Southport, CT Homes

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  $649,500

  • 2 Beds
  • 2.5 Baths
  • 1,731 Sq Ft

  80 Bywater Ln, Bridgeport, CT 06605

  A UNIQUE OPPORTUNITY OF GREAT VALUE AWAITS IN THIS DESIGNER HOME IN A PRIME BLACK ROCK LOCATION - Welcome Home to 80 Bywater Lane. Move right into this Voguish, NY chic styled, completely updated townhouse offering 3 spacious levels of comfortable living. Nestled in & surrounded by both nature & seasonal water views. This peaceful home offers total serenity while lounging on 1 of your 3 decks.

  

  Jackie Davis

  William Raveis Real Estate

  (203) 354-7242

  80 Bywater Ln, Bridgeport, CT 06605
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  /36

  $5,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,201 Sq Ft
  • House for Rent

  167 North Ave Unit Cottage, Westport, CT 06880

  Charming two-bedroom carriage house filled with natural light, set on two private acres. This beautifully renovated home offers an open-concept layout, featuring a brand-new kitchen and updated bathroom. Situated on two picturesque acres in the sought-after Coleytown neighborhood, while still just minutes from downtown Westport, shopping, dining, and transportation.

  

  Brittany Strouse

  Coldwell Banker Realty

  (203) 759-8916

  167 North Ave Unit Cottage, 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 $552,633

  Last Listing Agent Karim Douich William Raveis Real Estate

  26 Crescent Park Rd, Westport, CT 06880
• 

  Est $1,808,662 Not Listed For Sale

  29 Woods Grove Rd, Westport, CT 06880

  • 4 Beds
  • 3 Baths
  • 2,279 Sq Ft
  • Built 1952

  29 Woods Grove Rd, Westport, CT 06880

  Last Sold Summary

  • 2% Above List Price
  • $779/SF
  • 40 Days On Market

  • Last Sold Price $1,775,000
  • Apr 28, 2025

  Last Listing Agent Doug Bross Coldwell Banker Realty
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  $3,550,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,602 Sq Ft

  10 Winding Ln, Westport, CT 06880

  Experience the pinnacle of luxury living in this exceptional 4,600 sq ft, 5-bedroom home, ideally located in highly sought-after Old Hill. Perfectly positioned on a pristine 1-acre lot, this stunning home offers a rare "walk-to-everything" lifestyle-just steps from shopping, top-rated restaurants, and Earthplace. Designed for both elegant entertaining and everyday comfort, the home features an

  

  Susan Lieberman

  The Riverside Realty Group

  (475) 255-2758

  10 Winding Ln, Westport, CT 06880
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  /35

  Starting at $1,995

  Total Monthly Price

  • 1 Bed

  585 Ellsworth St, Bridgeport, CT 06605

  Mid-Rise Building with Elevator - 1 bedroom apartment in Beautiful Black Rock. Vinyl floors, granite countertops, updated appliances, and intercom system Heat, hot water, and cooking gas are included. Parking and a storage unit is included. Laundry, electric car chargers, and fitness center are on-site Cypress Apartments is ideally located just minutes from top-tier restaurants, trendy

  Cypress Apartments

  (475) 265-5678

  

  585 Ellsworth St, Bridgeport, CT 06605
• 

  $590,000 Sold Oct 02, 2025

  293 Barryscott Dr, Fairfield, CT 06825

  • 3 Beds
  • 1.5 Baths
  • 1,412 Sq Ft
  • Built 1953

  Last Sold Summary

  • 12% Above List Price
  • $418/SF
  • 71 Days On Market

  Current Estimated Value $495,959

  Last Listing Agent Stacey DiDio Coldwell Banker Realty

  293 Barryscott Dr, Fairfield, CT 06825
• 

  Est $7,198,935 Not Listed For Sale

  6 Pond Edge Rd, Westport, CT 06880

  • 5 Beds
  • 8.5 Baths
  • 10,324 Sq Ft
  • Built 2014

  6 Pond Edge Rd, Westport, CT 06880

  Last Sold Summary

  • 4% Above List Price
  • $668/SF
  • 33 Days On Market

  • Last Sold Price $6,900,000
  • May 08, 2025

  Last Listing Agent Kim Harizman Compass Connecticut, LLC
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  /39

