Southport, CT Homes

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  /40

  $7,750,000 Pending

  • 6 Beds
  • 8 Baths
  • 9,238 Sq Ft

  319 Bayberry Ln, Westport, CT 06880

  This exceptional Modern estate, originally crafted by Skyview as the builder's own residence, is available in as-new condition and enhanced by inspired customization. Set on 2+/- private acres in Coleytown, adjacent to the Paul Newman-Poses Nature Preserve, the home is approached by a long, gated drive that opens to a motorcourt ideal for grand entertaining. Triple-glazed Klar Studio windows

  Doug Bross Coldwell Banker Realty

  319 Bayberry Ln, Westport, CT 06880
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  /27

  $8,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 3,178 Sq Ft
  • House for Rent

  28 Punch Bowl Dr, Westport, CT 06880

  Dramatic Contemporary Colonial with soaring ceilings, hardwood floors, sun-drenched large rooms with open floor plan. Eat-in kitchen has Bosch double convection oven, glass cooktop, newer frig & newer washer/dryer. Huge living room with wood-burning fireplace, high ceilings, skylights & windows abound! Separate formal dining room & additional separate family room create easy flow for today's

  Debbie Fisher William Raveis Real Estate

  28 Punch Bowl Dr, Westport, CT 06880
• 

  $790,000 Sold Sep 03, 2025

  84 Edison Ave, Fairfield, CT 06825

  • 4 Beds
  • 2.5 Baths
  • 1,904 Sq Ft
  • Built 1998

  Last Sold Summary

  • $415/SF
  • 27 Days On Market

  Current Estimated Value $804,096

  Last Listing Agent Denise Curcio William Raveis Real Estate

  84 Edison Ave, Fairfield, CT 06825
• 

  Est $565,319 Not Listed For Sale

  12 Cross Hwy Unit A, Westport, CT 06880

  • 1 Bed
  • 1 Bath
  • 977 Sq Ft
  • Built 1900

  12 Cross Hwy Unit A, Westport, CT 06880

  Last Sold Summary

  • 10% Above List Price
  • $527/SF
  • 88 Days On Market

  • Last Sold Price $515,000
  • Apr 08, 2024

  Last Listing Agent Abigail Delise William Raveis Real Estate
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  /36

  $729,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft

  99 Judd St, Fairfield, CT 06824

  Welcome to this charming and spacious 3-bedroom, 2 full bath Cape Cod home located in Fairfield's desirable University area. Set on a corner lot, this thoughtfully updated and maintained home features a private, fully fenced backyard with mature landscaping, gardens, and a fire pit area - perfect for relaxing or entertaining. Freshly painted, the interior of this picture-perfect home offers

  Carrie Sakey Coldwell Banker Realty

  99 Judd St, Fairfield, CT 06824
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  /28

  $7,500 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,518 Sq Ft
  • House for Rent

  20 Chelsea St, Fairfield, CT 06824

  Located in one of Fairfield's most coveted neighborhoods, this charming Colonial in the desirable Riverhurst enclave offers the perfect blend of convenience and tranquility. Enjoy an easy walk to schools, Metro-North, and downtown Fairfield, while still feeling tucked away in a peaceful residential setting. Inside, the home features a classic and functional layout with a formal living room with a

  Jennifer Thomas-Heath Houlihan Lawrence

  20 Chelsea St, Fairfield, CT 06824
• 

  $546,000 Sold Oct 27, 2025

  299 Marlborough Terrace, Fairfield, CT 06825

  • 2 Beds
  • 1.5 Baths
  • 1,268 Sq Ft
  • Built 1947

  Last Sold Summary

  • $431/SF
  • 60 Days On Market

  Current Estimated Value $548,270

  Last Listing Agent Deborah Merlino William Raveis Real Estate

  299 Marlborough Terrace, Fairfield, CT 06825
• 

  Est $2,852,967 Not Listed For Sale

  8 Sandhopper Trail, Westport, CT 06880

  • 4 Beds
  • 2.5 Baths
  • 5,055 Sq Ft
  • Built 2006

  8 Sandhopper Trail, Westport, CT 06880

  Last Sold Summary

  • 21% Above List Price
  • $465/SF
  • 23 Days On Market

  • Last Sold Price $2,350,000
  • Sep 30, 2024

  Last Listing Agent Judy Michaelis Coldwell Banker Realty
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  /38

