35,315

Southport, CT Homes

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  • /38

    $3,695,000

    • 4 Beds
    • 4.5 Baths
    • 3,744 Sq Ft

    110 Judson Rd, Fairfield, CT 06824

    Nestled on one of Fairfield Beach's most coveted streets, this exceptional new construction blends timeless coastal architecture with sophisticated design in a location that's simply hard to duplicate. Just moments from the beach, town, train, schools, and parks, 110 Judson offers the rare convenience today's buyers seek without sacrificing privacy or tranquility. Thoughtfully positioned at a

    Cindy Raney Coldwell Banker Realty

    110 Judson Rd, Fairfield, CT 06824
  • /12

    $2,100

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft
    • Condo for Rent

    112 Bennett St Unit 112 Bennett Street 1st floor, Bridgeport, CT 06605

    FIRST FLOOR RENOVATED BLACK ROCK APARTMENT OFFERS REMODELED EAT IN KITCHEN WITH PANTRY AND WASHER/DRYER, UPDATED FULL BATH ALONG WITH 2 BEDROOMS WITH EXTRA AND DEEP CLOSETS PLUS OFF STREET PARKING. STEPS TO DINING/RESTAURANTS, RETAIL/SHOPPING, ENTERTAINMENT AND NIGHT-LIFE, METRO NORTH TRAIN STATIONS AND ST. MARY'S BY THE SEA WITH EASY ACCESS TO I-95, RT 25/8 AND RT 15 MERRITT PARKWAY. TENANT TO

    112 Bennett St Unit 112 Bennett Street 1st floor, Bridgeport, CT 06605
  • 147 Carriage Dr, Southport, CT 06890

    $1,913,022

    Sold Jun 11, 2026

    147 Carriage Dr, Southport, CT 06890

    • 4 Beds
    • 2.5 Baths
    • 2,682 Sq Ft
    • Built 1959

    Last Sold Summary

    • 13% Above List Price
    • $713/SF
    • 8 Days On Market

    Current Estimated Value $1,788,574

    Last Listing Agent Jackie Davis William Raveis Real Estate

    147 Carriage Dr, Southport, CT 06890
    • 205 Szost Dr, Fairfield, CT 06824

      Est $1,442,473

      Not Listed For Sale

      205 Szost Dr, Fairfield, CT 06824

      • 3 Beds
      • 3 Baths
      • 2,248 Sq Ft
      • Built 1953
      205 Szost Dr, Fairfield, CT 06824

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Stacey DiDio Coldwell Banker Realty

  • /37

    $6,495,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 3,260 Sq Ft

    16 Westport Ave, Westport, CT 06880

    Experience the future of coastal living in this brand-new smart home located just steps from the sands of Compo Beach. 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, radiant

    Karen Scott Compass Connecticut, LLC

    16 Westport Ave, Westport, CT 06880
  • /6

    $2,600

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,150 Sq Ft
    • Condo for Rent

    510 Commerce Dr Unit 510 Commerce Drive, Fairfield, CT 06825

    510 Commerce Dr Unit 510 Commerce Drive, Fairfield, CT 06825
  • 2821 Congress St, Fairfield, CT 06824

    $2,700,000

    Sold Oct 30, 2025

    2821 Congress St, Fairfield, CT 06824

    • 5 Beds
    • 4.5 Baths
    • 3,703 Sq Ft
    • Built 1835

    Last Sold Summary

    • 2% Above List Price
    • $729/SF
    • 42 Days On Market

    Last Listing Agent Andrew Whiteley Brown Harris Stevens

    2821 Congress St, Fairfield, CT 06824
    • 385 Brookside Dr, Fairfield, CT 06824

      Est $1,620,802

      Not Listed For Sale

      385 Brookside Dr, Fairfield, CT 06824

      • 4 Beds
      • 2.5 Baths
      • 3,040 Sq Ft
      • Built 1784
      385 Brookside Dr, Fairfield, CT 06824

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Lara Hoey William Raveis Real Estate

