Westport CT Real Estate

Introduction

Westport CT Real Estate represents one of the most desirable coastal markets in Fairfield County. Located along Long Island Sound and between New York City and New Haven, Westport offers a rare combination of coastal beauty, cultural energy, and high-quality suburban living.

With its strong schools, vibrant downtown, and waterfront lifestyle, Westport continues to attract buyers searching for homes for sale in Westport CT and long-term lifestyle value.

An Overview of Life in Westport

Life in Westport is defined by balance, convenience, and lifestyle quality. The town features a lively downtown filled with restaurants, cafés, boutiques, and services, along with quiet residential neighborhoods ranging from inland streets to coastal communities.

Westport supports both an active and relaxed lifestyle, with easy access to beaches, parks, schools, and transportation throughout the town.

Downtown Westport, Culture & Local Landmarks

Downtown Westport serves as the cultural and commercial center of the town. It is known for walkable streets, boutique shopping, and dining options that create a vibrant community atmosphere.

Westport is also a major cultural destination, anchored by:

Westport Country Playhouse
Levitt Pavilion for the Performing Arts

These institutions contribute to Westport’s reputation as one of the most culturally active towns in Connecticut.

Westport CT Real Estate continues to attract luxury buyers seeking waterfront homes, cultural living, and strong school districts.

Beaches, Parks & Outdoor Living

Westport offers extensive coastal access and outdoor recreation opportunities.

Key destinations include:

Compo Beach
Sherwood Island State Park
Longshore Club Park

These locations provide beaches, golf, tennis, walking trails, and waterfront recreation, making Westport CT Real Estate highly desirable for lifestyle-focused buyers.

Schools in Westport CT

Westport is known for its top-rated education system through Westport Public Schools, which includes strong academics, arts, and extracurricular programs.

The district includes:

5 elementary schools
2 middle schools
Staples High School

This strong education system is a major driver of demand for homes for sale in Westport CT.

Transportation & NYC Access

Westport offers convenient commuting access to New York City via the Metro-North New Haven Line.

With direct service to Grand Central Terminal and easy access to I-95 and the Merritt Parkway, Westport is highly attractive for professionals working in NYC while living in Connecticut.

Westport CT Real Estate & Lifestyle

Westport CT Real Estate includes a wide range of properties, from luxury waterfront estates to classic New England homes and modern residences.

Buyers are drawn to Westport for:

Coastal living
Strong school system
Cultural lifestyle
High-end housing market
NYC commuter convenience

Why Choose Westport CT Real Estate

Westport stands out for its combination of coastal beauty, cultural richness, and premium lifestyle offerings.

For buyers seeking luxury living with access to beaches, arts, top schools, and New York City, Westport remains one of the most desirable real estate markets in Fairfield County.

Westport CT Real Estate offers a perfect balance of coastal living, luxury homes, and easy access to New York City.

Around Town Gallery

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Properties for sale in Westport

