Southport, CT Homes

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  $2,345,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,218 Sq Ft

  86 Maple Ave S, Westport, CT 06880

  Renovated, refreshed, and move-in ready, this sunfilled Greens Farms gem offers the perfect blend of charm, style, and modern comfort. Set on a beautifully landscaped, level acre with gunite pool and expansive patio, the outdoor living experience is exceptional. Fresh paint inside and out, a new pergola, and thoughtful landscaping create irresistible curb appeal. Step inside and feel instantly at

  Jaclyn Picarillo Higgins Group Bedford Square

  86 Maple Ave S, Westport, CT 06880
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  $2,900 total monthly price

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

  528 Black Rock Turnpike Unit 108, Fairfield, CT 06825

  Experience all-inclusive, maintenance-free living in this brand-new 23-unit apartment building just a short walk from the Fairfield Metro Train Station. This spacious two-bedroom, one-bath residence features an open floor plan with sleek, modern finishes. Enjoy a stylish eat-in kitchen complete with quartz countertops and stainless-steel appliances, as well as a generously sized bathroom. The

  Sara Santos Coldwell Banker Realty

  528 Black Rock Turnpike Unit 108, Fairfield, CT 06825
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  $700,000 Sold Jun 09, 2025

  271 Seaside Ave, Bridgeport, CT 06605

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft
  • Built 1939

  Last Sold Summary

  • 23% Above List Price
  • $561/SF
  • 5 Days On Market

  Current Estimated Value $685,664

  Last Listing Agent Nannette Fatigate Berkshire Hathaway NE Prop.

  271 Seaside Ave, Bridgeport, CT 06605
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  Est $5,571,709 Not Listed For Sale

  39 Maple Ave S, Westport, CT 06880

  • 6 Beds
  • 7.5 Baths
  • 8,080 Sq Ft
  • Built 2023

  39 Maple Ave S, Westport, CT 06880

  Last Sold Summary

  • 11% Above List Price
  • $619/SF
  • 48 Days On Market

  Last Sold Price $5,004,000

  Last Listing Agent Kelly Loucas Compass Connecticut, LLC
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  $4,300,000

  • 6 Beds
  • 6 Baths
  • 6,000 Sq Ft

  394 Penfield Rd, Fairfield, CT 06824

  IMAGES FROM BUILDER'S PORTFOLIO.Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7

  Helene Salerno Ogents, LLC

  394 Penfield Rd, Fairfield, CT 06824
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  $2,300 total monthly price

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

  350 Grovers Ave Unit 1C, Bridgeport, CT 06605

  The Anchorage a Spectacular Resort like Condominium Complex on Black Rock Harbor! This first floor unit with no units above offers a spacious open living/dining area with NuCore Performance vinyl flooring which is also in the bedroom. The kitchen and bathroom have both been updated and there is an assigned parking space in the garage. Relax by the pool or on the sandy beach watching the boats

  John Kleps Berkshire Hathaway NE Prop.

  350 Grovers Ave Unit 1C, Bridgeport, CT 06605
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  $1,100,000 Sold Jan 12, 2026

  179 Verna Hill Rd, Fairfield, CT 06824

  • 5 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 1885

  Last Sold Summary

  • 19% Above List Price
  • $458/SF
  • 30 Days On Market

  Current Estimated Value $961,745

  Last Listing Agent Ellen Balazs Berkshire Hathaway NE Prop.

  179 Verna Hill Rd, Fairfield, CT 06824
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  Est $1,860,719 Not Listed For Sale

  12 Rocky Ridge Rd, Westport, CT 06880

  • 4 Beds
  • 4 Baths
  • 3,800 Sq Ft
  • Built 1944

  12 Rocky Ridge Rd, Westport, CT 06880

  Last Sold Summary

  • 29% Above List Price
  • $378/SF
  • 65 Days On Market

  Last Sold Price $1,437,500

  Last Listing Agent Karen Liss-uomoleale Coldwell Banker Realty
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  $1,475,000

  • Land
  • 1.05 Acres
  • $1,404,762 per Acre

  50 Sylvan Rd N, Westport, CT 06880

  DREAM YOUR TOMORROW This 1.05 acre of dry, level land that is available for sale, is beautifully sited in the middle of Westport's Old Hill and awaits your imagination. Enter through the original gates of the 1928 Arthur Whiteside Estate at 50 Sylvan North --- the park-like entry to the 25-acre estate built for Whiteside, who founded and headed the commercial credit rating firm of Dun &

  Martha Eidman Coldwell Banker Realty

  50 Sylvan Rd N, Westport, CT 06880
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  $4,100 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 3,182 Sq Ft
  • House for Rent

  61 Villa Ave, Fairfield, CT 06825

  Step into timeless elegance with this beautifully maintained center hall Colonial located in the beautiful Brooklawn neighborhood of Fairfield. Rich in Old World charm, this bright and spacious home welcomes you through a gracious foyer that opens to a sunlit, front-to-back living room featuring a wood-burning fireplace and access to a serene screened-in three-season porch overlooking lush,

