Moving from Connecticut

Moving from Connecticut to Palm Beach County

Most Connecticut buyers start in Palm Beach (if you love Greenwich), North Palm Beach (Darien and Rowayton), Jupiter Island (New Canaan) or Palm Beach Gardens (the Fairfield County clubs). Florida has no income or estate tax; Connecticut’s top rate is 6.99% and its median property tax rate is 1.54%. JetBlue flies nonstop to Westchester and Hartford.

Moving from Connecticut

Which Palm Beach County Towns Feel Most Like Connecticut?

Western Connecticut, the planning region that runs from Greenwich and Stamford to Westport and Danbury, sends more people to Palm Beach and Martin counties than any other part of the state. Greenwich and Palm Beach have shared winters for a century, so the move is a short step: the same clubs, the same kind of harbor, warmer water.

For a Connecticut buyer leaving Greenwich, start with Palm Beach; leaving Darien and Rowayton, North Palm Beach; leaving New Canaan, Jupiter Island; leaving the Fairfield County clubs, Palm Beach Gardens. To weigh every town at once by water, clubs, downtowns, commute and live prices, see Where to Live in Palm Beach County: The Towns Compared.

Where Connecticut buyers start, by what they are leaving (updated November 2026)
If you are leavingStart withWhy it fits
GreenwichPalm BeachBelle Haven and Round Hill find their match in Palm Beach's ocean-to-lake estates, and Greenwich Avenue's shops in Worth Avenue.
Darien and RowaytonNorth Palm BeachIf home is a dock on Long Island Sound, North Palm Beach will feel familiar: canal homes, marinas and a village golf club, a few minutes from the inlet and open ocean.
New CanaanJupiter IslandNew Canaan's quiet, green back roads and big lots have their counterpart on Jupiter Island: estate homes between the ocean and the Intracoastal, preserved land and the Jupiter Island Club.
The Fairfield County clubsPalm Beach GardensIf your week is built around the club, Palm Beach Gardens has private golf clubs across the city, with the homes inside the gate., with the homes inside the gate.
Stamford and South NorwalkWest Palm BeachStamford's new towers and SoNo's restaurants point to West Palm Beach: new buildings on the Intracoastal, finance offices downtown and restaurants within a walk.
Litchfield County horse countryWellingtonLitchfield's farms and riding trails have a winter counterpart in Wellington, with the show-jumping and polo seasons running through the coldest months.
Essex and Old SaybrookTequestaEssex's river village and boatyards have a match in Tequesta: a small village on the Loxahatchee River, close to the inlet, with parks, docks and a slow pace.
GreenwichPalm BeachThe two have shared winters for a century: ocean-to-lake estates, Worth Avenue for Greenwich Avenue, and beach, golf and social clubs.
  • No state income taxConnecticut's top rate is 6.99%; Florida has none.
  • Lower property taxesConnecticut's median rate is 1.54%; Palm Beach County's is 0.82%.
  • No estate or gift taxConnecticut taxes estates above $15 million and gifts too; Florida does not.
  • Westchester nonstopJetBlue to HPN, plus Hartford and New Haven.
  • Boating all yearThe Intracoastal never freezes.

Find Your Match: 7 Places to Start

Where Your Matches Are

Tap a pin to jump to that match. Map data © OpenStreetMap contributors.

Client reviews

What Out-of-State Clients Say About Working With Monika

Verbatim reviews from Zillow and Google, from clients who bought, sold or rented here while living somewhere else.

Buying from out of state

We Are Your Eyes and Ears Down Here

Most of our relocation clients start from a distance. Before you fly down, my team and I walk the communities, video the homes, read the documents and the club rules, and send you notes.

When you visit, the days are planned around what is left to decide. After the offer, we line up the inspections and insurance quotes and stay on top of every step to closing, whether you are here or in Connecticut.

Reviews are verbatim from Zillow and Google; some predate Monika’s move to Douglas Elliman.

Clients who bought, sold or rented from out of state
350+Closings
165+Five-star reviews
5.0Zillow and Google
“We were buying from out of state and she went to potential homes to video apartments we saw online… we finally decided to move from NY to Florida.”
Bought a condo, Northwood Harbor, West Palm Beach · Zillow review
“Moved from out of state and had constant communication before I arrived for a site visit… She is a great local resource!!”
Moved from out of state · Google review
“We were from out of state and only had 2 days to look at homes. Monika was able to orient us to the area very quickly.”
Bought a single-family home, Old Palm, Palm Beach Gardens · Zillow review
“We were moving from the Northeast to the Jupiter area and needed knowledgeable help to guide us through the process since we were not on the ground.”
Rented a single-family home, Rialto, Jupiter · Zillow review
“Monika single-handedly made my move to Florida possible, that is not an exaggeration!!”
Moved to Florida · Google review
“She took the lead and we were able to follow, even from quite a distance away. She made everything smooth and easy.”
Bought a single-family home, Palm Beach Gardens · Zillow review
“What truly set her apart was the level of care and support she provided while I was out of state.”
Sold a condo from out of state · Google review
“Monika made it very easy for us by being our eyes and ears at the site… without us having to make any trips to the area.”
Sold a single-family home, Paloma, Palm Beach Gardens · Zillow review
“I accepted a job in West Palm Beach and had 3 weeks to find an apartment and move down from NY… I can't thank Monika enough.”
Rented a home, West Palm Beach · Zillow review
“I also really appreciated how well informed she kept me- despite me being out of state during this process.”
Sold a home from out of state · Google review
“I sold my property in Florida whilst living overseas with Monika's help!!”
Sold a townhouse, Villages of Palm Beach Lakes, West Palm Beach · Zillow review
Read Client Reviews →

Selected verbatim reviews from Zillow and Google, October 2026; some predate Monika’s move to Douglas Elliman. No reviewer was paid. Individual experiences; results vary.

Match 1 of 7Greenwich → Palm BeachAll matches ↑

If You Love Greenwich, You’ll Love Palm Beach

Greenwich and Palm Beach have long shared winter residents. Belle Haven and Round Hill find their match in Palm Beach's ocean-to-lake estates, and Greenwich Avenue's shops in Worth Avenue.

New: Phipps Ocean Park is being rebuilt with restored dunes, 80,000 native plants, a relocated Little Red Schoolhouse and new beach pavilions (WLRN, November 2025). (WLRN (opens in a new tab), 2025-11-18)

Palm Beach grew from a pioneer settlement on the lake into a resort town in a single generation. The railroad, the hotels and the bridges set the shape of the island, and the Town still guards it today.

Every home for sale in Palm Beach (opens in a new tab) The Palm Beach guide 246 for sale now (live from BeachesMLS; changes through the day)

See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions

Side by side

Greenwich and Palm Beach

If you loveGreenwich
You’ll lovePalm Beach
The vibe
GreenwichGreenwich Avenue shops, estate sections and the harbor
Palm BeachWorth Avenue shops, estate sections, the lake and the ocean
The beaches
GreenwichTown beaches on Long Island Sound, like Greenwich Point
Palm BeachOcean beaches along the island, including Midtown Beach in the middle of town
On the water
GreenwichGreenwich Harbor and Long Island Sound, boating in season
Palm BeachThe Intracoastal on one side and the Atlantic on the other, boating all year
Golf and clubs
GreenwichPrivate clubs like the Round Hill Club and the Belle Haven Club
Palm BeachPrivate clubs like the Everglades Club, the Bath and Tennis Club and Palm Beach Country Club
Evenings out
GreenwichA pint at The Ginger Man on Greenwich Avenue, wine at L'Escale on the harbor
Palm BeachDrinks at Ta-boó on Worth Avenue, cocktails at HMF in The Breakers
The homes
GreenwichWaterfront estates, back-country acreage and in-town houses
Palm BeachOcean-to-lake estates, postwar co-ops, condominiums and in-town houses
Getting back to Greenwich
GreenwichYou are already there; Westchester County Airport is about 15 minutes away
Palm BeachAbout 15 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN)

What to do and see

If You Love It There, Try This Here

Restaurants

4 matches
If you loveL'Escale (opens in a new tab)Greenwich

Hotel dining rooms right on the water, harbor there, Atlantic here.

If you loveTerra (opens in a new tab)Greenwich

Italian dinners on or just off the main shopping street.

Dinner rooms in the center of town for a dressed-up night out.

Local favorites on or just off the main shopping avenue.

Nightlife

2 matches
If you loveThe Ginger Man (opens in a new tab)Greenwich (64 Greenwich Avenue)
TryTa-boó (opens in a new tab)Palm Beach (Worth Avenue)

Bars right on the main shopping avenue for a drink before or after dinner.

If you loveL'Escale wine lounge (opens in a new tab)Greenwich Harbor (500 Steamboat Road)

Hotel lounges with a deep wine list for a dressed-up evening.

Coffee

2 matches

European-style café counters with pastries made in-house.

Small cafés on the main street for coffee, juices and a light bite.

Beaches, Parks and the Water

2 matches

Town-run public beaches close to the main shopping street.

