35,438

Southport, CT Homes

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  • /40

    $429,900

    Pending
    • 2 Beds
    • 1 Bath
    • 791 Sq Ft

    165 Bennett St, Bridgeport, CT 06605

    Nestled in the heart of Black Rock.......Welcome to Evergreen Cottage! The perfect blend of Simplicity, comfort & Tranquility! Beautifully maintained and rich in details such as high ceilings, craftsman-style moldings , crisp decor & an abundance of natural light in every room. Updated kitchen and bath, gas furnace & sewer line. Roof fully replaced 2021. Original cedar clapboards and trim

    Mary Amenda William Pitt Sotheby's Int'l

    165 Bennett St, Bridgeport, CT 06605
  • /16

    $2,875 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,310 Sq Ft
    • Townhouse for Rent

    42 Ferris St, Bridgeport, CT 06605

    Terrific cul-de-sac location. Light, bright and spacious Duplex unit with views of Black Rock Harbor. Welcoming front porch. Open layout first floor with Kitchen and Family Room, Half Bath with new washer & dryer. Slider to rear deck and partially fenced back yard. The second floor features the primary bedroom with deck offering views of Black Rock Harbor and an additional nice size bedroom and

    Sandy Ruta Higgins Group Real Estate

    42 Ferris St, Bridgeport, CT 06605
  • 181 Lakewood Dr, Fairfield, CT 06824

    $1,400,000

    Sold Jul 16, 2025

    181 Lakewood Dr, Fairfield, CT 06824

    • 5 Beds
    • 3.5 Baths
    • 4,138 Sq Ft
    • Built 1993

    Last Sold Summary

    • 14% Above List Price
    • $338/SF
    • 12 Days On Market

    Current Estimated Value $1,451,029

    Last Listing Agent Denise Walsh William Raveis Real Estate

    181 Lakewood Dr, Fairfield, CT 06824
    • 3 Mystic Ln, Westport, CT 06880

      Est $1,632,809

      Not Listed For Sale

      3 Mystic Ln, Westport, CT 06880

      • 4 Beds
      • 3.5 Baths
      • 2,913 Sq Ft
      • Built 1965
      3 Mystic Ln, Westport, CT 06880

      Last Sold Summary

      • $559/SF
      • 17 Days On Market
      • Last Sold Price $1,629,000
      • Jan 10, 2025

      Last Listing Agent Jaclyn Picarillo Higgins Group Bedford Square

  • /39

    $2,100,000

    Under Contract
    • 4 Beds
    • 4.5 Baths
    • 4,494 Sq Ft

    276 Flintlock Rd, Southport, CT 06890

    Stunning in Southport! Nestled in a sought-after enclave of quiet streets and cul-de-sacs, lined with blooming Dogwood trees, this beautifully renovated 4 bed, 4.5 bath Colonial is ready to be enjoyed! The dream kitchen boasts a massive island, top of the line appliances, and a large sunny eating area with sliders to the deck! The open kitchen flows to the airy family room, living room and

    Leslie Clarke Compass Connecticut, LLC

    276 Flintlock Rd, Southport, CT 06890
  • /14

    $1,700 Per Month

    • 2 Beds
    • 1 Bath
    • 2,332 Sq Ft
    • Apartment for Rent

    7 Wilson St Unit 3, Bridgeport, CT 06605

    This well-maintained 3rd-floor apartment offers a comfortable and spacious layout featuring two generously sized bedrooms and ample living space. Finished in, great condition, the unit provides a clean, modern feel with plenty of natural light. Located in a desirable area, it offers convenience, accessibility, and a welcoming neighborhood atmosphere--making it an excellent rental option.