  $3,250,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 5,616 Sq Ft

  119 Long Lots Rd, Westport, CT 06880

  In Westport's coveted Long Lots neighborhood, this residence makes a striking first impression, set back in quiet privacy behind mature trees and landscaped grounds. Reimagined and expanded in 2010, the home offers sunlit rooms of impressive scale ideal for both memorable entertaining and everyday luxury, with high-end updates and amenities at every turn. An inviting first-floor lounge with pool

  Cyd Hamer William Pitt Sotheby's Int'l

  119 Long Lots Rd, Westport, CT 06880
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  /11

  $4,300 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,060 Sq Ft
  • Townhouse for Rent

  175 Alvin St Unit 175, Fairfield, CT 06825

  Great condition energy efficient town house with 3 bds 2.5bath, on quite street, classic huge master suite w/ his and hers walk-in closet, gas heat, c/a, city water, hardwood flr, gas fireplace, kitchen with granite top, large island, ss appliance, laundry on 2nd flr, basement for storage, conveniently located near shopping, a train station, and highway

  Jae Ahn William Raveis Real Estate

  175 Alvin St Unit 175, Fairfield, CT 06825
• 

  $11,000,000 Sold Mar 02, 2026

  39 Compo Pkwy, Westport, CT 06880

  • 6 Beds
  • 9 Baths
  • 11,150 Sq Ft
  • Built 2017

  Last Sold Summary

  • 15% Below List Price
  • $987/SF
  • 33 Days On Market

  Current Estimated Value $7,783,359

  Last Listing Agent Michelle Genovesi William Raveis Real Estate

  39 Compo Pkwy, Westport, CT 06880
• 

  Est $3,119,280 Not Listed For Sale

  9 Wheeler Gate, Westport, CT 06880

  • 5 Beds
  • 5 Baths
  • 3,770 Sq Ft
  • Built 1994

  9 Wheeler Gate, Westport, CT 06880

  Last Sold Summary

  • 4% Above List Price
  • $798/SF
  • 6 Days On Market

  • Last Sold Price $3,010,000
  • Oct 09, 2024

  Last Listing Agent Judy Michaelis Coldwell Banker Realty
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  /35

  $496,500 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,510 Sq Ft

  155 Moody Ave, Fairfield, CT 06825

  START YOUR NEW YEAR, MAKE YOUR OFFER AND SCHEDULE THE MOVERS TO SETTLE RIGHT INTO YOUR 3+ BEDROOM COLONIAL OFFERING AN IDEAL, CONVENIENT LOCATION CLOSE TO SCHOOLS, RETAIL/SHOPPING, PARKS AND REC, BEACHES, TOWN CENTER, METRO NORTH TRAIN STATIONS WITH EASY ACCESS TO I-95 AND RT 15 MERRITT PARKWAY. MAIN LEVEL FEATURES YOUR SUN FILLED LIVING ROOM WITH FIREPLACE, OFFICE/DEN, FORMAL DINING ROOM AND

  John Hackett William Raveis Real Estate

  155 Moody Ave, Fairfield, CT 06825
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  /11

  $2,300 Per Month

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • House for Rent

  124 Harborview Ave Unit 126, Bridgeport, CT 06605

  Enjoy the best of Black Rock living in this charming 2-bedroom, 1-bath first-floor apartment, perfectly situated just steps from Harborview Deli and the neighborhood's popular bars and restaurants. This bright, well-maintained unit offers a spacious layout, a full kitchen with ample cabinetry, updated kitchen flooring and countertop, and beautifully polished wood floors throughout. The

  John Steven Rios Ki Property Group

  124 Harborview Ave Unit 126, Bridgeport, CT 06605
• 

  $3,000,000 Sold Apr 16, 2026

  1380 Old Academy Rd, Fairfield, CT 06824

  • 4 Beds
  • 5.5 Baths
  • 3,961 Sq Ft
  • Built 2000

  Last Sold Summary

  • 16% Above List Price
  • $757/SF
  • 8 Days On Market

  Current Estimated Value $2,577,759

  Last Listing Agent Cindy Raney Coldwell Banker Realty

  1380 Old Academy Rd, Fairfield, CT 06824
• 

  Est $3,724,856 Not Listed For Sale

  28 Flower Farm Cir, Westport, CT 06880

  • 5 Beds
  • 5.5 Baths
  • 5,058 Sq Ft
  • Built 1995

  28 Flower Farm Cir, Westport, CT 06880

  Last Sold Summary

  • 15% Above List Price
  • $643/SF
  • 12 Days On Market

  • Last Sold Price $3,250,000
  • Jun 16, 2023

  Last Listing Agent Alex Chingas Coldwell Banker Realty
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  /38