  Sarah Harrower Sarah Harrower Realty

  61 Villa Ave, Fairfield, CT 06825
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  $468,000 Sold Jan 08, 2026

  245 Unquowa Rd Unit 34, Fairfield, CT 06824

  • 1 Bed
  • 1 Bath
  • 956 Sq Ft
  • Built 1964

  Last Sold Summary

  • 8% Above List Price
  • $490/SF
  • 4 Days On Market

  Current Estimated Value $449,248

  Last Listing Agent James Millington William Raveis Real Estate

  245 Unquowa Rd Unit 34, Fairfield, CT 06824
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  Est $2,876,264 Not Listed For Sale

  2 Smokey Ln, Westport, CT 06880

  • 4 Beds
  • 5 Baths
  • 5,516 Sq Ft
  • Built 1996

  2 Smokey Ln, Westport, CT 06880

  Last Sold Summary

  • 5% Above List Price
  • $496/SF
  • 13 Days On Market

  Last Sold Price $2,735,000

  Last Listing Agent Doug Bross Coldwell Banker Realty
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  $2,399,000

  • 3 Beds
  • 3.5 Baths
  • 3,328 Sq Ft

  2 Elmwood Dr Unit 2, Southport, CT 06890

  Rare opportunity in sought-after Southport Green-just steps to Southport Village and Metro-North. One of only two stand-alone residences in this 24-unit enclave, this home offers the privacy of a single-family lifestyle with the ease of condominium living. The townhouse-style residence spans three levels and features 3 bedrooms, 3 renovated full and 1 half baths, plus a coveted attached two-car

  Wendy Ryan Brown Harris Stevens

  2 Elmwood Dr Unit 2, Southport, CT 06890
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  $1,995 total monthly price

  • 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
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  $625,000 Sold Oct 15, 2025

  4 Heather Hill, Westport, CT 06880

  • 4 Beds
  • 1.5 Baths
  • 1,567 Sq Ft
  • Built 1955

  Last Sold Summary

  • 24% Below List Price
  • $399/SF
  • 95 Days On Market

  Current Estimated Value $675,426

  Last Listing Agent Matthew Loverci Coldwell Banker Realty

  4 Heather Hill, Westport, CT 06880
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  Est $2,662,162 Not Listed For Sale

  17 Gault Park Dr, Westport, CT 06880

  • 4 Beds
  • 4 Baths
  • 4,285 Sq Ft
  • Built 1952

  17 Gault Park Dr, Westport, CT 06880

  Last Sold Summary

  • 9% Above List Price
  • $572/SF
  • 7 Days On Market

  Last Sold Price $2,450,000

  Last Listing Agent Jeannette Floto Compass Connecticut, LLC
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  $705,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,421 Sq Ft

  148 Millspaugh Dr, Fairfield, CT 06824

  University Neighborhood Cape on a group of quiet and peaceful streets and cul-de-sacs. Perfect for walking, running, and bike riding, yet close to town, train, and schools! Expanded Cape, 3 bedroom, 2 full baths, with great Sunroom and a charming Screened in Porch, overlooking a lovely private backyard. Beautiful hardwood floors through out (bedrooms upstairs have hardwood under the wall to wall

  Terry Keegan Fairfield County Real Estate

  148 Millspaugh Dr, Fairfield, CT 06824
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  $9,850 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft
  • House for Rent

  656 Fairfield Beach Rd, Fairfield, CT 06824

  Introducing "The Reeds," Fairfield Beach's newest furnished rental. NOW AVAILABLE FROM 2/1/26-6/30/26 & JULY 2026 SUMMER RENTAL (PRICING VARIES), FLEX TERM/SHORT-TERM, MONTH-TO-MONTH. ACADEMIC LEASES ARE NOW IN PLACE FROM 2026-2029. ACADEMIC AVAILABLE 9/1/29. MANY FLEXIBLE OPTIONS. Totally renovated, 4 bedroom, 2.5 bath with amazing views from nearly every room. The best of both worlds, with

  Jessica Walsh William Raveis Real Estate

  656 Fairfield Beach Rd, Fairfield, CT 06824
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  $265,000 Sold Nov 05, 2025

  96 Davis Ave, Bridgeport, CT 06605

  • 2 Beds
  • 2 Baths
  • 931 Sq Ft
  • Built 1905

  Last Sold Summary

  • 8% Below List Price
  • $285/SF
  • 102 Days On Market

  Current Estimated Value $294,783

  Last Listing Agent Bogdan Stefanide KW Legacy Partners

  96 Davis Ave, Bridgeport, CT 06605
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  Est $5,151,669 Not Listed For Sale

  11 Burnham Hill, Westport, CT 06880

  • 5 Beds
  • 6.5 Baths
  • 6,185 Sq Ft
  • Built 1966

  11 Burnham Hill, Westport, CT 06880

  Last Sold Summary

  • 26% Above List Price
  • $663/SF
  • 34 Days On Market

  Last Sold Price $4,100,000

  Last Listing Agent Meredith Kamo Compass Connecticut, LLC

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