Southport, CT Homes

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  /40

  $5,725,000 Pending

  • 7 Beds
  • 9 Baths
  • 13,615 Sq Ft

  9 Greenbrier Rd, Westport, CT 06880

  A RARE SECOND CHANCE. This estate drew multiple offers within days, then sellers pressed pause. With plans now finalized, it's back on the market. Charming. Unique. Soulful. These are the words the current owner uses to describe this exceptional estate-and from the moment you arrive, you'll understand why. Poised on 2.85 private acres, this exceptional estate seamlessly weaves timeless heritage

  Cindy Raney Coldwell Banker Realty

  9 Greenbrier Rd, Westport, CT 06880
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  $7,500 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • House for Rent

  87 Old Dam Rd, Fairfield, CT 06824

  Hard to find direct waterfront rental home featuring private dock, Long Island Sound access & deeded Fairfield beach access. Full home renovation recently completed including new kitchen & baths, freshly painted interior/exterior, shining HW floors & new efficient mechanicals. Bright open floor plan includes spacious kitchen, dining area & living room with fireplace & soaring vaulted ceiling.

  Katie O'Grady Compass Connecticut, LLC

  87 Old Dam Rd, Fairfield, CT 06824
• 

  $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 $832,801

  Last Listing Agent Katie O'Grady Compass Connecticut, LLC

  985 S Pine Creek Rd, Fairfield, CT 06824
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  Est $2,887,356 Not Listed For Sale

  10 Evergreen Ave, Westport, CT 06880

  • 4 Beds
  • 4.5 Baths
  • 4,982 Sq Ft
  • Built 1993

  10 Evergreen Ave, Westport, CT 06880

  Last Sold Summary

  • 3% Above List Price
  • $562/SF
  • 70 Days On Market

  Last Sold Price $2,800,000

  Last Listing Agent Emily Gordon Coldwell Banker Realty
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  /40

  $1,250,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,688 Sq Ft

  164 Farist Rd, Fairfield, CT 06825

  Timeless 1896 Colonial Farmhouse with Renovated Barn in the heart of Fairfield. Step into the charm of a bygone era with the comforts of modern living in this beautiful, preserved Vintage home, thoughtfully expanded and updated. Rich in character, the home features soaring ceilings, original beams and vaulted ceilings, 2 staircases, one elegantly curved, gleaming hardwood floors, wide plank

  Bette Gigliotti William Raveis Real Estate

  164 Farist Rd, Fairfield, CT 06825
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  /16

  $2,300 total monthly price

  • 2 Beds
  • 1 Bath
  • 3,350 Sq Ft
  • House for Rent

  2449 North Ave Unit 2, Bridgeport, CT 06604

  Spacious and light-filled 2-bedroom rental located in a well-maintained multi-family home. This large unit features high ceilings that create an open, airy feel throughout. Enjoy comfortable living in a convenient location close to shopping, dining, and everyday amenities. A great opportunity for those seeking space, charm, and easy access to everything you need. 2nd floor unit access to covered

  Bobbie Poeltl Abagnale William Pitt Sotheby's Int'l

  2449 North Ave Unit 2, Bridgeport, CT 06604
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  $3,240,000 Sold Mar 28, 2025

  1 Sturges Hwy, Westport, CT 06880

  • 6 Beds
  • 6 Baths
  • 5,790 Sq Ft
  • Built 1955

  Last Sold Summary

  • 2% Below List Price
  • $560/SF
  • 31 Days On Market

  Last Listing Agent Annie Klyver Higgins Group Real Estate

  1 Sturges Hwy, Westport, CT 06880
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  Est $3,388,765 Not Listed For Sale

  184 Cross Hwy, Westport, CT 06880

  • 5 Beds
  • 6 Baths
  • 6,010 Sq Ft
  • Built 1998

  184 Cross Hwy, Westport, CT 06880

  Last Sold Summary

  • 9% Above List Price
  • $516/SF
  • 15 Days On Market

  Last Sold Price $3,100,000

  Last Listing Agent Annette Coplit Coldwell Banker Realty
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  /15

  $1,200,000

  • 4 Beds
  • 2.5 Baths
  • 2,084 Sq Ft

  5 Inwood Ln, Westport, CT 06880

  Walk to beach, Compo Beach neighborhood. Inwood Lane is off of Hale Road, off of Hillspoint Road. The backyard of this home views lovely homes on Loretta Court. Charming, with four bedrooms and a large family room. Lovely deck overlooking the backyard with flowers and fauna. The master suite has it's own wing, with fireplace, walk in closet, and full bath, and is accessible to the large deck

  Charlotte Cotton William Raveis Real Estate

  5 Inwood Ln, Westport, CT 06880
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  /20

  $5,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,053 Sq Ft
  • Apartment for Rent

  180 Ruane St Unit 1, Fairfield, CT 06824

  SUMMER 2026 ONLY JULY & AUGUST - fully furnished rental. Completely updated first floor unit with Bosch appliances, quartz countertops, inset electric fireplace, hardwood floors and luxury finishes throughout. Walk to train, town and beach.

