Southport, CT Homes for Sale

/23
$420,000

Open Sat 1PM - 3PM
- 3 Beds
- 1.5 Baths
- 1,232 Sq Ft
106 Brittin Ave, Bridgeport, CT 06605

Tucked away at the end of a cul-de-sac in highly desirable Black Rock. Right around the corner from Fairfield Ave. known for its energetic and welcoming vibe. With the great restaurants cafe's and pubs residents enjoy the active community. Close to St. Marys by the Sea, this spacious 3 bedroom duplex offers comfort, convenience and plenty of room to spread out. Enjoy the bright, sunny interior

Sandy Petrino William Pitt Sotheby's Int'l

106 Brittin Ave, Bridgeport, CT 06605
/40
$6,495,000

New Construction Open Sun 1PM - 3PM $1M PRICE DROP
- 4 Beds
- 4.5 Baths
- 3,260 Sq Ft
16 Westport Ave, Westport, CT 06880

Brand-new coastal smart home, steps from Compo Beach, built to run quietly through whatever Long Island Sound throws at it. This is the only just-completed residence on the Compo Beach side of Westport delivered as a fully integrated, self-monitoring home: rooftop solar power w/battery storage, intelligent load management, leak detection w/automatic water shutoff, energy-recovery ventilation,

Karen Scott Compass Connecticut, LLC

16 Westport Ave, Westport, CT 06880
/31
$314,999
- 2 Beds
- 1.5 Baths
- 1,138 Sq Ft
2660 North Ave Unit 211, Bridgeport, CT 06604

Come check out this updated 2-bedroom, 1.5-bathroom unit located in a quiet gated community with two assigned parking spaces. Features include hardwood floors, high ceilings with multiple skylights, elevator access, a courtyard, and an Amazon Lockers hub in the lobby. The primary bedroom includes a loft area that can be used as a home office, guest bedroom, or additional living space. The home

Sasha Iyamu ERIS, LLC

2660 North Ave Unit 211, Bridgeport, CT 06604
/22
$4,995,700

New Construction
- 4 Beds
- 4.5 Baths
- 4,000 Sq Ft
22 Dawn Dr, Westport, CT 06880

Come walk this stunning 1.5 acre lot with me - totally private, tucked at the end of a cul de sac in Long Lots. Peace, quiet, and the highest quality custom home spec'd to your wishlist by Coastal Luxury Homes is yours at 22 Dawn Drive. Go bigger/smaller, add an in-law suite or extra bedroom, an art studio, include a pool/spa, pickle court... let's discuss all the possibilities. Square footage

Jaclyn Picarillo Higgins Group Bedford Square

22 Dawn Dr, Westport, CT 06880
/6
$1,250,000

$240K PRICE DROP
- Land
- 6,534 Sq Ft
- $8,333,333 per Acre
15 Gorham Ave, Westport, CT 06880

Nestled on a charming historic street in one of Westport's most desirable neighborhoods, 15 Gorham Avenue offers a rare opportunity to build your dream home just moments from the heart of town. This exceptional property allows for the construction of a approximately 2,500+/- square foot residence, perfectly suited for today's lifestyle while blending beautifully with the character of the

Peter Lane Ogents, LLC

15 Gorham Ave, Westport, CT 06880
/6
$9,860,000

New Construction
- 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
$1,025,000

Open Sun 1PM - 3PM
- 3 Beds
- 2.5 Baths
- 2,300 Sq Ft
153 Woody Ln, Fairfield, CT 06825

Welcome to 153 Woody Lane, an exceptional Split Style home nestled on a quiet cul-de-sac in Fairfield. This property sits on a generous Half acre lot, offering both tranquility and privacy. With recent updates including new modern design kitchen, 3 Spacious bedrooms and 2.5 bathrooms, sunroom for year-round enjoyment, and a partially finished basement, this home is a perfect blend of modern