    Angel Mora eXp Realty

    7 Wilson St Unit 3, Bridgeport, CT 06605
  • 41 Richmondville Ave Unit 206, Westport, CT 06880

    $1,950,000

    Sold Jul 31, 2025

    41 Richmondville Ave Unit 206, Westport, CT 06880

    • 2 Beds
    • 2 Baths
    • 1,530 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Below List Price
    • $1,275/SF
    • 92 Days On Market

    Last Listing Agent Doug Bross Coldwell Banker Realty

    41 Richmondville Ave Unit 206, Westport, CT 06880
    • 3 Meeker Rd, Westport, CT 06880

      Est $2,218,390

      Not Listed For Sale

      3 Meeker Rd, Westport, CT 06880

      • 5 Beds
      • 4 Baths
      • 6,042 Sq Ft
      • Built 1952
      3 Meeker Rd, Westport, CT 06880

      Last Sold Summary

      • 17% Above List Price
      • $314/SF
      • 52 Days On Market
      • Last Sold Price $1,900,000
      • Jun 28, 2023

      Last Listing Agent Michael Dinshaw Berkshire Hathaway Home Services

  • /14

    $999,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,756 Sq Ft

    201 Bradley Ln Unit 201, Westport, CT 06880

    Welcome to Bradley Commons, a private gated enclave in the heart of Westport's vibrant Saugatuck neighborhood-just minutes to the train, Compo Beach, top-rated schools, and premier dining and shopping. This exceptional end-unit townhome features a bright open floor plan with hardwood floors, high ceilings, and abundant natural light. The chef's kitchen offers granite countertops, gas range,

    Maxxwell Crowley S.C.A. Crowley Real Estate

    201 Bradley Ln Unit 201, Westport, CT 06880
  • /38

    $16,000 Per Month

    • 4 Beds
    • 4.5 Baths
    • 3,360 Sq Ft
    • House for Rent

    110 Smith St, Fairfield, CT 06824

    Available beginning 7/15/26. 1-2 year term. Exceptional newer construction in Fairfield's coveted beach area, ideally located on a quiet, low-traffic street just moments from the beach, train, downtown Fairfield, and schools. A true neighborhood setting where neighbors gather, children ride bikes in the street, and coastal living feels effortless. Thoughtfully designed with timeless architecture

    Kate Cacciatore William Raveis Real Estate

    110 Smith St, Fairfield, CT 06824
  • 2660 North Ave Unit 217, Bridgeport, CT 06604

    $300,000

    Sold Jan 29, 2026

    2660 North Ave Unit 217, Bridgeport, CT 06604

    • 2 Beds
    • 1.5 Baths
    • 1,138 Sq Ft
    • Built 1992

    Last Sold Summary

    • $264/SF
    • 55 Days On Market

    Current Estimated Value $301,501

    Last Listing Agent Michael Barbaro Huntsman,Meade & Partners Comp

    2660 North Ave Unit 217, Bridgeport, CT 06604
    • 34 Silent Grove, Westport, CT 06880

      Est $1,260,664

      Not Listed For Sale

      34 Silent Grove, Westport, CT 06880

      • 2 Beds
      • 3 Baths
      • 1,973 Sq Ft
      • Built 1930
      34 Silent Grove, Westport, CT 06880

      Last Sold Summary

      • 10% Above List Price
      • $582/SF
      • 17 Days On Market
      • Last Sold Price $1,149,000
      • Nov 01, 2024

      Last Listing Agent Mary Phelps William Pitt

  • /17

    $249,999

    • 2 Beds
    • 2 Baths
    • 1,363 Sq Ft

    25 Cartright St Unit 7E, Bridgeport, CT 06604

    Stunning end unit 2-bedroom, 2-bath condo located in the desirable Brooklawn area of Bridgeport near the Fairfield line. This spacious 1,363 sq ft 7th-floor unit features wood flooring throughout and a bright, open-concept living and dining area. Enjoy treetop views from your private balcony. The unit offers an updated kitchen and bathrooms, a large primary suite with full bath, and generous

    Sasha Iyamu ERIS, LLC

    25 Cartright St Unit 7E, Bridgeport, CT 06604
  • /15

    $8,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • House for Rent

    799 Rowland Rd, Fairfield, CT 06824

    Spend the month of August at a desirable Long Island Sound Location! Excellent condition property located directly across from sandy beach, 6 rooms, 3 bedrooms, 2 baths, all appliances and utilities included, lots of town amenities. Please note: this rental is available for the month of August 2026 only. Don't miss this opportunity to relax and enjoy the Summer!

