Southport, CT Homes

/39
$3,995,000
- 6 Beds
- 5.5 Baths
- 5,682 Sq Ft
1061 Cedar Rd, Southport, CT 06890

Tucked behind mature landscaping on a beautifully private 1 acre setting, this extraordinary Southport residence is a home that reveals itself slowly, filled with warmth, character, and timeless craftsmanship. Designed for both everyday living and effortless entertaining, the nearly 6,000 SF home offers 6 bedrooms, 5.5 baths, soaring beamed ceilings, reclaimed wood, antique doors, wide-plank

Libby Tritschler

William Raveis Real Estate

1061 Cedar Rd, Southport, CT 06890
/21
$3,700 Per Month
- 2 Beds
- 2 Baths
- 960 Sq Ft
- House for Rent
25 Oakview Cir, Westport, CT 06880

Prime neighborhood in sought-after Westport, CT. 2 beds and 2 baths single family home with abundant natural light and a private patio in a quiet community. Vaulted ceiling living room open to dining room. Primary bedroom with bathroom and walk-in closet. Hardwood floors throughout. Amble storage space. Top-rated public school. Convenient location minutes to the quaint and beautiful downtown.

Richard Breglia

Coldwell Banker Realty

25 Oakview Cir, Westport, CT 06880
$1,800,000

Sold Jul 29, 2026

469 Woodridge Ave, Fairfield, CT 06825
- 5 Beds
- 4.5 Baths
- 3,458 Sq Ft
- Built 2019
Last Sold Summary
- 22% Above List Price
- $521/SF
- 14 Days On Market
Current Estimated Value $1,522,403

Last Listing Agent Jackie Davis William Raveis Real Estate

469 Woodridge Ave, Fairfield, CT 06825

Est $2,457,036

Not Listed For Sale

7 Sherwood Farms, Westport, CT 06880
- 6 Beds
- 4.5 Baths
- 4,471 Sq Ft
- Built 1993
7 Sherwood Farms, Westport, CT 06880

Last Sold Summary
- 55 Days On Market
Last Listing Agent Alex Chingas Coldwell Banker Realty

/38
$559,000
- 1 Bed
- 1.5 Baths
- 1,155 Sq Ft
50 Stone Ridge Way Unit 2A, Fairfield, CT 06824

Luxury Living in Fairfield! Welcome to sophisticated living in the sought-after gated community of Stone Ridge, ideally located directly across from the Fairfield-Black Rock Train Station and just moments from Whole Foods, shopping, restaurants, and downtown Fairfield. This beautifully appointed 1 bedroom, 1.5 bathroom residence offers elegant design, exceptional finishes, and a bright, open feel

Maria Graham-Baptist

Coldwell Banker Realty

50 Stone Ridge Way Unit 2A, Fairfield, CT 06824
/43
Starting at $4,120 Plus Fees
- 1 - 3 Beds
85 Post Rd W, Westport, CT 06880

Set along the banks of the Saugatuck River, Riverhouse introduces a fresh new standard of boutique luxury living in Westport. This brand-new rental community was thoughtfully designed for those who value effortless sophistication, blending elevated apartment homes with curated lifestyle amenities in one of Connecticut’s most desirable coastal towns — with the rare opportunity to be among the very

Riverhouse

85 Post Rd W, Westport, CT 06880
$3,500,000

Sold Sep 22, 2025

6 Florian Ct, Westport, CT 06880
- 5 Beds
- 6.5 Baths
- 7,970 Sq Ft
- Built 2007
Last Sold Summary
- 10% Below List Price
- $439/SF
- 88 Days On Market
Current Estimated Value $3,706,801

Last Listing Agent Lori Popkin Coldwell Banker Realty

6 Florian Ct, Westport, CT 06880

Est $2,439,287

Not Listed For Sale

7 Mansfield Place, Westport, CT 06880
- 4 Beds
- 4 Baths
- 3,270 Sq Ft
- Built 1900
7 Mansfield Place, Westport, CT 06880

Last Sold Summary
- 34 Days On Market
Last Listing Agent Judy Michaelis Coldwell Banker Realty

/37
$2,800,000

Under Contract
- 4 Beds
- 2 Baths
- 2,102 Sq Ft
1871 Fairfield Beach Rd, Fairfield, CT 06824

Premier direct waterfront living w/ ownership extending to the creek side, miles of sandy beach for endless walks, spectacular water views & a pristine 4 bedroom home - Welcome to 1871/1872 Fairfield Beach Road. Set on a .22, level acre w/ additional creek side parking for convenience. From the moment you arrive, the covered wraparound porch invites you to relax & enjoy the gorgeous water views.