  Ryan Ciambriello Houlihan Lawrence

  180 Ruane St Unit 1, Fairfield, CT 06824
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  $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 $993,820

  Last Listing Agent Pam Toner Berkshire Hathaway NE Prop.

  36 Rayfield Rd, Westport, CT 06880
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  Est $1,901,927 Not Listed For Sale

  60 Edgewater Commons Ln, Westport, CT 06880

  • 4 Beds
  • 2.5 Baths
  • 3,036 Sq Ft
  • Built 1999

  60 Edgewater Commons Ln, Westport, CT 06880

  Last Sold Summary

  • 27% Above List Price
  • $494/SF
  • 6 Days On Market

  Last Sold Price $1,500,000

  Last Listing Agent Leslie Clarke Compass Connecticut, LLC
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  /15

  $1,399,999 New Construction

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

  28 Country Rd, Fairfield, CT 06824

  Take me home Country Road...... Local builder with proven excellence in masterfully crafted homes is nearing completion on the newest project. Country Estates, soon to be completed. These townhomes (2)are adjoined only by garages, meaning no shared interior walls for maximum privacy. Tucked away on a charming half circle street in the University area, this home offers a seamless design for the

  Denise Daniels-biagi Coldwell Banker Realty

  28 Country Rd, Fairfield, CT 06824
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  /12

  $2,400 total monthly price

  • 3 Beds
  • 1 Bath
  • 2,676 Sq Ft
  • Townhouse for Rent

  725 Beechwood Ave Unit 1, Bridgeport, CT 06605

  Beautifully renovated first-floor apartment featuring 3 spacious bedrooms and 1 full bathroom, offering modern finishes and comfortable living. Fully updated, this unit boasts a brand-new kitchen with stylish cabinets, sleek countertops, and new appliances, along with a modern bathroom designed with contemporary fixtures. Enjoy luxury vinyl flooring, fresh neutral paint, and recessed lighting

  Angel Mora eXp Realty

  725 Beechwood Ave Unit 1, Bridgeport, CT 06605
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  $1,625,000 Sold Mar 25, 2025

  255 Hillside Rd, Fairfield, CT 06824

  • 4 Beds
  • 3.5 Baths
  • 3,918 Sq Ft
  • Built 1995

  Last Sold Summary

  • 2% Above List Price
  • $415/SF
  • 24 Days On Market

  Current Estimated Value $1,648,998

  Last Listing Agent Cindy Raney Coldwell Banker Realty

  255 Hillside Rd, Fairfield, CT 06824
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  Est $1,518,867 Not Listed For Sale

  329 Lansdowne, Westport, CT 06880

  • 2 Beds
  • 2 Baths
  • 2,450 Sq Ft
  • Built 1986

  329 Lansdowne, Westport, CT 06880

  Last Sold Summary

  • 1% Above List Price
  • $612/SF
  • 16 Days On Market

  Last Sold Price $1,500,000

  Last Listing Agent Kathleen DeRossi William Pitt
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  /40

  $1,430,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,416 Sq Ft

  783 Post Rd E Unit 201, Westport, CT 06880

  AMAZING NEW CONSTRUCTION! Located in the heart of Westport, The Gables of Westport presents a collection of eight townhomes and five flats, blending sophisticated design with the ease of in-town living. Enjoy close proximity to Metro-North, major highways, Longshore Club & Park, Compo Beach, Levitt Pavilion, Westport Country Playhouse, fine dining, shopping, and entertainment. Crafted by local

  Todd Gibbons Boost Real Estate Group

  783 Post Rd E Unit 201, Westport, CT 06880
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  /21

  $1,895 total monthly price

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

  2806 Fairfield Ave Unit 302, Bridgeport, CT 06605

  The Newly Renovated Wanis Building! Spectacular third floor, one bedroom, one bathroom end unit available for March 1st occupancy! The unit has been professionally cleaned and offers 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

  John Kleps Berkshire Hathaway NE Prop.

