Colonial Homes for Sale in Southport, CT

/40
$2,650,000
- 4 Beds
- 5 Baths
- 5,394 Sq Ft
3007 Redding Rd, Fairfield, CT 06824

A gorgeous Farmhouse Colonial tucked away on 2+ picturesque acres & minutes to Fairfield & Westport town await. Natural beauty, brilliant architecture, craftmanship & updates combine to make this home a standout. Featuring 12 rooms flooded w/ light over 3 levels of living. Enjoy views of a serene fallow field, a gentle stream, wildlife & stunning seasonal changes from vibrant autumn colors to

Jackie Davis

William Raveis Real Estate

(475) 255-0748

3007 Redding Rd, Fairfield, CT 06824
/38
$2,800,000

Open Thu 11AM - 2PM
- 4 Beds
- 3.5 Baths
- 3,241 Sq Ft
7 Short St, Westport, CT 06880

Premier in-town location & exceptional craftsmanship come together in this stunning custom-built home by a respected local luxury builder. Just 2 years young, this exquisite home is ideally situated at the end of a quiet cul-de-sac, offering privacy & convenience while only 4 minutes from town - Welcome home to 7 Short Street. Presenting 3 levels of beautifully finished living space, this

Jackie Davis

William Raveis Real Estate

(475) 255-6549

7 Short St, Westport, CT 06880
/39
$2,275,000
- 4 Beds
- 4.5 Baths
- 4,641 Sq Ft
161 Sherwood Dr, Southport, CT 06890

Enjoy the summer at 161 Sherwood Drive, a beautifully expanded and extensively updated residence located in the desirable Southport neighborhood. Offering approximately 3,679 square feet of thoughtfully designed living space, this home blends comfort, functionality, and inviting indoor-outdoor living in a private setting. The home features 4 spacious bedrooms, 4 full baths, and 1 half bath,

Pam Toner

Berkshire Hathaway NE Prop.

(475) 348-8287

161 Sherwood Dr, Southport, CT 06890
/40
$1,799,900

$75K PRICE DROP
- 5 Beds
- 3 Baths
- 3,032 Sq Ft
82 Lee Dr, Fairfield, CT 06824

Ideally located in the highly sought-after Sasco Hill neighborhood, this exceptional coastal home offers the rare advantage of beach-area living outside the flood zone-no flood insurance required. Perfectly positioned between town and shoreline, the property features a stunning second-floor addition completed in 2025 with over $200,000 invested, including a rooftop deck with beautiful Long Island

Jacek Mikolajczyk

Berkshire Hathaway NE Prop.

(475) 269-6318

82 Lee Dr, Fairfield, CT 06824
/40
$1,574,999

$25K PRICE DROP
- 3 Beds
- 3 Baths
- 2,443 Sq Ft
313 Old Post Rd, Fairfield, CT 06824

Welcome to 313 Old Post Road, a timeless Fairfield residence blending classic charm with an unbeatable location in one of the town's most desirable coastal neighborhoods. This beautifully maintained home offers inviting living spaces, abundant natural light, and the perfect balance of comfort and convenience. Recent improvements include updated AC units in 2023, new wiring in the detached heated

Joel Grispino

Drawbridge Realty

(475) 256-6136

313 Old Post Rd, Fairfield, CT 06824
/36
$2,495,000
- 6 Beds
- 5.5 Baths
- 3,700 Sq Ft
40 Richmondville Ave, Westport, CT 06880

Built in 2022, 40 Richmondville Avenue offers generous scale, a thoughtful layout, and true move-in-ready ease. Bright, open-concept main level connects kitchen, dining, and living spaces, with high ceilings and oversized windows throughout. The kitchen features a full Thermador appliance suite, large island with integrated outlets, extensive cabinetry, walk-in pantry, and mudroom with built-ins.

