35,300

Southport, CT Homes

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  • /39

    $2,195,000

    Under Contract
    • 5 Beds
    • 4.5 Baths
    • 4,512 Sq Ft

    50 Brookbend Rd, Fairfield, CT 06824

    An extraordinarily rare opportunity in Fairfield's coveted Winton Park Association. Offered for the first time in over 4 decades, this timeless 5-bedroom, 4.5-bath Colonial is set on nearly 2 breathtaking, park-like acres, offering estate-like privacy w/an unparalleled walk-to-town lifestyle. A gracious foyer welcomes you inside, where a magnificent staircase, wide-plank hardwood floors &

    Kate Cacciatore William Raveis Real Estate

    50 Brookbend Rd, Fairfield, CT 06824
  • /22

    $2,100 Per Month

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

    112 Bennett St Unit 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

    John Hackett William Raveis Real Estate

    112 Bennett St Unit 2nd floor, Bridgeport, CT 06605
  • 16 Mayflower Cir, Fairfield, CT 06824

    $890,000

    Sold Jun 25, 2026

    16 Mayflower Cir, Fairfield, CT 06824

    • 3 Beds
    • 2.5 Baths
    • 1,640 Sq Ft
    • Built 1960

    Last Sold Summary

    • $543/SF
    • 40 Days On Market

    Current Estimated Value $905,614

    Last Listing Agent Chrissie Rodriguez Higgins Group Real Estate

    16 Mayflower Cir, Fairfield, CT 06824
    • 30 Hogan Trail, Westport, CT 06880

      Est $1,312,019

      Not Listed For Sale

      30 Hogan Trail, Westport, CT 06880

      • 3 Beds
      • 2 Baths
      • 1,934 Sq Ft
      • Built 1950
      30 Hogan Trail, Westport, CT 06880

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Toni Mickiewicz William Pitt Sotheby's Int'l

  • /30

    $309,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    2612 North Ave Unit E9, Bridgeport, CT 06604

    NO STAIRS ...End unit with Private entrance. Come and see this beautiful open, spacious 2 Bedroom condominium. First floor, (NO STAIRS), Brand new flooring in the Kitchen, dining area Living room and Hallways. Hardwoods in both bedrooms. An abundance of light from the ample number of windows. Plenty of closet and storage space. Appliances all in good condition. Newer (Bosch) stainless tub

    Stacey Schwartz Coldwell Banker Realty

    2612 North Ave Unit E9, Bridgeport, CT 06604
  • /17

    $2,700 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,316 Sq Ft
    • House for Rent

    64 Nash Ln, Bridgeport, CT 06605

    Hard to find Black Rock 1st floor three bedroom, 1.5 bath apartment renovated in 2017 with a new eat in kitchen with stainless appliances, granite counters and a breakfast bar open to dining area. Spacious rooms, plenty of closet space, basement storage, basement laundry, off street parking. Walk to train, beach, shopping and restaurants. Must have very good credit, first month rent, two months

    John Kleps Berkshire Hathaway NE Prop.

    64 Nash Ln, Bridgeport, CT 06605
  • 34 Hanford Ave, Bridgeport, CT 06605

    $645,000

    Sold Oct 10, 2025

    34 Hanford Ave, Bridgeport, CT 06605

    • 5 Beds
    • 3 Baths
    • 2,215 Sq Ft
    • Built 1907

    Last Sold Summary

    • 3% Below List Price
    • $291/SF
    • 34 Days On Market

    Current Estimated Value $675,380

    Last Listing Agent Valerie Alvarez Serhant Connecticut, LLC

    34 Hanford Ave, Bridgeport, CT 06605
    • 6 Stonybrook Rd, Westport, CT 06880

      Est $5,251,132

      Not Listed For Sale

      6 Stonybrook Rd, Westport, CT 06880

      • 6 Beds
      • 8 Baths
      • 8,957 Sq Ft
      • Built 2011
      6 Stonybrook Rd, Westport, CT 06880