Waterfront green space by the town docks, a walk from the shops.

Things to Do

2 matches

Town cultural campuses with galleries, lectures and changing exhibitions.

Historic houses open as museums, telling each town's Gilded Age and art-colony story.

Neighborhoods

Neighborhoods, Side by Side

GreenwichPalm BeachWhat they share
Belle Haven
Gated peninsula of waterfront estates on the harbor and the Sound.
Primavera Estates
See homes in this community (opens in a new tab)
Large houses on avenues running from the lake to the ocean, a short walk from Worth Avenue.
Downtown Greenwich
In-town houses and apartments on the streets around Greenwich Avenue.
Royal Park Addition
See homes in this community (opens in a new tab)
Houses and apartments within a walk of the main shopping street.
Riverside
Shoreline section of houses on coves and the harbor.
Ibis Isle
See homes in this community (opens in a new tab)
A small island of houses and condominium buildings on the lagoon, reached by one road.

More to explore

More Neighborhoods Worth Noting in Palm Beach

For the beach lover

Sloan's Curve: Gated oceanfront condominiums on South Ocean Boulevard.

See homes in Sloan's Curve (opens in a new tab) 8 for sale now

Two North Breakers Row: Oceanfront residences on The Breakers grounds.

See homes in Two North Breakers Row (opens in a new tab) 3 for sale now

For walking everywhere

Palm Beach Towers: An in-town condominium on Cocoanut Row, near Royal Poinciana Way.

See homes in Palm Beach Towers (opens in a new tab) 6 for sale now

Royal Park Addition: Houses and apartments on the avenues between Royal Palm Way and Worth Avenue.

See homes in Royal Park Addition (opens in a new tab) 27 for sale now

For ocean-to-lake estates

Primavera Estates: Estate lots on Clarke, Barton and Primavera Avenues, in lake front, middle and ocean sections.

See homes in Primavera Estates (opens in a new tab) 4 for sale now

For life on the lagoon

Ibis Isle: Houses and condominiums on an island in the Lake Worth Lagoon.

See homes in Ibis Isle (opens in a new tab) 7 for sale now

Questions

Questions About Palm Beach If You Love Greenwich

Is Palm Beach like Greenwich?

Greenwich and Palm Beach have long shared winter residents. Belle Haven and Round Hill find their match in Palm Beach's ocean-to-lake estates, and Greenwich Avenue's shops in Worth Avenue.

Where should I eat in Palm Beach if I love the restaurants in Greenwich?

If you love L'Escale in Greenwich, try The Seafood Bar at The Breakers. If you love Terra in Greenwich, try Renato's. If you love Mediterraneo in Greenwich, try Café L'Europe.

What is the nightlife like in Palm Beach compared with Greenwich?

If The Ginger Man in Greenwich (64 Greenwich Avenue) is your kind of night, try Ta-boó: bars right on the main shopping avenue for a drink before or after dinner. If L'Escale wine lounge in Greenwich Harbor (500 Steamboat Road) is your kind of night, try HMF at The Breakers: hotel lounges with a deep wine list for a dressed-up evening.

What are the coffee shops, beaches and parks like in Palm Beach compared with Greenwich?

Which Palm Beach neighborhoods feel like Greenwich?

Belle Haven: look at Primavera Estates (Large houses on avenues running from the lake to the ocean, a short walk from Worth Avenue). Downtown Greenwich: look at Royal Park Addition (Houses and apartments within a walk of the main shopping street). Riverside: look at Ibis Isle (A small island of houses and condominium buildings on the lagoon, reached by one road). See every one in our Palm Beach neighborhood guides.

What is different about living in Palm Beach compared with Greenwich?

The vibe: Greenwich Avenue shops, estate sections and the harbor in Greenwich; Worth Avenue shops, estate sections, the lake and the ocean in Palm Beach. The beaches: Town beaches on Long Island Sound, like Greenwich Point in Greenwich; Ocean beaches along the island, including Midtown Beach in the middle of town in Palm Beach. On the water: Greenwich Harbor and Long Island Sound, boating in season in Greenwich; The Intracoastal on one side and the Atlantic on the other, boating all year in Palm Beach. Golf and clubs: Private clubs like the Round Hill Club and the Belle Haven Club in Greenwich; Private clubs like the Everglades Club, the Bath and Tennis Club and Palm Beach Country Club in Palm Beach. Evenings out: A pint at The Ginger Man on Greenwich Avenue, wine at L'Escale on the harbor in Greenwich; Drinks at Ta-boó on Worth Avenue, cocktails at HMF in The Breakers in Palm Beach. The homes: Waterfront estates, back-country acreage and in-town houses in Greenwich; Ocean-to-lake estates, postwar co-ops, condominiums and in-town houses in Palm Beach. Getting back to Greenwich: You are already there; Westchester County Airport is about 15 minutes away in Greenwich; About 15 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN) in Palm Beach.

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Match 2 of 7Darien and Rowayton → North Palm BeachAll matches ↑

If You Love Darien and Rowayton, You’ll Love North Palm Beach

If home is a dock on Long Island Sound, North Palm Beach will feel familiar: canal homes, marinas and a village golf club, a few minutes from the inlet and open ocean.

New: Village Place, the proposed redevelopment of the old Twin City Mall site at US-1 and Northlake Boulevard (hotel, residences, retail, civic space), is on hold pending the developer's lawsuit with the village over building heights. (Stet News (opens in a new tab), 2026-08-24)

North Palm Beach is a planned village of the 1950s, laid out on land that changed hands several times before it was dredged into canals. The golf course, the waterfront and the postwar plan still shape its neighborhoods today.

Every home for sale in North Palm Beach (opens in a new tab) The North Palm Beach guide 261 for sale now (live from BeachesMLS; changes through the day)

See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions

Side by side

Darien and Rowayton and North Palm Beach

If you loveDarien and Rowayton
You’ll loveNorth Palm Beach
The vibe
Darien and RowaytonShoreline villages, yacht clubs and the Five Mile River
North Palm BeachA canal village of docks and marinas, with a village golf club
The beaches
Darien and RowaytonTown beaches on the Sound, like Weed Beach in Darien
North Palm BeachOcean beaches minutes away in Juno Beach and at John D. MacArthur Beach State Park
On the water
Darien and RowaytonLong Island Sound, boating spring to fall
North Palm BeachThe Intracoastal, the Palm Beach Inlet and the Atlantic, boating all year
Golf and clubs
Darien and RowaytonClubs like Wee Burn Country Club and the Noroton Yacht Club
North Palm BeachThe village-owned North Palm Beach Country Club, with private clubs next door in Palm Beach Gardens
Evenings out
Darien and RowaytonOysters at Rowayton Seafood on the river, concerts at District Music Hall in Norwalk
North Palm BeachDrinks on the dock at Frigate's, concerts at Harbourside Place in Jupiter
The homes
Darien and RowaytonShingle houses and waterfront colonials
North Palm BeachCanal homes with docks and marina condominiums
Getting back to Greenwich
Darien and RowaytonAbout 15 to 20 minutes by car or Metro-North
North Palm BeachAbout 25 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN)

What to do and see

If You Love It There, Try This Here

Restaurants

2 matches

Casual seafood on the water where boats tie up alongside.

Neighborhood food markets with a counter for lunch.

Nightlife

2 matches
If you loveRowayton Seafood (opens in a new tab)Rowayton (on the Five Mile River)

Waterfront spots with their own docks, so you can arrive by boat for drinks and seafood.

TryHarbourside Place amphitheater (opens in a new tab)Jupiter, about 15 minutes north

Concert stages a short drive from home for an evening show.

Coffee

2 matches

Independent espresso bars in the middle of town.

Casual local cafés on the main road for coffee and breakfast.

Beaches, Parks and the Water

2 matches

Beach parks a few minutes from home, with room to walk the shore.

Waterfront town parks with a boat launch.

Things to Do

2 matches

Harbors where boating sets the rhythm of the week.

Golf courses a short drive from the docks.

Neighborhoods

Neighborhoods, Side by Side

Darien and RowaytonNorth Palm BeachWhat they share
Tokeneke
Darien shoreline section of estates on the Sound with a private beach association.
Lost Tree Village
See homes in this community (opens in a new tab)
Estates between the ocean and the Intracoastal behind a guard gate, with a club only residents may join.
Noroton Bay
Darien beach association of houses along the Sound.
Seminole Landing
See homes in this community (opens in a new tab)
Homes beside a shared private beach.

More to explore

More Neighborhoods Worth Noting in North Palm Beach

For golf and club life

Lost Tree: Gated homes from ocean to Intracoastal around a private club.

See homes in Lost Tree (opens in a new tab) 17 for sale now

For boaters

Old Port Cove: Condominiums around a marina with slips to 200 feet.

See homes in Old Port Cove (opens in a new tab) 29 for sale now

Harbour Isles: Single-family homes built in the early 2000s.

See homes in Harbour Isles (opens in a new tab) 5 for sale now

For the beach lover

Seminole Landing: Gated homes by the ocean with a private beach.

