Colonial Homes for Sale in Westport, CT

/36
$2,997,000

Open Sun 1PM - 3PM
- 5 Beds
- 4 Baths
- 3,255 Sq Ft
4 Bradley St, Westport, CT 06880

Just 383 steps from the sands of Compo Beach, this storied 1920s residence claims one of Westport's most sought-after addresses. Approximately 3,255 square feet hold five bedrooms and four baths. An open, updated kitchen with top-tier appliances flows into the living and gathering areas. The primary suite is a generous retreat with vaulted ceilings, a spa bath, and a walk-in closet. Four

Hyleri Katzenberg

Compass Connecticut, LLC

4 Bradley St, Westport, CT 06880
/36
$2,395,000

$100K PRICE DROP
- 6 Beds
- 5.5 Baths
- 3,700 Sq Ft
40 Richmondville Ave, Westport, CT 06880

Built in 2022, this 6-bedroom, 5.5-bath home offers four finished levels of flexible living just minutes from downtown Westport. Open-concept main level features high ceilings, oversized windows, and a Thermador kitchen with large island, walk-in pantry, and mudroom with built-ins. Upstairs includes a primary suite with heated floors, soaking tub, and oversized shower. Two bedrooms share a Jack

Jessica Lane

Serhant Connecticut LLC

40 Richmondville Ave, Westport, CT 06880
/17
$7,926,000

New Construction
- 6 Beds
- 7 Baths
- 7,200 Sq Ft
0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880

Set within Westport's most prestigious private estate enclave, surrounded by grand coastal estates and quintessential antique treasures, this exceptional Greens Farms 2+ acre* new construction offering is poised to become one of Fairfield County's most coveted addresses. Perfectly positioned, moments from beaches, downtown boutiques, vibrant dining scene, and just an express train to Manhattan,

Brett Lieberman

The Riverside Realty Group

0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880
/19
$4,250,000

New Construction
- 6 Beds
- 9 Baths
- 7,499 Sq Ft
6 Janson Dr, Westport, CT 06880

Exceptional new construction by AR Luxury Homes with 7,500+/- square feet of thoughtfully designed living space across four finished levels in a prime Westport location. This 6-bedroom, 6 full and 3 half bath residence blends refined craftsmanship with modern functionality, featuring an open-concept layout ideal for both everyday living and entertaining. The heart of the home is a custom-designed

Brett Lieberman

The Riverside Realty Group

6 Janson Dr, Westport, CT 06880
/40
$2,795,000

$55K PRICE DROP
- 6 Beds
- 7 Baths
- 9,454 Sq Ft
25 Hermit Ln, Westport, CT 06880

Experience timeless elegance in this extraordinary Colonial estate nestled in Westport's coveted Red Coat neighborhood. Offering more than 7,000sf of beautiful living space, plus an additional 2,400sf in the finished lower level, this exceptional residence combines luxury, comfort, and functionality. Featuring 6 spacious bedrooms and 5.2 baths, the home is thoughtfully designed for both everyday

Paul Cranick eXp Realty

25 Hermit Ln, Westport, CT 06880
/40
$2,999,000

New Construction Open Sat 2PM - 4PM
- 6 Beds
- 6 Baths
- 4,922 Sq Ft
36 E Main St, Westport, CT 06880

Nestled in the heart of Westport, Connecticut, this stunning new construction residence redefines elegant suburban living with unparalleled sophistication, timeless grace and is complete and ready for immediate occupancy. Boasting six generous bedrooms and six luxurious bathrooms, the home features soaring nine-foot ceilings that bathe its expansive interiors in natural light and create an

Paul Plonsky Realty ONE Group Connect

36 E Main St, Westport, CT 06880
/40
$8,450,000

New Construction
- 6 Beds
- 8 Baths
- 9,893 Sq Ft
10 Beltas Farm Ln, Westport, CT 06880