  $625,000 Open Sat 1PM - 3PM

  • 2 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  54 Bunnell Cir, Fairfield, CT 06825

  Nestled on a peaceful cul-de-sac and set on .50 acres very close to Lake Mohegan, this charming ranch-style home offers privacy, comfort, and stunning sunset views from its elevated sloping property. Featuring an open floor plan with beautiful hardwood floors throughout, the inviting living room is highlighted by a cozy fireplace and flows seamlessly into the dining area and kitchen-perfect for

  

  Amy Waugh Curry ABR CRS GRI

  Berkshire Hathaway NE Prop.

  (475) 242-5707

  54 Bunnell Cir, Fairfield, CT 06825
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  $12,500 Per Month

  • 5 Beds
  • 3.5 Baths
  • 6,310 Sq Ft
  • House for Rent

  71 High Point Rd, Westport, CT 06880

  Light-filled ranch style contemporary nestled at the end of one of Westport's most sought-after cul-de-sacs, close to schools, beaches and shopping. The main floor boasts open, airy rooms with niche spaces, all thoughtfully designed on one level. The kitchen has been tastefully renovated, complete with ample cabinetry, granite counters, a center island, and stainless steel appliances. The kitchen

  

  Hyleri Katzenberg

  Compass Connecticut, LLC

  (475) 290-6137

  71 High Point Rd, Westport, CT 06880
• 

  $1,190,000 Sold Jul 08, 2025

  94 Orchard Hill Dr, Fairfield, CT 06824

  • 4 Beds
  • 3 Baths
  • 2,740 Sq Ft
  • Built 1954

  Last Sold Summary

  • 6% Above List Price
  • $434/SF
  • 5 Days On Market

  Current Estimated Value $1,217,505

  Last Listing Agent Tammy Edwards Coldwell Banker Realty

  94 Orchard Hill Dr, Fairfield, CT 06824
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  Est $2,918,092 Not Listed For Sale

  15 Sunrise Rd, Westport, CT 06880

  • 5 Beds
  • 6.5 Baths
  • 5,407 Sq Ft
  • Built 2025

  15 Sunrise Rd, Westport, CT 06880

  Last Sold Summary

  • 5% Above List Price
  • $512/SF
  • 22 Days On Market

  • Last Sold Price $2,769,000
  • Apr 30, 2025

  Last Listing Agent Lisa Jones Higgins Group Bedford Square
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  $4,200,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 4,866 Sq Ft

  153 Birch Rd, Fairfield, CT 06824

  Location, Location, Location plus an exceptional design all come together at 153 Birch Road. Ideally located in one of the most sought-after Beach neighborhoods, this FEMA compliant home sits on a rare level, stunning, .34-acre lot and offers over 4800 square feet of high end, solid construction and brilliant architecture. Features that make this home a true stand out include 11 spacious rooms

  

  Jackie Davis

  William Raveis Real Estate

  (203) 514-7172

  153 Birch Rd, Fairfield, CT 06824
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  Starting at $3,275

  Total Monthly Price

  • Studio - 2 Beds

  665 Commerce Dr, Fairfield, CT 06825

  Trademark living is quintessentially connected; adjacent to the Fairfield Metro station,atop a curated collection of shops, and moments from downtown Fairfields restaurant-lined main street.

  Trademark Fairfield

  (475) 265-5263

  

  665 Commerce Dr, Fairfield, CT 06825
• 

  $642,000 Sold Apr 17, 2026

  115 King St Unit 117, Bridgeport, CT 06605

  • 4 Beds
  • 2 Baths
  • 2,632 Sq Ft
  • Built 1970

  Last Sold Summary

  • 1% Below List Price
  • $244/SF
  • 44 Days On Market

  Current Estimated Value $645,047

  Last Listing Agent Jeff Romatzick William Raveis Real Estate

  115 King St Unit 117, Bridgeport, CT 06605
• 

  Est $3,260,717 Not Listed For Sale

  10 Bauer Place, Westport, CT 06880

  • 6 Beds
  • 5.5 Baths
  • 5,951 Sq Ft
  • Built 2025

  10 Bauer Place, Westport, CT 06880

  Last Sold Summary

  • 5% Above List Price
  • $521/SF
  • 10 Days On Market

  • Last Sold Price $3,100,000
  • Apr 28, 2025

  Last Listing Agent Doug Bross Coldwell Banker Realty
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  $119,900 Pending

