Colonial Homes for Sale in Southport, CT

/36
$2,997,000
- 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
/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
/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
/2
$2,275,000

New Construction
- 4 Beds
- 3.5 Baths
- 3,744 Sq Ft
75 Spinning Wheel Rd, Fairfield, CT 06824

Another exceptional new construction by a well-known local builder! Now is the perfect opportunity to meet with the builder and customize this beautifully designed home to suit your lifestyle. Offering approximately 2700 square feet of thoughtfully designed living space, plus additional finished space in the basement, this home features 4 levels of living, 4 spacious bedrooms, and 3.5 luxurious

Bette Gigliotti

William Raveis Real Estate

75 Spinning Wheel Rd, Fairfield, CT 06824
/37
$2,399,000

New Construction
- 4 Beds
- 3.5 Baths
- 2,950 Sq Ft
96 Clinton St, Fairfield, CT 06824

One of only two new construction homes currently available in Fairfield's coveted Beach neighborhood, an incredible opportunity w/ outstanding market value & just steps to the beach - Welcome Home to 96 Clinton Street. 4 levels of living w/ 2950 sf, elevator shaft ready, 4 bedrooms, 3.5 bath & high end finishes throughout. The open concept main level features custom finishes w/ a chef's kitchen

Jackie Davis

William Raveis Real Estate

96 Clinton St, Fairfield, CT 06824
/40
$2,999,000

New Construction
- 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
/38
$3,695,000
- 4 Beds
- 4.5 Baths
- 3,744 Sq Ft
110 Judson Rd, Fairfield, CT 06824

Nestled on one of Fairfield Beach's most coveted streets, this exceptional new construction blends timeless coastal architecture with sophisticated design in a location that's simply hard to duplicate. Just moments from the beach, town, train, schools, and parks, 110 Judson offers the rare convenience today's buyers seek without sacrificing privacy or tranquility. Thoughtfully positioned at a

Cindy Raney Coldwell Banker Realty

110 Judson Rd, Fairfield, CT 06824
/40
$4,500,000

$490K PRICE DROP
- 5 Beds
- 4 Baths
- 4,144 Sq Ft
1149 Fairfield Beach Rd, Fairfield, CT 06824

A rare opportunity to own a premier BEACHFRONT residence offering compelling value in today's luxury market with updated guest home....All BEAUTIFULLY appointed & MOVE IN READY! 60 MINS to NYC! BEACHFRONT Home~1149 Walk-Out-To-Sand Waterfront AND Guest Home ~1148 fun & updated (2022) just steps to your Private BEACH. Enjoy true beachfront living w/no steps from your main level family room to an

Christine Magliocco Higgins Group Real Estate

1149 Fairfield Beach Rd, Fairfield, CT 06824
/23
$1,575,000
- 5 Beds
- 3.5 Baths
- 3,596 Sq Ft
35 S Benson Commons, Fairfield, CT 06824

Nestled on a quiet cul-de-sac just minutes from town, train, and beach, this beautifully crafted Colonial offers the perfect blend of elegance, comfort, and convenience. A charming front porch welcomes you into a light-filled home featuring a dramatic two-story foyer, a chef's kitchen, granite countertops, and premium Viking, Wolf, and Sub-Zero stainless steel appliances. The adjoining family

Katie O'Grady Compass Connecticut, LLC

35 S Benson Commons, Fairfield, CT 06824
/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
/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
/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
/39
$2,699,000

$251K 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
/36
$5,995,000

$504K PRICE DROP
- 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
/39
$1,548,000
- 4 Beds
- 2.5 Baths
- 3,665 Sq Ft
485 Mountain Laurel Rd, Fairfield, CT 06824

Picture coming home to your own Custom Colonial sitting on over half a private acre on a quiet, tree-lined street in lower Greenfield Hill, where you're minutes from everything but feel worlds away. An expansive front porch invites you to slow down the second you pull in. Inside, sunlight pours through every room and hardwood floors gleam underfoot. The high-end, spacious kitchen is made for

Patricia Shea Coldwell Banker Realty

485 Mountain Laurel 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
/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
/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
/36
$4,900,000
- 6 Beds
- 8 Baths
- 7,801 Sq Ft
80 Governors Ln, Fairfield, CT 06824

As you enter 80 Governors Lane down a private driveway, discover an 8.5-acre estate blending timeless elegance with serene privacy. This circa 1933 farmhouse, designed by architect Jack Franzen and beautifully restored, features wide plank black walnut floors, exposed beams, and a bread oven fireplace. Six spacious bedrooms include a luxurious Primary Suite with vaulted ceilings, carved mantle

Lis Reed Coldwell Banker Realty

80 Governors Ln, Fairfield, CT 06824
/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
$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
/14
$1,799,000

New Construction
- 5 Beds
- 4.5 Baths
- 4,093 Sq Ft
83 Morehouse Hwy, Fairfield, CT 06825

Brand-NEW construction Home underway in Fairfield's highly sought-after Lake Mohegan neighborhood, crafted by local builders known for exceptional quality and design. There is still time for buyers to personalize select finishes and create the home of their dreams! Offering over 4,000 square feet of thoughtfully designed living space, this stunning residence is situated on a rare, level .89-acre