Extraordinary New Construction home on one of Westport's newest premier cul-de-sacs. Offering nearly 10,000 SF of impeccably finished living space, this exceptional home blends timeless elegance w/ modern luxury & showcases the finest craftsmanship throughout.Designed with an uncompromising attention to detail, features include exquisite millwork, stunning custom cabinetry, spectacular ceiling

Linda Skolnick Coldwell Banker Realty

10 Beltas Farm Ln, Westport, CT 06880
/32
$2,950,000
- 4 Beds
- 3 Baths
- 2,778 Sq Ft
6 Canal Rd, Westport, CT 06880

Wake up each morning to breathtaking 270-degree views of Long Island Sound, where sailboats, paddleboarders, and ever-changing waterfront activity create a stunning backdrop to everyday life. Located in the heart of Saugatuck, this beautifully renovated home blends coastal charm with modern convenience. Thoughtfully reimagined by a talented local photographer with an eye for design, the home

Lynne Nolan Compass Connecticut, LLC

6 Canal Rd, Westport, CT 06880
/40
$6,795,000
- 7 Beds
- 6.5 Baths
- 9,209 Sq Ft
21 Compo Pkwy, Westport, CT 06880

A rare offering in Westport's coveted Compo Beach neighborhood, this extraordinary estate sits on a prized double lot just moments from Compo Beach, Longshore Club, train & vibrant downtown. Featured in Westport Magazine, the property masterfully blends the charm of a beautifully preserved historic residence from 1928 w/ a remarkable 6,000 sq ft addition completed in 2008. The result is a

Sarah Fair William Raveis Real Estate

21 Compo Pkwy, Westport, CT 06880
/38
$1,999,000
- 5 Beds
- 3.5 Baths
- 2,864 Sq Ft
110 Cross Hwy, Westport, CT 06880

Experience modern luxury in this beautifully reimagined home, set on 1.57 scenic, park-like acres. Thoughtfully renovated, this 2,864 sq ft residence offers open-concept living spaces filled with natural light and sophisticated finishes throughout. The designer kitchen features a stunning island and premium cabinetry, flowing seamlessly into the dining and living areas with a dramatic linear

Stephanie Ferreira BHGRE Gaetano Marra Homes

110 Cross Hwy, Westport, CT 06880
/27
$3,685,000

New Construction
- 4 Beds
- 5.5 Baths
- 4,204 Sq Ft
3 Laurel Ln, Westport, CT 06880

Welcome to this new construction project which is currently underway, with an expected completion date in the Summer of 2026. Discover the epitome of elegance and sophistication on a quiet street, in a coveted area in Westport! Stunning new luxury construction designed by renowned Coastal Luxury Homes. Known for their architectural brilliance & unparalleled craftsmanship, Coastal Luxury Homes are

Julie Vanderblue Higgins Group Real Estate

3 Laurel Ln, Westport, CT 06880
/22
$4,995,000

New Construction
- 5 Beds
- 7 Baths
- 5,550 Sq Ft
1 Coastal Ct, Westport, CT 06880

Introducing 1 Coastal Court, a rare opportunity to own in Westport's only gated community, an exclusive four-lot enclave envisioned and built by Joe Feinleib, founder of Coastal Luxury Homes and one of Fairfield County's most respected builders.This private neighborhood blends timeless architecture with modern luxury. Each custom residence, ranging from 5,000 to 7,500 square feet, plus generous

Julie Vanderblue Higgins Group Real Estate

1 Coastal Ct, Westport, CT 06880
/14
$6,650,000

New Construction
- 5 Beds
- 7 Baths
- 11,000 Sq Ft
4 Lantern Hill Rd, Westport, CT 06880

An exceptional opportunity to create a custom luxury residence on 1.2 acres in Westport. With approved plans and permits already in place, buyers may bring their preferred builder and collaborate with the project architect to tailor the home to their vision. The property offers a streamlined path toward creating a distinctive residence while retaining flexibility in design, specifications, and