Jessica Lane

Serhant Connecticut, LLC

(475) 244-9410

40 Richmondville Ave, Westport, CT 06880
/15
$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

(475) 203-1918

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

(475) 330-3787

6 Janson Dr, Westport, CT 06880
/25
$1,250,000
- 2 Beds
- 2 Baths
- 1,400 Sq Ft
119 Kings Hwy N, Westport, CT 06880

House and land are fully available. Build your dream house on this beautiful lot in the Old Hill section of Westport. The small single-family home was converted into two apartments in the 1930s by its then-owners. The land is in a Residential AA zone and any construction needs to follow all the towns regulations. Walk to town from this generous .87 acre lot that has views of the town and river in

Helen Cusa Brown Harris Stevens

119 Kings Hwy N, Westport, CT 06880
/9
$3,750,000

New Construction
- 5 Beds
- 5.5 Baths
- 5,000 Sq Ft
22 Brett Rd, Fairfield, CT 06824

Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among

Andrew Whiteley Brown Harris Stevens

22 Brett Rd, Fairfield, CT 06824
/28
$2,100,000
- 5 Beds
- 3.5 Baths
- 3,782 Sq Ft
34 Pequot Trail, Westport, CT 06880

Discover this serene setting in a sought after Old Hill neighborhood. Two thoughtful and beautifully executed additions have made this sprawling 12 room home flow with the versatility to fit today's varied lifestyles. Comfortable open living spaces have been designed with the flexibility to offer multi-generational spaces, a home office or simply to allow for room to grow in the way that pleases

Lynn Fraund William Pitt Sotheby's Int'l

34 Pequot Trail, Westport, CT 06880
/40
$2,650,000

Open Thu 11AM - 2PM
- 5 Beds
- 5.5 Baths
- 7,055 Sq Ft
53 Clinton Ave, Westport, CT 06880

SHOWINGS BEGIN WEDNESDAY, JUNE 17 - MORE PHOTOS SOON. Incredibly located moments from town and convenient to schools, shopping, commuting options and more, this sparking home showcases pride of ownership. A new 2026 driveway leads to the landscaped setting, where this gracious home with an in-ground Wagner pool is set amid .74+/- acre. The two-story foyer introduces crisp, timeless spaces, and a

Alex Chingas Coldwell Banker Realty

53 Clinton Ave, 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
/39
$2,799,000

$151K PRICE DROP
- 5 Beds
- 4 Baths
- 2,188 Sq Ft
1235 Fairfield Beach Rd, Fairfield, CT 06824

TWO incredible waterside opportunities await! That's right, not one, but TWO fantastic beach area homes are offered! With their direct waterfront locations (1235 - beachfront/LI Sound; 1236 - canal side), both homes have amazing water views, beach access and a convenient, fantastic location all in one! Both homes also offer excellent investment/rental opportunities. #1235 is rented for the

John Foran Compass Connecticut, LLC

1235 Fairfield Beach Rd, Fairfield, CT 06824
/29
$2,200,000

$550K 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
/40
$2,199,000
- 5 Beds
- 4.5 Baths
- 3,380 Sq Ft
24 Burr School Rd, Westport, CT 06880

Tucked away towards the end of a quiet cul-de-sac in a prime central Westport location, this beautifully updated home offers the perfect blend of privacy, convenience, and lifestyle. Set on 1.05 acres and just moments from town, close to schools, shopping, and commuting options, this five-bedroom residence is designed for both everyday living and effortless entertaining. The heart of the home is

Julia Broder Coldwell Banker Realty

24 Burr School Rd, Westport, CT 06880
/36
$6,499,000
- 5 Beds
- 7 Baths
- 6,189 Sq Ft
775 Sasco Hill Rd, Fairfield, CT 06824

775 Sasco Hill Road is an extraordinary estate where timeless elegance meets modern luxury. Impeccably renovated and beautifully curated by the current owners, this sophisticated residence offers three full levels of refined living set across five private, park-like acres. A dramatic cathedral foyer and soaring 9-foot ceilings create an immediate sense of scale and light, while the thoughtfully