  $978,000

  • 4 Beds
  • 2 Baths
  • 1,735 Sq Ft

  52 Robin Ln, Fairfield, CT 06824

  Immaculate University area split level home on beautiful lot which is just over one third of an acre. Perfect opportunity to rebuild completely on one of the most generously-sized parcels on this street. Or, to renovate, expand, and reimagine your own dream, simply enjoying its comfort as it was built. Tremendous backyard with classic stone wall. Top-rated schools, close to shopping, and less

  Janet Warren William Raveis Real Estate

  52 Robin Ln, Fairfield, CT 06824
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  /7

  $1,100 Per Month

  • 1 Bath
  • 300 Sq Ft
  • Apartment for Rent

  89-91 Jetland Place Unit 93, Bridgeport, CT 06605

  Well-maintained first-floor studio located on a quiet street in the desirable Black Rock area. This clean and efficient unit offers a practical layout, ideal for someone looking for an affordable and comfortable living space. Conveniently situated within walking distance to shops, restaurants, and everyday necessities. A great option for anyone seeking a safe, low-maintenance place to live while

  Jeff P Puciato Realty Group

  89-91 Jetland Place Unit 93, Bridgeport, CT 06605
• 

  $810,000 Sold Jul 01, 2025

  985 S Pine Creek Rd, Fairfield, CT 06824

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft
  • Built 1982

  Last Sold Summary

  • 5% Above List Price
  • $567/SF
  • 55 Days On Market

  Current Estimated Value $849,617

  Last Listing Agent Katie O'Grady Compass Connecticut, LLC

  985 S Pine Creek Rd, Fairfield, CT 06824
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  Est $2,668,894 Not Listed For Sale

  26 Flower Farm Cir, Westport, CT 06880

  • 5 Beds
  • 5 Baths
  • 4,230 Sq Ft
  • Built 1996

  26 Flower Farm Cir, Westport, CT 06880

  Last Sold Summary

  • 11% Above List Price
  • $567/SF
  • 15 Days On Market

  • Last Sold Price $2,400,000
  • Jun 04, 2024

  Last Listing Agent Karen Scott Compass Connecticut, LLC
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  /32

  $795,000 Under Contract

  • 2 Beds
  • 3.5 Baths
  • 1,600 Sq Ft

  3 Ocean Reef Dr Unit 3, Fairfield, CT 06824

  OCEAN REEF - Perfectly positioned on a cul de sac within an impeccably maintained 11-unit Townhouse community in the coveted Fairfield Beach area, 3 Ocean Reef Drive offers refined coastal living at its best. Beautifully updated and filled with natural light, this exceptional residence features two to three bedrooms and three-and-a-half baths, thoughtfully designed for both comfort and style.

  Victoria Fingelly Higgins Group Real Estate

  3 Ocean Reef Dr Unit 3, Fairfield, CT 06824
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  /20

  $3,750 Per Month

  • 3 Beds
  • 2 Baths
  • 1,412 Sq Ft
  • Apartment for Rent

  228 Jennings Rd, Fairfield, CT 06825

  AVAILABLE JULY 1ST! This beautifully updated 2nd-floor apartment, located in a peaceful, quiet neighborhood. This bright and airy home features light-colored hardwood floors throughout, creating a fresh and modern feel the moment you walk in.*Enjoy a big eat-in kitchen fully equipped with granite countertops, sleek stainless steel appliances, and a dishwasher for easy cleanup.*Primary Suite: The

  Burcin Kaya Keller Williams Realty

  228 Jennings Rd, Fairfield, CT 06825
• 

  $915,000 Sold Jul 01, 2025

  36 Rayfield Rd, Westport, CT 06880

  • Land
  • 1.1 Acres
  • $831,818 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 85 Days On Market

  Current Estimated Value $1,041,990

  Last Listing Agent Pam Toner Berkshire Hathaway NE Prop.