  • /6

    $455,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,210 Sq Ft

    141 Berwick Ave, Fairfield, CT 06825

    Situated on a quiet dead-end street in the desirable town of Fairfield, this well-maintained 3-bedroom, 2 full-bath single-family home offers comfort, efficiency, and convenience. With approximately 1,200 square feet of living space, the home features a functional layout with bright, inviting rooms throughout. The first-floor living room includes a wood-burning stove, creating a warm and

    Derek Greene Derek Greene

    141 Berwick Ave, Fairfield, CT 06825
  • /21

    $2,000

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 750 Sq Ft
    • Condo for Rent

    21 Davenport Ave Unit 3, Westport, CT 06880

    Spacious one bedroom apartment, large bedroom with huge closet, separate eat-in kitchen. Convenient Westport location, access to compo Beach close to train, private, quiet neighborhood. Unfurnished.

    21 Davenport Ave Unit 3, Westport, CT 06880
  • 32 Whitney Glen Unit 32, Westport, CT 06880

    $520,000

    Sold Jul 31, 2026

    32 Whitney Glen Unit 32, Westport, CT 06880

    • 1 Bed
    • 2 Baths
    • 949 Sq Ft
    • Built 1982

    Last Sold Summary

    • 13% Above List Price
    • $548/SF
    • 14 Days On Market

    Current Estimated Value $536,103

    Last Listing Agent Stephen Pratt Keller Williams Realty

    32 Whitney Glen Unit 32, Westport, CT 06880
    • 147 Trillium Rd, Fairfield, CT 06824

      Est $1,840,942

      Not Listed For Sale

      147 Trillium Rd, Fairfield, CT 06824

      • 4 Beds
      • 4 Baths
      • 4,176 Sq Ft
      • Built 1971
      147 Trillium Rd, Fairfield, CT 06824

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Robert Richter Coldwell Banker Realty

  • /20

    $550,000

    • 8 Beds
    • 3 Baths
    • 2,679 Sq Ft

    18-20 Clinton Ave, Bridgeport, CT 06605

    This very large 2,679 sqft 2 family property is perfect for any home owner or investor. The 1st floor unit consists of 3 bedrooms and 1 bathroom. The 2nd unit is a very spacious two floor apartment that has 5 bedrooms and 2 bathrooms that was recently updated. Conveniently located just minutes from I-95 and I-91. Schedule your showing today!!!

    Thomas Payne Century 21 Scala Group

    18-20 Clinton Ave, Bridgeport, CT 06605
  • /14

    $2,100

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft
    • Condo for Rent

    114 Bennett St Unit 112-114 Bennett St 2nd floor, Bridgeport, CT 06605

    MAKE YOUR OFFER AND MOVE RIGHT INTO THIS RENOVATED, BRIGHT AND SUNNY 2ND FLOOR 2 BEDROOM BLACK ROCK APARTMENT FEATURING DESIGNER EAT IN KITCHEN WITH WASHER/DRYER, REMODELED FULL BATH, EXTRA AND DEEP CLOSETS PLUS FRONT AND REAR DECKS AND OFF STREET PARKING. ENJOY THE RESTAURANTS, RETAIL/SHOPPING, NIGHT LIFE AND ST. MARY'S BY THE SEA ALL STEPS FROM YOUR NEW HOME ALONG WITH EASY ACCESS TO METRO

    114 Bennett St Unit 112-114 Bennett St 2nd floor, Bridgeport, CT 06605
  • 65 Thorpe St Unit 65, Fairfield, CT 06824

    $915,000

    Sold Mar 27, 2026

    65 Thorpe St Unit 65, Fairfield, CT 06824

    • 3 Beds
    • 2.5 Baths
    • 2,303 Sq Ft
    • Built 2003

    Last Sold Summary

    • 6% Above List Price
    • $397/SF
    • 63 Days On Market

    Current Estimated Value $979,057

    Last Listing Agent David Harmuth Coldwell Banker Realty

    65 Thorpe St Unit 65, Fairfield, CT 06824
    • 142 Trillium Rd, Fairfield, CT 06824

      Est $1,387,439

      Not Listed For Sale

      142 Trillium Rd, Fairfield, CT 06824

      • 4 Beds
      • 2.5 Baths
      • 3,050 Sq Ft
      • Built 1971
      142 Trillium Rd, Fairfield, CT 06824

