Southport, CT Homes

/34
$2,600,000 Under Contract
- 5 Beds
- 5.5 Baths
- 5,008 Sq Ft
10 Wakenor Rd, Westport, CT 06880

Exceptional new build just completed by SIR Development, Westport's premier builder w/ 30+ yrs experience & 300+ homes. Leave the city for the burbs but keep the conveniences. Just a short walk to Starbucks, Stiles Market, Aux Delice, Little Barn & Big Y Plaza. Short ride to great schools, train & beach. This award winning layout and design has 5 BDRMs and is beautifully detailed across 4

Julie Haroun Westport Residential, LLC.

10 Wakenor Rd, Westport, CT 06880
/33
$5,200 total monthly price
- 3 Beds
- 2 Baths
- 1,056 Sq Ft
- House for Rent
26 Hiawatha Lane Extension, Westport, CT 06880

Welcome to this updated and move-in ready rental in sought-after Westport, offering a bright open layout and modern finishes throughout. The main level features a sun-filled living room with a fireplace, flowing seamlessly into the dining area and updated kitchen with granite counters, white cabinetry, and stainless appliances - ideal for everyday living and entertaining. The home offers three

Lisa Ronzello Coldwell Banker Realty

26 Hiawatha Lane Extension, Westport, CT 06880
$2,120,000 Sold Jun 05, 2025

35 Pumpkin Hill Rd, Westport, CT 06880
- 4 Beds
- 4 Baths
- 3,562 Sq Ft
- Built 1963
Last Sold Summary
- 12% Above List Price
- $595/SF
- 28 Days On Market
Current Estimated Value $2,110,490

Last Listing Agent Linda Skolnick Coldwell Banker Realty

35 Pumpkin Hill Rd, Westport, CT 06880

Est $3,414,139 Not Listed For Sale

10 Tranquility Ln, Westport, CT 06880
- 5 Beds
- 6 Baths
- 5,643 Sq Ft
- Built 1999
10 Tranquility Ln, Westport, CT 06880

Last Sold Summary
- 12% Above List Price
- $541/SF
- 6 Days On Market
Last Sold Price $3,055,000

Last Listing Agent Krista Alecia Coldwell Banker Realty

/39
$574,900
- 4 Beds
- 1.5 Baths
- 1,462 Sq Ft
1 Overlook Ave, Fairfield, CT 06824

Welcome to 1 Overlook in Fairfield - a charming Farmhouse Colonial offering 4 bedrooms, 1.5 baths, and a perfect blend of timeless character and modern-day comfort. From the moment you step inside, you'll appreciate the warm and inviting layout filled with natural light, spacious bedrooms, and flexible living spaces. The true standout feature is the incredible backyard oasis - a rare and

Skylar Smith William Raveis Real Estate

1 Overlook Ave, Fairfield, CT 06824
/8
$2,800 total monthly price
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Condo for Rent
292 Berkeley Rd Unit 292 BERKELEY RD, Fairfield, CT 06825

This property is an amazing 2 bedroom 1 bathroom apartment with all new appliances and vinyl flooring. It is 900 square foot with plenty of room. Ideal for singles and couples. Furthermore, there is ALDI, Planet Fitness, Subway, Dunkin Donuts, and Stop & Shop within walking distance. This rental is available starting September 1, 2025.

292 Berkeley Rd Unit 292 BERKELEY RD, Fairfield, CT 06825
$1,699,000 Sold Aug 20, 2025

1846 Mill Plain Rd, Fairfield, CT 06824
- 5 Beds
- 4 Baths
- 4,250 Sq Ft
- Built 2025
Last Sold Summary
- $400/SF
- 28 Days On Market
Current Estimated Value $1,613,284

Last Listing Agent Jacob Bivona Keller Williams Prestige Prop.