Aziz Seyal William Raveis Real Estate

153 Woody Ln, Fairfield, CT 06825
/4
$5,999,999

New Construction Coming Soon
- 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 8,800+/- 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
$4,990,000

Open Sun 1PM - 3PM
- 5 Beds
- 4 Baths
- 5,779 Sq Ft
1149 & 1148 Fairfield Beach Rd, Fairfield, CT 06824

Toes in the sand! Welcome to direct BEACHFRONT Living where the best beach memories are made&every day feels like summer....BEAUTIFULLY appointed & MOVE IN READY! Main Home~1149 w/Walk-Out-To-Sand Waterfront AND Guest Home ~1148~A fun & updated (2022) 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

Christine Magliocco Higgins Group Real Estate

1149 & 1148 Fairfield Beach Rd, Fairfield, CT 06824
/40
$999,000

Open Sat 1PM - 4PM
- 3 Beds
- 2.5 Baths
- 1,999 Sq Ft
252 Shoreham Village Dr, Fairfield, CT 06824

Wake up to gorgeous creek views, perennial gardens and the sounds of nature in this Nantucket-inspired 3-bedroom colonial. Filled with timeless charm and character throughout, this one is truly special. Relax by the wood-burning fireplace in the living room, framed by beautiful arched doorways. Read or work in the stunning library with custom wall-to-wall built-ins, a vaulted ceiling, and sliding

Carrie Sakey Coldwell Banker Realty

252 Shoreham Village Dr, Fairfield, CT 06824
/17
$1,275,000
- 4 Beds
- 3 Baths
- 2,270 Sq Ft
32 Morningside Dr N, Westport, CT 06880

4 Bedroom 3 Bath Farmhouse in the heart of Westport set on a picturesque level .5 acre. Full of potential, this home awaits your creative vision. Flat, pretty property with city water and sewer available nearby. Detached one car garage. Ideally located in the coveted Long Lots neighborhood, minutes to the train, restaurants, schools, shops, Burying Hill Beach, Sherwood Island Park, Compo Beach,

Patricia Shea Coldwell Banker Realty

32 Morningside Dr N, Westport, CT 06880
/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
/35
$800,000

Open Sun 11AM - 1PM
- 4 Beds
- 2.5 Baths
- 2,070 Sq Ft
77 Round Hill Rd, Fairfield, CT 06824

Fabulous 4-bedroom expanded Cape in a highly sought-after location within walking distance to train, beloved downtown amenities like restaurants and shopping, and Fairfield schools! This charming home offers wonderful curb appeal and a fully fenced yard, perfect for outdoor enjoyment, pets, or play! Inside, you'll find a warm and inviting layout featuring a spacious Living Room, bright Kitchen

Julie Vanderblue Higgins Group Real Estate

77 Round Hill Rd, Fairfield, CT 06824
/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
/14
$899,000

$76K PRICE DROP
- 2 Beds
- 2 Baths
- 1,182 Sq Ft
20 Cross St Unit 7, Westport, CT 06880

This beautiful condo/townhouse is located conveniently within a 5 min walk to downtown Westport. The upstairs features 2 spacious bedrooms with walk in closets and a full bathroom. The main level has a sun-filled living room and a dining room with a view of a cozy backyard accompanied by another full bathroom and a walk in pantry. The kitchen is well appointed with all thick marble countertops

Steven Koleno Beycome of Connecticut

20 Cross St Unit 7, 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
/18
$1,475,000
- Land
- 1.05 Acres
- $1,404,762 per Acre
50 Sylvan Rd N, Westport, CT 06880

ATTENTION BUYERS : FLAT DRY, ONE -OF-A-KIND LAND OPPORTUNITY NOW HUGELY IMPROVED WITH WELL DEFINED SITE PLAN. Do you hope for new custom construction no bigger than "about" 4500sf, yet continue to see 7000sf and larger get the edge? Stop wishing for it and take action! Bring your architect or builder to consider a new home that meets your dream to be practically-sized for every life stage. No