Suzy Ryan William Raveis Real Estate

775 Sasco Hill Rd, Fairfield, CT 06824
/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
/32
$949,000

$20K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,068 Sq Ft
370 Nepas Rd, Fairfield, CT 06825

Recently updated and freshly painted, this bright and welcoming Colonial sits on a picturesque .57-acre property surrounded by vibrant gardens, and charming, walkable streets. Whether you enjoy an active lifestyle or quiet retreat, this location offers the best of both. An easy stroll to the lake with sandy beach, scenic hiking trails, new splash pad, playground, annual events, and the Cascades

Denise Walsh William Raveis Real Estate

370 Nepas Rd, Fairfield, CT 06825
/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
/12
$2,199,999

New Construction $201K PRICE INCREASE
- 6 Beds
- 7 Baths
- 4,709 Sq Ft
280 Tuckahoe Ln, Fairfield, CT 06824

Exceptional new construction in the desirable University area, scheduled for completion in Fall 2026. Built by an experienced local builder known for quality craftsmanship and thoughtful design, this impressive home offers 4,709 square feet across four levels, including a walk-out lower level. Designed for modern living, the home features 6 bedrooms and 5.5 baths, providing flexibility for

Elizabeth Casey William Raveis Real Estate

280 Tuckahoe Ln, Fairfield, CT 06824
/40
$6,500,000
- 6 Beds
- 10 Baths
- 9,349 Sq Ft
124 Hillandale Rd, Westport, CT 06880

An exceptional home in coveted Greens Farms, 124 Hillandale Road captures the essence of classic Connecticut living. Timeless, elegant, and impeccably maintained, this beautiful estate is surrounded by mature landscaping and a peaceful, private setting, while remaining just minutes from everything Westport has to offer. Spanning four finished levels connected by an elevator, the home seamlessly

Meredith Cohen Serhant Connecticut, LLC

124 Hillandale Rd, Westport, CT 06880
/22
$375,000

$25K PRICE DROP
- 3 Beds
- 1 Bath
- 1,751 Sq Ft
527 Colorado Ave, Bridgeport, CT 06605

Well-located Colonial in Bridgeport's desirable West Side/West End, just minutes to the Fairfield border and close to Black Rock. This spacious 3-bedroom home offers approximately 1,750 sq ft of living space with a functional layout, generously sized rooms, and great natural flow throughout. The main level features a large living area, formal dining room, and an eat-in kitchen with plenty of

Sasha McLeain Coldwell Banker Realty

527 Colorado Ave, Bridgeport, CT 06605
/38
$4,050,000
- 6 Beds
- 9 Baths
- 9,525 Sq Ft
278 North Ave, Westport, CT 06880

Set in one of Westport's most prestigious estate enclaves, this exceptional shingle-style residence defines luxury living with a rare emphasis on multi-generational comfort, timeless architecture, and impeccable craftsmanship. Designed and built by a renowned architect and builder for a Fortune 500 CEO, the home reflects uncompromising quality, enduring design, and gracious curb appeal that

Cyd Hamer William Pitt Sotheby's Int'l

278 North Ave, Westport, CT 06880
/40
$1,790,000

New Construction
- 5 Beds
- 6 Baths
- 4,821 Sq Ft
309 Hunyadi Ave, Fairfield, CT 06824

Set on a cul-de-sac in Fairfield's sought-after University area, this custom-built 5-bedroom, 6-bath residence was originally designed as the developer's own home, with a focus on natural light, architectural detail, and elevated everyday living. The primary suite features soaring 18-foot cathedral ceilings, a custom white oak ceiling treatment, an 11-foot picture window, and a spa-inspired bath.