1846 Mill Plain Rd, Fairfield, CT 06824

Est $3,353,733 Not Listed For Sale

8 Tranquility Ln, Westport, CT 06880
- 4 Beds
- 5 Baths
- 6,225 Sq Ft
- Built 1999
8 Tranquility Ln, Westport, CT 06880

Last Sold Summary
- 17% Above List Price
- $462/SF
- 129 Days On Market
Last Sold Price $2,875,000

Last Listing Agent Michelle Genovesi William Raveis Real Estate

/30
$1,500,000 Pending
- 3 Beds
- 3 Baths
- 2,107 Sq Ft
5 Over Rock Ln, Westport, CT 06880

A rare offering providing the best of both worlds! Enter through stone pillars to find this well built ranch set on large, professionally landscaped property in a multi-million dollar neighborhood near town, train and beach. A spacious front to back great room with wood burning fireplace, built-ins and hardwood floors under the carpet, features walls of windows overlooking the lovely property

Laura Sydney William Pitt Sotheby's Int'l

5 Over Rock Ln, Westport, CT 06880
/14
$2,200 total monthly price
- 1 Bed
- 1 Bath
- 600 Sq Ft
- House for Rent
195 Laurel Place, Bridgeport, CT 06604

Beautifully renovated 1 bedroom, 1 bathroom apartment in the desirable Brooklawn neighborhood of Bridgeport. This fully updated unit features brand new stainless steel appliances, sleek countertops, white shaker cabinets, and gleaming hardwood floors throughout. A brand new central air and heating system with smart thermostat allows you to control the temperature right from your phone. In-unit

Chris Eanniello William Raveis Real Estate

195 Laurel Place, Bridgeport, CT 06604
$1,150,000 Sold Jul 18, 2025

407 Meadowbrook Rd, Fairfield, CT 06824
- 5 Beds
- 2.5 Baths
- 2,840 Sq Ft
- Built 1927
Last Sold Summary
- 15% Above List Price
- $405/SF
- 10 Days On Market
Current Estimated Value $1,136,916

Last Listing Agent Skylar Smith William Raveis Real Estate

407 Meadowbrook Rd, Fairfield, CT 06824

Est $1,843,181 Not Listed For Sale

44 Bridge St, Westport, CT 06880
- 4 Beds
- 3.5 Baths
- 4,549 Sq Ft
- Built 1999
44 Bridge St, Westport, CT 06880

Last Sold Summary
- 34% Above List Price
- $303/SF
- 37 Days On Market
Last Sold Price $1,380,000

Last Listing Agent Adrienne Durkin Compass Connecticut, LLC

/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
/13
$11,000 total monthly price
- 4 Beds
- 3 Baths
- 1,700 Sq Ft
- House for Rent
296 Reef Rd, Fairfield, CT 06824

Tastefully FURNISHED 9 month rental beginning September 2027. Viking appliances. Spa showers. Patio. Easy stroll to downtown, train, shopping and beach. Up to 5 unrelated tenants. Subject to credit report and employment verification; co-signers accepted.

296 Reef Rd, Fairfield, CT 06824
$3,700,000 Sold Jun 02, 2025

612 Penfield Rd, Fairfield, CT 06824
- 5 Beds
- 4.5 Baths
- 4,501 Sq Ft
- Built 2014
Last Sold Summary
- $822/SF
- 15 Days On Market
Current Estimated Value $3,777,728

Last Listing Agent Jane Jones Berkshire Hathaway NE Prop.

612 Penfield Rd, Fairfield, CT 06824

Est $3,827,037 Not Listed For Sale

19 Woody Ln, Westport, CT 06880
- 6 Beds
- 9 Baths
- 8,928 Sq Ft
- Built 1997
19 Woody Ln, Westport, CT 06880

Last Sold Summary
- 23% Above List Price
- $347/SF
- 36 Days On Market
Last Sold Price $3,100,000

Last Listing Agent Linda Skolnick Coldwell Banker Realty

/38
$799,000 Open Thu 10:30AM - 2PM
- 3 Beds
- 1.5 Baths
- 1,652 Sq Ft
188 Henderson Rd, Fairfield, CT 06824