  36 Rayfield Rd, Westport, CT 06880
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  Est $3,207,793 Not Listed For Sale

  269 Sturges Hwy, Westport, CT 06880

  • 5 Beds
  • 7 Baths
  • 5,009 Sq Ft
  • Built 1997

  269 Sturges Hwy, Westport, CT 06880

  Last Sold Summary

  • 7% Above List Price
  • $599/SF
  • 67 Days On Market

  • Last Sold Price $3,000,000
  • Dec 02, 2024

  Last Listing Agent Susan Vanech Compass Connecticut, LLC
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  /31

  $429,900

  • 3 Beds
  • 2 Baths
  • 1,293 Sq Ft

  245 Sunnyridge Ave Unit 1, Fairfield, CT 06824

  Invest in a seamless, income-generating asset with this exceptional end-unit townhouse. Located on the highest level of the complex, this home truly defines the name Sunnyridge, offering immediate cash flow with a tenant already in place. This ensures a turnkey transition for any investor looking to avoid vacancy periods and marketing costs. The interior features an open layout with gleaming

  Sang Jee Eagle Eye Realty PLLC

  245 Sunnyridge Ave Unit 1, Fairfield, CT 06824
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  /27

  $6,000 Per Month

  • 3 Beds
  • 3 Baths
  • 1,894 Sq Ft
  • House for Rent

  798 Mill Plain Rd, Fairfield, CT 06824

  Walk to town and train from this conveniently located 3+bedroom colonial. The main living level features a living room with a fireplace, open dining room, remodeled kitchen with granite counter tops and stainless steel appliances, a half bath and spacious family room with sliders that open to the deck and over-sized backyard. The upper living level features two bedrooms and a full bathroom as

  Stacey DiDio Coldwell Banker Realty

  798 Mill Plain Rd, Fairfield, CT 06824
• 

  $930,000 Sold Jun 27, 2025

  154 Warsaw St, Fairfield, CT 06825

  • 3 Beds
  • 3 Baths
  • 2,829 Sq Ft
  • Built 1956

  Last Sold Summary

  • 3% Above List Price
  • $329/SF
  • 48 Days On Market

  Current Estimated Value $906,809

  Last Listing Agent Valerie Alvarez Serhant Connecticut, LLC

  154 Warsaw St, Fairfield, CT 06825
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  Not Listed For Sale

  8 Cunningham Place, Westport, CT 06880

  • 2 Beds
  • 3 Baths
  • 1,614 Sq Ft
  • Built 1924

  8 Cunningham Place, Westport, CT 06880

  Last Sold Summary

  • $589/SF
  • 11 Days On Market

  • Last Sold Price $950,000
  • Apr 22, 2024

  Last Listing Agent Linda Dunsmore Coldwell Banker Realty
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  /29

  $194,900 Pending

  • 1 Bed
  • 1 Bath
  • 817 Sq Ft

  132 Bennett St Unit 302, Bridgeport, CT 06605

  Recently remodeled 3rd-floor unit offering a functional open layout with a living room, dining area, kitchen, and one bedroom. The kitchen was updated by the current owner in 2023, adding a modern touch to the space. Includes two assigned parking spaces and an ideal location for commuters, with easy access to the train, public transportation, and nearby towns. Enjoy being just a short walk from

  Deborah Angal Coldwell Banker Realty

  132 Bennett St Unit 302, Bridgeport, CT 06605
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  /38

  $15,000 Per Month

  • 5 Beds
  • 6 Baths
  • 3,148 Sq Ft
  • House for Rent

  18 Danbury Ave, Westport, CT 06880

  One week only including 2 weekends- price is for the week - Designer's own home with Gunite pool steps from Compo Beach. This modern completely renovated home is elegantly designed and decorated. Large main level has open Kitchen and Family Room leading to gorgeous patio, private yard and custom Pool with auto cover. There are 5 bedrooms including a stunning Primary Suite. It's only a few homes

  Linda Skolnick Coldwell Banker Realty

  18 Danbury Ave, Westport, CT 06880
• 

  $1,835,000 Sold Sep 12, 2025

  69 River St, Southport, CT 06890

  • 2 Beds
  • 2.5 Baths
  • 1,868 Sq Ft
  • Built 1904

  Last Sold Summary

  • 15% Above List Price
  • $982/SF
  • 16 Days On Market

  Current Estimated Value $1,796,523

  Last Listing Agent Wendy Ryan Brown Harris Stevens

  69 River St, Southport, CT 06890
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  Est $2,337,872 Not Listed For Sale