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Bobbie Poeltl Abagnale William Pitt Sotheby's Int'l

  • /40

    $8,450,000

    New Construction
    • 6 Beds
    • 8 Baths
    • 9,893 Sq Ft

    10 Beltas Farm Ln, Westport, CT 06880

    Extraordinary New Construction home on one of Westport's newest premier cul-de-sacs. Offering nearly 10,000 SF of impeccably finished living space, this exceptional home blends timeless elegance w/ modern luxury & showcases the finest craftsmanship throughout.Designed with an uncompromising attention to detail, features include exquisite millwork, stunning custom cabinetry, spectacular ceiling

    Linda Skolnick Coldwell Banker Realty

    10 Beltas Farm Ln, Westport, CT 06880
  • /13

    $2,385

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    34 Kenwood Ave Unit 34 Kenwood Avenue, Fairfield, CT 06824

    Designed for comfort, freshly updated throughout with an unbeatable WATER VIEW. Ultra-quiet, this bright, private upper level unit feels like a retreat, not just a rental. Discover this 2 bedroom, 1 bath gem right on the water with a peaceful backyard. Available immediately, this apartment is situated in a prime location close to I-95, within walking distance to the train, nature trail, shopping,

    34 Kenwood Ave Unit 34 Kenwood Avenue, Fairfield, CT 06824
  • 27 Nash Ln Unit 5, Bridgeport, CT 06605

    $242,000

    Sold Jun 12, 2026

    27 Nash Ln Unit 5, Bridgeport, CT 06605

    • 1 Bed
    • 1 Bath
    • 755 Sq Ft
    • Built 1918

    Last Sold Summary

    • 3% Below List Price
    • $321/SF
    • 117 Days On Market

    Last Listing Agent Gail Robinson William Raveis Real Estate

    27 Nash Ln Unit 5, Bridgeport, CT 06605
    • 33 Alexandria Ct, Fairfield, CT 06824

      Est $1,118,340

      Not Listed For Sale

      33 Alexandria Ct, Fairfield, CT 06824

      • 4 Beds
      • 2.5 Baths
      • 2,310 Sq Ft
      • Built 1994
      33 Alexandria Ct, Fairfield, CT 06824

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Susan Morelli Coldwell Banker Realty

  • /19

    $319,900

    $26K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,145 Sq Ft

    3250 Fairfield Ave Unit 206, Bridgeport, CT 06605

    Welcome to The Village at Black Rock. This bright 2BR/2BA second-floor unit offers serene water views from nearly every room and a private deck ideal for morning coffee or sunset unwinding. The open layout features a combined living/dining area with a wall of windows overlooking Ash Creek and a spacious kitchen with ample storage, great counter space, and a breakfast bar. The primary bedroom

    Patrick Laufer Laufer Real Estate

    3250 Fairfield Ave Unit 206, Bridgeport, CT 06605
  • /27

    $4,300

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,365 Sq Ft
    • Condo for Rent

    245 Unquowa Rd Unit 132, Fairfield, CT 06824

    Welcome to Mosswood Condominiums a bright and beautifully updated 2-bedroom, 2-bath condo with 1,365 square feet of inviting living space in one of Fairfield's most convenient locations. This unfurnished home showcases a stylish renovated kitchen with stainless steel appliances, farmhouse sink, custom-style open shelving, and abundant prep and storage space. The sun-filled layout includes a

    245 Unquowa Rd Unit 132, Fairfield, CT 06824
  • 24 Burr School Rd, Westport, CT 06880

    $2,325,000

    Sold Jul 15, 2026

    24 Burr School Rd, Westport, CT 06880

    • 5 Beds
    • 4.5 Baths
    • 3,380 Sq Ft
    • Built 1965

    Last Sold Summary

    • 6% Above List Price
    • $688/SF
    • 47 Days On Market

    Current Estimated Value $2,194,871

    Last Listing Agent Julia Broder Coldwell Banker Realty

    24 Burr School Rd, Westport, CT 06880
    • 110 Florence Ln, Fairfield, CT 06824

      Est $1,736,839

      Not Listed For Sale

      110 Florence Ln, Fairfield, CT 06824

      • 3 Beds
      • 3.5 Baths
      • 3,366 Sq Ft
      • Built 1961
      110 Florence Ln, Fairfield, CT 06824