      Last Sold Summary

      • 93 Days On Market

      Last Listing Agent Meredith Kamo Compass Connecticut, LLC

  • /37

    $1,599,000

    Pending
    • 3 Beds
    • 3 Baths
    • 2,424 Sq Ft

    75 Millard St, Fairfield, CT 06824

    Fairfield Beach Neighborhood! Nestled in the heart of Fairfield's highly sought-after Beach Area, this wonderful Colonial was totally rebuilt in 2008 and offers an unparalleled lifestyle just moments from Sherman Elementary, public beaches, bocce/tennis courts, the tot lot, Town Hall, downtown Fairfield's acclaimed restaurants, boutique shopping, library, & the Metro-North train station. This

    Christi McEldowney William Raveis Real Estate

    75 Millard St, Fairfield, CT 06824
  • /39

    $14,850 Per Month

    • 4 Beds
    • 4.5 Baths
    • 4,449 Sq Ft
    • House for Rent

    222 Compo Rd S, Westport, CT 06880

    Set well back from the road at the end of a long, tree-lined drive, this private Contemporary residence offers a rare pairing of seclusion and central Westport convenience. A short stroll from the Metro-North station, Compo Beach, and Longshore Club Park, the home rests on a level, professionally landscaped 1.05-acre lot in the coveted Compo Beach neighborhood - and, notably, sits comfortably

    Elizabeth Anrig Coach Lamp Living

    222 Compo Rd S, Westport, CT 06880
  • 32 Webb Rd, Westport, CT 06880

    $4,100,000

    Sold Jul 15, 2026

    32 Webb Rd, Westport, CT 06880

    • 8 Beds
    • 9 Baths
    • 8,412 Sq Ft
    • Built 2026

    Last Sold Summary

    • 2% Below List Price
    • $487/SF
    • 47 Days On Market

    Current Estimated Value $4,131,341

    Last Listing Agent Judy Michaelis Coldwell Banker Realty

    32 Webb Rd, Westport, CT 06880
    • 179 Bayberry Ln, Westport, CT 06880

      Est $1,126,272

      Not Listed For Sale

      179 Bayberry Ln, Westport, CT 06880

      • 3 Beds
      • 2.5 Baths
      • 1,656 Sq Ft
      • Built 1940
      179 Bayberry Ln, Westport, CT 06880

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Jane Jones Berkshire Hathaway NE Prop.

  • /39

    $2,995,000

    Under Contract
    • 4 Beds
    • 4.5 Baths
    • 5,629 Sq Ft

    166 Long Lots Rd, Westport, CT 06880

    Your private oasis awaits! This beautifully renovated home offers an ideal location with easy access to town, shopping, and the beach. Designed with comfort and style in mind, the home features inviting living spaces including a two-story family room with an open staircase. The gourmet eat-in kitchen is open to a sitting area with a corner fireplace. Two family bedrooms with en-suite baths

    Michelle Genovesi William Raveis Real Estate

    166 Long Lots Rd, Westport, CT 06880
  • /39

    $5,950 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,904 Sq Ft
    • Apartment for Rent

    450 Center St Unit 15, Southport, CT 06890

    Experience luxury living in the heart of Fairfield with this exceptional three level condominium that blends timeless elegance with modern convenience. From the moment you step inside, you'll be welcomed by soaring ceilings, rich hardwood floors, crown molding, and recessed lighting that create a bright, sophisticated atmosphere throughout. The open concept main level is designed for both

    Daniel Leyden KW Legacy Partners

    450 Center St Unit 15, Southport, CT 06890
  • 790 Cedar Brook Ln, Southport, CT 06890

    $2,755,000

    Sold Jul 08, 2026

    790 Cedar Brook Ln, Southport, CT 06890

    • 5 Beds
    • 4.5 Baths
    • 6,022 Sq Ft
    • Built 1972

    Last Sold Summary

    • 10% Above List Price
    • $457/SF
    • 6 Days On Market

    Last Listing Agent Cindy Raney Coldwell Banker Realty

    790 Cedar Brook Ln, Southport, CT 06890
    • 5 Country Ln, Westport, CT 06880

      Est $3,805,778

      Not Listed For Sale

      5 Country Ln, Westport, CT 06880

      • 5 Beds
      • 7 Baths
      • 5,955 Sq Ft
      • Built 1951
      5 Country Ln, Westport, CT 06880

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Susan Seath Compass Connecticut, LLC

  • /11

    $1,749,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    54 Timothy St, Fairfield, CT 06824