Julie Vanderblue Higgins Group Real Estate

309 Hunyadi Ave, Fairfield, CT 06824
/38
$975,000
- 3 Beds
- 3.5 Baths
- 3,191 Sq Ft
35 Crystal Ln, Fairfield, CT 06824

Welcome to this beautiful home perfectly situated at the end of a quiet cul-de-sac in a prime university neighborhood off of Mill Plain Road. This pristine property features 3 bedrooms and 3.5 baths, offering an exceptional blend of comfort, style, and modern convenience. The main living areas feature gleaming hardwood floors that have just been redone throughout the house. The heart of the home

Lindsey Rosen William Pitt Sotheby's Int'l

35 Crystal Ln, Fairfield, CT 06824
/7
$2,495,000

New Construction
- 5 Beds
- 5.5 Baths
- 5,900 Sq Ft
108 Old Farm Rd, Fairfield, CT 06825

108 Old Farm Road is a stunning new construction currently underway in one of Weston's most desirable settings. This five-bedroom, 5.5-bath home offers 4,568 square feet above grade plus a 1,400 square foot finished heated lower level with home theater, totaling nearly 6,000 square feet of exceptional living space. The main level features soaring two-story ceilings, a formal dining room, home

Alex De Camargo eXp Realty

108 Old Farm Rd, Fairfield, CT 06825
/38
$5,199,000

New Construction $400K PRICE DROP
- 6 Beds
- 6.5 Baths
- 7,387 Sq Ft
36 Maple Ave S, Westport, CT 06880

Beautiful Georgian Colonial style home in desired Greens Farms neighborhood design by renowned architect Judith Larson. A fabulous Redcoat design team make this home a must, perfect for todays's lifestyle with a classic feel. This 6 bedroom residence is set on a flat, level.70 acre property embodying a perfect synergy of architectural excellence and an enviable location. Crafted for modern living

Kelly Loucas Compass Connecticut, LLC

36 Maple Ave S, 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
/32
$849,000

$26K PRICE DROP
- 4 Beds
- 1.5 Baths
- 1,990 Sq Ft
163 Windsor Rd, Fairfield, CT 06824

Move-in ready. Energy-efficient. Rarely available prime Fairfield location. Enter this home to an open-concept layout with a cozy living room, dedicated coffee bar, dining area, & fully renovated kitchen. With four thoughtfully designed levels of of versatile living space, this property offers comfort now with room to grow * Renovated kitchen with stainless steel appliances, quartz countertops,

Valerie Applebaum Berkshire Hathaway NE Prop.

163 Windsor Rd, Fairfield, CT 06824
/40
$25,000,000
- 6 Beds
- 11 Baths
- 19,569 Sq Ft
1131 Sasco Hill Rd, Fairfield, CT 06824

Sasco Point- A Rare Waterfront Estate. Perched on over 11 acres with 450 feet directly on Long Island Sound, Sasco Point is an extraordinary coastal retreat. Nestled at the end of prestigious Sasco Hill Road, this architecturally stunning estate blends Swedish, Dutch, and Moorish influences, creating a residence that is as elegant as it is timeless. A discreet gated entrance leads to a winding

Andrew Whiteley Brown Harris Stevens

1131 Sasco Hill Rd, Fairfield, CT 06824
/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, thoughtfully reimagined with an array of stunning features and superior craftsmanship. Sited on 2 private acres, this extraordinary property offers priceless panoramic views of a 7-acre nature preserve, affording permanent tranquility and a sense of wonder. The meticulous renovations center around a

Carol Langeland William Pitt Sotheby's Int'l

4 Charcoal Ln, Westport, CT 06880
/40
$4,250,000
- 4 Beds
- 8 Baths
- 8,546 Sq Ft
800 Verna Hill Rd, Fairfield, CT 06824

Set on one of Fairfield's most coveted streets, this is the kind of home families spend years hoping will become available. Set on 3.35 acres on prestigious Verna Hill Road, adjacent to Fairfield Country Day School, this is the kind of property that becomes the backdrop for decades of memories. Summer afternoons by the pool and spa. Holiday dinners that bring everyone together. At the center of