Experience the unbeatable location of 188 Henderson Rd. Imagine starting your perfect day with a short stroll to Starbucks and Pop Up Bagels. After enjoying your morning treats, you can walk a few doors down to Mill River and easily launch your kayak or canoe right at the water's edge. For lunch, grab a delicious sandwich at No Pine Creek Deli. Just a short walk away is the Sportsplex, where

Helene Daly Compass Connecticut, LLC

188 Henderson Rd, Fairfield, CT 06824
/21
$2,950 total monthly price
- 2 Beds
- 1 Bath
- 1,100 Sq Ft
- House for Rent
108 Wilson St Unit B, Bridgeport, CT 06605

Spectacular new construction, second floor, two bedroom, 1 bathroom apartment with a den and open floor plan. The property is ideally located in the Black Rock restaurant and entertainment district and convenient to the Black Rock Train Station, I-95, St. Mary's By The Sea, Captain's Cove Seaport and offers two off street parking spaces. The owner meticulously renovated with high end finishes

John Kleps Berkshire Hathaway NE Prop.

108 Wilson St Unit B, Bridgeport, CT 06605
$2,700,000 Sold Jan 26, 2026

26 Hitchcock Rd, Westport, CT 06880
- 5 Beds
- 5 Baths
- 4,549 Sq Ft
- Built 2025
Last Sold Summary
- $594/SF
- 224 Days On Market
Current Estimated Value $2,298,758

Last Listing Agent Mar Jennings Higgins Group Bedford Square

26 Hitchcock Rd, Westport, CT 06880

Est $3,020,324 Not Listed For Sale

5 Windrush Ln, Westport, CT 06880
- 5 Beds
- 5.5 Baths
- 5,424 Sq Ft
- Built 1995
5 Windrush Ln, Westport, CT 06880

Last Sold Summary
- 10% Above List Price
- $505/SF
- 17 Days On Market
Last Sold Price $2,737,500

Last Listing Agent Jillian Klaff Coldwell Banker Realty

/35
$1,599,000 Open Thu 10:30AM - 1:30PM
- 4 Beds
- 3.5 Baths
- 3,636 Sq Ft
11 Tuckahoe Ln, Fairfield, CT 06824

WELCOME HOME to 11 Tuckahoe Lane. A Fabulous like new 4/5 bedroom colonial in the popular Osborn Hill/FFLD Woods/FFld Ludlowe district! Stately double entry doors - perfect first impression for this beautifully appointed University area colonial, inside & out. One Owner & good as new! Open floor plan for the modern homeowner has a sought after open concept! Kitchen w/center island, WetBar &

Christine Magliocco Higgins Group Real Estate

11 Tuckahoe Ln, Fairfield, CT 06824
/11
$2,300 total monthly price
- 3 Beds
- 1 Bath
- 834 Sq Ft
- House for Rent
969 Maplewood Ave, Bridgeport, CT 06605

MUST SEE, this cozy one family house. renovated with hard wood floors throughout the house. Freshly painted throughout. Washer and dryer hookup. Reach out if interested.

969 Maplewood Ave, Bridgeport, CT 06605
$360,000 Sold Oct 17, 2025

2612 North Ave Unit D7, Bridgeport, CT 06604
- 2 Beds
- 2.5 Baths
- 1,410 Sq Ft
- Built 1988
Last Sold Summary
- 3% Above List Price
- $255/SF
- 39 Days On Market
Current Estimated Value $358,769

Last Listing Agent Bozena Tisch Coldwell Banker Realty

2612 North Ave Unit D7, Bridgeport, CT 06604

Est $4,285,054 Not Listed For Sale

21 Daniel Ct, Westport, CT 06880
- 6 Beds
- 6.5 Baths
- 7,575 Sq Ft
- Built 1995
21 Daniel Ct, Westport, CT 06880

Last Sold Summary
- 14% Above List Price
- $495/SF
- 4 Days On Market
Last Sold Price $3,750,000

Last Listing Agent Debra Carson William Raveis Real Estate

/35
$650,000 Under Contract
- 4 Beds
- 2 Baths
- 1,942 Sq Ft
1 Garden Dr, Fairfield, CT 06825