See homes in Seminole Landing (opens in a new tab) 1 for sale now

Questions

Questions About North Palm Beach If You Love Darien and Rowayton

Is North Palm Beach like Darien and Rowayton?

If home is a dock on Long Island Sound, North Palm Beach will feel familiar: canal homes, marinas and a village golf club, a few minutes from the inlet and open ocean.

Where should I eat in North Palm Beach if I love the restaurants in Darien and Rowayton?

If you love Rowayton Seafood in Rowayton, try Frigates Waterfront Bar & Grill. If you love Rowayton Market in Rowayton, try Cod & Capers Seafood.

What is the nightlife like in North Palm Beach compared with Darien and Rowayton?

If Rowayton Seafood in Rowayton (on the Five Mile River) is your kind of night, try Frigate's Waterfront Bar & Grill: waterfront spots with their own docks, so you can arrive by boat for drinks and seafood. If District Music Hall in Norwalk is your kind of night, try Harbourside Place amphitheater: concert stages a short drive from home for an evening show.

What are the coffee shops, beaches and parks like in North Palm Beach compared with Darien and Rowayton?

Which North Palm Beach neighborhoods feel like Darien and Rowayton?

Tokeneke: look at Lost Tree Village (Estates between the ocean and the Intracoastal behind a guard gate, with a club only residents may join). Noroton Bay: look at Seminole Landing (Homes beside a shared private beach). See every one in our North Palm Beach neighborhood guides.

What is different about living in North Palm Beach compared with Darien and Rowayton?

The vibe: Shoreline villages, yacht clubs and the Five Mile River in Darien and Rowayton; A canal village of docks and marinas, with a village golf club in North Palm Beach. The beaches: Town beaches on the Sound, like Weed Beach in Darien in Darien and Rowayton; Ocean beaches minutes away in Juno Beach and at John D. MacArthur Beach State Park in North Palm Beach. On the water: Long Island Sound, boating spring to fall in Darien and Rowayton; The Intracoastal, the Palm Beach Inlet and the Atlantic, boating all year in North Palm Beach. Golf and clubs: Clubs like Wee Burn Country Club and the Noroton Yacht Club in Darien and Rowayton; The village-owned North Palm Beach Country Club, with private clubs next door in Palm Beach Gardens in North Palm Beach. Evenings out: Oysters at Rowayton Seafood on the river, concerts at District Music Hall in Norwalk in Darien and Rowayton; Drinks on the dock at Frigate's, concerts at Harbourside Place in Jupiter in North Palm Beach. The homes: Shingle houses and waterfront colonials in Darien and Rowayton; Canal homes with docks and marina condominiums in North Palm Beach. Getting back to Greenwich: About 15 to 20 minutes by car or Metro-North in Darien and Rowayton; About 25 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN) in North Palm Beach.

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Match 3 of 7New Canaan → Jupiter Island and Hobe SoundAll matches ↑

If You Love New Canaan, You’ll Love Jupiter Island and Hobe Sound

New Canaan's quiet, green back roads and big lots have their counterpart on Jupiter Island: estate homes between the ocean and the Intracoastal, preserved land and the Jupiter Island Club.

New: A mixed-use project is proposed at 9025 SE Bridge Road in downtown Hobe Sound: about 4,399 sq ft of restaurant and retail space, three apartments and six townhouses (Martin County applications, February 2026). (TreasureCoast.com (opens in a new tab), 2026-02)

Jupiter Island was a Spanish land grant, a pineapple venture and a winter resort before it became a town. The club, the preserves and the beach program that shape it today date from the 1930s to the 1980s.

Every home for sale in Jupiter Island and Hobe Sound (opens in a new tab) 18 for sale now (live from BeachesMLS; changes through the day)

See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions

Side by side

New Canaan and Jupiter Island and Hobe Sound

If you loveNew Canaan
You’ll loveJupiter Island and Hobe Sound
The vibe
New CanaanGreen back roads, big lots and a walkable Elm Street
Jupiter Island and Hobe SoundQuiet, green roads of estate homes and preserved land, with no shopping district
The beaches
New CanaanSound beaches a drive away in Darien and Norwalk
Jupiter Island and Hobe SoundOcean beaches on the east side, and the rock shoreline at Blowing Rocks Preserve
On the water
New CanaanPonds and reservoirs, with the Sound about 15 minutes south
Jupiter Island and Hobe SoundThe Intracoastal on the west side with private docks; the Jupiter Inlet just south
Golf and clubs
New CanaanPrivate clubs like the Country Club of New Canaan
Jupiter Island and Hobe SoundThe Jupiter Island Club, with more clubs nearby in Hobe Sound and Jupiter
Evenings out
New CanaanDinner at Gates, a drink at the South End Bar off Elm Street
Jupiter Island and Hobe SoundQuiet evenings on the island; live music at Tiki 52 in Tequesta, a short drive south
The homes
New CanaanColonials and modern houses on acreage
Jupiter Island and Hobe SoundEstate homes on large lots between the ocean and the Intracoastal
Getting back to Greenwich
New CanaanAbout 25 to 30 minutes by car
Jupiter Island and Hobe SoundAbout 45 to 55 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN)

What to do and see

If You Love It There, Try This Here

Nightlife

2 matches
If you loveGATES Restaurant & Bar (opens in a new tab)New Canaan (Forest Street)

Relaxed restaurant bars where locals meet for a drink and dinner.

If you loveThe South End Bar @ The Back End (opens in a new tab)New Canaan (17 Elm Street)

Casual bars a short drive from home for a drink on a weekend night.

Beaches, Parks and the Water

2 matches

Protected land with quiet trails close to home.

TryBlowing Rocks Preserve (opens in a new tab)Jupiter Island and Hobe Sound

Open landscapes with walking paths and a visitor building to start from.

Neighborhoods

Neighborhoods, Side by Side

New CanaanJupiter Island and Hobe SoundWhat they share
Oenoke Ridge
Estate homes on large, wooded lots north of town.
Jupiter IslandLarge estate lots, quiet roads and a lot of green.
Country Club of New Canaan area
Homes on the roads around the town's private club.
Jupiter Island Club
See homes in this community (opens in a new tab)
Island life built around one private club.

More to explore

More Neighborhoods Worth Noting in Jupiter Island and Hobe Sound

For quiet and privacy

Jupiter Island Club: A 1944 club at the center of a 2.7-square-mile town.

See homes in Jupiter Island Club (opens in a new tab) 13 for sale now

For boaters

Loblolly: In Hobe Sound across the Intracoastal from Jupiter Island: homes on the Intracoastal with a private marina and club.

See homes in Loblolly (opens in a new tab) 6 for sale now

Questions

Questions About Jupiter Island and Hobe Sound If You Love New Canaan

Is Jupiter Island and Hobe Sound like New Canaan?

New Canaan's quiet, green back roads and big lots have their counterpart on Jupiter Island: estate homes between the ocean and the Intracoastal, preserved land and the Jupiter Island Club.

What is the nightlife like in Jupiter Island and Hobe Sound compared with New Canaan?

If GATES Restaurant & Bar in New Canaan (Forest Street) is your kind of night, try Tiki 52 Bar & Grill: relaxed restaurant bars where locals meet for a drink and dinner. If The South End Bar @ The Back End in New Canaan (17 Elm Street) is your kind of night, try Square Grouper Tiki Bar: casual bars a short drive from home for a drink on a weekend night.

What are the coffee shops, beaches and parks like in Jupiter Island and Hobe Sound compared with New Canaan?

Which Jupiter Island and Hobe Sound neighborhoods feel like New Canaan?

Oenoke Ridge: look at Jupiter Island (Large estate lots, quiet roads and a lot of green). Country Club of New Canaan area: look at Jupiter Island Club (Island life built around one private club). See every one in our Jupiter Island and Hobe Sound neighborhood guides.

What is different about living in Jupiter Island and Hobe Sound compared with New Canaan?

The vibe: Green back roads, big lots and a walkable Elm Street in New Canaan; Quiet, green roads of estate homes and preserved land, with no shopping district in Jupiter Island and Hobe Sound. The beaches: Sound beaches a drive away in Darien and Norwalk in New Canaan; Ocean beaches on the east side, and the rock shoreline at Blowing Rocks Preserve in Jupiter Island and Hobe Sound. On the water: Ponds and reservoirs, with the Sound about 15 minutes south in New Canaan; The Intracoastal on the west side with private docks; the Jupiter Inlet just south in Jupiter Island and Hobe Sound. Golf and clubs: Private clubs like the Country Club of New Canaan in New Canaan; The Jupiter Island Club, with more clubs nearby in Hobe Sound and Jupiter in Jupiter Island and Hobe Sound. Evenings out: Dinner at Gates, a drink at the South End Bar off Elm Street in New Canaan; Quiet evenings on the island; live music at Tiki 52 in Tequesta, a short drive south in Jupiter Island and Hobe Sound. The homes: Colonials and modern houses on acreage in New Canaan; Estate homes on large lots between the ocean and the Intracoastal in Jupiter Island and Hobe Sound. Getting back to Greenwich: About 25 to 30 minutes by car in New Canaan; About 45 to 55 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN) in Jupiter Island and Hobe Sound.