Martha Eidman Coldwell Banker Realty

50 Sylvan Rd N, Westport, CT 06880
/16
$379,000

Open Sat 11AM - 1PM
- 2 Beds
- 1 Bath
- 1,036 Sq Ft
150 Beachview Ave Unit 290, Bridgeport, CT 06605

Welcome to 150 Beachview Ave, Unit 290, located in the sought-after Black Rock area of Bridgeport. This beautiful first-floor unit offers two bedrooms, one bathroom, and a convenient in-unit laundry room. Set within a gated waterfront community, it features a private covered deck and direct access to a ramp for kayaking or paddleboarding. With one dedicated parking space plus visitor parking,

Walter Montero Keller Williams Realty

150 Beachview Ave Unit 290, Bridgeport, CT 06605
/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
/26
$1,175,000

$75K PRICE DROP
- 6 Beds
- 3 Baths
- 2,870 Sq Ft
21 Ardmore St, Fairfield, CT 06824

Fairfield Three-Family | Prime Location, Steady Income A well positioned income producing property in one of Fairfield's most convenient pockets. All three units are currently occupied, offering an investor immediate cash flow from day one. The first and second floor units each offer two bedrooms, 5 rooms total, and over 1,100 square feet of living space, solid footprints that attract long term

Jennifer Lockwood Coldwell Banker Realty

21 Ardmore St, Fairfield, CT 06824
/32
$2,200,000

$199K PRICE DROP
- 3 Beds
- 3.5 Baths
- 3,328 Sq Ft
2 Elmwood Dr Unit 2, Southport, CT 06890

Rare opportunity in sought-after Southport Green-just steps to Southport Village and Metro-North. One of only two stand-alone residences in this 24-unit enclave, this home offers the privacy of a single-family lifestyle with the ease of condominium living. The townhouse-style residence spans three levels and features 3 bedrooms, 3 renovated full and 1 half baths, plus a coveted attached two-car

Wendy Ryan Brown Harris Stevens

2 Elmwood Dr Unit 2, Southport, CT 06890
/40
$2,790,000
- 5 Beds
- 3 Baths
- 3,072 Sq Ft
56 Charcoal Hill Rd, Westport, CT 06880

A rare opportunity to own one of Charcoal Hill's signature properties, this exceptional Frazier Peters stone home pairs historic craftsmanship with a level of care and refinement that is increasingly hard to find. Set atop 2.3 +/- gated acres and introduced through a stunning circular drive, the residence showcases Peters' hallmark use of native stone, warm wood tones, and artisan detail,

Doug Bross Coldwell Banker Realty

56 Charcoal Hill Rd, Westport, CT 06880
/39
$1,495,000

Open Sun 1AM - 3PM
- 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
/40
$2,895,000

Open Sun 1PM - 3PM
- 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
/37
$650,000
- 4 Beds
- 3 Baths
- 2,074 Sq Ft
430 Berkeley Rd, Fairfield, CT 06825

Lovely 4 Bedrooms and 3 Full Bath Cape built in 1986 is ready to move-in. House has many updates including new Kitchen countertops, Newer roof, water heater and much more. Private deck converted to paved parking and play area for children and finished basement. The house offers Spacious primary bedroom and full bathroom on first floor along with updated kitchen - new Quartz countertops, newer

Aziz Seyal William Raveis Real Estate

430 Berkeley Rd, Fairfield, CT 06825
/26
$599,000
- 3 Beds
- 1 Bath
- 1,760 Sq Ft
81 Shoreham Terrace, Fairfield, CT 06824

Discover the opportunity to create your own coastal retreat in this 3-bedroom home ideally situated in Fairfield's desirable shoreline area. Approximately 50 miles from New York City, this property presents an opportunity to customize and update a home in a sought-after location that offers commutability, coastal charm, flexibility, and convenience. Offering approximately 1,760 total finished