Ian Defronze Serhant Connecticut, LLC

4 Lantern Hill Rd, Westport, CT 06880
/37
$899,000
- 2 Beds
- 1.5 Baths
- 1,047 Sq Ft
3 Madeline Ave, Westport, CT 06880

The beach lifestyle, water views, natural light, and endless possibilities await at 3 Madeline Avenue. Freshly painted and furnished, this charming 2-3 bedroom cottage offers an open and inviting floor plan featuring refinished hardwood floors, expansive windows, and a sun-filled living space one house from the waterfront. The kitchen is equipped with granite countertops and ample cabinetry,

Karen Liss-uomoleale Coldwell Banker Realty

3 Madeline Ave, Westport, CT 06880
/25
$1,150,000
- 2 Beds
- 2 Baths
- 1,400 Sq Ft
119 Kings Hwy N, Westport, CT 06880

Build your dream house on this beautiful property close to town in the Old Hill section of Westport. This .87 acre lot in a AA zone has views of town and river through the trees. There is a small single-family home that was converted into two apartments in the 1930s by its then-owners. This can be a perfect ADU opportunity as part of a new house to be built. Have an office on one level and an

Helen Cusa Brown Harris Stevens

119 Kings Hwy N, Westport, CT 06880
/40
$2,799,000

Open Sun 12PM - 2PM
- 5 Beds
- 3.5 Baths
- 4,471 Sq Ft
4 Crawford Rd, Westport, CT 06880

Privately nestled in Westport's coveted Old Hill neighborhood, this extraordinary five-bedroom New England residence offers a rare opportunity to own a home where timeless character & modern comfort come together beautifully. Thoughtfully updated while preserving its remarkable architectural details, the residence features sun-filled interiors, beautifully scaled rooms, & an inviting warmth

Barbara Sweeney Coldwell Banker Realty

4 Crawford Rd, Westport, CT 06880
/11
$5,990,000

New Construction
- 6 Beds
- 6.5 Baths
- 6,900 Sq Ft
10 Mary Jane Ln, Westport, CT 06880

New construction by renowned Red Coat Homes, ideally set on a quiet cul-de-sac in a premier Westport neighborhood. Designed by architect Judith Larson, this exceptional home offers over 7,000 sq ft of refined living space on more than one acre, complete with a resort-style pool. Timeless architecture and sophisticated finishes create spaces ideal for entertaining, work, and everyday living, with

Danna Rogers Higgins Group Bedford Square

10 Mary Jane Ln, Westport, CT 06880
/40
$3,450,000

$225K PRICE DROP
- 5 Beds
- 4.5 Baths
- 6,015 Sq Ft
4 Charcoal Ln, Westport, CT 06880

A rare offering indeed! Welcome to 4 Charcoal Lane, an unrivaled multi-generational estate mere minutes from top-rated schools, shopping, restaurants and all that Westport has to offer. Sited on 2 private acres, this extraordinary property offers panoramic views of a 7-acre nature preserve, affording permanent tranquility. The meticulous renovations center around a gracious farmhouse-style

Carol Langeland William Pitt Sotheby's Int'l

4 Charcoal Ln, Westport, CT 06880
/40
$4,450,000

New Construction Open Sun 12PM - 4PM
- 6 Beds
- 8 Baths
- 8,356 Sq Ft
159 Easton Rd, Westport, CT 06880

Are you dreaming of an estate property? Something a bit more than the generic flat acre on a cul de sac? How do two acres on the Aspetuck River sound to you? With views from your bedroom? The sounds of a waterfall next door lulling you to sleep? Having sunnies tickle your toes in the summertime? Maybe a bit of fly fishing for trout? Or perhaps some paddleboarding? Yes, of course, there's a 20x40