  • Studio
  • 1 Bath
  • 384 Sq Ft

  25 Ellsworth St Unit 17, Bridgeport, CT 06605

  Why rent when you can own? This freshly painted studio unit, with heat and hot water included in the HOA, is ideally situated in the heart of the historic Black Rock neighborhood. The open living space opens to your private balcony overlooking Ellsworth Park, where you can relax and watch baseball games from home. The lower level features a shared laundry room and a separate storage unit. A short

  

  Sue Varrone

  Coldwell Banker Realty

  (475) 253-8245

  25 Ellsworth St Unit 17, Bridgeport, CT 06605
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  $3,000 Per Month

  • 3 Beds
  • 1 Bath
  • 971 Sq Ft
  • House for Rent

  218 Melville Ave, Fairfield, CT 06825

  Charming 3 bedroom, 1 bath rental property in the heart of Fairfield. This property offers almost 1,000 sq ft of living space between two-levels, and provides the perfect balance of comfort and convenience. Located near local parks, vibrant dining, boutique shopping and entertainment. Great commuter location with easy access to both the Merritt Parkway and I-95.

  

  Tammy Edwards

  Coldwell Banker Realty

  (203) 890-0217

  218 Melville Ave, Fairfield, CT 06825
• 

  $1,640,000 Sold Sep 12, 2025

  248 Mayweed Rd, Fairfield, CT 06824

  • 4 Beds
  • 4.5 Baths
  • 4,075 Sq Ft
  • Built 2019

  Last Sold Summary

  • 4% Below List Price
  • $402/SF
  • 49 Days On Market

  Current Estimated Value $1,670,770

  Last Listing Agent Christopher Maroc Coldwell Banker Realty

  248 Mayweed Rd, Fairfield, CT 06824
• 

  Est $2,987,015 Not Listed For Sale

  200 Jessica Ln, Southport, CT 06890

  • 5 Beds
  • 4.5 Baths
  • 6,466 Sq Ft
  • Built 1995

  200 Jessica Ln, Southport, CT 06890

  Last Sold Summary

  • 3% Above List Price
  • $448/SF
  • 25 Days On Market

  • Last Sold Price $2,900,000
  • Apr 30, 2025

  Last Listing Agent Laura Kottler Compass Connecticut, LLC
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  $645,000 Pending

  • 8 Beds
  • 2 Baths
  • 2,849 Sq Ft

  74 Carleton Ave, Bridgeport, CT 06604

  Fully renovated two-family home with new floors and fresh paint. Each unit offers a bright living room with high ceilings and in-unit laundry hookups. The location is ideal and close to schools, shopping, and public transportation. Minutes from Metro North, I-95, grocery stores, restaurants, bus lines, and near Fairfield amenities. Seaside Park is a short drive for waterfront views and outdoor

  

  Rudy Pierre

  YellowBrick Real Estate LLC

  (475) 242-5962

  74 Carleton Ave, Bridgeport, CT 06604
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  Starting at $2,299

  Total Monthly Price

  • 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

  (475) 258-7455

  

  1177 Post Rd E, Westport, CT 06880
• 

  $875,000 Sold Jan 06, 2026

  162 Country Rd Unit 162, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 2,516 Sq Ft
  • Built 2004

  Last Sold Summary

  • 6% Above List Price
  • $348/SF
  • 54 Days On Market

  Last Listing Agent Maria Tziolis William Pitt Sotheby's Int'l

  162 Country Rd Unit 162, Fairfield, CT 06824
• 

  Est $924,725 Not Listed For Sale

  35 John St, Southport, CT 06890

  • 3 Beds
  • 1.5 Baths
  • 2,481 Sq Ft
  • Built 1924

  35 John St, Southport, CT 06890

  Last Sold Summary

  • 16% Above List Price
  • $322/SF
  • 94 Days On Market

  • Last Sold Price $800,000
  • Apr 29, 2025

  Last Listing Agent Ellen Balazs-Byington Berkshire Hathaway Home Services
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  $1,549,000