Jackie Davis

William Raveis Real Estate

1871 Fairfield Beach Rd, Fairfield, CT 06824
/17
$12,000 Per Month
- 5 Beds
- 4.5 Baths
- 4,029 Sq Ft
- House for Rent
10 Fernwood Rd, Westport, CT 06880

Luxury In-Town Rental in the Heart of Westport Tucked away at the end of a peaceful cul-de-sac, this exceptional five-bedroom Colonial offers the rare combination of complete privacy, expansive living spaces, and an unbeatable in-town Westport location. Set on 1.5+ meticulously landscaped acres, this custom home was thoughtfully rebuilt in 2010 and is designed for effortless everyday living and

Jennifer Runnette

Brown Harris Stevens

10 Fernwood Rd, Westport, CT 06880
$2,425,000

Sold Jun 23, 2026

171 Compo Rd S, Westport, CT 06880
- 4 Beds
- 5 Baths
- 3,800 Sq Ft
- Built 2026
Last Sold Summary
- 1% Below List Price
- $638/SF
- 35 Days On Market
Last Listing Agent Tanya Sprague Coldwell Banker Realty

171 Compo Rd S, Westport, CT 06880

Est $3,024,700

Not Listed For Sale

33 Woody Ln, Westport, CT 06880
- 5 Beds
- 3.5 Baths
- 4,554 Sq Ft
- Built 1970
33 Woody Ln, Westport, CT 06880

Last Sold Summary
- 2 Days On Market
Last Listing Agent Michelle Genovesi William Raveis Real Estate

/28
$739,000

Under Contract
- 3 Beds
- 2 Baths
- 2,276 Sq Ft
9 Wildwood Rd, Fairfield, CT 06825

Ideally situated in Fairfield's sought after Fairfield Woods neighborhood, this impeccably maintained home offers the perfect blend of comfort, functionality, and convenience. Located just minutes from schools, parks, shopping, restaurants, and major commuting routes, the location is as desirable as the home itself. Thoughtfully updated over the years, the home features a finished lower level

Libby Tritschler

William Raveis Real Estate

9 Wildwood Rd, Fairfield, CT 06825
/67
Starting at $2,315

Total Monthly Price
- Studio - 2 Beds
1401 Kings Hwy, Fairfield, CT 06824

A unique fusion of convenience and luxuryyoull find the home, amenities, and location youve been dreaming of at ALTO Fairfield Metro. Discover what it feels like to love where you livemodern, spacious open-layout apartments boasting stunning quartz countertops, stainless steel appliances, floor-to-ceiling windows, hardwood-style plank flooring, and full-size washers and dryers. Discover The ALTO

Alto Fairfield Metro

1401 Kings Hwy, Fairfield, CT 06824
$1,225,000

Sold Jul 16, 2026

936 S Pine Creek Rd, Fairfield, CT 06824
- 3 Beds
- 5 Baths
- 2,740 Sq Ft
- Built 1988
Last Sold Summary
- 2% Above List Price
- $447/SF
- 43 Days On Market
Current Estimated Value $1,200,288

Last Listing Agent Jackie Davis William Raveis Real Estate

936 S Pine Creek Rd, Fairfield, CT 06824

Est $3,936,355

Not Listed For Sale

2A Whippoorwill Ln, Westport, CT 06880
- 6 Beds
- 8 Baths
- 8,558 Sq Ft
- Built 2007
2A Whippoorwill Ln, Westport, CT 06880

Last Sold Summary
- 22 Days On Market
Last Listing Agent Leslie Clarke Compass Connecticut, LLC

/40
$949,000

Under Contract
- 3 Beds
- 3.5 Baths
- 2,304 Sq Ft
25 Beaumont St, Fairfield, CT 06824

Spectacular luxury townhouse with a sophisticated New York loft feel! This stunning 3-bedroom, 3.5-bath residence showcases custom finishes throughout, hardwood flooring on the upper levels, and heated tile flooring on the entry level. A private elevator services all floors, providing effortless access from the tandem 2-car garage with additional storage. The chef's kitchen features premium

Patricia Moreggi

Coldwell Banker Realty

25 Beaumont St, Fairfield, CT 06824
/10
$2,100 Per Month
- 3 Beds
- 1 Bath
- 1,100 Sq Ft
- House for Rent
166 Dewey St Unit 1, Bridgeport, CT 06605

Move right in to this completely renovated 2/3 bedroom apartment. Spacious livingroom/dining room can be used as the third bedroom. Close to schools, shopping, transportation. A must see!