    Experience refined luxury in this custom new construction offering 3,200 sqft. of thoughtfully designed living space, situated on a cul-de-sac just moments from downtown Fairfield, premier dining, boutique shopping & beautiful beaches. Step inside to discover exceptional millwork & upscale finishes. The main level features a spacious dining room complemented by a wet bar, perfect for

    Anthony Fabrizio Coldwell Banker Realty

    54 Timothy St, Fairfield, CT 06824
  • /20

    $15,000 Per Month

    • 5 Beds
    • 2.5 Baths
    • 2,376 Sq Ft
    • House for Rent

    989 Fairfield Beach Rd, Fairfield, CT 06824

    Trade the ordinary for a winter by the water in this incredible beachfront Colonial on Long Island Sound. Available as an unfurnished winter/academic rental, this spacious 5-bedroom home offers panoramic water views, direct beach access, and a front-row seat to spectacular sunrises and peaceful coastal living. Filled with classic beach house charm, the home features an updated kitchen with quartz

    Jean Marie Sutton William Pitt Sotheby's Int'l

    989 Fairfield Beach Rd, Fairfield, CT 06824
  • 28 Ferry Ln E, Westport, CT 06880

    $6,100,000

    Sold Jul 10, 2026

    28 Ferry Ln E, Westport, CT 06880

    • 5 Beds
    • 9 Baths
    • 8,466 Sq Ft
    • Built 2014

    Last Sold Summary

    • 2% Below List Price
    • $721/SF
    • 21 Days On Market

    Current Estimated Value $6,232,625

    Last Listing Agent Susan Lieberman The Riverside Realty Group

    28 Ferry Ln E, Westport, CT 06880
    • 25 Hale St, Westport, CT 06880

      Est $1,144,474

      Not Listed For Sale

      25 Hale St, Westport, CT 06880

      • 3 Beds
      • 2.5 Baths
      • 1,650 Sq Ft
      • Built 1997
      25 Hale St, Westport, CT 06880

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Christy Syrrist Higgins Group Bedford Square

  • /33

    $4,699,000

    $50K PRICE DROP Pending
    • 6 Beds
    • 8 Baths
    • 8,190 Sq Ft

    19 Mortar Rock Rd, Westport, CT 06880

    Stunning modern transitional home built by Compo Luxury Homes in 2024 and ideally located just minutes to downtown Westport, Compo Beach, and the train. Set on .65 acres with city water, sewer, and natural gas, this beautifully designed residence offers over 8,000 square feet across four finished levels with 6 bedrooms, 6 full and 2 half baths. The open floor plan features a chef's kitchen with

    Danna Rogers Higgins Group Bedford Square

    19 Mortar Rock Rd, Westport, CT 06880
  • /16

    $6,500 Per Month

    • 3 Beds
    • 3 Baths
    • 1,456 Sq Ft
    • House for Rent

    17 Long Lots Rd, Westport, CT 06880

    Enjoy this sun-drenched renovated contemporary split-level home with open floor plan.finished walk out lower level adds 500square ft. Featuring a private, fenced in yard, this inviting renovated property offers the perfect blend of style, comfort and convenience, just minutes from town, beaches, shopping, dining, schools, train and all that Westport has to offer.

    Georgia Wasserman Coldwell Banker Realty

    17 Long Lots Rd, Westport, CT 06880
  • 245 Unquowa Rd Unit 2, Fairfield, CT 06824

    $701,000

    Sold Mar 06, 2026

    245 Unquowa Rd Unit 2, Fairfield, CT 06824

    • 2 Beds
    • 2 Baths
    • 1,058 Sq Ft
    • Built 1964

    Last Sold Summary

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

    Current Estimated Value $691,434

    Last Listing Agent Lisa Mancini William Raveis Real Estate

    245 Unquowa Rd Unit 2, Fairfield, CT 06824
    • 37 Park Ln, Westport, CT 06880

      Est $1,622,584

      Not Listed For Sale

      37 Park Ln, Westport, CT 06880

      • 4 Beds
      • 3 Baths
      • 2,419 Sq Ft
      • Built 1960
      37 Park Ln, Westport, CT 06880

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Gina Hackett Compass Connecticut, LLC

  • /39

    $7,350,000

    • 6 Beds
    • 6.5 Baths
    • 6,585 Sq Ft

    69 Beachside Ave, Westport, CT 06880

    Set behind gates on over four exquisitely landscaped acres in Westport's coveted Beachside enclave, 69 Beachside Avenue is a private coastal estate offering a rare blend of scale, privacy, and resort-style living just moments from the shoreline. A long, gracious approach leads to a timeless residence defined by exceptional craftsmanship and sun-filled interiors. Expansive living spaces feature

    John Raus Berkshire Hathaway NE Prop.

