Colonial Homes for Sale in Southport, CT

/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
/4
$4,950,000

Coming Soon
- 5 Beds
- 4.5 Baths
- 4,875 Sq Ft
6 Gray Ln, Westport, CT 06880

A rare WATERFRONT offering in one of Westport's most coveted enclaves. This beautifully composed estate is gracefully sited on more than two private, tree-lined acres, encompassing sweeping views of Sasco Creek, Southport Beach, and Long Island Sound while preserving an exceptional sense of seclusion. Designed to maximize its remarkable setting, the home captures water views from nearly every

Christine McKinney William Raveis Real Estate

6 Gray Ln, Westport, CT 06880
/23
$1,799,000

Open Sat 1PM - 3PM
- 4 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
/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
/40
$4,100,000

$400K PRICE DROP
- 5 Beds
- 8 Baths
- 9,819 Sq Ft
1 Flower Farm Ln, Westport, CT 06880

Absolutely exquisite colonial is located on one of the most sought after neighborhoods. This home will greet you w/a mahogany front porch that leads inside to a grand foyer. This timeless residence boasts a custom kitchen w/high-end appliances, a Butler's pantry, large island & the convenience of a desk station. The elegant formal living room features a cozy fireplace, while the family room

Heather Fitzgerald Coldwell Banker Realty

1 Flower Farm Ln, Westport, CT 06880
/39
$2,395,000
- 4 Beds
- 4.5 Baths
- 3,978 Sq Ft
298 S Benson Rd, Fairfield, CT 06824

Savor the coastal lifestyle in this beautifully designed, light-filled home in Fairfield's sought-after Beach neighborhood. Ideally located just a half-mile stroll from Jennings Beach, Jennings Pavilion, the Fairfield Marina, and Sand Castle park, this home offers the perfect blend of comfort & convenience. The open-concept main level features a spacious living room that flows seamlessly into the

Katie O'Grady Compass Connecticut, LLC

298 S Benson Rd, Fairfield, CT 06824
/4
$6,495,000

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

New Construction by Westport Family Homes - Elevator, July Completion. Privately set at the end of a quiet cul-de-sac in the coveted Long Lots neighborhood, this 2.3-acre, flat, tree-lined property offers a rare combination of privacy and endless possibilities for creating a luxury compound. Introducing a truly exceptional estate by award-winning Builder, Westport Family Homes. The residence

Lori Popkin Coldwell Banker Realty

5 Baldwin Place, Westport, CT 06880
/37
$4,799,000

New Construction
- 5 Beds
- 5.5 Baths
- 7,583 Sq Ft
11 Wake Robin Rd, Westport, CT 06880

Just completed and ready for immediate occupancy, this beautifully crafted new construction home is set on a quiet cul-de-sac in the desirable Greens Farms area. Situated on a level one-acre property with a pool, the home is filled with abundant natural light and offers a thoughtful, well-balanced layout designed for both everyday living and entertaining. The stunning kitchen opens to a dramatic

Judi Lake The Riverside Realty Group

11 Wake Robin Rd, Westport, CT 06880
/7
$4,100,000

New Construction
- 6 Beds
- 5.5 Baths
- 6,244 Sq Ft
48 Woodside Ave, Westport, CT 06880

A rare opportunity to own new construction in Westport's coveted Old Hill neighborhood, offering refined design, a swimming pool, and a walkable lifestyle near Post Road and downtown. Tucked within one of Westport's most sought-after enclaves, this newly constructed 6-bedroom, 5.5-bath home blends architectural sophistication with modern livability. Natural light, clean lines, and

Judy Michaelis Coldwell Banker Realty

48 Woodside Ave, Westport, CT 06880
/37
$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
/38
$475,000

$25K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,564 Sq Ft
111 Elmwood Place, Bridgeport, CT 06605

Welcome to this beautiful spacious 5 bedroom Colonial offering over 2,500+ sq ft of beautifully laid-out living space in the heart of Bridgeport. This 5 bedroom home blends classic charm with modern comfort, featuring a warm and welcoming living area with fireplace and a stunning dinning space highlighted by large windows overlooking the backyard perfect for gatherings and everyday enjoyment.