  3 Maple Ln, Westport, CT 06880

  • 5 Beds
  • 5.5 Baths
  • 5,268 Sq Ft
  • Built 1986

  3 Maple Ln, Westport, CT 06880

  Last Sold Summary

  • 18% Above List Price
  • $375/SF
  • 16 Days On Market

  • Last Sold Price $1,975,000
  • Jul 16, 2024

  Last Listing Agent Michael Lissack The Virtual Realty Group
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  /26

  $8,995,000

  • 8 Beds
  • 10 Baths
  • 15,172 Sq Ft

  2 Judy Point Ln, Westport, CT 06880

  Set on over 3 private acres with sweeping water views, 2 Judy Point Lane is a remarkable Westport waterfront estate offering approximately 14,000 square feet of living space and a rare compound-style layout. The property consists of two substantial residences connected by a breezeway, creating exceptional flexibility for multi-generational living, extended guests, or a private guest house.

  Daniel Kramp Christie's International Real Estate

  2 Judy Point Ln, Westport, CT 06880
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  /6

  $1,100 Per Month

  • 1 Bath
  • 300 Sq Ft
  • Apartment for Rent

  89-91 Jetland Place Unit 42, Bridgeport, CT 06605

  Well-maintained first-floor studio located on a quiet street in the desirable Black Rock area. This clean and efficient unit offers a practical layout, ideal for someone looking for an affordable and comfortable living space. Conveniently situated within walking distance to shops, restaurants, and everyday necessities. A great option for anyone seeking a safe, low-maintenance place to live while

  Jeff P Puciato Realty Group

  89-91 Jetland Place Unit 42, Bridgeport, CT 06605
• 

  $1,400,000 Sold Nov 10, 2025

  17 Grays Farm Rd, Weston, CT 06883

  • 4 Beds
  • 3.5 Baths
  • 3,166 Sq Ft
  • Built 1963

  Last Sold Summary

  • 12% Below List Price
  • $442/SF
  • 106 Days On Market

  Current Estimated Value $1,425,504

  Last Listing Agent Mary Palmieri Gai Berkshire Hathaway NE Prop.

  17 Grays Farm Rd, Weston, CT 06883
• 

  Est $850,574 Not Listed For Sale

  230 Saugatuck Ave Unit 20, Westport, CT 06880

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

  230 Saugatuck Ave Unit 20, Westport, CT 06880

  Last Sold Summary

  • 17% Above List Price
  • $608/SF
  • 125 Days On Market

  • Last Sold Price $730,000
  • Sep 18, 2024

  Last Listing Agent Mary Kate Klemish-Boehm Brown Harris Stevens
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  /35

  $969,000 Open Sat 12PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 2,068 Sq Ft

  370 Nepas Rd, Fairfield, CT 06825

  Welcome to "The Nature House": Nestled in the highly sought-after Lake Mohegan area, this bright and welcoming Colonial sits on a picturesque .57-acre property surrounded by vibrant gardens, and charming, walkable streets. Whether you enjoy an active lifestyle or quiet retreat, this location offers the best of both. An easy stroll to the lake with sandy beach, scenic hiking trails, new splash

  Denise Walsh William Raveis Real Estate

  370 Nepas Rd, Fairfield, CT 06825
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  /14

  $2,000 Per Month

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

  195 Laurel Place, Bridgeport, CT 06604

  Beautifully renovated 1 bedroom, 1 bathroom apartment in the desirable Brooklawn neighborhood of Bridgeport. This fully updated unit features brand new stainless steel appliances, sleek countertops, white shaker cabinets, and gleaming hardwood floors throughout. A brand new central air and heating system with smart thermostat allows you to control the temperature right from your phone. In-unit

  Chris Eanniello William Raveis Real Estate

  195 Laurel Place, Bridgeport, CT 06604
• 

  $1,550,000 Sold Nov 20, 2025

  8 Washington Ave, Westport, CT 06880

  • 5 Beds
  • 3 Baths
  • 3,090 Sq Ft
  • Built 1890

  Last Sold Summary

  • 6% Below List Price
  • $502/SF
  • 84 Days On Market

  Last Listing Agent Susan Vanech Compass Connecticut, LLC

  8 Washington Ave, Westport, CT 06880
• 

  Est $798,033 Not Listed For Sale

  230 Saugatuck Ave Unit 8, Westport, CT 06880

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

  230 Saugatuck Ave Unit 8, Westport, CT 06880

  Last Sold Summary

  • 6% Above List Price
  • $629/SF
  • 32 Days On Market

  • Last Sold Price $755,000
  • Sep 23, 2024

  Last Listing Agent Scott Wright RE/MAX

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