  • 5 Beds
  • 4.5 Baths
  • 4,451 Sq Ft

  155 Labbance Ln, Fairfield, CT 06824

  A once-in-a-generation Japanese-inspired 3 acre sanctuary on the coveted Westport side of Greenfield Hill, this extraordinary property offers a rare fusion of architecture, artistry, and landscape. Designed by the owner, a master gardener, the grounds unfold as a private retreat where the Sasco River winds through natural boulders, hand-laid stone walls, flowering specimen trees, terraced

  

  Amy Waugh Curry ABR CRS GRI

  Berkshire Hathaway NE Prop.

  (475) 260-9629

  155 Labbance Ln, Fairfield, CT 06824
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  $2,100 Plus Fees

  • 3 Beds
  • 1 Bath
  • Condo for Rent

  139 Poplar St Unit 2nd floor, Bridgeport, CT 06605

  Property Id: 1079538Wonderful cozy property kept clean and nice for a wonderful family or couple

  (475) 476-1534

  139 Poplar St Unit 2nd floor, Bridgeport, CT 06605
• 

  $672,000 Sold Jul 07, 2025

  51 Laurel St, Fairfield, CT 06825

  • 4 Beds
  • 3 Baths
  • 2,208 Sq Ft
  • Built 1930

  Last Sold Summary

  • 1% Below List Price
  • $304/SF
  • 34 Days On Market

  Current Estimated Value $2,318,099

  Last Listing Agent Christopher Giolitto William Raveis Real Estate

  51 Laurel St, Fairfield, CT 06825
• 

  Est $2,420,329 Not Listed For Sale

  1 Church St, Southport, CT 06890

  • 5 Beds
  • 5.5 Baths
  • 4,243 Sq Ft
  • Built 1831

  1 Church St, Southport, CT 06890

  Last Sold Summary

  • 3% Above List Price
  • $551/SF
  • 14 Days On Market

  • Last Sold Price $2,340,000
  • Apr 28, 2025

  Last Listing Agent Amy Waugh Curry ABR CRS GRI Berkshire Hathaway Home Services
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  $1,150,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,705 Sq Ft

  126 Ann St, Fairfield, CT 06824

  BEST AND FINAL OFFERS DUE MONDAY 5/27 @ 5PM. Enjoy the best of Fairfield living at 126 Ann Street, ideally located in highly sought-after walkable beachside neighborhood. Just minutes to the train, downtown, and beaches, this charming 3-bedroom, 1 full and 1 half bath Colonial offers an exceptional walk-to-everything lifestyle in a prime commuter location. Built in 1948 and thoughtfully updated

  

  Brett Lieberman

  The Riverside Realty Group

  (475) 253-3411

  126 Ann St, Fairfield, CT 06824
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  /12

  $14,000 Plus Fees

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft
  • House for Rent

  25 Penfield Place, Fairfield, CT 06824

  Property Id: 1724828Water views and short steps to a private beach; very quiet private street in the middle of everything (1 mile to town/train). Newly-built modern home, fully furnished, with a location that can't be beat! Option for a 4th bedroom if needed. Please feel free to reach out to discuss!

  (475) 471-1481

  25 Penfield Place, Fairfield, CT 06824
• 

  $3,400,000 Sold Feb 03, 2026

  1 Boxwood Ln, Westport, CT 06880

  • 5 Beds
  • 8 Baths
  • 7,359 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $462/SF
  • 11 Days On Market

  Last Listing Agent Julie Vanderblue Higgins Group Real Estate

  1 Boxwood Ln, Westport, CT 06880
• 

  Not Listed For Sale

  319 Harbor Rd, Southport, CT 06890

  • 5 Beds
  • 5 Baths
  • 3,580 Sq Ft
  • Built 1918

  319 Harbor Rd, Southport, CT 06890

  Last Sold Summary

  • $838/SF
  • 189 Days On Market

  • Last Sold Price $3,000,000
  • May 02, 2025

  Last Listing Agent Andrew Whiteley Brown Harris Stevens
• 

  /2

  $949,000 Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,684 Sq Ft

  54 Elm St, Fairfield, CT 06824

  Conveniently located in Fairfield's highly sought-after University Area and just a short walk to the train. Nestled on a quiet street, this 3-bedroom, 1.5-bath home sits on an expansive .63-acre lot, providing rare space and privacy in an unbeatable location. Enjoy close proximity to Fairfield's top-rated schools, and vibrant downtown. With easy access to major highways it makes travel a breeze