PRICE

$798,000 $9,860,000

LIVING AREA

<792 sqft 9,349+ sqft

5 DRUMLIN ROAD

5 DRUMLIN ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 4 BA | 2,884 SQ.FT.

$1,795,000

16 WESTPORT AVENUE

16 WESTPORT AVENUE, WESTPORT, CONNECTICUT 06880

4 BD | 5 BA | 2,180 SQ.FT.

$6,495,000

3 MADELINE AVENUE

3 MADELINE AVENUE, WESTPORT, CONNECTICUT 06880

2 BD | 2 BA | 1,047 SQ.FT.

$899,000

107 ROSEVILLE ROAD

107 ROSEVILLE ROAD, WESTPORT, CONNECTICUT 06880

3 BD | 3 BA | 1,572 SQ.FT.

$1,199,000

110 CROSS HIGHWAY

110 CROSS HIGHWAY, WESTPORT, CONNECTICUT 06880

5 BD | 4 BA | 2,408 SQ.FT.

$1,999,000

2 HALF MILE COMMON

2 HALF MILE COMMON, WESTPORT, CONNECTICUT 06880

4 BD | 5 BA | 4,339 SQ.FT.

$3,100,000

9 N RIDGE ROAD

9 N RIDGE ROAD, WESTPORT, CONNECTICUT 06880

6 BD | 7 BA | 5,251 SQ.FT.

$3,550,000

18 SILVER BROOK ROAD

18 SILVER BROOK ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 5 BA | 4,013 SQ.FT.

$2,350,000

10 BELTAS FARM LANE

10 BELTAS FARM LANE, WESTPORT, CONNECTICUT 06880

6 BD | 8 BA | 6,655 SQ.FT.

$8,450,000

38 PROSPECT ROAD

38 PROSPECT ROAD, WESTPORT, CONNECTICUT 06880

6 BD | 9 BA

$9,200,000

4 HEATHER HILL

4 HEATHER HILL, WESTPORT, CONNECTICUT 06880

4 BD | 2 BA | 1,567 SQ.FT.

$1,179,000

5 LEHN FARM ROAD

5 LEHN FARM ROAD, WESTPORT, CONNECTICUT 06880

3 BD | 2 BA | 1,352 SQ.FT.

$1,299,000

34 WOODSIDE AVENUE

34 WOODSIDE AVENUE, WESTPORT, CONNECTICUT 06880

4 BD | 5 BA | 2,801 SQ.FT.

$2,699,000

6 LOREN LANE

6 LOREN LANE, WESTPORT, CONNECTICUT 06880

4 BD | 3 BA | 2,012 SQ.FT.

$1,195,000

18 VANI COURT

18 VANI COURT, WESTPORT, CONNECTICUT 06880

3 BD | 4 BA | 1,734 SQ.FT.

$1,795,000

119 KINGS HIGHWAY NORTH

119 KINGS HIGHWAY NORTH, WESTPORT, CONNECTICUT 06880

2 BD | 2 BA | 1,400 SQ.FT.

$1,150,000

3 KELLER LANE

3 KELLER LANE, WESTPORT, CONNECTICUT 06880

2 BD | 1 BA | 792 SQ.FT.

$798,000

27 WOODY LANE

27 WOODY LANE, WESTPORT, CONNECTICUT 06880

5 BD | 5 BA | 6,166 SQ.FT.

$3,400,000

157 NEWTOWN TURNPIKE

157 NEWTOWN TURNPIKE, WESTPORT, CONNECTICUT 06880

3 BD | 3 BA | 2,642 SQ.FT.

$1,580,000

2 QUARTER MILE ROAD

2 QUARTER MILE ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 4 BA | 2,124 SQ.FT.

$1,050,000

48 BAYBERRY LANE

48 BAYBERRY LANE, WESTPORT, CONNECTICUT 06880

6 BD | 6 BA | 5,325 SQ.FT.

$4,449,000

6 CANAL ROAD

6 CANAL ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 3 BA | 2,778 SQ.FT.

$2,950,000

240 NORTH AVENUE

240 NORTH AVENUE, WESTPORT, CONNECTICUT 06880

4 BD | 5 BA | 3,049 SQ.FT.

$3,499,000

13 EDGEMARTH HILL ROAD

13 EDGEMARTH HILL ROAD, WESTPORT, CONNECTICUT 06880

7 BD | 8 BA

$5,999,999

25 OLD ROAD

25 OLD ROAD, WESTPORT, CONNECTICUT 06880

5 BD | 5 BA | 4,474 SQ.FT.

$2,200,000

32 MORNINGSIDE DRIVE NORTH

32 MORNINGSIDE DRIVE NORTH, WESTPORT, CONNECTICUT 06880

4 BD | 3 BA | 2,270 SQ.FT.

$1,275,000

6 GRAY LANE

6 GRAY LANE, WESTPORT, CONNECTICUT 06880

5 BD | 5 BA | 4,875 SQ.FT.

$4,950,000

359 GREENS FARMS ROAD

359 GREENS FARMS ROAD, WESTPORT, CONNECTICUT 06880