Sara Barnaba Century 21 Scala Group

111 Elmwood Place, Bridgeport, CT 06605
/40
$15,000,000
- 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
/22
$1,175,000

Open Thu 10AM - 1PM Coming Soon
- 2 Beds
- 2 Baths
- 1,055 Sq Ft
119 Old Dam Rd, Fairfield, CT 06824

Delightful waterfront oasis offering direct access to Long Island Sound and includes deeded Fairfield beach access. This jewel box home has a bright, open floor plan, fully renovated with a coastal style. The kitchen flows seamlessly to the dining area and living room. Glass doors bring the outside in an lead to a spacious deck and property that culminates at the waterfront and dock. The primary

Katie O'Grady Compass Connecticut, LLC

119 Old Dam Rd, Fairfield, CT 06824
/40
$1,845,000
- 4 Beds
- 3.5 Baths
- 3,239 Sq Ft
7 Ennis Ln, Fairfield, CT 06824

Let's focus on one of the best lifestyles in Fairfield-come home to 7 Ennis Lane. More than just a house, this is a home that has been filled w/ love & laughter. Warm, open & welcoming, its spaces create an atmosphere that is both inviting, comfortable & elevated. With an optimal location at the end of a small cul de sac surrounded by beautiful marshland in Center/Beach/Sasco areas, this property

Jessica Walsh William Raveis Real Estate

7 Ennis Ln, Fairfield, CT 06824
/40
$3,275,000
- 5 Beds
- 8 Baths
- 8,279 Sq Ft
111 Golden Pond Ln, Fairfield, CT 06824

111 Golden Pond Lane is the rare luxury home that feels as welcoming as it is impressive. Tucked at the end of a quiet, tree-lined cul-de-sac, the home opens with an undeniable scale - soaring 19-foot ceilings, a dramatic two-story entry, sweeping staircases, and natural light that moves effortlessly throughout the day. Yet what makes the home memorable is not its grandeur alone, but the warmth

Cindy Raney Coldwell Banker Realty

111 Golden Pond Ln, Fairfield, CT 06824
/5
$2,050,000
- 5 Beds
- 3.5 Baths
- 2,509 Sq Ft
79 Fairfield Place, Fairfield, CT 06824

Set on a level and flat .24-acre lot in the highly sought-after Sasco Hill area of Fairfield, this charming home offers endless opportunities to customize and create your dream living space. Boasting 2,500 square feet of versatile living area, plus a full unfinished basement, a deck, and an outdoor shed, this property perfectly balances comfort and potential. Enjoy a unique dual-street frontage,

Phyllis Doonan William Raveis Real Estate

79 Fairfield Place, Fairfield, CT 06824
/40
$3,300,000

New Construction Open Sat 12PM - 3PM
- 4 Beds
- 5 Baths
- 3,943 Sq Ft
920 Old Post Rd, Fairfield, CT 06824

Experience coastal luxury in this exceptional new construction home ideally located in Fairfield's coveted beach/center location. Thoughtfully designed with outstanding craftsmanship & high-end finishes throughout, this stunning residence offers four levels of beautifully appointed living space with 4 bedrooms, 3 full & 2 half baths. The heart of the home is an impressive chef's kitchen featuring

Julie Vanderblue Higgins Group Real Estate

920 Old Post Rd, Fairfield, CT 06824
/7
$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
/6
$9,860,000

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

An exceptional modern residence by Compo Luxury Homes, designed by renowned architect Tanner White, set on over two private acres just minutes from downtown Westport, Compo Beach, and the train-approximately one hour from NYC. This 6-bedroom home spans approximately 9,200 square feet and showcases custom European windows and doors, sophisticated interiors, and seamless indoor-outdoor living. At