    Barbara Whelan Coldwell Banker Realty

    799 Rowland Rd, Fairfield, CT 06824
  • Unlisted Address

    $1,395,000

    Sold Apr 13, 2026

    Unlisted Address

    • 3 Beds
    • 3.5 Baths
    • 3,785 Sq Ft
    • Built 1985

    Last Sold Summary

    • $369/SF
    • 30 Days On Market

    Current Estimated Value $1,414,725

    Last Listing Agent Julia Broder Coldwell Banker Realty

    Unlisted Address
    • 5 Deerwood Rd, Westport, CT 06880

      Est $2,186,257

      Not Listed For Sale

      5 Deerwood Rd, Westport, CT 06880

      • 4 Beds
      • 2.5 Baths
      • 3,182 Sq Ft
      • Built 1967
      5 Deerwood Rd, Westport, CT 06880

      Last Sold Summary

      • 2% Above List Price
      • $676/SF
      • 7 Days On Market
      • Last Sold Price $2,150,000
      • Aug 08, 2024

      Last Listing Agent Jennifer Twombly Compass Connecticut, LLC

  • /3

    $1,699,000

    New Construction
    • 4 Beds
    • 4 Baths
    • 3,700 Sq Ft

    217 Fairland Dr, Fairfield, CT 06825

    This stunning 3,700 square foot new construction Colonial features 4 spacious bedrooms and 4 full baths. The home is thoughtfully designed for today's lifestyle. The open-concept kitchen boasts a large quartz center island and flows seamlessly into the eating area and dramatic cathedral-ceiling family room. The primary suite is a true retreat, featuring cathedral ceilings, oversized walk-in

    Madeline O'Shea Coldwell Banker Realty

    217 Fairland Dr, Fairfield, CT 06825
  • /13

    $2,800 Per Month

    • 3 Beds
    • 1 Bath
    • 2,889 Sq Ft
    • House for Rent

    82-86 Waldorf Ave, Bridgeport, CT 06605

    Welcome to this beautifully renovated 3 bedroom apartment, where modern finishes meet unbeatable convenience. Enjoy a sleek kitchen with stainless steel appliances, the ease of laundry in unit, and a thoughtfully updated layout. Ideally located just minutes from I-95, grocery stores and popular dining options, everything you need is right at your doorstep. A perfect blend of comfort, style and

    Nadia Almezy Larracuente & Johnson Realty, LLC

    82-86 Waldorf Ave, Bridgeport, CT 06605
  • 387 Main St, Westport, CT 06880

    $2,100,000

    Sold May 14, 2025

    387 Main St, Westport, CT 06880

    • 4 Beds
    • 4 Baths
    • 3,016 Sq Ft
    • Built 1840

    Last Sold Summary

    • 7% Below List Price
    • $696/SF
    • 28 Days On Market

    Current Estimated Value $2,133,409

    Last Listing Agent Ryan Sullivan Berkshire Hathaway NE Prop.

    387 Main St, Westport, CT 06880
    • 35 Old Rd, Westport, CT 06880

      Est $1,749,880

      Not Listed For Sale

      35 Old Rd, Westport, CT 06880

      • 5 Beds
      • 4.5 Baths
      • 3,844 Sq Ft
      • Built 1941
      35 Old Rd, Westport, CT 06880

      Last Sold Summary

      • 10% Above List Price
      • $412/SF
      • 28 Days On Market
      • Last Sold Price $1,584,000
      • Apr 08, 2024

      Last Listing Agent Karen Liss-uomoleale Coldwell Banker Realty

  • /20

    $2,800,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    53 Cross Hwy, Westport, CT 06880

    Proposed New Construction, build this beautiful home or let's design your dream home!! 1 acre lot with a brook sets up perfectly for a walk-out basement. Great location close to everything. Quality custom home builder with 25 years experience and over 150 homes built. Existing home to be torn down, taxes shown reflect existing home.