6 BD | 8 BA | 7,748 SQ.FT.

$5,499,000

2 CHARCOAL LANE

2 CHARCOAL LANE, WESTPORT, CONNECTICUT 06880

3 BD | 3 BA | 1,905 SQ.FT.

$2,100,000

7 HIGH GATE ROAD

7 HIGH GATE ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 3 BA | 1,704 SQ.FT.

$1,699,000

16 HARBOR ROAD

16 HARBOR ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 4 BA | 3,150 SQ.FT.

$2,995,000

4 SYCAMORE DRIVE

4 SYCAMORE DRIVE, WESTPORT, CONNECTICUT 06880

6 BD | 8 BA

$5,199,000

30 SAINT JOHNS PLACE

30 SAINT JOHNS PLACE, WESTPORT, CONNECTICUT 06880

5 BD | 4 BA | 3,999 SQ.FT.

$2,895,000

124 HILLANDALE ROAD

124 HILLANDALE ROAD, WESTPORT, CONNECTICUT 06880

6 BD | 10 BA | 9,349 SQ.FT.

$6,500,000

143 NORTH AVENUE

143 NORTH AVENUE, WESTPORT, CONNECTICUT 06880

3 BD | 3 BA | 2,192 SQ.FT.

$1,699,000

25 HERMIT LANE

25 HERMIT LANE, WESTPORT, CONNECTICUT 06880

6 BD | 7 BA | 7,054 SQ.FT.

$2,795,000

18 RIVER LANE

18 RIVER LANE, WESTPORT, CONNECTICUT 06880

5 BD | 6 BA | 3,435 SQ.FT.

$2,100,000

2 WINDY HILL ROAD

2 WINDY HILL ROAD, WESTPORT, CONNECTICUT 06880

6 BD | 8 BA

$4,795,000

9 OVER ROCK LANE

9 OVER ROCK LANE, WESTPORT, CONNECTICUT 06880

6 BD | 8 BA

$9,860,000

, WESTPORT, CONNECTICUT 06880

3 BD | 2 BA | 1,244 SQ.FT.

$1,499,000

3 LAUREL LANE

3 LAUREL LANE, WESTPORT, CONNECTICUT 06880

4 BD | 6 BA | 1,686 SQ.FT.

$3,685,000

72 COMPO ROAD NORTH

72 COMPO ROAD NORTH, WESTPORT, CONNECTICUT 06880

5 BD | 7 BA | 4,855 SQ.FT.

$2,950,000

36 FILLOW STREET

36 FILLOW STREET, WESTPORT, CONNECTICUT 06880

3 BD | 3 BA | 1,554 SQ.FT.

$1,199,000

21 COMPO PARKWAY

21 COMPO PARKWAY, WESTPORT, CONNECTICUT 06880

7 BD | 7 BA | 7,209 SQ.FT.

$6,795,000

53 CLINTON AVENUE

53 CLINTON AVENUE, WESTPORT, CONNECTICUT 06880

5 BD | 6 BA | 5,319 SQ.FT.

$2,650,000

422 RIVERSIDE AVENUE

422 RIVERSIDE AVENUE, WESTPORT, CONNECTICUT 06880

5 BD | 4 BA | 3,345 SQ.FT.

$1,800,000

71 HIGH POINT ROAD

71 HIGH POINT ROAD, WESTPORT, CONNECTICUT 06880

5 BD | 4 BA | 3,615 SQ.FT.

$1,995,000

22 STURGES COMMONS

22 STURGES COMMONS, WESTPORT, CONNECTICUT 06880

5 BD | 8 BA | 4,911 SQ.FT.

$3,295,000

31 STONYBROOK ROAD

31 STONYBROOK ROAD, WESTPORT, CONNECTICUT 06880

5 BD | 8 BA | 6,503 SQ.FT.

$5,750,000

34 PEQUOT TRAIL

34 PEQUOT TRAIL, WESTPORT, CONNECTICUT 06880

5 BD | 4 BA | 3,782 SQ.FT.

$2,100,000

10 SIDE HILL ROAD

10 SIDE HILL ROAD, WESTPORT, CONNECTICUT 06880

6 BD | 6 BA | 5,666 SQ.FT.

$3,250,000

36 TURKEY HILL ROAD NORTH

36 TURKEY HILL ROAD NORTH, WESTPORT, CONNECTICUT 06880

5 BD | 4 BA | 3,220 SQ.FT.

$1,790,000

5 W BRANCH ROAD

5 W BRANCH ROAD, WESTPORT, CONNECTICUT 06880

6 BD | 9 BA | 6,455 SQ.FT.

$5,599,000

18 HALES ROAD

18 HALES ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 3 BA | 1,092 SQ.FT.

$1,250,000

7 MORTAR ROCK ROAD

7 MORTAR ROCK ROAD, WESTPORT, CONNECTICUT 06880

6 BD | 8 BA | 5,499 SQ.FT.

$3,799,000

2 GRASSY PLAINS ROAD

2 GRASSY PLAINS ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 4 BA | 1,849 SQ.FT.

$1,699,000

CLAPBOARD HILL ROAD (NEW BUILD)