Danna Rogers Higgins Group Bedford Square

9 Over Rock Ln, Westport, CT 06880
/34
$1,599,876

$75K PRICE DROP
- 5 Beds
- 4 Baths
- 3,156 Sq Ft
30 Pequot Trail, Westport, CT 06880

Coveted Old Hill neighborhood! This stone and shingle 10 room colonial is detailed with custom millwork, recessed lighting and beautiful hardwood floors throughout. The front to back living room with marble fireplace offers peaceful views through expansive windows. The formal dining room with picture window is adjacent to a generous country kitchen featuring a bay window, granite countertops, a

Lynn Fraund William Pitt Sotheby's Int'l

30 Pequot Trail, Westport, CT 06880
/40
$4,990,000

Open Sat 11AM - 2PM
- 5 Beds
- 4 Baths
- 5,779 Sq Ft
1149 & 1148 Fairfield Beach Rd, Fairfield, CT 06824

Toes in the sand! Welcome to 1149 & 1148 Fairfield Beach Rd where the best beach memories are made&every day feels like summer....2 wonderful homes:Main Home~1149 w/direct waterfront & private sandy beach AND 1148~A fun updated (2022) guest home just steps across the street. Enjoy true beachfront living w/no steps from your main level family room to an expansive patio (see video) where you can

Christine Magliocco Higgins Group Real Estate

1149 & 1148 Fairfield Beach Rd, Fairfield, CT 06824
/5
$2,950,000
- 4 Beds
- 4.5 Baths
- 3,611 Sq Ft
169 Compo Rd S, Westport, CT 06880

Stunning New Construction in highly desirable Compo South neighborhood! Introducing 169 Compo Rd.S. a tucked away hidden gem, superbly designed and presently being impeccably built by local HOME Design & Build. Set in an incredible natural and private setting amid woods, ledge and open space, this home offers three levels of sun-filled open-concept living. Timeless architectural details blend

Tanya Sprague Coldwell Banker Realty

169 Compo Rd S, Westport, CT 06880
/40
$3,850,000
- 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
/40
$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
/11
$1,899,000
- 4 Beds
- 3.5 Baths
- 3,514 Sq Ft
36 Lyons Plain Rd, Westport, CT 06880

Lovely 2.36 acres of river front land in Westport, with 300 ft. frontage on the Aspetuck River. Four large bedrooms including Primary with fireplace and full bath. Large kitchen, Great Room with a fireplace that opens to the deck and views of the river. Lots of privacy, and a beautiful setting! A wonderful opportunity for a renovation as is, or new build. Town appraisal is $1,898,400.00. Must

Charlotte Cotton William Raveis Real Estate

36 Lyons Plain Rd, Westport, CT 06880
/36
$1,395,000
- 3 Beds
- 3.5 Baths
- 3,203 Sq Ft
1180 Merwins Ln, Fairfield, CT 06824

Private Greenfield Hill Retreat on 2+ Acres with Guest Suite, Modern Updates & Equestrian Potential.Tucked away on a quiet cul-de-sac in the heart of Greenfield Hill, this rare property offers privacy, flexibility, and modern comfort. From the moment you enter, the craftsmanship is unmistakable featuring a handcrafted staircase, custom millwork, built-ins, and a dramatic barrel ceiling living

Jennifer Lockwood Coldwell Banker Realty

1180 Merwins Ln, Fairfield, CT 06824
/38
$1,495,000

Coming Soon
- 4 Beds
- 2.5 Baths
- 3,163 Sq Ft
26 Spruce St, Southport, CT 06890

SOUTHPORT VILLAGE ITALIANATE VICTORIAN - The Legrand Sherwood | William Northrop House - Circa 1872. Ideally located in Southport Village, this exceptional 3,163 square foot, four bedroom Italianate Victorian has been thoughtfully restored and sensitively updated, blending exceptional architectural elements with beautiful interiors. Designer finishes (marble, tiles, fixtures and hardware),