Maryann Levanti Higgins Group Bedford Square

159 Easton Rd, Westport, CT 06880
/40
$3,400,000
- 5 Beds
- 4.5 Baths
- 6,166 Sq Ft
27 Woody Ln, Westport, CT 06880

This beautifully renovated Ward French custom home offers elegant formal spaces, a chef's kitchen, flexible guest and office accommodations, a luxury primary suite, fitness studio and sitting room with balcony. The home's 2,442 square foot lower level offers tremendous untapped potential, providing an opportunity to create customized luxury amenities such as a home theater, golf simulator, wine

Allan Styer Compass Connecticut, LLC

27 Woody Ln, Westport, CT 06880
/40
$5,895,000

$100K PRICE DROP
- 4 Beds
- 6 Baths
- 5,567 Sq Ft
46 Compo Mill Cove, Westport, CT 06880

Set within Compo Mill Cove, a rare private association where homes are accessed only by footbridge and no cars are permitted, this Brooke Girty-designed shingle-style residence offers 5,567 SF of true coastal sanctuary. The footbridge approach immediately separates the home from daily life, delivering a level of seclusion few coastal properties can match. Interiors are warm, considered, and

Evangela Brock Douglas Elliman of Connecticut

46 Compo Mill Cove, Westport, CT 06880
/40
$10,500,000

$5M PRICE DROP
- 7 Beds
- 6.5 Baths
- 6,215 Sq Ft
4 Sherwood Island Ln, Westport, CT 06880

Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected

Andrew Whiteley Brown Harris Stevens

4 Sherwood Island Ln, Westport, CT 06880
/13
$7,990,000

New Construction
- 6 Beds
- 8 Baths
- 6,000 Sq Ft
4 Compo Pkwy, Westport, CT 06880

Build your coastal dream home on a rare, full acre* property along one of Compo Beach's most coveted cul-de-sacs, where opportunities of this caliber seldom become available. Ideally positioned just across from Longshore and moments from the shoreline, this extraordinary setting places Westport's most treasured amenities at your fingertips: golf, tennis, swimming, boating, beaches, playgrounds,

Jaclyn Picarillo Higgins Group Bedford Square

4 Compo Pkwy, Westport, CT 06880
/40
$4,795,000

New Construction
- 6 Beds
- 8 Baths
- 8,185 Sq Ft
2 Windy Hill Rd, Westport, CT 06880

Resort-style living meets modern luxury at 2 Windy Hill Road. Set on a private landscaped acre, this newly completed 8,100+ SF estate by HOBI Award-winning builder Cypress Development was thoughtfully designed for the way today's luxury buyer lives, entertains, and unwinds. A dramatic two-story foyer introduces light-filled interiors highlighted by soaring ceilings, white oak flooring, natural

Jacob Bivona Keller Williams Prestige Prop.

2 Windy Hill Rd, Westport, CT 06880
/35
$1,425,000

Open Sun 1PM - 3PM
- 5 Beds
- 2.5 Baths
- 3,246 Sq Ft
19 Vineyard Ln, Westport, CT 06880

Get ready to make 19 Vineyard Lane home! This wonderful family home is ideally situated in the heart of Westport, offering 5 bedrooms and 2.5 baths designed for comfortable, everyday living and effortless entertaining alike. Lovingly cared for by its current owner for 50 years, this home features a first-floor office, while the partially finished basement offers space for a gym or playroom. Set

Polly Sykes Compass Connecticut, LLC

19 Vineyard Ln, Westport, CT 06880
/8
$9,860,000

New Construction
- 6 Beds
- 9 Baths
- 9,200 Sq Ft
9 Over Rock Ln, Westport, CT 06880

Newly completed by Compo Luxury Homes, this exceptional modern estate offers approximately 9,200 square feet on 2.1 private acres just minutes from downtown Westport, Compo Beach, and Metro-North. Thoughtfully designed with European craftsmanship, premium finishes, and sophisticated smart-home technology, the home blends timeless design with exceptional functionality. A dramatic floating

Danna Rogers Higgins Group Bedford Square

9 Over Rock Ln, Westport, CT 06880
/38
$5,999,999

New Construction Open Sun 1PM - 3PM
- 7 Beds
- 7.5 Baths
- 8,700 Sq Ft
13 Edgemarth Hill Rd, Westport, CT 06880

Set on 1.70 private acres in the heart of Greens Farms, this distinctive new construction by Dwell offers a rare combination of timeless design, exceptional privacy, and resort-caliber outdoor living. Offering 8,700+/- sq ft, this exceptional residence features 7 bedrooms, 8 bathrooms, and thoughtfully designed living spaces crafted with an emphasis on enduring design rather than passing trends.