CLAPBOARD HILL ROAD (NEW BUILD), WESTPORT, CONNECTICUT 06880

6 BD | 7 BA

$7,926,000

299 SAUGATUCK AVENUE

299 SAUGATUCK AVENUE, WESTPORT, CONNECTICUT 06880

4 BD | 6 BA | 4,854 SQ.FT.

$2,799,000

22 EVERGREEN AVENUE

22 EVERGREEN AVENUE, WESTPORT, CONNECTICUT 06880

5 BD | 5 BA | 4,377 SQ.FT.

$4,850,000

36 LYONS PLAIN ROAD

36 LYONS PLAIN ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 4 BA

$1,899,000

20 FRESENIUS ROAD

20 FRESENIUS ROAD, WESTPORT, CONNECTICUT 06880

7 BD | 9 BA

$4,000,000

UNDER CONTRACT - CONTINUE TO SHOW

4 BAYWOOD LANE

4 BAYWOOD LANE, WESTPORT, CONNECTICUT 06880

5 BD | 3 BA | 1,316 SQ.FT.

$1,600,000

80 BAYBERRY LANE

80 BAYBERRY LANE, WESTPORT, CONNECTICUT 06880

6 BD | 7 BA | 6,769 SQ.FT.

$3,995,000

23 W PARISH ROAD

23 W PARISH ROAD, WESTPORT, CONNECTICUT 06880

3 BD | 2 BA | 1,187 SQ.FT.

$999,000

22 DAWN DRIVE

22 DAWN DRIVE, WESTPORT, CONNECTICUT 06880

4 BD | 5 BA

$4,995,700

24 WASHINGTON AVENUE

24 WASHINGTON AVENUE, WESTPORT, CONNECTICUT 06880

4 BD | 4 BA | 3,430 SQ.FT.

$2,850,000

48 WOODSIDE AVENUE

48 WOODSIDE AVENUE, WESTPORT, CONNECTICUT 06880

6 BD | 6 BA | 1,853 SQ.FT.

$4,100,000

2 MORTAR ROCK ROAD

2 MORTAR ROCK ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 6 BA | 3,312 SQ.FT.

$2,999,000

10 GRIST MILL LANE

10 GRIST MILL LANE, WESTPORT, CONNECTICUT 06880

3 BD | 3 BA | 2,138 SQ.FT.

$1,689,000

7 KELLER LANE

7 KELLER LANE, WESTPORT, CONNECTICUT 06880

6 BD | 3 BA

$1,325,000

5 FARNHAM COURT

5 FARNHAM COURT, WESTPORT, CONNECTICUT 06880

5 BD | 5 BA | 3,988 SQ.FT.

$2,099,000

159 EASTON ROAD

159 EASTON ROAD, WESTPORT, CONNECTICUT 06880

6 BD | 8 BA | 3,243 SQ.FT.

$4,450,000

19 MORTAR ROCK ROAD

19 MORTAR ROCK ROAD, WESTPORT, CONNECTICUT 06880

6 BD | 8 BA | 5,975 SQ.FT.

$4,699,000

15 ROOSEVELT ROAD

15 ROOSEVELT ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 5 BA | 3,562 SQ.FT.

$5,100,000

278 NORTH AVENUE

278 NORTH AVENUE, WESTPORT, CONNECTICUT 06880

6 BD | 9 BA | 7,227 SQ.FT.

$4,050,000

170 IMPERIAL AVENUE

170 IMPERIAL AVENUE, WESTPORT, CONNECTICUT 06880

3 BD | 2 BA | 1,902 SQ.FT.

$1,098,000

UNDER CONTRACT - CONTINUE TO SHOW

6 TWIN CIRCLE DRIVE

6 TWIN CIRCLE DRIVE, WESTPORT, CONNECTICUT 06880

6 BD | 7 BA | 6,166 SQ.FT.

$5,000,000

8 PLEASANT VALLEY LANE

8 PLEASANT VALLEY LANE, WESTPORT, CONNECTICUT 06880

7 BD | 9 BA | 1,462 SQ.FT.

$5,650,000

1 TWIN OAKS LANE

1 TWIN OAKS LANE, WESTPORT, CONNECTICUT 06880

5 BD | 6 BA | 5,792 SQ.FT.

$5,500,000

221 GREENS FARMS ROAD

221 GREENS FARMS ROAD, WESTPORT, CONNECTICUT 06880

5 BD | 6 BA | 5,789 SQ.FT.