Susan Hanson

William Raveis Real Estate

166 Dewey St Unit 1, Bridgeport, CT 06605
$5,575,000

Sold Aug 26, 2025

29 Sturges Commons, Westport, CT 06880
- 6 Beds
- 9 Baths
- 8,817 Sq Ft
- Built 2012
Last Sold Summary
- 6% Below List Price
- $632/SF
- 110 Days On Market
Current Estimated Value $6,112,438

Last Listing Agent Doug Bross Coldwell Banker Realty

29 Sturges Commons, Westport, CT 06880

Est $4,980,024

Not Listed For Sale

108 Clapboard Hill Rd, Westport, CT 06880
- 5 Beds
- 4.5 Baths
- 5,312 Sq Ft
- Built 1920
108 Clapboard Hill Rd, Westport, CT 06880

Last Sold Summary
- 7 Days On Market
Last Listing Agent Lynne Nolan Compass Connecticut, LLC

/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
Starting at $1,988

Total Monthly Price
- Studio - 2 Beds
306 Canfield Ave, Bridgeport, CT 06605

Tucked along the winding shores of Ash Creek, Canfield Park at Fairfield Metro is just 0.5 miles from Fairfield-Black Rock Metro Train Station, with express rides to and from NYC and Stamford. Head a few blocks in the other direction on foot or by bike, and find yourself in the heart of Black Rock, with its charming coffee shops, fabled restaurants, bars and more. While at home, enjoy gourmet

Canfield Park

306 Canfield Ave, Bridgeport, CT 06605
$625,000

Sold Oct 22, 2025

270 Oakwood Dr, Fairfield, CT 06824
- 3 Beds
- 1 Bath
- 1,056 Sq Ft
- Built 1960
Last Sold Summary
- 4% Above List Price
- $592/SF
- 17 Days On Market
Current Estimated Value $678,948

Last Listing Agent Elizabeth Altobelli William Raveis Real Estate

270 Oakwood Dr, Fairfield, CT 06824

Est $4,159,812

Not Listed For Sale

19 Center St, Westport, CT 06880
- 6 Beds
- 8 Baths
- 7,861 Sq Ft
- Built 2017
19 Center St, Westport, CT 06880

Last Sold Summary
- 18 Days On Market
Last Listing Agent Brett Lieberman The Riverside Realty Group

/37
$755,000

$20K PRICE DROP
- 4 Beds
- 2 Baths
- 1,524 Sq Ft
241 Old Stratfield Rd, Fairfield, CT 06825

!!!ASSUMABLE 3% VA LOAN - APPROX. $468,000 BALANCE!!! A rare opportunity to secure a substantial portion of your financing at just 3% on this fully renovated Fairfield two-family! Current rents total $4,650/month and are believed to be below market, creating a compelling opportunity for owner-occupants and investors alike. Live in one unit and let the other help offset your housing costs or add a

Andrei Balaj

Higgins Group Real Estate

241 Old Stratfield Rd, Fairfield, CT 06825
/28
$17,000 Per Month
- 6 Beds
- 6 Baths
- 5,190 Sq Ft
- House for Rent
2 Bluewater Hill S, Westport, CT 06880

Steps from Compo Beach sits this 5000 Square Foot 6 Bedroom and 6 Bath Home with Water Views from most rooms. Incredible open floor plan with great entertaining spaces inside & out including a fabulous pool with spa. Finished Lower Level with Bed, Bath and Playroom. Term is September 3, 2026 - thru June 10, 2027.THIS IS AN ACADEMIC TERM FURNISHED RENTAL ONLY. Price is per month.

Susan Lieberman

The Riverside Realty Group

2 Bluewater Hill S, Westport, CT 06880
$587,000

Sold Jul 27, 2026

265 Shelter Rock Rd, Fairfield, CT 06825
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
- Built 1961
Last Sold Summary
- 5% Below List Price
- $582/SF
- 55 Days On Market
Current Estimated Value $600,591

Last Listing Agent Pamela Fernberg Coldwell Banker Realty

265 Shelter Rock Rd, Fairfield, CT 06825

Est $3,627,881

Not Listed For Sale

99 Hillspoint Rd, Westport, CT 06880
- 5 Beds
- 6 Baths
- 6,027 Sq Ft
- Built 2022
99 Hillspoint Rd, Westport, CT 06880

Last Sold Summary
- 38 Days On Market
Last Listing Agent Susan Lieberman The Riverside Realty Group

/39
$1,349,000

Under Contract
- 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

313 Old Post Rd, Fairfield, CT 06824
/35
Starting at $1,895 Plus Fees
- 1 Bed
575 Ellsworth St, Bridgeport, CT 06605

SPECIAL DEAL: One month FREE in rent credit on any new 12 month lease! Welcome to RockRidge Place, a newly and fully renovated pet-friendly community offering modern luxury living. RockRidge Place is comprised of one three-story building featuring one-bedroom and two-bedroom apartments, as well as outdoor amenities such as a pet play area and a community grilling and patio area.