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Match 4 of 7The Fairfield County clubs → Palm Beach GardensAll matches ↑

If You Love The Fairfield County clubs, You’ll Love Palm Beach Gardens

If your week is built around the club, Palm Beach Gardens has private golf clubs across the city, with the homes inside the gate., with the homes inside the gate.

New: Publix opened May 21, 2026 at Avenir Town Center on Northlake Boulevard. (Publix Corporate Newsroom (opens in a new tab), 2026-05-21)

Palm Beach Gardens was a plan on paper before it was a place. One landowner’s idea of a garden city, and the golf that followed, shaped the neighborhoods buyers choose between today.

Every home for sale in Palm Beach Gardens (opens in a new tab) The Palm Beach Gardens guide 603 for sale now (live from BeachesMLS; changes through the day)

See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions

Side by side

The Fairfield County clubs and Palm Beach Gardens

If you loveThe Fairfield County clubs
You’ll lovePalm Beach Gardens
The vibe
The Fairfield County clubsLong-established towns, country clubs and wooded lots
Palm Beach GardensA planned city of gated club communities, with shopping on PGA Boulevard
The beaches
The Fairfield County clubsSound beaches in towns like Westport, Fairfield and Greenwich
Palm Beach GardensJuno Beach and Singer Island about 10 to 15 minutes away
On the water
The Fairfield County clubsLong Island Sound, boating spring to fall
Palm Beach GardensThe Intracoastal on the city's east side, boating all year
Golf and clubs
The Fairfield County clubsPrivate clubs like Round Hill, Wee Burn and the Country Club of Fairfield, April to October
Palm Beach GardensClubs like PGA National, BallenIsles and Old Palm, played all year
Evenings out
The Fairfield County clubsConcerts at Fairfield Theatre Company, a pint at Two Roads in Stratford
Palm Beach GardensConcerts at Harbourside Place in Jupiter, a pint at Twisted Trunk Brewing
The homes
The Fairfield County clubsColonials and estates
Palm Beach GardensClub homes and custom estates inside gated communities
Getting back to Greenwich
The Fairfield County clubsAbout 15 to 45 minutes by car, depending on the town
Palm Beach GardensAbout 20 to 25 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN)

What to do and see

If You Love It There, Try This Here

Restaurants

2 matches

Seafood with a view of boats on the water.

If you loveKawa Ni (opens in a new tab)Westport

Chef-run restaurants with short, changing menus.

Nightlife

2 matches
TryHarbourside Place amphitheater (opens in a new tab)Jupiter, about 15 minutes north

Close-to-home stages for an evening concert without driving into the city.

TryTwisted Trunk Brewing (opens in a new tab)Palm Beach Gardens (PGA Boulevard)

Local craft breweries with taprooms for a pint with friends.

Coffee

1 match

Local bakeries with bread from their own ovens and coffee to go.

Things to Do

1 match

Enclosed malls anchored by department stores.

Neighborhoods

Neighborhoods, Side by Side

The Fairfield County clubsPalm Beach GardensWhat they share
Wee Burn Country Club
Long-established Darien golf club with homes on the surrounding roads.
BallenIsles
See homes in this community (opens in a new tab)
An established club with golf at the center of the neighborhood.
Shorehaven Golf Club
East Norwalk club where the course runs beside the Sound.
Frenchman's Creek
See homes in this community (opens in a new tab)
Golf and deep water in the same club.
The Stanwich Club
Greenwich golf club known for a demanding course in the back country.
Old Palm Golf Club
See homes in this community (opens in a new tab)
A golf-first club with a demanding course.

More to explore

More Neighborhoods Worth Noting in Palm Beach Gardens

For golf and club life

BallenIsles: Three courses and an equity club.

See homes in BallenIsles (opens in a new tab) 28 for sale now

Old Palm: About 300 homes on 650 acres around one private course.

See homes in Old Palm (opens in a new tab) 5 for sale now

Mirasol: Two courses and 23 neighborhoods.

See homes in Mirasol (opens in a new tab) 10 for sale now

For boaters

Frenchman's Creek: Deep-water lots, 36 holes and a beach club.

See homes in Frenchman's Creek (opens in a new tab) 17 for sale now

For golf without a required membership

PGA National: Four championship courses plus a par-3, thousands of homes, with club membership optional.

See homes in PGA National (opens in a new tab) 102 for sale now

For no club at all

Evergrene: Homes around Lake Dorothy, with no club equity.

See homes in Evergrene (opens in a new tab) 22 for sale now

Questions

Questions About Palm Beach Gardens If You Love The Fairfield County clubs

Is Palm Beach Gardens like The Fairfield County clubs?

If your week is built around the club, Palm Beach Gardens has private golf clubs across the city, with the homes inside the gate., with the homes inside the gate.

Where should I eat in Palm Beach Gardens if I love the restaurants in The Fairfield County clubs?

If you love The Whelk in Westport, try Waterway Cafe. If you love Kawa Ni in Westport, try Coolinary and The Parched Pig.

What is the nightlife like in Palm Beach Gardens compared with The Fairfield County clubs?

If Fairfield Theatre Company in Fairfield is your kind of night, try Harbourside Place amphitheater: close-to-home stages for an evening concert without driving into the city. If Two Roads Brewing in Stratford is your kind of night, try Twisted Trunk Brewing: local craft breweries with taprooms for a pint with friends.

What are the coffee shops, beaches and parks like in Palm Beach Gardens compared with The Fairfield County clubs?

Which Palm Beach Gardens neighborhoods feel like The Fairfield County clubs?

Wee Burn Country Club: look at BallenIsles (An established club with golf at the center of the neighborhood). Shorehaven Golf Club: look at Frenchman's Creek (Golf and deep water in the same club). The Stanwich Club: look at Old Palm Golf Club (A golf-first club with a demanding course). See every one in our Palm Beach Gardens neighborhood guides.

What is different about living in Palm Beach Gardens compared with The Fairfield County clubs?

The vibe: Long-established towns, country clubs and wooded lots in The Fairfield County clubs; A planned city of gated club communities, with shopping on PGA Boulevard in Palm Beach Gardens. The beaches: Sound beaches in towns like Westport, Fairfield and Greenwich in The Fairfield County clubs; Juno Beach and Singer Island about 10 to 15 minutes away in Palm Beach Gardens. On the water: Long Island Sound, boating spring to fall in The Fairfield County clubs; The Intracoastal on the city's east side, boating all year in Palm Beach Gardens. Golf and clubs: Private clubs like Round Hill, Wee Burn and the Country Club of Fairfield, April to October in The Fairfield County clubs; Clubs like PGA National, BallenIsles and Old Palm, played all year in Palm Beach Gardens. Evenings out: Concerts at Fairfield Theatre Company, a pint at Two Roads in Stratford in The Fairfield County clubs; Concerts at Harbourside Place in Jupiter, a pint at Twisted Trunk Brewing in Palm Beach Gardens. The homes: Colonials and estates in The Fairfield County clubs; Club homes and custom estates inside gated communities in Palm Beach Gardens. Getting back to Greenwich: About 15 to 45 minutes by car, depending on the town in The Fairfield County clubs; About 20 to 25 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN) in Palm Beach Gardens.

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Match 5 of 7Stamford and South Norwalk → West Palm BeachAll matches ↑

If You Love Stamford and South Norwalk, You’ll Love West Palm Beach

Stamford's new towers and SoNo's restaurants point to West Palm Beach: new buildings on the Intracoastal, finance offices downtown and restaurants within a walk.

New: The Nora District enters its third phase with Nora House, an 11-story building of 117 condos; groundbreaking expected 2027, completion 2029. (WFLX (opens in a new tab), 2026-04-10)

West Palm Beach began as Henry Flagler’s town across the lake from his Palm Beach hotels. The railroad, the boom and the bust, and the arts that came later shaped the neighborhoods buyers look at today.

Every home for sale in West Palm Beach (opens in a new tab) The West Palm Beach guide 1,670 for sale now (live from BeachesMLS; changes through the day)

See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions

Side by side

Stamford and South Norwalk and West Palm Beach

If you loveStamford and South Norwalk
You’ll loveWest Palm Beach
The vibe
Stamford and South NorwalkNew towers, corporate offices and the restaurants of Washington Street in SoNo
West Palm BeachNew towers on the Intracoastal, finance offices and restaurants on Clematis Street
The beaches
Stamford and South NorwalkSound beaches like Cummings Park in Stamford and Calf Pasture in Norwalk
West Palm BeachOcean beaches across the bridge in Palm Beach, about 10 minutes away
On the water
Stamford and South NorwalkStamford Harbor and Norwalk Harbor on Long Island Sound
West Palm BeachThe Intracoastal along Flagler Drive, with marinas downtown
Golf and clubs
Stamford and South NorwalkPublic courses and private clubs across the county
West Palm BeachPrivate clubs a short drive away in Palm Beach and Palm Beach Gardens
Evenings out
Stamford and South NorwalkA beer at Half Full Brewery in Stamford, concerts at District Music Hall in Norwalk
West Palm BeachA beer at Steam Horse Brewing, shows at the Kravis Center, Thursday concerts at Clematis by Night
The homes
Stamford and South NorwalkCondominium towers, townhouses and older neighborhoods
West Palm BeachCondominium towers on Flagler Drive and 1920s houses in historic districts
Getting back to Greenwich
Stamford and South NorwalkAbout 15 to 25 minutes by car or Metro-North
West Palm BeachAbout 10 to 15 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN)

What to do and see

If You Love It There, Try This Here

Restaurants

2 matches
If you loveMatch (opens in a new tab)South Norwalk

Chef-driven American cooking in a lively neighborhood dining room.