Melissa Montagno Higgins Group Real Estate

83 Morehouse Hwy, Fairfield, CT 06825
/40
$2,950,000

$175K PRICE DROP
- 6 Beds
- 6.5 Baths
- 5,320 Sq Ft
420 Morehouse Ln, Southport, CT 06890

Nestled on a private lane, this Southport luxury estate offers a pin-drop quiet setting just minutes from Southport Village, Southport Harbor, the Southport train station, I-95, and the Merritt Parkway. Set on over two level acres, it blends tranquility and convenience. The home features six bedrooms, including a gracious first-floor primary suite with a fireplace, dual spa-like bathrooms,

Amanda Heyn William Raveis Real Estate

420 Morehouse Ln, Southport, CT 06890
/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
$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 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
/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
/39
$2,195,000
- 5 Beds
- 4.5 Baths
- 4,512 Sq Ft
50 Brookbend Rd, Fairfield, CT 06824

An extraordinarily rare opportunity in Fairfield's coveted Winton Park Association. Offered for the first time in over 4 decades, this timeless 5-bedroom, 4.5-bath Colonial is set on nearly 2 breathtaking, park-like acres, offering estate-like privacy w/an unparalleled walk-to-town lifestyle. A gracious foyer welcomes you inside, where a magnificent staircase, wide-plank hardwood floors &

Kate Cacciatore William Raveis Real Estate

50 Brookbend Rd, 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
/40
$4,450,000

New Construction
- 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
$3,399,900
- 5 Beds
- 8 Baths
- 8,657 Sq Ft
344 Fence Row Dr, Fairfield, CT 06824

Old-world craftsmanship meets modern indulgence. Set on a peaceful, tree-lined street,this home offers total privacy and timeless curb appeal. Soaring ceilings, hand-finished millwork, and custom detail are evident throughout. This grand 5BR/6.5BA light filled residence pairs classic entertaining spaces - formal LR, formal DR, & a wood-paneled library w/wet bar & full BA-with modern amenities

Krista Alecia Coldwell Banker Realty

344 Fence Row Dr, Fairfield, CT 06824
/39
$875,655
- 2 Beds
- 2 Baths
- 2,324 Sq Ft
1 Campfield Dr, Fairfield, CT 06825

Completely renovated and move-in ready, this stunning modern Colonial is located in Fairfield's desirable Tunxis Hill neighborhood. Meticulously remodeled from top to bottom, the home seamlessly blends contemporary style with timeless charm. Featuring 3 bedrooms with lots of natural light, an additional flexible office space and 2 full baths, the thoughtfully designed interior showcases a chef's

Catherine Aaron Berkshire Hathaway NE Prop.

1 Campfield Dr, Fairfield, CT 06825
/39
$3,400,000
- 5 Beds
- 5.5 Baths
- 6,753 Sq Ft
1760 Hillside Rd, Fairfield, CT 06824

Privately sited in the heart of Greenfield Hill, this updated home blends European-inspired architecture with the modern comforts today's luxury buyers value most. Rich in character, it offers soaring ceilings with exposed wood beams and skylights, wide-plank hardwood floors, custom built-ins, antique mantels, and repurposed antique doors throughout. The dramatic family room flows to a private

Andrew Whiteley Brown Harris Stevens

1760 Hillside Rd, Fairfield, CT 06824
/39
$3,850,000
- 5 Beds
- 4.5 Baths
- 3,921 Sq Ft
406 Harbor Rd, Southport, CT 06890

This is why so many people fall in love with Southport. Set on an extraordinary .83-acre parcel in the heart of the Village, this circa 1874 residence captures the charm, character, and lifestyle that have made Southport one of New England's most treasured coastal communities. Approached by a long drive and set well back from Harbor Road, the home enjoys a level of privacy rarely found in the

Wendy Ryan Brown Harris Stevens

406 Harbor Rd, Southport, CT 06890
/35
$989,000

Open Wed 7PM - 7:30PM
- 4 Beds
- 3 Baths
- 2,326 Sq Ft
133 Alma Dr, Fairfield, CT 06824

Gambrel style Colonial and features 8 Rooms, 4 Bedrooms, 3 Bathrooms, 1 Car Garage. NOTED FEATURES that the whole family will enjoy; 262 square foot Gym or Playroom in the lower level, 252 square foot Main level Bedroom, 183 square foot Sunroom off the kitchen, 408 square foot Patio with movable fireplace, 540 square foot Pool deck for summer fun and 252 square feet expansion possibilities above

Paul Ferreira RE/MAX Right Choice

133 Alma Dr, Fairfield, CT 06824
/40
$2,199,000

Coming Soon
- 4 Beds
- 3.5 Baths
- 3,519 Sq Ft
245 N Cedar Rd, Fairfield, CT 06824

Rarely do you find a house that needs nothing. Look no further than this Southport gem. Set on a gentle knoll at the end of a long gated driveway, past your sprawling front lawn and dreamy treehouse, 2-car garage, and sportcourt. The interior has been tweaked by the best quality construction to the kitchen, bathrooms, sunroom, and basement. The rear property's stone patio, gunite pool, and pool

Michael Traum RE/MAX Heritage

245 N Cedar Rd, Fairfield, CT 06824

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