    69 Beachside Ave, Westport, CT 06880
  • /33

    $16,000 Per Month

    • 6 Beds
    • 3 Baths
    • 2,500 Sq Ft
    • House for Rent

    12 Sandy Way, Fairfield, CT 06824

    Welcome to Yai Yai Beach House! 12 Sandy Way offers the ultimate Fairfield summer escape. 2024 construction ideally located on the corner of Sandy Way and Reef Road, less than a half-mile to the beach and an easy walk to both downtown and the shoreline. Just a 30-second stroll to Bud's Deli and one minute to Veteran's Park, this location is second to none. This beautifully furnished 6-bedroom, 3

    Anthony Gigliotti Keller Williams Realty

    12 Sandy Way, Fairfield, CT 06824
  • 60 Sylvan Rd N, Westport, CT 06880

    $2,199,000

    Sold Nov 12, 2025

    60 Sylvan Rd N, Westport, CT 06880

    • 4 Beds
    • 3.5 Baths
    • 3,430 Sq Ft
    • Built 1963

    Last Sold Summary

    • $641/SF
    • 56 Days On Market

    Current Estimated Value $2,389,542

    Last Listing Agent Judy Michaelis Coldwell Banker Realty

    60 Sylvan Rd N, Westport, CT 06880
    • 64 Wright St, Westport, CT 06880

      Est $3,526,220

      Not Listed For Sale

      64 Wright St, Westport, CT 06880

      • 5 Beds
      • 4.5 Baths
      • 3,805 Sq Ft
      • Built 1840
      64 Wright St, Westport, CT 06880

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Joelle Malec William Raveis Real Estate

  • /4

    $1,100,000

    • Land
    • 2.65 Acres
    • $415,094 per Acre

    22 Brett Rd, Fairfield, CT 06824

    An exceptional opportunity to build your dream home on one of the most desirable and scenic settings in Fairfield. This beautiful, flat 2.65-acre parcel-approved by the Wetlands Com. for a 5-bedroom, 5-bathroom residence with a pool and pool house-offers both privacy and prestige. The property is situated in the estate section of Greenfield Hill. With its driveway access on Brett Road, a

    Andrew Whiteley Brown Harris Stevens

    22 Brett Rd, Fairfield, CT 06824
  • /13

    $2,800 Per Month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Apartment for Rent

    36 Churchill St, Fairfield, CT 06824

    Newly Renovated 2 bedroom apartment- Walk to train..Stainless steel appliances, recessed lighting, spacious pantry, and two large bedrooms. Hardwood floors throughout the entire unit accented by a beautiful shiplap finish interior trim. Units own washer and dryer in the basement, large storage unit in the basement, garden bed, fenced in back yard, plenty of street parking. 10 minute walk to

    Raymond Foote Divided Sky Realty

    36 Churchill St, Fairfield, CT 06824
  • 165 Hemlock Hills Rd S, Fairfield, CT 06824

    $2,335,000

    Sold Jun 16, 2026

    165 Hemlock Hills Rd S, Fairfield, CT 06824

    • 5 Beds
    • 4 Baths
    • 5,158 Sq Ft
    • Built 1977

    Last Sold Summary

    • 11% Above List Price
    • $453/SF
    • 12 Days On Market

    Current Estimated Value $2,178,877

    Last Listing Agent Lois Lehman William Raveis Real Estate

    165 Hemlock Hills Rd S, Fairfield, CT 06824
    • 5 Canning Ln, Westport, CT 06880

      Est $1,506,622

      Not Listed For Sale

      5 Canning Ln, Westport, CT 06880

      • 3 Beds
      • 2 Baths
      • 2,599 Sq Ft
      • Built 1963
      5 Canning Ln, Westport, CT 06880

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Thomas Broadbent William Pitt Sotheby's Int'l