TryGrato (opens in a new tab)West Palm Beach

Neighborhood Italian with pasta and a lively room.

Nightlife

2 matches
If you loveHalf Full Brewery (opens in a new tab)Stamford (575 Pacific Street)
TrySteam Horse Brewing (opens in a new tab)West Palm Beach (Warehouse District)

Brewery taprooms in a revived neighborhood near downtown, busy in the evenings.

Downtown stages for touring concerts and comedy, close to dinner.

Coffee

2 matches

Local roasters pouring their own beans in town.

If you loveHoney Joe'sStamford

Independent cafés for coffee and a quick bite.

Beaches, Parks and the Water

1 match

Downtown green space along the water with events through the year.

Things to Do

1 match

Downtown stages for touring shows, concerts and comedy.

Neighborhoods

Neighborhoods, Side by Side

Stamford and South NorwalkWest Palm BeachWhat they share
Harbor Point
New towers along the marina in Stamford's South End.
One Watermark Place
See homes in this community (opens in a new tab)
Residences on the water with a private marina at the door.
Downtown Stamford
High-rise apartments and condos near the station and offices.
CityPlace South Tower
See homes in this community (opens in a new tab)
Tower living over a walkable downtown of shops and offices.
SoNo
South Norwalk's historic brick blocks around Washington Street.
Northwood Village
No homes are listed for sale here right now. New listings come up through the year; ask me to watch for one.
Historic main-street blocks with restaurants and galleries.
Shippan Point
Stamford peninsula of houses on the Sound.
El Cid
See homes in this community (opens in a new tab)
Older houses on streets along the water near downtown.

More to explore

More Neighborhoods Worth Noting in West Palm Beach

For something new

The Bristol: A 25-story tower on South Flagler Drive, completed 2019.

See homes in The Bristol (opens in a new tab) 4 for sale now

La Clara: 83 residences on South Flagler, closings from 2023.

See homes in La Clara (opens in a new tab) 3 for sale now

Forté on Flagler: A 25-story tower on South Flagler, with closings since July 2025.

See homes in Forté on Flagler (opens in a new tab) 5 for sale now

For boaters

One Watermark Place: Large residences above a 22-slip marina.

See homes in One Watermark Place (opens in a new tab) 1 for sale now

For old Florida charm

El Cid: A historic district of 1920s and postwar homes along South Flagler Drive.

See homes in El Cid (opens in a new tab) 9 for sale now

Flamingo Park: A 1920s historic district just south of downtown.

See homes in Flamingo Park (opens in a new tab) 9 for sale now

Old Northwood: A 1920s land-boom historic district north of downtown.

See homes in Old Northwood (opens in a new tab) 9 for sale now

For a newer single-family home

Banyan Cay: Single-family homes inside Banyan Cay Resort, on the former President Country Club land.

See homes in Banyan Cay (opens in a new tab) 22 for sale now

Questions

Questions About West Palm Beach If You Love Stamford and South Norwalk

Is West Palm Beach like Stamford and South Norwalk?

Stamford's new towers and SoNo's restaurants point to West Palm Beach: new buildings on the Intracoastal, finance offices downtown and restaurants within a walk.

Where should I eat in West Palm Beach if I love the restaurants in Stamford and South Norwalk?

If you love Match in South Norwalk, try Kitchen. If you love Cafe Silvium in Stamford, try Grato.

What is the nightlife like in West Palm Beach compared with Stamford and South Norwalk?

If Half Full Brewery in Stamford (575 Pacific Street) is your kind of night, try Steam Horse Brewing: brewery taprooms in a revived neighborhood near downtown, busy in the evenings. If District Music Hall in Norwalk is your kind of night, try Kravis Center: downtown stages for touring concerts and comedy, close to dinner.

What are the coffee shops, beaches and parks like in West Palm Beach compared with Stamford and South Norwalk?

Which West Palm Beach neighborhoods feel like Stamford and South Norwalk?

Harbor Point: look at One Watermark Place (Residences on the water with a private marina at the door). Downtown Stamford: look at CityPlace South Tower (Tower living over a walkable downtown of shops and offices). SoNo: look at Northwood Village (Historic main-street blocks with restaurants and galleries). Shippan Point: look at El Cid (Older houses on streets along the water near downtown). See every one in our West Palm Beach neighborhood guides.

What is different about living in West Palm Beach compared with Stamford and South Norwalk?

The vibe: New towers, corporate offices and the restaurants of Washington Street in SoNo in Stamford and South Norwalk; New towers on the Intracoastal, finance offices and restaurants on Clematis Street in West Palm Beach. The beaches: Sound beaches like Cummings Park in Stamford and Calf Pasture in Norwalk in Stamford and South Norwalk; Ocean beaches across the bridge in Palm Beach, about 10 minutes away in West Palm Beach. On the water: Stamford Harbor and Norwalk Harbor on Long Island Sound in Stamford and South Norwalk; The Intracoastal along Flagler Drive, with marinas downtown in West Palm Beach. Golf and clubs: Public courses and private clubs across the county in Stamford and South Norwalk; Private clubs a short drive away in Palm Beach and Palm Beach Gardens in West Palm Beach. Evenings out: A beer at Half Full Brewery in Stamford, concerts at District Music Hall in Norwalk in Stamford and South Norwalk; A beer at Steam Horse Brewing, shows at the Kravis Center, Thursday concerts at Clematis by Night in West Palm Beach. The homes: Condominium towers, townhouses and older neighborhoods in Stamford and South Norwalk; Condominium towers on Flagler Drive and 1920s houses in historic districts in West Palm Beach. Getting back to Greenwich: About 15 to 25 minutes by car or Metro-North in Stamford and South Norwalk; About 10 to 15 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN) in West Palm Beach.

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Match 6 of 7Litchfield County horse country → WellingtonAll matches ↑

If You Love Litchfield County horse country, You’ll Love Wellington

Litchfield's farms and riding trails have a winter counterpart in Wellington, with the show-jumping and polo seasons running through the coldest months.

New: Related Ross bought 32 acres near State Road 7 for Village Landing, planned with a 180-room hotel and 300,000+ square feet of shops, offices and restaurants. (Commercial Observer (opens in a new tab), 2026-09-01)

Wellington is one of the newest towns in the county: a ranch in the 1950s, a planned community in the 1970s and a village since 1995. Horses came with the polo club and never left.

See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions

Side by side

Litchfield County horse country and Wellington

If you loveLitchfield County horse country
You’ll loveWellington
The vibe
Litchfield County horse countryFarms, stone walls and small New England towns
WellingtonHorse farms, show grounds and polo fields, busiest in the winter season
The outdoors
Litchfield County horse countryHiking trails, lakes and state forests
WellingtonBridle trails through the equestrian district and village parks
Horses and riding
Litchfield County horse countrySummer and fall shows and trail riding
WellingtonThe Winter Equestrian Festival at Wellington International, January to April, and the polo season
Golf and clubs
Litchfield County horse countryCountry clubs and a few public courses
WellingtonClubs like The Wanderers Club and Palm Beach Polo
Evenings out
Litchfield County horse countryPiano nights at Fife 'n Drum in Kent, summer concerts at Music Mountain
WellingtonLive bands at Copper Blues, weekend concerts at the Wellington Amphitheater
The homes
Litchfield County horse countryFarms and country houses on acreage
WellingtonFarms and estates in an equestrian zoning district, plus club homes
Getting back to Greenwich
Litchfield County horse countryAbout 1.5 hours by car
WellingtonAbout 20 to 30 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN)

What to do and see

If You Love It There, Try This Here

Restaurants

2 matches

New American dining in the middle of horse country.

Local restaurants that have been town gathering places for years.

Nightlife

2 matches

Live music with dinner and drinks on weekend nights.

If you loveMusic Mountain (opens in a new tab)Falls Village

Weekend concert series in season, a short drive from the farms.

Coffee

1 match

Farm-minded cafés with coffee, breakfast and fresh ingredients.

Beaches, Parks and the Water

1 match

Wetland boardwalks and trails for birdwatching.