Doug Bross Coldwell Banker Realty

13 Edgemarth Hill Rd, Westport, CT 06880
/40
$3,795,000

$55K PRICE DROP
- 4 Beds
- 3.5 Baths
- 3,418 Sq Ft
61 Clapboard Hill Rd, Westport, CT 06880

Located in prestigious Greens Farms, this European-inspired Colonial offers a rare opportunity to enjoy immediate charm while planning for the future. Set behind private gates on expansive, picturesque grounds, the property is surrounded by multimillion-dollar estates-making it an exceptional canvas for new construction or a significant estate expansion. The existing home is beautifully

Lorelei Atwood Higgins Group Real Estate

61 Clapboard Hill Rd, Westport, CT 06880
/39
$5,925,000
- 6 Beds
- 9 Baths
- 6,561 Sq Ft
3 Stony Point W, Westport, CT 06880

Located within the highly desirable Stony Point association, this exceptional home offers a rare combination of privacy, water views, and convenience just moments from the train, local restaurants, and everyday amenities. This particular home enjoys private dock membership, providing summer boat access just steps from your door. Completely transformed and expanded in 2016, the home features over

Debra Shaughnessy Coldwell Banker Realty

3 Stony Point W, Westport, CT 06880
/16
$1,899,000
- 4 Beds
- 3.5 Baths
- 3,514 Sq Ft
36 Lyons Plain Rd, Westport, CT 06880

Rarely does an opportunity like this become available in Westport. Set on 2.36 private acres with approximately 300 feet along the scenic Aspetuck River, this exceptional property offers a remarkable setting to renovate, expand, or create the custom estate you've always envisioned. The existing four-bedroom residence features a spacious primary suite with fireplace, an expansive kitchen, and a

Charlotte Cotton William Raveis Real Estate

36 Lyons Plain Rd, Westport, CT 06880
/20
$6,495,000

New Construction
- 6 Beds
- 8 Baths
- 9,062 Sq Ft
5 Baldwin Place, Westport, CT 06880

Rarely does a new construction home and property like this come on the market in Westport. Set at the end of a cul-de-sac, in the coveted Long Lots neighborhood, this 2.3-acre, flat property offers a rare combination of privacy and convenience to town. The property features a resort-style, saltwater pool w/spa and automatic safety cover, expansive covered and open-air patios, and a fully equipped

Lori Popkin Coldwell Banker Realty

5 Baldwin Place, Westport, CT 06880
/27
$2,100,000

$100K PRICE DROP
- 5 Beds
- 4.5 Baths
- 6,330 Sq Ft
25 Old Rd, Westport, CT 06880

Set in Westport's sought-after Hunt Club neighborhood, this European-inspired Colonial offers over 6,300 square feet across three finished levels, including expansive recreation spaces and a dedicated home theater. A dramatic two-story entry introduces refined formal and informal rooms, including a fireplaced living room, formal dining room, private office, and an expansive eat-in kitchen with

Zach Wright William Pitt Sotheby's Int'l

25 Old Rd, Westport, CT 06880
/36
$5,750,000
- 5 Beds
- 8 Baths
- 6,503 Sq Ft
31 Stonybrook Rd, Westport, CT 06880

Tucked behind a gated entry in Old Hill, this stunning 5 bedroom, 6.2 bath home offers a rare blend of elegance, privacy and natural beauty. The property has multiple serene water features-a heated saltwater gunite pool with hot tub, a tranquil private pond with fountain and picturesque Stony Brook. The stately stone and wood exterior blends seamlessly with the lush surroundings, while inside, an