Terrific owner occupied or investor opportunity! Corner lot means 2 separate addresses and entrances! Owners unit enters at 218 Melville and boasts an updated eat in kitchen and open floor plan with front to back dining area and living room. Main level washer and dryer. Upstairs you will find an updated full bath and 2 good sized bedrooms PLUS an open office with potential for a 3rd bedroom (no

Patricia Cardozo Coldwell Banker Realty

1 Garden Dr, Fairfield, CT 06825
/18
$3,000 total monthly price
- 3 Beds
- 2 Baths
- 1,755 Sq Ft
- Apartment for Rent
25 Cartright St Unit 2D, Bridgeport, CT 06604

3-bedroom/2-bathroom condo rental in the Brooklawn section of Bridgeport near Fairfield. Tenant pays electricity only; heat and water included. Building has 24-hour lobby doorman/security and common-area laundry in the basement. Unit updated with parquet flooring throughout and new appliances. Convenient access to I-95 and Metro-North: Fairfield Metro Station (2.0 mi), Bridgeport Station (2.3

Yasmina Delacruz-Bailey BHGRE Gaetano Marra Homes

25 Cartright St Unit 2D, Bridgeport, CT 06604
$580,000 Sold Apr 25, 2025

126 Churchill St, Fairfield, CT 06824
- 4 Beds
- 1 Bath
- 1,787 Sq Ft
- Built 1953
Last Sold Summary
- 23% Above List Price
- $325/SF
- 16 Days On Market
Current Estimated Value $579,768

Last Listing Agent Benjamin Howell Coldwell Banker Realty

126 Churchill St, Fairfield, CT 06824

Est $755,526 Not Listed For Sale

14 Cross Hwy Unit D, Westport, CT 06880
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 1900
14 Cross Hwy Unit D, Westport, CT 06880

Last Sold Summary
- 17% Above List Price
- $538/SF
- 16 Days On Market
Last Sold Price $645,000

Last Listing Agent Georgia Wasserman Coldwell Banker Realty

/23
$649,900
- 4 Beds
- 2 Baths
- 1,612 Sq Ft
9 Garden Ct, Fairfield, CT 06825

Welcome to 9 Garden Court, a tastefully updated two family duplex consisting of two townhouse style units located in the highly sought after Stratfield neighborhood. A perfect opportunity for an owner-occupant or investor seeking to expand their portfolio. The home features two mirror image side by side two story units with private opposing entrances via a porch. Each unit boasts hardwood floors

Adam Roy BHGRE Gaetano Marra Homes

9 Garden Ct, Fairfield, CT 06825
/10
$8,500 total monthly price
- 4 Beds
- 1 Bath
- 1,100 Sq Ft
- House for Rent
417 Reef Rd, Fairfield, CT 06824

2028-2029 FURNISHED 4BR Cape Cod charmer with central A/C and lush backyard with furnished patio. Easy stroll to the beach, train and downtown Fairfield shopping and restaurants. MBR has queen size bed and the other 3 BR's have full size beds. Maximum 4 unrelated tenants. Co-signers accepted.

417 Reef Rd, Fairfield, CT 06824
$635,000 Sold Sep 25, 2025

125 Vesper St, Fairfield, CT 06825
- 3 Beds
- 2 Baths
- 1,896 Sq Ft
- Built 1919
Last Sold Summary
- 2% Above List Price
- $335/SF
- 21 Days On Market
Current Estimated Value $630,048

Last Listing Agent Max Dober Keller Williams Prestige Prop.