Jennifer McCoy Coldwell Banker Realty

81 Shoreham Terrace, Fairfield, CT 06824
/27
$2,200,000
- 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
$1,199,000

Open Sat 1PM - 3PM
- 3 Beds
- 2.5 Baths
- 2,773 Sq Ft
41 Pepperbush Ln, Fairfield, CT 06824

Welcome home to this fully renovated Colonial in one of Fairfield's most desirable neighborhoods! Comprehensively updated with high-quality finishes throughout, this 3-bedroom, 2.5-bath home offers move-in ready living w/ nothing left to do but unpack. Brand-new open concept kitchen over looks dining room & features modern shaker-style cabinetry, quartz countertops, & all-new st/st appliances,

Max Dober Keller Williams Prestige Prop.

41 Pepperbush Ln, Fairfield, CT 06824
/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
/35
$899,000
- Land
- 2.08 Acres
- $432,212 per Acre
101 Hubbell Ln, Fairfield, CT 06824

Rare opportunity to create a custom residence on 2.08 acres in coveted lower Greenfield Hill. Set on beautiful Hubbell Lane, this raw land parcel offers 258.45 feet of frontage and a special chance to build in one of Fairfield's most desirable neighborhoods, where open building lots are increasingly difficult to find. Site work and preliminary environmental review have been completed, including

Tara Hawley Coldwell Banker Realty

101 Hubbell Ln, 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
/7
$479,500
- 6 Beds
- 2 Baths
- 3,419 Sq Ft
52-54 Clinton Ave, Bridgeport, CT 06605

INVESTMENT OPPORTUNITY!! Don't miss this versatile two-family offering strong income potential. Featuring six Bedrooms Two full baths. Offers flexible with expansion. Attic offers added value. Roof is two years old. Mechanics all in working order. Property being sold As-Is. Bring your ideas and unlock the full potential this income-producing property!

William Ferguson Brown Harris Stevens

52-54 Clinton Ave, Bridgeport, CT 06605
/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 Sun 1PM - 3PM
- 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
/22
$995,000

Open Sat 1:30PM - 3PM $100K PRICE DROP
- 3 Beds
- 2 Baths
- 2,400 Sq Ft
18 Hurd St, Fairfield, CT 06824

Welcome home to this charming and beautifully maintained 3-bedroom, 2-full-bath ranch offering the perfect blend of comfort, convenience, and lifestyle. Ideally situated just moments from the beach, downtown, and the train, this home puts everything you love right at your fingertips. Step inside to discover a warm and inviting floor plan designed for easy everyday living. The spacious living area

Adam Wagner Keller Williams Prestige Prop.

18 Hurd St, Fairfield, CT 06824
/29
$1,200,000
- 4 Beds
- 2.5 Baths
- 1,406 Sq Ft
97 Fayerweather Terrace, Bridgeport, CT 06605

Fabulous Remodeled 4 Bedroom main house with Open floor plan. Partially finished basement. New Energy Star Appliances, Solar and beautifully appointed. Detached 2 Car Garage with One bedroom one bath unit above. Close to train, restaurants, St. Mary's by the Sea.

Steven Koleno Beycome of Connecticut

97 Fayerweather Terrace, Bridgeport, CT 06605
/3
$999,000
- Land
- 13,068 Sq Ft
- $3,330,000 per Acre
20 Woods Grove Rd, Westport, CT 06880

Set on a picturesque 0.30-acre lot, this ranch-style home is full of potential and waiting for your creative vision. While the home is being sold as-is the possibilities are endless. Whether you're an investor, a builder, or a homeowner with a vision, this property offers the perfect canvas to bring your ideas to life. Situated in a sought-after neighborhood with close proximity to downtown,

Miki Scarfo Compass Connecticut, LLC

20 Woods Grove Rd, Westport, CT 06880
/29
$1,899,000

Open Sat 11AM - 1PM
- 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
/40
$3,499,000

Open Sun 1PM - 3PM
- 4 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

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