    Phil Pedros Philips Real Estate

    53 Cross Hwy, Westport, CT 06880
  • /2

    $3,750 Per Month

    • 3 Beds
    • 1 Bath
    • 2,372 Sq Ft
    • House for Rent

    318 Grovers Ave Unit 2nd floor, Bridgeport, CT 06605

    This first-floor unit is located in the highly sought-after Black Rock area of Bridgeport. It features a well-maintained interior with 3 bedrooms, 1 bathroom, a spacious living room, and a clean eat-in kitchen. A washer, dryer, and dishwasher are included in the unit for the tenant's convenience. The property also offers a 1-car garage and 1 off-street parking space. The location is within

    Pascale Millien-Faustin Guy Bocicaut Real Estate

    318 Grovers Ave Unit 2nd floor, Bridgeport, CT 06605
  • 127 College Park Dr, Fairfield, CT 06824

    $1,800,000

    Sold Aug 21, 2025

    127 College Park Dr, Fairfield, CT 06824

    • 4 Beds
    • 2.5 Baths
    • 2,704 Sq Ft
    • Built 1980

    Last Sold Summary

    • 24% Above List Price
    • $666/SF
    • 8 Days On Market

    Current Estimated Value $1,807,292

    Last Listing Agent Chrissie Rodriguez Higgins Group Real Estate

    127 College Park Dr, Fairfield, CT 06824
    • 64 Bayberry Ln, Westport, CT 06880

      Est $3,193,135

      Not Listed For Sale

      64 Bayberry Ln, Westport, CT 06880

      • 4 Beds
      • 7 Baths
      • 6,678 Sq Ft
      • Built 2004
      64 Bayberry Ln, Westport, CT 06880

      Last Sold Summary

      • 20% Above List Price
      • $397/SF
      • 32 Days On Market
      • Last Sold Price $2,650,000
      • Oct 26, 2023

      Last Listing Agent Robert Appell Coldwell Banker Realty

  • /38

    $1,599,000

    Open Sun 1PM - 3PM
    • 3 Beds
    • 3.5 Baths
    • 3,012 Sq Ft

    71 Aberdeen Way Unit 71, Southport, CT 06890

    Beautiful End Unit, Perfectly situated in Southport, this beautifully appointed 3-bedroom, 3.5-bath Colonial townhouse end unit offers an exceptional lifestyle just moments from village shops, restaurants, Southport Harbor, and the Metro-North train. Thoughtfully updated, the remodeled kitchen features quartz countertops, a sleek backsplash, and premium Bosch appliances, centered around a

    Michael Ferraro Compass Connecticut, LLC

    71 Aberdeen Way Unit 71, Southport, CT 06890
  • /11

    $2,200 Per Month

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

    206 Scofield Ave, Bridgeport, CT 06605

    Charming 2-bedroom, 1st floor Apartment in BlackRock, Connecticut. This Inviting apartment offers central air for your comfort and a dishwasher for easy cleanup. Nestled in the vibrant Blackrock Area, you're just steps away from shops, eateries, and parks. This apartment is perfect for those seeking a blend of convenience and comfort. Reach out today to schedule a viewing

    Lacie Malcolm Keller Williams Realty Prtnrs.