Wendy Ryan Brown Harris Stevens

800 Verna Hill Rd, Fairfield, CT 06824
/17
$1,989,000

New Construction
- 5 Beds
- 4.5 Baths
- 4,110 Sq Ft
301 Godfrey Rd, Fairfield, CT 06825

Be inspired to live your best life in this to-be-built Colonial, sited on a beautifully level and private .46-acre lot, an increasingly rare offering in the coveted Lake Mohegan area of Fairfield. Offering Spring 2027 occupancy, this home blends quality craftsmanship with a thoughtfully designed floor plan that evolves with you. The home unfolds with a seamless flow of light-filled spaces, where

Dominika Wojciechowski Houlihan Lawrence

301 Godfrey Rd, Fairfield, CT 06825
/37
$1,599,000

Open Sat 11AM - 2PM Coming Soon
- 3 Beds
- 3 Baths
- 2,424 Sq Ft
75 Millard St, Fairfield, CT 06824

Fairfield Beach Neighborhood! Nestled in the heart of Fairfield's highly sought-after Beach Area, this wonderful Colonial offers an unparalleled lifestyle just moments from Sherman Elementary, public beaches, bocce/tennis courts, the tot lot, Town Hall, downtown Fairfield's acclaimed restaurants, boutique shopping, library, & the Metro-North train station. This beautifully appointed 9-room, 3-4

Christi McEldowney William Raveis Real Estate

75 Millard St, Fairfield, CT 06824
/11
$1,749,000

New Construction
- 4 Beds
- 3.5 Baths
- 3,200 Sq Ft
54 Timothy St, Fairfield, CT 06824

Experience refined luxury in this custom new construction offering 3,200 sqft. of thoughtfully designed living space, situated on a cul-de-sac just moments from downtown Fairfield, premier dining, boutique shopping & beautiful beaches. Step inside to discover exceptional millwork & upscale finishes. The main level features a spacious dining room complemented by a wet bar, perfect for

Anthony Fabrizio Coldwell Banker Realty

54 Timothy St, Fairfield, CT 06824
/33
$4,699,000

$50K PRICE DROP
- 6 Beds
- 8 Baths
- 8,190 Sq Ft
19 Mortar Rock Rd, Westport, CT 06880

Stunning modern transitional home built by Compo Luxury Homes in 2024 and ideally located just minutes to downtown Westport, Compo Beach, and the train. Set on .65 acres with city water, sewer, and natural gas, this beautifully designed residence offers over 8,000 square feet across four finished levels with 6 bedrooms, 6 full and 2 half baths. The open floor plan features a chef's kitchen with

Danna Rogers Higgins Group Bedford Square

19 Mortar Rock Rd, Westport, CT 06880
/40
$4,450,000

New Construction Open Sun 1PM - 3PM
- 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
/20
$3,900,000

Coming Soon
- 5 Beds
- 4.5 Baths
- 4,849 Sq Ft
36 Otter Trail, Westport, CT 06880

Welcome to riverfront living in the heart of Westport. Set along the beautiful Saugatuck River, this five-bedroom, five-bath Colonial offers a breathtaking setting with the perfect blend of privacy, charm, and convenience. The flat, fully fenced yard is ideal for playing, entertaining, or simply relaxing by the water, while the patio features a built-in barbecue and outdoor fireplace - the

Benjamin Howell Coldwell Banker Realty

36 Otter Trail, Westport, CT 06880
/40
$1,649,000

New Construction Open Sun 1PM - 3PM
- 4 Beds
- 4 Baths
- 3,700 Sq Ft
217 Fairland Dr, Fairfield, CT 06825

This stunning 3,700 square foot new construction Colonial features 4 spacious bedrooms and 4 full baths. The home is thoughtfully designed for today's lifestyle. The open-concept kitchen boasts a large quartz center island and flows seamlessly into the eating area and dramatic cathedral-ceiling family room. The primary suite is a true retreat, featuring cathedral ceilings, oversized walk-in

Madeline O'Shea Coldwell Banker Realty

217 Fairland Dr, Fairfield, CT 06825

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