  

  Thomas Bepko

  YellowBrick Real Estate LLC

  (475) 259-2738

  54 Elm St, Fairfield, CT 06824
• 

  

  /3

  $2,000 Plus Fees

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  137 Poplar St Unit 1 floor, Bridgeport, CT 06605

  Property Id: 865006Warm cozy comfortable apt great location close to transportation and schools and downtown area

  (203) 433-6130

  137 Poplar St Unit 1 floor, Bridgeport, CT 06605
• 

  $1,500,000 Sold Feb 13, 2026

  101 Brambley Hedge Cir, Fairfield, CT 06824

  • 5 Beds
  • 6 Baths
  • 5,136 Sq Ft
  • Built 1990

  Last Sold Summary

  • 12% Below List Price
  • $292/SF
  • 86 Days On Market

  Current Estimated Value $1,724,881

  Last Listing Agent Akenmisire Musa The Agency

  101 Brambley Hedge Cir, Fairfield, CT 06824
• 

  Est $7,549,094 Not Listed For Sale

  640 Sasco Hill Rd, Fairfield, CT 06824

  • 8 Beds
  • 16 Baths
  • 17,736 Sq Ft
  • Built 1990

  640 Sasco Hill Rd, Fairfield, CT 06824

  Last Sold Summary

  • 27% Below List Price
  • $586/SF
  • 306 Days On Market

  • Last Sold Price $10,400,000
  • Apr 29, 2025

  Last Listing Agent Cindy Raney Coldwell Banker Realty
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  $2,495,000 Open Sat 12PM - 2PM

  • 6 Beds
  • 5.5 Baths
  • 3,700 Sq Ft

  40 Richmondville Ave, Westport, CT 06880

  Built in 2022, 40 Richmondville Avenue offers generous scale, a thoughtful layout, and true move-in-ready ease. Bright, open-concept main level connects kitchen, dining, and living spaces, with high ceilings and oversized windows throughout. The kitchen features a full Thermador appliance suite, large island with integrated outlets, extensive cabinetry, walk-in pantry, and mudroom with built-ins.

  Jessica Lane

  Serhant Connecticut, LLC

  (475) 244-9410

  40 Richmondville Ave, Westport, CT 06880
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  /20

  $19,000 Plus Fees

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • House for Rent

  2155 Fairfield Beach Rd, Fairfield, CT 06824

  Property Id: 162681PLEASE CONTACT MARK FOR DETAILS: . VOTED BEST ROOFTOP DECK ON FAIRFIELD BEACH! Feels like living on a boat from the comfort of your own home; surrounded by water! Beautiful newly-constructed beach home with modern finishes and appliances directly on the water! Only minutes to vibrant downtown Fairfield with countless restaurants, nightlife and great access to Manhattan!

  (475) 476-1507

  2155 Fairfield Beach Rd, Fairfield, CT 06824
• 

  $605,000 Sold Oct 01, 2025

  261 Colony St, Fairfield, CT 06824

  • 4 Beds
  • 1 Bath
  • 1,446 Sq Ft
  • Built 1936

  Last Sold Summary

  • 1% Above List Price
  • $418/SF
  • 49 Days On Market

  Current Estimated Value $650,856

  Last Listing Agent Christine Howard William Raveis Real Estate

  261 Colony St, Fairfield, CT 06824
• 

  Est $863,439 Not Listed For Sale

  58 Southfield Rd, Fairfield, CT 06824

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • Built 1938

  58 Southfield Rd, Fairfield, CT 06824

  Last Sold Summary

  • 4% Above List Price
  • $663/SF
  • 59 Days On Market

  • Last Sold Price $827,500
  • May 05, 2025

  Last Listing Agent Ken Banks William Raveis Real Estate

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