    206 Scofield Ave, Bridgeport, CT 06605
  • 230 Saugatuck Ave Unit 6, Westport, CT 06880

    $740,000

    Sold Nov 19, 2025

    230 Saugatuck Ave Unit 6, Westport, CT 06880

    • 2 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • Built 1988

    Last Sold Summary

    • 1% Above List Price
    • $617/SF
    • 75 Days On Market

    Last Listing Agent Scott Wright RE/MAX Right Choice

    230 Saugatuck Ave Unit 6, Westport, CT 06880
    • 2 Bonnie Brook Rd, Westport, CT 06880

      Est $601,819

      Not Listed For Sale

      2 Bonnie Brook Rd, Westport, CT 06880

      • 5 Beds
      • 3 Baths
      • 4,257 Sq Ft
      • Built 1960
      2 Bonnie Brook Rd, Westport, CT 06880

      Last Sold Summary

      • 66% Below List Price
      • $411/SF
      • 23 Days On Market
      • Last Sold Price $1,750,000
      • Nov 17, 2023

      Last Listing Agent Susan Herrmann William Raveis Real Estate

  • /7

    $725,000

    $70K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,483 Sq Ft

    855 Brewster St Unit 857, Bridgeport, CT 06605

    An incredible investment opportunity in a highly desirable Black Rock Neighborhood. This well maintained 3 Family property is perfect for investors or owner occupied. Ideally located within walking distance to the Fairfield Metro Train Station, shops and restaurants along Fairfield Ave. It's a short drive to I-95 and Downtown Fairfield and Black Rock Turnpike. This 3 Family home has 5 Bedrooms, 3

    Doug Munson Munson Real Estate

    855 Brewster St Unit 857, Bridgeport, CT 06605
  • /17

    $5,800 Per Month

    • 3 Beds
    • 2.5 Baths
    • 3,500 Sq Ft
    • Townhouse for Rent

    62 Soundview Ave, Fairfield, CT 06825

    Brand New Contemporary Townhouse never occupied! All new kitchen and appliances! Large pantry and wine chiller in kitchen. Open floor plan. Office space on main floor. Half bath on main floor. Light bearing room living room. Slider to private patio on main floor. 3 Bedrooms upstairs with large closets. Main Bedroom with ensuite. Finished lower level with 1 car garage under the house. Spacious,

    Roseanne Ganim Berkshire Hathaway NE Prop.

    62 Soundview Ave, Fairfield, CT 06825
  • 2031 Redding Rd, Fairfield, CT 06824

    $2,270,000

    Sold May 29, 2025

    2031 Redding Rd, Fairfield, CT 06824

    • 7 Beds
    • 6 Baths
    • 5,291 Sq Ft
    • Built 1810

    Last Sold Summary

    • 1% Below List Price
    • $429/SF
    • 102 Days On Market

    Last Listing Agent Katie O'Grady Compass Connecticut, LLC

    2031 Redding Rd, Fairfield, CT 06824
    • 25 Soundview Dr, Westport, CT 06880

      Est $580,929

      Not Listed For Sale

      25 Soundview Dr, Westport, CT 06880

      • 4 Beds
      • 4.5 Baths
      • 3,492 Sq Ft
      • Built 1920
      25 Soundview Dr, Westport, CT 06880

      Last Sold Summary

      • 90% Below List Price
      • $1,586/SF
      • 15 Days On Market
      • Last Sold Price $5,540,000
      • Dec 02, 2024

      Last Listing Agent Leslie Clarke Compass Connecticut, LLC

  • /26

    $884,900

    Coming Soon
    • 3 Beds
    • 1.5 Baths
    • 1,008 Sq Ft

    76 Geneva Terrace, Fairfield, CT 06824

    76 Geneva Terrace is a sweet 1,008-square-foot Ranch that delivers effortless one-level living on a peaceful, tree-lined side street. Situated just off the main road, this location provides exceptional access to Fairfield's renowned beaches, the train station, and the vibrant town center. Recently renovated throughout, including floors, the bathroom, and kitchen - cabinets, countertops and

    Zach Pinto Alpha Capital Realty, LLC

    76 Geneva Terrace, Fairfield, CT 06824
  • /32

    $3,700 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,750 Sq Ft
    • Townhouse for Rent

    2 Beacon Square Unit 3, Fairfield, CT 06825

    Welcome to the beautifully maintained complex known as Beacon Square in Fairfield. Each unit has its own individual garage with interior entrance to the ground level. On the entry level, you'll find a large room that can be used as a guest bedroom, office, playroom...whatever you need. This ground level has a generous foyer with ample closets. Up one level is the main living area with a large

    Lauren Dunne Berkshire Hathaway NE Prop.