$2,995,000

4 CARDINAL LANE

4 CARDINAL LANE, WESTPORT, CONNECTICUT 06880

4 BD | 4 BA | 4,103 SQ.FT.

$2,199,000

3 BOWLING LANE

3 BOWLING LANE, WESTPORT, CONNECTICUT 06880

6 BD | 6 BA | 1,236 SQ.FT.

$3,450,000

7 POND EDGE ROAD

7 POND EDGE ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 6 BA

$4,495,000

5 BALDWIN PLACE

5 BALDWIN PLACE, WESTPORT, CONNECTICUT 06880

6 BD | 8 BA

$6,495,000

28 BULKLEY AVENUE NORTH

28 BULKLEY AVENUE NORTH, WESTPORT, CONNECTICUT 06880

5 BD | 5 BA | 3,917 SQ.FT.

$2,400,000

61 CLAPBOARD HILL ROAD

61 CLAPBOARD HILL ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 4 BA | 3,418 SQ.FT.

$3,795,000

UNDER CONTRACT - CONTINUE TO SHOW

30 PEQUOT TRAIL

30 PEQUOT TRAIL, WESTPORT, CONNECTICUT 06880

5 BD | 4 BA | 2,706 SQ.FT.

$1,599,876

UNDER CONTRACT - CONTINUE TO SHOW

7 LINCOLN STREET

7 LINCOLN STREET, WESTPORT, CONNECTICUT 06880

4 BD | 3 BA | 1,443 SQ.FT.

$949,000

32 HALE STREET

32 HALE STREET, WESTPORT, CONNECTICUT 06880

4 BD | 5 BA | 2,298 SQ.FT.

$1,799,900

6 JANSON DRIVE

6 JANSON DRIVE, WESTPORT, CONNECTICUT 06880

6 BD | 9 BA

$4,250,000

4 CHARCOAL LANE

4 CHARCOAL LANE, WESTPORT, CONNECTICUT 06880

5 BD | 5 BA | 4,527 SQ.FT.

$3,450,000

107 COMPO ROAD NORTH

107 COMPO ROAD NORTH, WESTPORT, CONNECTICUT 06880

4 BD | 3 BA | 1,810 SQ.FT.

$1,399,000

11 CLAPBOARD HILL ROAD

11 CLAPBOARD HILL ROAD, WESTPORT, CONNECTICUT 06880

6 BD | 8 BA

$3,995,000

11 WAKE ROBIN ROAD

11 WAKE ROBIN ROAD, WESTPORT, CONNECTICUT 06880

5 BD | 6 BA | 6,868 SQ.FT.

$4,799,000

24 BLUE RIBBON DRIVE

24 BLUE RIBBON DRIVE, WESTPORT, CONNECTICUT 06880

4 BD | 4 BA | 2,834 SQ.FT.

$2,349,000

56 CHARCOAL HILL ROAD

56 CHARCOAL HILL ROAD, WESTPORT, CONNECTICUT 06880

5 BD | 3 BA | 2,552 SQ.FT.

$2,790,000

3 VALLEY FIELD ROAD

3 VALLEY FIELD ROAD, WESTPORT, CONNECTICUT 06880

4 BD | 3 BA | 3,581 SQ.FT.

$2,349,000

46 COMPO MILL COVE

46 COMPO MILL COVE, WESTPORT, CONNECTICUT 06880

4 BD | 6 BA | 5,567 SQ.FT.

$5,895,000

21 COVLEE DRIVE

21 COVLEE DRIVE, WESTPORT, CONNECTICUT 06880

4 BD | 5 BA | 4,444 SQ.FT.

$6,875,000

69 BEACHSIDE AVENUE

69 BEACHSIDE AVENUE, WESTPORT, CONNECTICUT 06880

6 BD | 7 BA | 6,585 SQ.FT.

$7,350,000

3 TANGLEWOOD LANE

3 TANGLEWOOD LANE, WESTPORT, CONNECTICUT 06880

6 BD | 7 BA

$6,999,999

11 MANITOU COURT

11 MANITOU COURT, WESTPORT, CONNECTICUT 06880

7 BD | 9 BA | 2,826 SQ.FT.

$8,995,000

Overview for Westport, CT

$2.6m

Median Sale Price

80

Average Days on Market

48.10 %

Since March 2025

19.00 %

Since March 2025

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