Kristi Law William Pitt Sotheby's Int'l

31 Stonybrook Rd, Westport, CT 06880
/40
$3,499,000
- 5 Beds
- 4.5 Baths
- 3,778 Sq Ft
240 North Ave, Westport, CT 06880

"MEADOW WOOD" - Nearly two acres of Westport's most spectacular land is the setting for this storied estate, which has been completely remodeled, expanded and transformed for modern living. Totally fenced & screened w/privacy trees, this unique property offers rare sophistication with a stunning main residence, gunite pool, and a 2,447+/- sqft barn. Gated driveways lead to both the main house &

Doug Bross Coldwell Banker Realty

240 North Ave, Westport, CT 06880
/43
$14,900,000
- 5 Beds
- 8 Baths
- 9,546 Sq Ft
279 Saugatuck Ave, Westport, CT 06880

Panoramic vistas of Long Island Sound extend from this gated, resort-style estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool with

Joseph Barbieri Sotheby's International Realty

279 Saugatuck Ave, Westport, CT 06880
/40
$4,850,000
- 5 Beds
- 5 Baths
- 5,103 Sq Ft
22 Evergreen Ave, Westport, CT 06880

Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate

Valerie Alvarez Serhant Connecticut, LLC

22 Evergreen Ave, Westport, CT 06880
/34
$925,000

$24K PRICE DROP
- 4 Beds
- 3 Baths
- 2,166 Sq Ft
7 Lincoln St, Westport, CT 06880

Nestled in one of Westport's most sought-after in-town neighborhoods, 7 Lincoln Street offers a rare opportunity to own a home that has been lovingly maintained and quietly cherished for more than five decades. Just moments from the Saugatuck River, vibrant Main Street, Saugatuck Village, train to NYC, Compo Beach. Easy access to local schools without a car or bus. This property delivers a

Georgia Wasserman Coldwell Banker Realty

7 Lincoln St, Westport, CT 06880
/40
$2,400,000

$300K PRICE DROP
- 5 Beds
- 5 Baths
- 5,793 Sq Ft
28 Bulkley Ave N, Westport, CT 06880

Beautifully renovated 1799 antique Colonial offering timeless charm, modern luxury, flat pool-worthy property, and exceptional convenience, just one light to the Greens Farms train. This special home captures the soul of historic Westport while delivering the comfort of today's lifestyle. Thoughtfully renovated, it blends original character, architectural detail, warmth, and six fireplaces with

Judy Michaelis Coldwell Banker Realty

28 Bulkley Ave N, Westport, CT 06880
/22
$5,900,000
- 7 Beds
- 7.5 Baths
- 9,800 Sq Ft
22 Cavalry Rd, Westport, CT 06880

Set behind private gates in Westport's prestigious Red Coat estate area, this extraordinary luxury residence offers the utmost in privacy and sophisticated design. Thoughtfully conceived with elegant architecture, exceptional proportions, soaring 10-foot ceilings on the main level, 9-foot ceilings on the second floor and finished lower level, and light-filled interiors, the home blends

Cyd Hamer William Pitt Sotheby's Int'l

22 Cavalry Rd, Westport, CT 06880
/40
$2,195,000
- 5 Beds
- 5.5 Baths
- 5,131 Sq Ft
159 Newtown Turnpike, Weston, CT 06883

This exceptional 150-year-old antique estate in Lower Weston has been thoughtfully and stylishly reimagined, seamlessly blending timeless historic character with the luxurious amenities of contemporary living. The main residence strikes a perfect balance between grand, flowing entertaining spaces and cozy, intimate nooks tailored for remote work or quiet relaxation. At the heart of the home, an

Peter Depalo William Raveis Real Estate

159 Newtown Turnpike, Weston, CT 06883

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