RockRidge Place

575 Ellsworth St, Bridgeport, CT 06605
$485,000

Sold Dec 17, 2025

115 Denver Ave Unit 117, Bridgeport, CT 06605
- 6 Beds
- 2.5 Baths
- 3,382 Sq Ft
- Built 1900
Last Sold Summary
- 7% Below List Price
- $143/SF
- 21 Days On Market
Current Estimated Value $497,238

Last Listing Agent Joy Yen BHGRE Gaetano Marra Homes

115 Denver Ave Unit 117, Bridgeport, CT 06605

Est $3,041,815

Not Listed For Sale

54 North Ave, Westport, CT 06880
- 5 Beds
- 4.5 Baths
- 5,780 Sq Ft
- Built 2016
54 North Ave, Westport, CT 06880

Last Sold Summary
- 77 Days On Market
Last Listing Agent Leslie Clarke Compass Connecticut, LLC

/22
$589,000

$10K PRICE DROP
- 3 Beds
- 1.5 Baths
- 1,337 Sq Ft
245 Oakwood Dr, Fairfield, CT 06824

An amazing opportunity to own in a highly desirable University neighborhood - Welcome home to 245 Oakwood Drive. Distinguishable features include a picture perfect move in ready home, hardwood floors, an updated kitchen with granite countertops, freshly painted cabinetry and natural sunlight that brightens daily living. The main level presents beautifully with a bright and inviting living room,

Austin Reid

William Raveis Real Estate

245 Oakwood Dr, Fairfield, CT 06824
/38
$4,400 Per Month
- 3 Beds
- 2 Baths
- 1,690 Sq Ft
- House for Rent
111 Mill Hill Rd, Fairfield, CT 06824

Nestled on one of Southport's most beloved streets, 111 Mill Hill Road blends classic charm with turnkey comfort. This 3-bed, 2-bath Cape offers ~2,746 sq ft of living space on nearly an acre-so you get room to breathe, entertain, and unwind. The first level features newly finished hardwood floors and a newer kitchen, with updated baths that keep the day-to-day effortless. A flexible main-floor

Alan Stewart Jr.

ASJ Realty Partners

111 Mill Hill Rd, Fairfield, CT 06824
$620,000

Sold Oct 16, 2025

58 Post Rd, Fairfield, CT 06824
- 3 Beds
- 1.5 Baths
- 1,567 Sq Ft
- Built 1918
Last Sold Summary
- 1% Below List Price
- $396/SF
- 108 Days On Market
Current Estimated Value $660,823

Last Listing Agent Tammy Edwards Coldwell Banker Realty

58 Post Rd, Fairfield, CT 06824

Est $2,797,357

Not Listed For Sale

6 Weathervane Hill, Westport, CT 06880
- 4 Beds
- 3.5 Baths
- 4,771 Sq Ft
- Built 1949
6 Weathervane Hill, Westport, CT 06880

Last Sold Summary
- 29 Days On Market
Last Listing Agent Amy van Arsdale Compass Connecticut, LLC

/35
$329,900
- 2 Beds
- 2 Baths
- 1,145 Sq Ft
3250 Fairfield Ave Unit 110, Bridgeport, CT 06605

Easy living in the heart of Black Rock! Tucked into a desirable rear corner of the Village at Black Rock, this 2-bedroom, 2-full-bath condo offers approximately 1,145 square feet of comfortable one-level living with peaceful views overlooking Ash Creek. Step inside and you'll immediately appreciate the bright, open layout where the kitchen, dining, and living spaces come together-perfect for

Alan Stewart Jr.

ASJ Realty Partners

3250 Fairfield Ave Unit 110, Bridgeport, CT 06605
/28
Starting at $2,487 Plus Fees
- Studio - 1 Bed
1177 Post Rd E, Westport, CT 06880

Suburban comfort mixed with urban convenience. Ideally located north of the Long Island Sound and one hour away from New York, our studio and one-bedroom homes are the perfect place to live and thrive. These Westport, CT, apartments are ready to satisfy all your needs through a wide range of amenities and services. Flexible lease terms are also available!Modern and airy – our residences recreate

1177 Greens Farms

1177 Post Rd E, Westport, CT 06880
$568,000

Sold Mar 31, 2026

26 Crescent Park Rd, Westport, CT 06880
- 3 Beds
- 2 Baths
- 1,104 Sq Ft
- Built 1986
Last Sold Summary
- 3% Above List Price
- $514/SF
- 46 Days On Market
Current Estimated Value $604,541

Last Listing Agent Karim Douich William Raveis Real Estate

26 Crescent Park Rd, Westport, CT 06880

Est $2,531,544

Not Listed For Sale

378 Riverside Ave, Westport, CT 06880
- 4 Beds
- 6 Baths
- 4,700 Sq Ft
- Built 2014
378 Riverside Ave, Westport, CT 06880

Last Sold Summary
- 304 Days On Market
Last Listing Agent Peter Lane Ogents, LLC

Showing Results 1 - 40, Page 1 of 18

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Southport, CT Homes

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