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Ellen Fusco Compass Connecticut, LLC

  • /9

    $3,750,000

    New Construction
    • 5 Beds
    • 5.5 Baths
    • 5,000 Sq Ft

    22 Brett Rd, Fairfield, CT 06824

    Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among

    Andrew Whiteley Brown Harris Stevens

    22 Brett Rd, Fairfield, CT 06824
  • /13

    $11,000

    Total Monthly Price

    • 4 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    417 Reef Rd, Fairfield, CT 06824

    2029-2030 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
  • 550 Davis Rd, Fairfield, CT 06825

    $1,650,000

    Sold Sep 05, 2025

    550 Davis Rd, Fairfield, CT 06825

    • 5 Beds
    • 4.5 Baths
    • 3,927 Sq Ft
    • Built 2025

    Last Sold Summary

    • $420/SF
    • 50 Days On Market

    Current Estimated Value $1,727,798

    Last Listing Agent Carmen Desiato Serhant Connecticut, LLC

    550 Davis Rd, Fairfield, CT 06825
    • 184 Stillson Rd, Fairfield, CT 06825

      Est $1,227,403

      Not Listed For Sale

      184 Stillson Rd, Fairfield, CT 06825

      • 3 Beds
      • 3.5 Baths
      • 3,951 Sq Ft
      • Built 1995
      184 Stillson Rd, Fairfield, CT 06825

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Clyde Wauchope Coldwell Banker Realty

  • /28

    $2,100,000

    Pending
    • 5 Beds
    • 3.5 Baths
    • 3,782 Sq Ft

    34 Pequot Trail, Westport, CT 06880

    Discover this serene setting in a sought after Old Hill neighborhood. Two thoughtful and beautifully executed additions have made this sprawling 12 room home flow with the versatility to fit today's varied lifestyles. Comfortable open living spaces have been designed with the flexibility to offer multi-generational spaces, a home office or simply to allow for room to grow in the way that pleases

    Lynn Fraund William Pitt Sotheby's Int'l

    34 Pequot Trail, Westport, CT 06880
  • /32

    $4,700

    Total Monthly Price

    • 4 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Townhouse for Rent

    442 Surrey Ln, Fairfield, CT 06824

    **Beautifully Renovated 4BR Fairfield Home | Walk-Out Lower Level | 2-Car Garage | Smart Home Features**Welcome to this beautifully renovated 4-bedroom, 2.5-bath main home in one of Fairfield's most desirable residential neighborhoods. Offering approximately 2,000 square feet of thoughtfully updated living space, this home blends modern amenities with timeless charm and is just minutes

    442 Surrey Ln, Fairfield, CT 06824
  • 109 Green Acre Ln, Fairfield, CT 06824

    $963,000

    Sold Nov 07, 2025

    109 Green Acre Ln, Fairfield, CT 06824

    • 3 Beds
    • 3 Baths
    • 1,980 Sq Ft
    • Built 1959

    Last Sold Summary

    • 11% Above List Price
    • $486/SF
    • 9 Days On Market

    Current Estimated Value $1,022,283

    Last Listing Agent Lynn Dolan William Pitt Sotheby's Int'l

    109 Green Acre Ln, Fairfield, CT 06824
    • 301 Nepas Rd, Fairfield, CT 06825

      Est $790,714

      Not Listed For Sale

      301 Nepas Rd, Fairfield, CT 06825

      • 3 Beds
      • 2.5 Baths
      • 2,012 Sq Ft
      • Built 1971
      301 Nepas Rd, Fairfield, CT 06825

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Linda Finnie William Raveis Real Estate

  • /39

    $1,689,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,687 Sq Ft

    2477 Bronson Rd, Fairfield, CT 06824

    Nestled in the heart of historic Greenfield Hill, this special and timeless 1907 Queen Anne farmhouse provides an opportunity to own in one of the most desirable and coveted locations in Fairfield. The Clifford S. Banks house was once a farm where the owner raised turkeys, chickens, onions and bees. Situated on 2 acres of beautifully landscaped grounds that includes gardens and a barn- perfect