Neighborhoods

Neighborhoods, Side by Side

Litchfield County horse countryWellingtonWhat they share
Litchfield horse farms
Farms with barns, paddocks and riding trails outside the borough.
Palm Beach Point
See homes in this community (opens in a new tab)
Farms of several acres with barns and room to ride.
Washington and Roxbury
Estate homes and horse properties on rolling farmland.
Southfields
See homes in this community (opens in a new tab)
Estate homes and horse properties beside Palm Beach Polo.
Salisbury and Lakeville
Country lanes of farms and horse properties near the hills.
Saddle Trail Park
See homes in this community (opens in a new tab)
Acreage lots with barns and paddocks on quiet, ungated roads.

More to explore

More Neighborhoods Worth Noting in Wellington

For room to ride

Palm Beach Point: Farm parcels in Wellington’s equestrian district.

See homes in Palm Beach Point (opens in a new tab) 7 for sale now

Saddle Trail Park: Acreage lots in the equestrian district.

See homes in Saddle Trail Park (opens in a new tab) 11 for sale now

Next to the show grounds

Grand Prix Village: Horse farms near the Wellington International show grounds.

No homes are listed for sale here right now. New listings come up through the year; ask me to watch for one.

For polo

Southfields: Horse properties and estate homes near Palm Beach Polo Golf & Country Club.

See homes in Southfields (opens in a new tab) 5 for sale now

For golf

Binks Forest: Homes around Wellington National, a Johnny Miller course.

See homes in Binks Forest (opens in a new tab) 16 for sale now

Questions

Questions About Wellington If You Love Litchfield County horse country

Is Wellington like Litchfield County horse country?

Litchfield's farms and riding trails have a winter counterpart in Wellington, with the show-jumping and polo seasons running through the coldest months.

Where should I eat in Wellington if I love the restaurants in Litchfield County horse country?

If you love West Street Grill in Litchfield, try Stallion Restaurant. If you love The Village in Litchfield, try Oli's Fashion Cuisine.

What is the nightlife like in Wellington compared with Litchfield County horse country?

If Fife 'n Drum in Kent is your kind of night, try Copper Blues Rock Pub & Kitchen: live music with dinner and drinks on weekend nights. If Music Mountain in Falls Village is your kind of night, try Wellington Amphitheater weekend concerts: weekend concert series in season, a short drive from the farms.

What are the coffee shops, beaches and parks like in Wellington compared with Litchfield County horse country?

Which Wellington neighborhoods feel like Litchfield County horse country?

Litchfield horse farms: look at Palm Beach Point (Farms of several acres with barns and room to ride). Washington and Roxbury: look at Southfields (Estate homes and horse properties beside Palm Beach Polo). Salisbury and Lakeville: look at Saddle Trail Park (Acreage lots with barns and paddocks on quiet, ungated roads). See every one in our Wellington neighborhood guides.

What is different about living in Wellington compared with Litchfield County horse country?

The vibe: Farms, stone walls and small New England towns in Litchfield County horse country; Horse farms, show grounds and polo fields, busiest in the winter season in Wellington. The outdoors: Hiking trails, lakes and state forests in Litchfield County horse country; Bridle trails through the equestrian district and village parks in Wellington. Horses and riding: Summer and fall shows and trail riding in Litchfield County horse country; The Winter Equestrian Festival at Wellington International, January to April, and the polo season in Wellington. Golf and clubs: Country clubs and a few public courses in Litchfield County horse country; Clubs like The Wanderers Club and Palm Beach Polo in Wellington. Evenings out: Piano nights at Fife 'n Drum in Kent, summer concerts at Music Mountain in Litchfield County horse country; Live bands at Copper Blues, weekend concerts at the Wellington Amphitheater in Wellington. The homes: Farms and country houses on acreage in Litchfield County horse country; Farms and estates in an equestrian zoning district, plus club homes in Wellington. Getting back to Greenwich: About 1.5 hours by car in Litchfield County horse country; About 20 to 30 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN) in Wellington.

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Match 7 of 7Essex and Old Saybrook → TequestaAll matches ↑

If You Love Essex and Old Saybrook, You’ll Love Tequesta

Essex's river village and boatyards have a match in Tequesta: a small village on the Loxahatchee River, close to the inlet, with parks, docks and a slow pace.

New: The Village of Tequesta took ownership of Tequesta Park from the state and has an $8-10 million improvement plan, with planning money set aside but no construction funding yet. (WFLX (opens in a new tab), 2026-06-23)

Tequesta is younger than its neighbors: a 1950s plan along the river forks that became a village in two years. The river, the inlet and the lighthouse across the water were here long before it.

Every home for sale in Tequesta (opens in a new tab) The Tequesta guide 96 for sale now (live from BeachesMLS; changes through the day)

See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions

Side by side

Essex and Old Saybrook and Tequesta

If you loveEssex and Old Saybrook
You’ll loveTequesta
The vibe
Essex and Old SaybrookA river village of boatyards and old houses
TequestaA small river village of docks and parks, with mostly low-rise buildings
The beaches
Essex and Old SaybrookSound beaches in Old Saybrook, warm enough for summer
TequestaOcean beaches a few minutes away in Jupiter and on Jupiter Island
On the water
Essex and Old SaybrookThe Connecticut River and Long Island Sound
TequestaThe Loxahatchee River and the Jupiter Inlet, with offshore fishing all year
Golf and clubs
Essex and Old SaybrookYacht clubs and a few country clubs along the shore
TequestaThe Tequesta Country Club, with more clubs nearby in Jupiter
Evenings out
Essex and Old SaybrookLive music in the Griswold Inn Tap Room, concerts at The Kate in Old Saybrook
TequestaLive music at Tiki 52 on the water, concerts at Harbourside Place in Jupiter
The homes
Essex and Old SaybrookColonials and river houses
TequestaRiver homes, club homes and low-rise condominiums
Getting back to Greenwich
Essex and Old SaybrookAbout 1.5 hours by car on I-95, longer at rush hour
TequestaAbout 35 to 40 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN)

What to do and see

If You Love It There, Try This Here

Restaurants

3 matches

Casual marina dining right on the water.

If you loveJohnny Ad's (opens in a new tab)Old Saybrook

Casual seafood shacks on the main road.

Local seafood restaurants for a relaxed dinner in town.

Nightlife

2 matches
If you loveThe Griswold Inn Tap Room (opens in a new tab)Essex (36 Main Street)

Small-town bars with live music on a regular weekly schedule.

TryHarbourside Place amphitheater (opens in a new tab)Jupiter, about 10 minutes south

Small-town stages for an evening concert close to home.

Coffee

1 match

Local roasters with their own café.

Beaches, Parks and the Water

1 match
If you loveHarvey's BeachOld Saybrook

Small beaches a short drive from the river mouth.

Things to Do

1 match

Village art galleries with changing exhibitions.

Neighborhoods

Neighborhoods, Side by Side

Essex and Old SaybrookTequestaWhat they share
Essex Village
Historic river village of colonials, docks and boatyards on the Connecticut River.
Tequesta Country Club
See homes in this community (opens in a new tab)
Homes along the river with docks and river parks nearby.
Fenwick
Old Saybrook borough of shingle cottages around a nine-hole course on the Sound.
Turtle Creek Club
See homes in this community (opens in a new tab)
A golf course at the heart of one quiet community near the water.
Ivoryton
Wooded village section of Essex with a playhouse and older homes.
Jupiter Hills Club
See homes in this community (opens in a new tab)
Wooded, rolling sand ridges beside a state park.

More to explore

More Neighborhoods Worth Noting in Tequesta

For golf and club life

Jupiter Hills Club: Two Fazio courses behind a guard gate, just north of Tequesta.

See homes in Jupiter Hills Club (opens in a new tab) 6 for sale now

Turtle Creek: A 1969 Joe Lee course, with golf membership optional.

See homes in Turtle Creek (opens in a new tab) 6 for sale now

For life on the river

Tequesta Country Club: Homes near the Loxahatchee in the neighborhood Tequesta grew up around.

See homes in Tequesta Country Club (opens in a new tab) 12 for sale now

For easy condo living

Lighthouse Cove: Condominiums off Village Boulevard.

See homes in Lighthouse Cove (opens in a new tab) 9 for sale now

Questions

Questions About Tequesta If You Love Essex and Old Saybrook

Is Tequesta like Essex and Old Saybrook?

Essex's river village and boatyards have a match in Tequesta: a small village on the Loxahatchee River, close to the inlet, with parks, docks and a slow pace.

Where should I eat in Tequesta if I love the restaurants in Essex and Old Saybrook?

If you love Fresh Salt at Saybrook Point in Old Saybrook, try Tiki 52 Bar & Grill. If you love Johnny Ad's in Old Saybrook, try Hog Snappers Shack & Sushi. If you love Liv's Oyster Bar in Old Saybrook, try The Gallery Grille.

What is the nightlife like in Tequesta compared with Essex and Old Saybrook?

If The Griswold Inn Tap Room in Essex (36 Main Street) is your kind of night, try Tiki 52 Bar & Grill: small-town bars with live music on a regular weekly schedule. If The Kate (Katharine Hepburn Cultural Arts Center) in Old Saybrook is your kind of night, try Harbourside Place amphitheater: small-town stages for an evening concert close to home.