Victoria Fingelly Higgins Group Real Estate

26 Spruce St, Southport, CT 06890
/38
$2,895,000

Coming Soon
- 5 Beds
- 3.5 Baths
- 3,999 Sq Ft
30 Saint Johns Place, Westport, CT 06880

Saint John Place is the street people who know Westport quietly hope opens up. It almost never does. Reimagined in 2007 by Renato Gasparian Associates and refreshed in 2022, this house has all the right moves. Inside, the main level opens up the way you hope it will. The great room stretches nearly thirty-four feet and flows into the dining area and a kitchen built around a center island, with a

Carrie Perkins RE/MAX Heritage

30 Saint Johns Place, Westport, CT 06880
/19
$3,900,000

New Construction
- 5 Beds
- 4.5 Baths
- 4,100 Sq Ft
1008 Fairfield Beach Rd, Fairfield, CT 06824

1008 Fairfield Beach Road- A Masterpiece on Fairfield's Iconic Coastline. Where modern luxury meets coastal elegance. Presented by one of Fairfield County's premier celebrity developers, this extraordinary new construction beach home offers an unparalleled lifestyle with panoramic, unobstructed views of the Long Island Sound with jaw-dropping sunsets. Stand out in the neighborhood with one of the

Valerie Alvarez Serhant Connecticut, LLC

1008 Fairfield Beach Rd, Fairfield, CT 06824
/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
/39
$2,225,000

$25K PRICE INCREASE
- 6 Beds
- 2 Baths
- 2,180 Sq Ft
2142 Fairfield Beach Rd, Fairfield, CT 06824

OPPORTUNITY KNOCKS TWICE - A unique investment awaits with the only two-family home on the Fairfield Beach Road Peninsula featuring private beach access. This fully furnished property offers excellent rental income during the academic season and serves as a relaxing summer retreat for owners-or an additional rental opportunity. Unit 2142 is a spacious four-bedroom residence, each room furnished

Michael Menillo Collage Realty

2142 Fairfield Beach Rd, Fairfield, CT 06824
/40
$1,699,000

Open Thu 11AM - 2PM
- 4 Beds
- 3 Baths
- 2,604 Sq Ft
7 High Gate Rd, Westport, CT 06880

Hamptons sophistication meets timeless Westport charm in this exquisitely renovated 4-bedroom, 3-bath Colonial nestled at the end of a peaceful cul-de-sac on a double lot in the highly coveted Greens Farms neighborhood. Reimagined by acclaimed fashion designer Christian Siriano, this one-of-a-kind residence blends elevated design with exceptional craftsmanship throughout. The stunning new chef's

Linda Skolnick Coldwell Banker Realty

7 High Gate Rd, Westport, CT 06880
/30
$1,899,000

Open Thu 12PM - 3PM
- 3 Beds
- 2.5 Baths
- 3,338 Sq Ft
23 Old Dam Rd, Fairfield, CT 06824

Wonderful waterfront oasis offers direct access to Long Island Sound via a private dock and includes deeded Fairfield beach access. The home features a bright, open floor plan, creating an inviting coastal atmosphere. The primary bedroom boasts a sitting room, a walk-in closet, and a balcony overlooking the waterfront, providing stunning views of LI Sound & Pine Creek. The property promises

Katie O'Grady Compass Connecticut, LLC

23 Old Dam Rd, Fairfield, CT 06824
/35
$2,799,000
- 4 Beds
- 3.5 Baths
- 4,340 Sq Ft
42 Anvill Rd, Southport, CT 06890

What lifestyle can you expect when buying a home in Southport?When buying a home in Southport, you can expect a lifestyle centered on peaceful living in a charming, quiet neighborhood filled with tranquil streets and cul-de-sacs. Homes here, like 42 Anvil Road offer spacious and elegant living spaces designed for comfort and functionality. Imagine preparing meals in a gourmet kitchen with custom