    Marilyn Heffers Coldwell Banker Realty

    2477 Bronson Rd, Fairfield, CT 06824
  • /28

    $6,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,112 Sq Ft
    • Apartment for Rent

    45 Sherman St Unit B, Fairfield, CT 06824

    IN-TOWN LUXURY RETREAT/RENTAL just steps from the heart of downtown Fairfield. Walk to train, restaurants, parks and the beach! This is a 2nd floor apt with High ceilings, warmly stained hardwood floors and custom moldings throughout with walls of windows for natural light. Private entry from covered front porch. The stunning open floor plan includes gorgeous great room w/built-ins, flat screen

    Denise Walsh William Raveis Real Estate

    45 Sherman St Unit B, Fairfield, CT 06824
  • 3 Bolton Ln, Westport, CT 06880

    $3,470,000

    Sold Dec 02, 2025

    3 Bolton Ln, Westport, CT 06880

    • 6 Beds
    • 6.5 Baths
    • 7,899 Sq Ft
    • Built 2008

    Last Sold Summary

    • 9% Below List Price
    • $439/SF
    • 35 Days On Market

    Current Estimated Value $3,743,256

    Last Listing Agent Jen Kass Higgins Group Bedford Square

    3 Bolton Ln, Westport, CT 06880
    • 6 Thompson St, Fairfield, CT 06825

      Est $637,309

      Not Listed For Sale

      6 Thompson St, Fairfield, CT 06825

      • 5 Beds
      • 2 Baths
      • 1,514 Sq Ft
      • Built 1927
      6 Thompson St, Fairfield, CT 06825

      Last Sold Summary

      • 77 Days On Market

      Last Listing Agent Alan Hamilton William Raveis Real Estate

  • /40

    $11,995,000

    New Construction
    • 5 Beds
    • 7 Baths
    • 6,050 Sq Ft

    14 Owenoke Park, Westport, CT 06880

    Summer starts here. Set on prestigious Owenoke Park steps from Compo Beach, this brand-new 6,050 sqft coastal masterpiece delivers the ultimate Westport lifestyle - pool and spa, Gray's Creek waterfront access, Long Island Sound views throughout, and a rare 3-car garage. Five ensuite bedrooms, double-island kitchen with scullery, elevator, primary suite sauna, and a lower-level loggia built for

    Deirdre Andreoli Compass Connecticut, LLC

    14 Owenoke Park, Westport, CT 06880
  • /14

    $4,250

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • 3,250 Sq Ft
    • Condo for Rent

    42 Poe Ct Unit 42, Fairfield, CT 06825

    Remodeled from top to bottom and nestled at the end of a private driveway; this 3 Bedroom, 2.5 Baths apartment has it all. A bright, cheerful kitchen with stainless steel appliances, granite counters, hardwood floors and even a wine cooler. Perfect for entertaining or just enjoying a quiet evening at home, the peaceful ambiance of this hideaway will bring harmony and peace to your day. Close to

    42 Poe Ct Unit 42, Fairfield, CT 06825
  • 88 Overhill Rd, Fairfield, CT 06824

    $1,610,000

    Sold Apr 07, 2026

    88 Overhill Rd, Fairfield, CT 06824

    • 4 Beds
    • 3 Baths
    • 4,057 Sq Ft
    • Built 1931

    Last Sold Summary

    • 15% Above List Price
    • $397/SF
    • 11 Days On Market

    Current Estimated Value $1,567,462

    Last Listing Agent Cindy Raney Coldwell Banker Realty

    88 Overhill Rd, Fairfield, CT 06824
    • 435 Lenox Rd, Fairfield, CT 06825

      Est $637,327

      Not Listed For Sale

      435 Lenox Rd, Fairfield, CT 06825

      • 3 Beds
      • 1 Bath
      • 1,050 Sq Ft
      • Built 1937
      435 Lenox Rd, Fairfield, CT 06825

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Lorelei Atwood Higgins Group Real Estate

Showing Results 161 - 200, Page 5 of 18

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