What are the coffee shops, beaches and parks like in Tequesta compared with Essex and Old Saybrook?

Ashlawn Farm Coffee pairs with Oceana Coffee. Harvey's Beach pairs with Coral Cove Park.

Which Tequesta neighborhoods feel like Essex and Old Saybrook?

Essex Village: look at Tequesta Country Club (Homes along the river with docks and river parks nearby). Fenwick: look at Turtle Creek Club (A golf course at the heart of one quiet community near the water). Ivoryton: look at Jupiter Hills Club (Wooded, rolling sand ridges beside a state park). See every one in our Tequesta neighborhood guides.

What is different about living in Tequesta compared with Essex and Old Saybrook?

The vibe: A river village of boatyards and old houses in Essex and Old Saybrook; A small river village of docks and parks, with mostly low-rise buildings in Tequesta. The beaches: Sound beaches in Old Saybrook, warm enough for summer in Essex and Old Saybrook; Ocean beaches a few minutes away in Jupiter and on Jupiter Island in Tequesta. On the water: The Connecticut River and Long Island Sound in Essex and Old Saybrook; The Loxahatchee River and the Jupiter Inlet, with offshore fishing all year in Tequesta. Golf and clubs: Yacht clubs and a few country clubs along the shore in Essex and Old Saybrook; The Tequesta Country Club, with more clubs nearby in Jupiter in Tequesta. Evenings out: Live music in the Griswold Inn Tap Room, concerts at The Kate in Old Saybrook in Essex and Old Saybrook; Live music at Tiki 52 on the water, concerts at Harbourside Place in Jupiter in Tequesta. The homes: Colonials and river houses in Essex and Old Saybrook; River homes, club homes and low-rise condominiums in Tequesta. Getting back to Greenwich: About 1.5 hours by car on I-95, longer at rush hour in Essex and Old Saybrook; About 35 to 40 minutes to the West Palm Beach airport, then about 3 hours nonstop to Westchester (HPN) in Tequesta.

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In their words

What People Ask Before Moving from Connecticut

Questions and worries that come up again and again in forums and news coverage, with our answers. Quotes are from public posts and articles, linked to the source.

“Not having state income tax is a huge blessing.”

City-Data forum (a City-Data user) (opens in a new tab), 2008

Will Jupiter or Palm Beach cost what Greenwich does?

Palm Beach island can; Jupiter, Tequesta and Palm Beach Gardens cover a wide range. Ask us for current prices in the towns you are considering.

Will I miss Connecticut?

Many Connecticut buyers start with the village-scale towns, Tequesta, Hobe Sound and North Palm Beach, and with the boating.

How much more for car and home insurance?

Get quotes for each address; newer concrete construction and roof age move premiums the most. Citizens cut its 2026 rates, with a statewide average reduction of 8.7%.

Does Florida have an estate tax?

Florida has no state estate or inheritance tax. Connecticut taxes estates above $15 million for 2026 deaths.

The big question

Is It Worth Moving from Connecticut to Palm Beach County?

For most Connecticut buyers who can make Florida their real home, yes. Florida has no income, estate or gift tax, against Connecticut's 6.99% top rate and 12% estate tax above $15,000,000, and Westchester, Hartford and New Haven are about three hours nonstop; the trade is a higher insurance bill and a hot summer that is also hurricane season.

871 tax returns moved from Connecticut into Palm Beach and Martin counties in the 2022 to 2023 IRS county-to-county migration data, led by the Western Connecticut planning region (333), which takes in Greenwich and Stamford (IRS SOI migration data (opens in a new tab)).

What changes when you move (updated November 2026; sources in each section below)
What changesConnecticutPalm Beach County
State income tax, top rate6.99% above $500,000 single / $1,000,000 jointNone
Estate and gift taxEstates above $15,000,000 (2026), 12% flat; gifts count toward itNone
Median effective property tax1.54%Palm Beach County 0.82%; Martin County 0.76%
Leaving the tax systemConnecticut treats someone domiciled elsewhere as a resident if they keep a permanent home in the state and spend more than 183 days there.Driver license within 30 days, Declaration of Domicile, homestead by March 1
Home insuranceUsually the smaller billUsually the larger bill; wind and flood are priced house by house
Flights between the twoWestchester, Hartford and New HavenNonstop from West Palm Beach, about three hours
Home pricesVaries by townTown by town; see the live medians

Taxes and costs

How Do Connecticut and Florida Taxes Compare?

Florida has no state income, estate or gift tax. Connecticut’s top income tax rate is 6.99%, it taxes estates above $15,000,000 at a flat 12% in 2026 with lifetime gifts counted toward it, and its median effective property tax rate is 1.54%, against 0.82% in Palm Beach County.

Connecticut taxes income, estates and gifts; Florida taxes none of them. Run your own figures with your CPA.

ConnecticutFlorida
State income tax, top rate6.99% above $500,000 single / $1,000,000 jointNone
Estate and gift taxEstates above $15,000,000 (2026), 12% flat; gifts count toward it (CT DRS (opens in a new tab))None
Median effective property tax1.54% (Tax Foundation 2026 (opens in a new tab), 2024 data)Palm Beach County 0.82%; Martin County 0.76%
Primary home protectionsNo statewide homestead exemptionHomestead exemption on the first $25,000 plus a second, inflation-indexed $25,000 of assessed value; Save Our Homes 3% cap

Accessed October 2026. General information, not tax advice.

Florida’s constitution bars a state tax on the income of residents (Fla. Const. Art. VII, s.5 (opens in a new tab)). A home you own and live in as of January 1 can carry the homestead exemption: the first $25,000 of assessed value off all taxes and a second $25,000 (indexed to inflation) off non-school taxes on value above $50,000 (s.196.031 (opens in a new tab)). After the first year, Save Our Homes holds the yearly rise in assessed value to 3% or inflation, whichever is lower (s.193.155 (opens in a new tab)). A second home or rental gets no homestead; its non-school assessment increase is capped at 10% a year (s.193.1554 (opens in a new tab)).

On the November 3, 2026 ballot: Amendment 3 (opens in a new tab) would raise the non-school homestead exemption sharply from 2027 and lower the non-homestead cap from 10% to 5%. As passed by the Legislature, people who are not Florida residents on December 31, 2026 would get the current exemption for their first four years of homestead and the larger one from the fifth year, to the extent the U.S. Constitution allows. If it passes, we will update this page; if timing matters to you, talk to your tax advisor before you close.

Published rates as of October 2026. General information, not tax advice. Your result depends on your income and filing; confirm with your CPA.

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Making Florida home

When Does Connecticut Stop Treating Me as a Resident?

Connecticut treats someone domiciled elsewhere as a resident if they keep a permanent home in the state and spend more than 183 days there (CT DRS (opens in a new tab)). Keeping the house in Greenwich? Then the calendar matters. The Florida filings below build the record.

  1. Close on a home you will live inHomestead turns on owning and living in the home as your permanent residence on January 1.
  2. Florida driver license within 30 daysFlorida asks new residents to switch their license within 30 days of establishing residency (FLHSMV (opens in a new tab)).
  3. Insure, title and register your carFlorida insurance from a Florida-licensed agent, then title and registration within 10 days of establishing residency. A vehicle titled in another state needs a VIN verification.
  4. Register to vote at the new addressOnline, at the tax collector or at a driver license office (Florida Division of Elections (opens in a new tab)). The address should match the homestead.
  5. File a Declaration of DomicileA sworn statement recorded with the Clerk of the Circuit Court in your county (s.222.17 (opens in a new tab)): Palm Beach County Clerk (opens in a new tab) or Martin County Clerk (opens in a new tab).
  6. Apply for homestead by March 1With the Palm Beach County Property Appraiser (opens in a new tab) or the Martin County Property Appraiser (opens in a new tab). Miss March 1 and the exemption waits a year.

We coordinate closing dates with your attorney and CPA so the January 1 homestead date and your Connecticut records line up.

Florida filings show intent but do not by themselves end residency in your current state. That state decides under its own rules, so get advice from a tax professional there before you rely on it.

Getting back

How Do I Get Back to Connecticut from Palm Beach?

Nonstop flights from West Palm Beach to Westchester, Hartford and New Haven take about three hours, and the airport is about 30 minutes from Jupiter.

West Palm Beach (DJT, formerly PBI) flies nonstop to Westchester on JetBlue, to Hartford on JetBlue and to New Haven on Avelo and Breeze (airport nonstop list (opens in a new tab), October 2026). LaGuardia and JFK are nonstop too.

From Jupiter the airport is about 30 minutes without traffic.

Nonstop from DJT, October 2026

  • Westchester (HPN): JetBlue
  • Hartford (BDL): JetBlue
  • New Haven (HVN): Avelo; Breeze (seasonal)
  • LaGuardia (LGA): American, Delta, JetBlue

Airlines change routes often; check with the airline before you plan around one.

Before you make an offer

What Should I Know About Insurance and Flood Zones Before I Make an Offer?