125 Vesper St, Fairfield, CT 06825

Est $574,284 Not Listed For Sale

14 Cross Hwy Unit B, Westport, CT 06880
- 2 Beds
- 1 Bath
- 800 Sq Ft
- Built 1900
14 Cross Hwy Unit B, Westport, CT 06880

Last Sold Summary
- 7% Above List Price
- $669/SF
- 40 Days On Market
Last Sold Price $535,000

Last Listing Agent Sandra Calise Cenatiempo Settlers & Traders

/39
$1,925,000
- 3 Beds
- 3.5 Baths
- 3,805 Sq Ft
485 Westway Rd Unit 485, Fairfield, CT 06890

Welcome to Village at Southport, a 16-home gated enclave of luxurious, turn-key homes right in "The Village." Pure easy living in this 3800+ square foot, three level townhome with every amenity desired. Just a few minutes to the gorgeous beach & harbor, library, restaurants & shops, ideally located close to commute & downtown living, yet quiet & private. This end unit is ideally set abutting the

Jessica Walsh William Raveis Real Estate

485 Westway Rd Unit 485, Fairfield, CT 06890
/38
$5,000 total monthly price
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
- House for Rent
322 Greenfield St, Fairfield, CT 06825

Ideal for LONG-TERM TENANTS, TRAVEL NURSES, and SACRED HEART COMMUTERS, this freshly updated rental is only a 10-15 MINUTE COMMUTE from Sacred Heart University and offers FLEXIBLE LEASE OPTIONS to fit your needs. Step inside 322 Greenfield St and enjoy soaring 12+ FT CEILINGS in the living room, creating a bright and open atmosphere. The BRAND-NEW KITCHEN features a modern BACKSPLASH, UPDATED

Rafael Suarez Yellowbrick Real Estate LLC

322 Greenfield St, Fairfield, CT 06825
$1,000,000 Sold Dec 15, 2025

2492 Congress St, Fairfield, CT 06824
- 4 Beds
- 3 Baths
- 2,273 Sq Ft
- Built 1929
Last Sold Summary
- 16% Above List Price
- $440/SF
- 47 Days On Market
Current Estimated Value $945,752

Last Listing Agent Tracie and Vicki Team William Raveis Real Estate

2492 Congress St, Fairfield, CT 06824

Est $653,442 Not Listed For Sale

12 Cross Hwy Unit C, Westport, CT 06880
- 2 Beds
- 1 Bath
- 1,074 Sq Ft
- Built 1900
12 Cross Hwy Unit C, Westport, CT 06880

Last Sold Summary
- 10% Above List Price
- $554/SF
- 45 Days On Market
Last Sold Price $595,000

Last Listing Agent Doug Rose Scalzo Real Estate

/23
$745,000 Pending
- 4 Beds
- 3 Baths
- 1,984 Sq Ft
329 Bronson Rd, Southport, CT 06890

Location, location and location! Here is a chance to build some sweet equity that you have been waiting for! With 4 Bedrooms and 3 full bathrooms there is room for all. Living room with a fireplace along with two additional sitting room to accommodate all your guests. Partially fenced in yard, detached garage. Central air, gas heat, tankless hot water heater and much more. Connecticut Choice

Masooma Ali Connecticut Choice Realty

329 Bronson Rd, Southport, CT 06890
/11
$14,000 total monthly price
- 4 Beds
- 4 Baths
- 2,200 Sq Ft
- Townhouse for Rent
928 Reef Rd, Fairfield, CT 06824

Newly constructed townhouse with 4 bedrooms ( each with its own bath ).Attic bedroom can accommodate two students.Totally furnished.

928 Reef Rd, Fairfield, CT 06824
$1,900,000 Sold Aug 11, 2025

1369 S Pine Creek Rd, Fairfield, CT 06824
- 4 Beds
- 2.5 Baths
- 2,521 Sq Ft
- Built 2025
Last Sold Summary
- $754/SF
- 141 Days On Market
Current Estimated Value $1,817,481

Last Listing Agent Veronica Monahan Compass Connecticut, LLC

1369 S Pine Creek Rd, Fairfield, CT 06824

Est $559,200 Not Listed For Sale

12 Cross Hwy Unit A, Westport, CT 06880
- 1 Bed
- 1 Bath
- 977 Sq Ft
- Built 1900
12 Cross Hwy Unit A, Westport, CT 06880

Last Sold Summary
- 9% Above List Price
- $527/SF
- 88 Days On Market
Last Sold Price $515,000

Last Listing Agent Abigail Delise William Raveis Real Estate

Showing Results 281 - 320, Page 8 of 18

Connecticut Fairfield County Southport

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage