35,315

Southport, CT Homes

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  • /38

    $4,950,000

    Pending
    • 5 Beds
    • 4.5 Baths
    • 4,875 Sq Ft

    6 Gray Ln, Westport, CT 06880

    **Sellers request all offers to be submitted by Sunday 6/28 at noon.** A WATERFRONT offering in one of Westport's most coveted enclaves. This beautifully composed estate is gracefully sited on more than two private, tree-lined acres, encompassing sweeping views of Sasco Creek, Southport Beach, and Long Island Sound while preserving an exceptional sense of seclusion. Designed to maximize its

    Christine McKinney William Raveis Real Estate

    6 Gray Ln, Westport, CT 06880
  • /34

    $8,500 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,624 Sq Ft
    • House for Rent

    287 Greens Farms Rd, Westport, CT 06880

    This light filled home is set on 2 acres finished on both levels with over 2300 sq ft of living space. Beautiful flat back yard for fun summer games. Just 3 minutes from the Metro North, and convenient to all the Westport amenities. TOTAL SQUARE FT IS 2308

    Georgia Wasserman Coldwell Banker Realty

    287 Greens Farms Rd, Westport, CT 06880
  • 204 Glen Ridge Rd, Fairfield, CT 06825

    $2,210,000

    Sold Apr 01, 2026

    204 Glen Ridge Rd, Fairfield, CT 06825

    • 5 Beds
    • 4.5 Baths
    • 4,474 Sq Ft
    • Built 2026

    Last Sold Summary

    • 11% Above List Price
    • $494/SF
    • 4 Days On Market

    Current Estimated Value $1,954,286

    Last Listing Agent Jennifer DeLaurentis Compass Connecticut, LLC

    204 Glen Ridge Rd, Fairfield, CT 06825
    • 9 Brookside Dr, Westport, CT 06880

      Est $4,780,478

      Not Listed For Sale

      9 Brookside Dr, Westport, CT 06880

      • 6 Beds
      • 11 Baths
      • 9,142 Sq Ft
      • Built 1938
      9 Brookside Dr, Westport, CT 06880

      Last Sold Summary

      • 309 Days On Market

      Last Listing Agent Kim Vartuli Keller Williams Realty

  • /40

    $3,399,900

    • 5 Beds
    • 8 Baths
    • 8,657 Sq Ft

    344 Fence Row Dr, Fairfield, CT 06824

    Old-world craftsmanship meets modern indulgence. Set on a peaceful, tree-lined street,this home offers total privacy and timeless curb appeal. Soaring ceilings, hand-finished millwork, and custom detail are evident throughout. This grand 5BR/6.5BA light filled residence pairs classic entertaining spaces - formal LR, formal DR, & a wood-paneled library w/wet bar & full BA-with modern amenities

    Krista Alecia Coldwell Banker Realty

    344 Fence Row Dr, Fairfield, CT 06824
  • /34

    $14,000 Per Month

    • 5 Beds
    • 4 Baths
    • 3,392 Sq Ft
    • House for Rent

    20 Joann Cir, Westport, CT 06880

    Enjoy Summer in Westport CT. Located on a quiet neighborhood street, this 5-bedroom home spans a full acre, offering a tranquil setting for your summer retreat. It's ideally positioned near all town amenities, perfect for enjoying Westport's lively summer scene. The home welcomes you with a spacious living room, large windows highlighting scenic views, and a dining area leading to a sunlit

    Jessica Brookbanks Coldwell Banker Realty

    20 Joann Cir, Westport, CT 06880
  • 145 Galloping Hill Rd, Fairfield, CT 06824

    $3,300,000

    Sold Jun 02, 2026

    145 Galloping Hill Rd, Fairfield, CT 06824

    • 5 Beds
    • 5.5 Baths
    • 8,925 Sq Ft
    • Built 2006

    Last Sold Summary

    • 18% Above List Price
    • $370/SF
    • 13 Days On Market

    Current Estimated Value $3,136,334

    Last Listing Agent Susan Gardella William Pitt Sotheby's Int'l

    145 Galloping Hill Rd, Fairfield, CT 06824
    • 1 Blue Ribbon Dr, Westport, CT 06880

      Est $2,180,314

      Not Listed For Sale

      1 Blue Ribbon Dr, Westport, CT 06880

      • 4 Beds
      • 3 Baths
      • 3,493 Sq Ft
      • Built 1930
      1 Blue Ribbon Dr, Westport, CT 06880

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Anne Frewen Coldwell Banker Realty

  • /31

    $1,199,000

    $150K PRICE DROP Under Contract
    • 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
  • /22

    $3,550 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    110 Southport Woods Dr Unit 110, Fairfield, CT 06825

    Beautiful apartment located in desirable Southport, CT. This property offers a wonderfully peaceful, safe and warm community setting. The apartment unit is exceptionally wellmanaged and meticulously caredfor, featuring freshly painted walls across the entire space, movein ready. It sits within a highlyrated school district. The elementary school is within walking distance, while middle and high

    Michael Jabick Keller Williams Realty

    110 Southport Woods Dr Unit 110, Fairfield, CT 06825
  • 102 Hansen Ave Unit 104, Bridgeport, CT 06605

    $390,000

    Sold Sep 08, 2025

    102 Hansen Ave Unit 104, Bridgeport, CT 06605

    • 6 Beds
    • 2 Baths
    • 2,511 Sq Ft
    • Built 1917

    Last Sold Summary

    • 5% Above List Price
    • $155/SF
    • 9 Days On Market

    Current Estimated Value $432,435

    Last Listing Agent John Armellino William Raveis Real Estate

    102 Hansen Ave Unit 104, Bridgeport, CT 06605
    • 39 Danbury Ave, Westport, CT 06880

      Est $4,961,493

      Not Listed For Sale

      39 Danbury Ave, Westport, CT 06880

      • 5 Beds
      • 5.5 Baths
      • 4,294 Sq Ft
      • Built 2007
      39 Danbury Ave, Westport, CT 06880

      Last Sold Summary

      • 188 Days On Market

      Last Listing Agent Karen Scott Compass Connecticut, LLC

  • /40

    $2,299,000

    New Construction Pending
    • 5 Beds
    • 4.5 Baths
    • 7,318 Sq Ft

    1054 Mill Plain Rd, Fairfield, CT 06824

    Welcome to 1054 Mill Plain Road! Exceptional craftsmanship and timeless design define this impressive center hall NEW CONSTRUCTION colonial! This open-concept floor plan is designed for seamless everyday living and effortless entertainment boasting 5,518 sq ft of living space and privately set on a rear lot in the sought-after Fairfield University neighborhood. This home presents 5 bedrooms, 4.5

    Tracey Jefferson eXp Realty

    1054 Mill Plain Rd, Fairfield, CT 06824
  • /20

    $2,600 Per Month

    • 2 Beds
    • 1 Bath
    • 925 Sq Ft
    • House for Rent

    287 Old Stratfield Rd, Fairfield, CT 06825

    Welcome to this beautifully maintained 2 bedroom, 1 bath home with a detached one-car garage, ideally situated in a desirable Fairfield neighborhood. The remodelled kitchen features granite countertops, stainless steel appliances and a breakfast bar that opens seamlessly to the living area, creating a bright and comfortable space for everyday living and entertaining. Additional highlights include

    Danielle McCain BHGRE Gaetano Marra Homes

    287 Old Stratfield Rd, Fairfield, CT 06825
  • 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 $306,772

    Last Listing Agent Michael Barbaro Huntsman,Meade & Partners Comp

    2660 North Ave Unit 217, Bridgeport, CT 06604
    • 3 Butternut Ln, Westport, CT 06880

      Est $1,961,489

      Not Listed For Sale

      3 Butternut Ln, Westport, CT 06880

      • 4 Beds
      • 2.5 Baths
      • 3,575 Sq Ft
      • Built 1964
      3 Butternut Ln, Westport, CT 06880

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Linda Dunsmore Coldwell Banker Realty

  • /22

    $699,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,570 Sq Ft

    247 Harborview Ave, Bridgeport, CT 06605

    247 Harborview Avenue, is quintesential Blaack Rock living. The home is exceptionally well-maintained in one of Black Rock's most desirable locations. Situated just steps from Harborview Market and minutes from St. Mary's By The Sea, Fairfield Avenue's restaurants, shops, this home offers the best of Black Rock living. The first floor features a warm and inviting open layout with hardwood floors,

    Aaron Goldberg Coldwell Banker Realty

    247 Harborview Ave, Bridgeport, CT 06605
  • /12

    $3,150 Per Month

    • 2 Beds
    • 1 Bath
    • 759 Sq Ft
    • House for Rent

    105 Churchill St Unit 1st Floor (103), Fairfield, CT 06824

    Spacious and Bright 2 Bedroom Apartment in Fairfield - Brand NEW and Ready for You! Discover the perfect blend of comfort and style in this newly and totally renovated 2-bedroom, 1st-floor apartment, located in a charming 3-family home. This spacious and bright apartment is now available for occupancy, offering a modern living experience with all the amenities you need. Step into the open floor

    Ellen Garcia Brown Harris Stevens

    105 Churchill St Unit 1st Floor (103), Fairfield, CT 06824
  • 693 S Benson Rd, Fairfield, CT 06824

    $2,100,000

    Sold May 11, 2026

    693 S Benson Rd, Fairfield, CT 06824

    • 4 Beds
    • 3 Baths
    • 2,533 Sq Ft
    • Built 1956

    Last Sold Summary

    • 24% Above List Price
    • $829/SF
    • 12 Days On Market

    Current Estimated Value $1,978,078

    Last Listing Agent Jackie Davis William Raveis Real Estate

    693 S Benson Rd, Fairfield, CT 06824
    • 219 Wilton Rd, Westport, CT 06880

      Est $1,223,651

      Not Listed For Sale

      219 Wilton Rd, Westport, CT 06880

      • 3 Beds
      • 2 Baths
      • 1,908 Sq Ft
      • Built 1973
      219 Wilton Rd, Westport, CT 06880

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Sandra Kinseley William Raveis Real Estate

  • /6

    $22,825,000

    • 8 Beds
    • 10 Baths
    • 12,946 Sq Ft

    11 Beachside Common, Westport, CT 06880

    Direct Waterfront | Greens Farms An extraordinary new waterfront estate by award-winning Coastal Luxury Homes is coming to one of the most coveted stretches of the Connecticut shoreline. Set in the heart of Greens Farms, this spectacular 12,948 square foot modern residence will span four levels and capture sweeping, unobstructed views across Sherwood Island, Burying Hill Beach, and Long Island

    Andrew Whiteley Brown Harris Stevens

    11 Beachside Common, Westport, CT 06880
  • /15

    $1,850 Per Month

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

    808 Mill Plain Rd Unit 2nd Floor, Fairfield, CT 06824

    Best deal in Fairfield! Very clean and move in condition second floor, one bedroom apartment with covered front porch available for immediate occupancy and conveniently located in walking distance to the town center and train station. Heat and hot water are included, shared washer and dryer in basement and off street parking. The owner requires good credit, no smoking, will consider a pet, first,

    John Kleps Berkshire Hathaway NE Prop.

    808 Mill Plain Rd Unit 2nd Floor, 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 $1,398,173

    Last Listing Agent Julia Broder Coldwell Banker Realty

    Unlisted Address
    • 337 Greens Farms Rd, Westport, CT 06880

      Est $1,840,447

      Not Listed For Sale

      337 Greens Farms Rd, Westport, CT 06880

      • 4 Beds
      • 3 Baths
      • 2,773 Sq Ft
      • Built 1964
      337 Greens Farms Rd, Westport, CT 06880

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Patricia Shea Coldwell Banker Realty

  • /36

    $665,000

    • 3 Beds
    • 2 Baths
    • 1,410 Sq Ft

    681 Jennings Rd, Fairfield, CT 06824

    Welcome to this beautiful home at 681 Jennings Rd, Fairfield, CT! This well-maintained property offers a flexible and functional layout with 3 bedrooms and 2 full bathrooms. The second floor features two spacious bedrooms, a full bathroom, and beautiful hardwood floors. The main level includes an additional bedroom, a bright living room and dining room with hardwood flooring, a beautifully

    EDUARDO SUAREZ William Pitt Sotheby's Int'l

    681 Jennings Rd, Fairfield, CT 06824
  • /24

    $8,500 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft
    • House for Rent

    108 New England Ave, Fairfield, CT 06824

    Brand-new 2026 construction offering over 3,200 square feet of thoughtfully designed living space-an exceptionally rare opportunity to rent a new construction home in Fairfield. This five-bedroom, four-and-a-half-bath residence features a highly functional modern layout with high-end finishes throughout, including hardwood floors, quartz countertops in the kitchen and bathrooms, custom cabinetry,

    Anthony Gigliotti Keller Williams Realty

    108 New England Ave, Fairfield, CT 06824
  • 527 Colorado Ave, Bridgeport, CT 06605

    $370,000

    Sold Jul 27, 2026

    527 Colorado Ave, Bridgeport, CT 06605

    • 3 Beds
    • 1 Bath
    • 1,751 Sq Ft
    • Built 1890

    Last Sold Summary

    • 8% Below List Price
    • $211/SF
    • 80 Days On Market

    Current Estimated Value $368,628

    Last Listing Agent Sasha McLeain Coldwell Banker Realty

    527 Colorado Ave, Bridgeport, CT 06605
    • /7

      Est $6,611,161

      Not Listed For Sale

      19 Old Hill Farms Rd, Westport, CT 06880

      • 5 Beds
      • 5.5 Baths
      • 7,595 Sq Ft
      • Built 2012
      19 Old Hill Farms Rd, Westport, CT 06880

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Jennifer Leahy Compass Connecticut, LLC

  • /40

    $2,850,000

    Pending
    • 5 Beds
    • 5 Baths
    • 4,922 Sq Ft

    55 Center St, Westport, CT 06880

    Located in Westport's coveted Greens Farms neighborhood, this light-filled home is perfectly sited high and dry on a private park-like acre with room for a pool and pool house. A renovated kitchen with top-of-the-line appliances and sunny breakfast nook opens to a spacious great room with stone fireplace and expansive deck overlooking the property, ideal for indoor-outdoor living. The flexible

    Mary Ann Lindwall The Riverside Realty Group

    55 Center St, Westport, CT 06880
  • /36

    $11,500 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft
    • House for Rent

    2149 Fairfield Beach Rd, Fairfield, CT 06824

    SPECTACULAR FAIRFIELD BEACH ACADEMIC YEAR RENTAL: September 1, 2028 till end of May 2029. BEACHFRONT PROPERTY! NICE OPEN FLOOR PLAN WITH ROOFTOP DECK, PARKING WASHER DRYER.

    Nick Khamarji New England Realty & Insurance

    2149 Fairfield Beach Rd, Fairfield, CT 06824
  • 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 $1,943,393

    Last Listing Agent Chrissie Rodriguez Higgins Group Real Estate

    127 College Park Dr, Fairfield, CT 06824
    • 5 Thomas Rd, Westport, CT 06880

      Est $2,291,778

      Not Listed For Sale

      5 Thomas Rd, Westport, CT 06880

      • 3 Beds
      • 4 Baths
      • 2,620 Sq Ft
      • Built 1934
      5 Thomas Rd, Westport, CT 06880

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Mersene Norbom William Pitt Sotheby's Int'l

  • /39

    $875,655

    • 2 Beds
    • 2 Baths
    • 2,324 Sq Ft

    1 Campfield Dr, Fairfield, CT 06825

    Completely renovated and move-in ready, this stunning modern Colonial is located in Fairfield's desirable Tunxis Hill neighborhood. Meticulously remodeled from top to bottom, the home seamlessly blends contemporary style with timeless charm. Featuring 3 bedrooms with lots of natural light, an additional flexible office space and 2 full baths, the thoughtfully designed interior showcases a chef's

    Catherine Aaron Berkshire Hathaway NE Prop.

    1 Campfield Dr, Fairfield, CT 06825
  • /7

    $2,200 Per Month

    • 2 Beds
    • 1 Bath
    • 2,459 Sq Ft
    • Apartment for Rent

    Unlisted Address

    4 Rooms Renovated Apartment for Rent, second floor of this beautiful Multifamily in very desirable neighborhood of Black Rock. Walk to Public Transportation, business area with plenty of restaurants, supermarkets, etc. Definitely a must see if you are looking for a rental. Street Parking. Show and Rent it.

    Elba Garcia Berkshire Hathaway NE Prop.

    Unlisted Address
  • 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
    • 25 Crescent Rd, Westport, CT 06880

      Est $1,026,227

      Not Listed For Sale

      25 Crescent Rd, Westport, CT 06880

      • 3 Beds
      • 1 Bath
      • 1,472 Sq Ft
      • Built 1954
      25 Crescent Rd, Westport, CT 06880

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Tara Chlupsa Coldwell Banker Realty

  • /39

    $3,400,000

    • 5 Beds
    • 5.5 Baths
    • 6,753 Sq Ft

    1760 Hillside Rd, Fairfield, CT 06824

    Privately sited in the heart of Greenfield Hill, this updated home blends European-inspired architecture with the modern comforts today's luxury buyers value most. Rich in character, it offers soaring ceilings with exposed wood beams and skylights, wide-plank hardwood floors, custom built-ins, antique mantels, and repurposed antique doors throughout. The dramatic family room flows to a private

    Andrew Whiteley Brown Harris Stevens

    1760 Hillside Rd, Fairfield, CT 06824
  • /38

    $6,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,076 Sq Ft
    • House for Rent

    71 Belmont St, Fairfield, CT 06824

    Rare opportunity to lease this beautifully maintained and updated Raised Ranch in one of Fairfield's most desirable beach-area neighborhoods. Just a short walk to Jennings Beach, Fairfield Train Station, downtown Fairfield, restaurants, shopping, parks, and all the amenities that make Fairfield one of Connecticut's most sought-after communities.This spacious home offers 3 bedrooms, 2 full

    William J. Gill Compass Connecticut, LLC

    71 Belmont St, Fairfield, CT 06824
  • 49 Hillspoint Rd, Westport, CT 06880

    $4,225,000

    Sold Jun 12, 2026

    49 Hillspoint Rd, Westport, CT 06880

    • 5 Beds
    • 7 Baths
    • 8,550 Sq Ft
    • Built 2015

    Last Sold Summary

    • 9% Below List Price
    • $494/SF
    • 88 Days On Market

    Current Estimated Value $4,301,301

    Last Listing Agent Michelle Genovesi William Raveis Real Estate

    49 Hillspoint Rd, Westport, CT 06880
    • 25 Colony Rd, Westport, CT 06880

      Est $2,112,341

      Not Listed For Sale

      25 Colony Rd, Westport, CT 06880

      • 4 Beds
      • 2.5 Baths
      • 3,548 Sq Ft
      • Built 1966
      25 Colony Rd, Westport, CT 06880

      Last Sold Summary

      • 81 Days On Market

      Last Listing Agent Marilyn Heffers Coldwell Banker Realty

Showing Results 601 - 640, Page 16 of 18

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