Insurance is one of the costs new arrivals most often underestimate, and it turns as much on the house as on the town: roof age and shape, opening protection, elevation and distance to the water all move the premium. We ask for quotes during the inspection period, not after it.

Look up the flood zone for the specific home: FEMA Flood Map Service Center (opens in a new tab), Palm Beach County flood maps (opens in a new tab) (new maps took effect December 20, 2024) or Martin County flood zones (opens in a new tab). A National Flood Insurance Program policy usually starts 30 days after purchase, unless it is bought with the mortgage (FloodSmart (opens in a new tab)).

Citizens Property Insurance is the state’s insurer of last resort. A primary home qualifies only when private offers run more than 20% above Citizens, and Citizens policies now require flood coverage, phased in by home value through January 1, 2027 (s.627.351 (opens in a new tab)).

Ask for these before you commit

  • A four-point and a wind mitigation inspection (insurers price the roof, openings and wiring)
  • The roof’s age and permit history
  • An elevation certificate if the home is in a flood zone
  • The seller’s current premium and carrier
  • For a condominium: the association’s master policy, reserves and milestone inspection status

Wind-mitigation features earn premium credits by law (s.627.0629 (opens in a new tab)). Homesteaded owners may qualify for a free inspection through My Safe Florida Home (opens in a new tab).

Not insurance advice. Eligibility, coverage and premiums are set by each carrier and by Citizens. Get quotes from a Florida-licensed agent and confirm the flood zone for the specific address.

Renting first

Should I Rent Before I Buy in Palm Beach County?

Many of our buyers rent first: a winter season, or a year, to learn the drive to the beach in March traffic, what August feels like, and which clubhouse they actually want to walk into. Many winter leases run January through April, and furnished homes for the season are often reserved months ahead.

We arrange the rental, and when the right home comes up we are already looking with you. How seasonal and annual rentals work here.

Search what is open now

Every luxury seasonal rental in Palm Beach County, furnished and priced by the month, live from the MLS. By town: Palm Beach · Jupiter · Palm Beach Gardens · Singer Island · West Palm Beach · Juno Beach.

A home can be committed for part of the season and still show as active, so send us your dates and we check each one with the listing agent. Leases of six months or less carry Florida sales tax and the county’s 6% tourist development tax.

Many condominiums and homeowner associations set a minimum lease term and limit how often a home can be leased each year, and some towns restrict short stays. Check the association and town rules for the specific home before you sign.

West Palm Beach averages about 66°F in January and 83°F in July, with about 62 inches of rain a year, most of it May through October (NOAA 1991-2020 normals (opens in a new tab)). Hurricane season runs June 1 to November 30 (National Hurricane Center (opens in a new tab)).

How we help

Who Helps With a Move from Connecticut to Palm Beach County?

My team and I scout first and send you video, notes and documents before you fly. We coordinate with your attorney and CPA on timing, line up insurance quotes and inspections, and stay with you through closing and the homestead filing.

Questions we hear

Moving from Connecticut: Questions

Where should I live in Palm Beach County if I'm moving from Connecticut?

Most Connecticut buyers start in Palm Beach (if you love Greenwich), North Palm Beach (Darien and Rowayton), Jupiter Island (New Canaan) or Palm Beach Gardens (the Fairfield County clubs). Florida has no income or estate tax; Connecticut’s top rate is 6.99% and its median property tax rate is 1.54%. JetBlue flies nonstop to Westchester and Hartford.

Which Palm Beach County town is most like Greenwich?

Palm Beach. Belle Haven and Round Hill find their match in Palm Beach’s ocean-to-lake estates, and Greenwich Avenue’s shops in Worth Avenue.

Which Palm Beach County town is most like Darien and Rowayton?

North Palm Beach. If home is a dock on Long Island Sound, North Palm Beach will feel familiar: canal homes, marinas and a village golf club, a few minutes from the inlet and open ocean.

Which Palm Beach County town is most like New Canaan?

Jupiter Island. New Canaan’s quiet, green back roads and big lots have their counterpart on Jupiter Island: estate homes between the ocean and the Intracoastal, preserved land and the Jupiter Island Club.

Which Palm Beach County town is most like The Fairfield County clubs?

Palm Beach Gardens. If your week is built around the club, Palm Beach Gardens has private golf clubs across the city, with the homes inside the gate., with the homes inside the gate.

Which Palm Beach County town is most like Stamford and South Norwalk?

West Palm Beach. Stamford’s new towers and SoNo’s restaurants point to West Palm Beach: new buildings on the Intracoastal, finance offices downtown and restaurants within a walk.

Which Palm Beach County town is most like Litchfield County horse country?

Wellington. Litchfield’s farms and riding trails have a winter counterpart in Wellington, with the show-jumping and polo seasons running through the coldest months.

Which Palm Beach County town is most like Essex and Old Saybrook?

Tequesta. Essex’s river village and boatyards have a match in Tequesta: a small village on the Loxahatchee River, close to the inlet, with parks, docks and a slow pace.

Which Palm Beach County town is most like Greenwich?

Palm Beach. The two have shared winters for a century: ocean-to-lake estates, Worth Avenue for Greenwich Avenue, and beach, golf and social clubs.

Can I fly nonstop to Westchester?

Yes. JetBlue flies nonstop from West Palm Beach to Westchester (HPN), and to Hartford.

Can I keep my Connecticut house?

Yes, but Connecticut can treat you as a resident if you keep a permanent home there and spend more than 183 days in the state. Plan it with your CPA.

How do I establish Florida residency if I'm leaving Connecticut?

Get a Florida driver license within 30 days, insure, title and register your car, register to vote at your new address, record a Declaration of Domicile with the county clerk, and file for homestead by March 1.

When is hurricane season, and how does it affect insurance?

June 1 to November 30. Insurers price wind risk by the house: roof age, opening protection and elevation. Ask for quotes and a wind mitigation inspection during the inspection period.

Is it worth moving from Connecticut to Palm Beach County?

For most Connecticut buyers who can make Florida their real home, yes. Florida has no income, estate or gift tax, against Connecticut's 6.99% top rate and 12% estate tax above $15,000,000, and Westchester, Hartford and New Haven are about three hours nonstop; the trade is a higher insurance bill and a hot summer that is also hurricane season.

How many people move from Connecticut to Palm Beach County?

871 tax returns moved from Connecticut into Palm Beach and Martin counties in the 2022 to 2023 IRS migration data, the most of them from the Western Connecticut region around Greenwich and Stamford.

Is Palm Beach County cheaper than Connecticut?

On taxes, yes for most buyers: no income, estate or gift tax, and a median property tax rate of 0.82% in Palm Beach County against 1.54% in Connecticut. Home insurance usually costs more here, and home prices vary widely by town; the towns compared shows each town's live median.

How long is the flight from Connecticut to Palm Beach?

About three hours nonstop from the airport in West Palm Beach (DJT, formerly PBI) to Westchester, Hartford and New Haven.

Who helps people relocating from Connecticut to Jupiter or Palm Beach Gardens?

Monika Phillips of Douglas Elliman Real Estate in Jupiter, licensed in Florida since 2009, works with buyers moving from Greenwich, Darien, New Canaan, the rest of Fairfield County and Litchfield County: community scouting and video before you fly down, then tours when you visit.

Your move, handled

Start Your Move from Connecticut

Tell us the places you love at home and how you want to live here. We will send a short list of towns and communities to start from.

Monika Phillips, Sales Associate, Douglas Elliman Real Estate

Resources

Resources and Sources

Every outside link we used to build this guide, plus the official sites you will need once you get here. Links open in a new tab.

Wellington photo: Pantagruel68, CC BY-SA 3.0, via Wikimedia Commons.

Tax, residency, insurance and legal information on this page is general, current as of October 2026, and is not tax, legal, insurance or financial advice. Laws and rates change. Before acting, confirm with a licensed CPA, an attorney licensed in Florida and in your current state, and a Florida-licensed insurance agent. Links to outside sites are for convenience; we do not control or endorse them. Restaurant, club and brand names belong to their owners and imply no affiliation. Listing counts are live from BeachesMLS, change throughout the day, include only listings available for internet display, and are deemed reliable but not guaranteed. All material presented herein is intended for information purposes only. While this information is believed to be correct; it is represented subject to errors, omission, changes, or withdrawal without notice. All property information, including, but not limited to square footage, room count, number of bedrooms and the school district in property listings are deemed reliable, but should be verified by the Agent’s own attorney, architect, or zoning expert. Monika Phillips, Sales Associate, Douglas Elliman Real Estate, 400 South US Highway 1, Suite C1, Jupiter, FL 33477. © 2026 Douglas Elliman Real Estate. All material presented herein is intended for information purposes only. While this information is believed to be correct, it is represented subject to errors, omissions, changes or withdrawal without notice. Equal Housing Opportunity.

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  • The towns that match the places you love, north to south
  • Your state vs Florida: taxes and the residency rules on the way out
  • Homestead, driver license and domicile steps, with deadlines
  • Insurance and flood questions to ask before you make an offer
  • A first-30-days checklist