    2 Beacon Square Unit 3, Fairfield, CT 06825
  • 105 Fox St Unit 107, Bridgeport, CT 06605

    $665,000

    Sold Jan 07, 2026

    105 Fox St Unit 107, Bridgeport, CT 06605

    • 6 Beds
    • 3 Baths
    • 3,258 Sq Ft
    • Built 1907

    Last Sold Summary

    • 1% Above List Price
    • $204/SF
    • 63 Days On Market

    Current Estimated Value $697,723

    Last Listing Agent John Kleps Berkshire Hathaway NE Prop.

    105 Fox St Unit 107, Bridgeport, CT 06605
    • 58 North Ave, Westport, CT 06880

      Est $2,633,809

      Not Listed For Sale

      58 North Ave, Westport, CT 06880

      • 6 Beds
      • 5.5 Baths
      • 4,210 Sq Ft
      • Built 1879
      58 North Ave, Westport, CT 06880

      Last Sold Summary

      • 3% Above List Price
      • $606/SF
      • 25 Days On Market
      • Last Sold Price $2,553,000
      • Sep 12, 2024

      Last Listing Agent Patricia Prenderville Higgins Group Real Estate

  • /30

    $1,349,000

    Open Sat 1:30PM - 3:30PM
    • 3 Beds
    • 3 Baths
    • 2,140 Sq Ft

    27 Brookdale Rd, Fairfield, CT 06824

    Turnkey, beautifully renovated & expanded...this home feels like NEW! This University home tucked away in one of the sweetest neighborhoods...so convenient to downtown, restaurants, train, beaches, shopping and walk to elementary, park, ballfield & pickleball. Featuring a flexible floor plan w/over 2,100 sq.ft. including 3 spacious bedrooms (main level option or office), 3 full designer

    Stacey DiDio Coldwell Banker Realty

    27 Brookdale Rd, Fairfield, CT 06824
  • /25

    $1,995 Per Month

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

    2806 Fairfield Ave Unit 101, Bridgeport, CT 06605

    The Newly Renovated Wanis Building! Spectacular first floor, one bedroom, one bathroom end unit! The unit has an open living, dining, kitchen area, the appliances are stainless steel and there is also a stackable washer and dryer. This nice and bright end unit with exposed brick is ideally located in the Black Rock restaurant and entertainment district and is convenient to the Black Rock Train

    John Kleps Berkshire Hathaway NE Prop.

    2806 Fairfield Ave Unit 101, Bridgeport, CT 06605
  • 61 Edgewater Commons Ln, Westport, CT 06880

    $1,769,000

    Sold Dec 19, 2025

    61 Edgewater Commons Ln, Westport, CT 06880

    • 4 Beds
    • 3.5 Baths
    • 3,397 Sq Ft
    • Built 1988

    Last Sold Summary

    • 31% Below List Price
    • $521/SF
    • 84 Days On Market

    Current Estimated Value $1,804,050

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

    61 Edgewater Commons Ln, Westport, CT 06880
    • 39 Guyer Rd, Westport, CT 06880

      Est $1,627,420

      Not Listed For Sale

      39 Guyer Rd, Westport, CT 06880

      • 5 Beds
      • 5 Baths
      • 4,303 Sq Ft
      • Built 1950
      39 Guyer Rd, Westport, CT 06880

      Last Sold Summary

      • 16% Above List Price
      • $325/SF
      • 17 Days On Market
      • Last Sold Price $1,400,000
      • Nov 12, 2024

      Last Listing Agent Catherine McGee Coldwell Banker Realty

Showing Results 601 - 640, Page 16 of 18

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