Lis Reed Coldwell Banker Realty

42 Anvill Rd, Southport, CT 06890
/40
$1,599,000

New Construction
- 4 Beds
- 4.5 Baths
- 4,007 Sq Ft
50 Lisbon Dr, Fairfield, CT 06825

Experience exceptional contemporary design and detail in this custom built home offering incredible flexible living spaces! A perfect blend of luxury and versatility, this stunning residence features 4 bedrooms, 4.5 bathrooms, including a Luxurious Primary suite complete with spa-like bathroom and dual walk in closets. The open-concept floor plan is anchored by a designer eat-in Kitchen complete

Melissa Montagno Higgins Group Real Estate

50 Lisbon Dr, Fairfield, CT 06825
/40
$1,199,000

Open Sat 1PM - 4PM
- 5 Beds
- 4 Baths
- 3,310 Sq Ft
120 Saddleview Rd, Fairfield, CT 06825

Exceptional 5-Bedroom Colonial in Fairfield's Desirable Lake Mohegan Neighborhood! Featuring 1st-Floor Bedrooms, 4 Full Baths, Impressive Private Fenced Yard, and Easy Access to Beaches, Commuter Rail, and Fairfield's Town Centers. Ideally located steps from the Lake with serene dog-friendly nature trails, fresh-water swimming beach, and sprinkler area, this beautifully updated home with 3,328

Linda Raymond William Raveis Real Estate

120 Saddleview Rd, Fairfield, CT 06825
/12
$309,900

$19K PRICE DROP
- 3 Beds
- 1 Bath
- 864 Sq Ft
969 Maplewood Ave, Bridgeport, CT 06605

Welcome Home! This charming, "move-in ready" fully updated 3-Bedroom, 1-bathroom single-family residence is a premier opportunity for a first-timer or investor. The 1st floor open floor plan allows everyone to share the same space. Some of the recent updates include a new roof, hot water heater, bathroom and new flooring through-out the home. The new fenced level-yard is perfect for pets,

Ortiz Jes Carrena Property Mgmt & Realty

969 Maplewood Ave, Bridgeport, CT 06605
/40
$3,295,000

Open Thu 11AM - 1PM $705K PRICE DROP
- 5 Beds
- 8 Baths
- 4,911 Sq Ft
22 Sturges Commons, Westport, CT 06880

22 Sturges Commons offers the rare combination of timeless elegance, true neighborhood living, and unmatched convenience in one of Westport's most sought-after locations near the Hunt Club. Just one traffic light to the Greens Farms Station train station, this home makes commuting to New York City effortless while allowing you to return home to a peaceful walking neighborhood where charming

Judy Michaelis Coldwell Banker Realty

22 Sturges Commons, Westport, CT 06880
/40
$5,750,000
- 4 Beds
- 4.5 Baths
- 3,800 Sq Ft
69 Birch Rd, Fairfield, CT 06824

Your new fully custom near beach luxury residence is ready for you now... Introducing "White Birch", a masterfully executed collaboration between Fairfield County's premier Architect, Builder, & Designer, sets a new benchmark for bespoke coastal living and the effortless estate lifestyle. Every detail has been thoughtfully curated, every finish intentionally elevated, every inch built with

Jaclyn Picarillo Higgins Group Bedford Square

69 Birch Rd, Fairfield, CT 06824
/17
$1,650,000
- 4 Beds
- 3.5 Baths
- 4,880 Sq Ft
101 Applegate Rd, Fairfield, CT 06825

Welcome to this exceptional fully reimagined home at 101 Applegate Road, perfectly set on a quiet, walkable horseshoe street just off Fairfield Woods Road in one of Fairfield's most desirable neighborhoods. This thoughtfully designed 4-bedroom, 3 full and 1 half bath home blends timeless style with modern functionality, offering the ideal layout for today's lifestyle. Step inside to a bright,

Alan Hamilton William Raveis Real Estate

101 Applegate Rd, Fairfield, CT 06825

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