  • /37

    $4,450,000

    New Construction
    • 6 Beds
    • 8 Baths
    • 8,356 Sq Ft

    159 Easton Rd, Westport, CT 06880

    Are you dreaming of an estate property? Something a bit more than the generic flat acre on a cul de sac? How do two acres on the Aspetuck River sound to you? With views from your bedroom? The sounds of a waterfall next door lulling you to sleep? Having sunnies tickle your toes in the summertime? Maybe a bit of fly fishing for trout? Or perhaps some paddleboarding? Yes, of course, there's a 20x40

    Maryann Levanti Higgins Group Bedford Square

    159 Easton Rd, Westport, CT 06880
  • /20

    $5,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,073 Sq Ft
    • House for Rent

    19 Hickory Dr, Westport, CT 06880

    Charming newly renovated house on a great quiet cul-de-sac. Convenient to schools, parks, shopping, and transportation. 4 bedrooms, 2 baths, wonderful screened porch, fenced yard updated kitchen and baths. Fantastic Long Island Sound community with outstanding school system and great recreational opportunities. Several pieces of furniture will stay.

    Elaine Schanzenbach William Raveis Real Estate

    19 Hickory Dr, Westport, CT 06880
  • 22 Knollwood Dr, Fairfield, CT 06824

    $1,275,000

    Sold May 26, 2026

    22 Knollwood Dr, Fairfield, CT 06824

    • 4 Beds
    • 3.5 Baths
    • 3,515 Sq Ft
    • Built 1987

    Last Sold Summary

    • 28% Above List Price
    • $363/SF
    • 1 Day On Market

    Current Estimated Value $1,234,573

    Last Listing Agent Melanie LeRoy William Raveis Real Estate

    22 Knollwood Dr, Fairfield, CT 06824
    • 12 Overlook Rd, Westport, CT 06880

      Est $2,424,963

      Not Listed For Sale

      12 Overlook Rd, Westport, CT 06880

      • 4 Beds
      • 2.5 Baths
      • 4,281 Sq Ft
      • Built 1929
      12 Overlook Rd, Westport, CT 06880

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Susan Vanech Barnes Connecticut LLC

  • /35

    $3,988,000

    • 4 Beds
    • 5.5 Baths
    • 7,971 Sq Ft

    475 Fence Row Dr, Fairfield, CT 06824

    Set within The Ridge in Greenfield Hill, Fairfield's gated residential community, this residence has been completely rebuilt and thoughtfully reimagined with the scale and finish of new construction. Spanning over 8,000 sq ft, the home offers four bedrooms and six full and two half baths, with wide plank oak floors, multiple fireplaces, and expansive windows that frame tranquil pond views. A

    Erin Melson The Agency

    475 Fence Row Dr, Fairfield, CT 06824
  • /16

    $15,500 Per Month

    • 5 Beds
    • 5 Baths
    • 4,605 Sq Ft
    • House for Rent

    15 Timber Ln, Westport, CT 06880

    15 Timber Lane, Westport, CT | School Year Furnished Rental Experience luxury living in the coveted Roseville neighborhood of Westport. Situated on 1.45 private acres at the end of a quiet cul-de-sac, this beautifully furnished 4-bedroom, 5-bath home offers the perfect school year retreat. Designed for comfortable living and entertaining, the home features two spacious primary suites with vaulted

    Cody Nizzardo Nizzardo Real Estate Services

    15 Timber Ln, Westport, CT 06880
  • 5 Compo Hill Ave, Westport, CT 06880

    $3,000,000

    Sold Sep 12, 2025

    5 Compo Hill Ave, Westport, CT 06880

    • 3 Beds
    • 2.5 Baths
    • 2,554 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $1,175/SF
    • 46 Days On Market

    Current Estimated Value $3,223,442

    Last Listing Agent Susan Lieberman The Riverside Realty Group

    5 Compo Hill Ave, Westport, CT 06880
    • 16 Morningside Ln, Westport, CT 06880

      Est $2,586,089

      Not Listed For Sale

      16 Morningside Ln, Westport, CT 06880

      • 4 Beds
      • 4.5 Baths
      • 3,764 Sq Ft
      • Built 2000
      16 Morningside Ln, Westport, CT 06880

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Karen Liss-uomoleale Coldwell Banker Realty

Showing Results 521 - 560, Page 14 of 18

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