  2806 Fairfield Ave Unit 302, Bridgeport, CT 06605
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  $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 $902,505

  Last Listing Agent Valerie Alvarez Serhant Connecticut, LLC

  154 Warsaw St, Fairfield, CT 06825
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  Est $1,583,158 Not Listed For Sale

  317 Lansdowne, Westport, CT 06880

  • 3 Beds
  • 3 Baths
  • 2,450 Sq Ft
  • Built 1986

  317 Lansdowne, Westport, CT 06880

  Last Sold Summary

  • 1% Below List Price
  • $654/SF
  • 16 Days On Market

  Last Sold Price $1,602,000

  Last Listing Agent Laurie Morris Compass Connecticut, LLC
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  /40

  $5,999,000 Pending

  • 6 Beds
  • 7 Baths
  • 6,100 Sq Ft

  9 Pond Edge Rd, Westport, CT 06880

  Experience the pinnacle of Compo Beach living at 9 Pond Edge Road, a rare coastal sanctuary offering immediate beach access with the peace of mind of an elevated, flood-safe setting. Spanning 6,100 square feet across four impeccably finished levels, this 6-bedroom home is designed for effortless entertaining and everyday relaxation. Sunlight fills the open great room (with WBF) and dining area,

  Meredith Kamo Compass Connecticut, LLC

  9 Pond Edge Rd, Westport, CT 06880
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  /27

  $3,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Townhouse for Rent

  215 York Rd, Fairfield, CT 06825

  Welcome to 215 York Road, a recently remodeled duplex that feels fresh, clean, and move-in ready. Nearly every surface has been thoughtfully updated, offering modern finishes and a comfortable, functional layout. The first floor features brand new luxury vinyl plank flooring, while the second level offers new plush carpeting. The kitchen has been completely renovated with new tile flooring,

  Alexander Walton RE/MAX Heritage

  215 York Rd, Fairfield, CT 06825
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  $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 $1,736,966

  Last Listing Agent Wendy Ryan Brown Harris Stevens

  69 River St, Southport, CT 06890
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  Est $798,932 Not Listed For Sale

  46 Edgewater Commons Ln, Westport, CT 06880

  • 2 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • Built 1985

  46 Edgewater Commons Ln, Westport, CT 06880

  Last Sold Summary

  • 9% Above List Price
  • $326/SF
  • 97 Days On Market

  Last Sold Price $730,000

  Last Listing Agent Mark Gilrain Brown Harris Stevens
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  /5

  $2,595,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,478 Sq Ft

  154 Gorham Rd, Fairfield, CT 06824

  Spectacular New Construction in the Sasco Beach Area. Don't miss the rare opportunity to customize and make this home your own.Located on almost a half acre of peaceful, private property, last house on a cul-de-sac, backing up to open land on Sasco Hill. Distant water views, serenity, extensively manicured yard and just steps to South Pine Creek Beach.. a very special quaint beach with life

  Bette Gigliotti William Raveis Real Estate

  154 Gorham Rd, Fairfield, CT 06824
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  $35,000 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,762 Sq Ft
  • House for Rent

  200 Hillspoint Rd, Westport, CT 06880

  Compo Beach, Westport | July 2026 Summer Rental Experience the magic of waterfront living at this 3BD | 2.2BA Compo Beach retreat-where sunrises and moonrises paint the sky from a stunning rooftop deck with wide, unobstructed views of the Sound. Designed for peace and comfort, this fully furnished home offers a zen-like atmosphere perfect for a cozy holiday stay or memorable Thanksgiving

  Kim Harizman Compass Connecticut, LLC

  200 Hillspoint Rd, Westport, CT 06880
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  $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 $1,425,506

  Last Listing Agent Mary Palmieri Gai Berkshire Hathaway NE Prop.

  17 Grays Farm Rd, Weston, CT 06883
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  Est $837,155 Not Listed For Sale

  8 Davenport Ave, Westport, CT 06880

  • 3 Beds
  • 1 Bath
  • 1,272 Sq Ft
  • Built 1951

  8 Davenport Ave, Westport, CT 06880

  Last Sold Summary

  • 21% Above List Price
  • $542/SF
  • 54 Days On Market

  Last Sold Price $690,000

  Last Listing Agent Shelly Olivadoti Berkshire Hathaway Home Services
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  /32

  $975,000

  • 3 Beds
  • 2 Baths
  • 1,183 Sq Ft

  65 W Parish Rd, Westport, CT 06880

  Bright, beautifully maintained home in Westport's desirable Greens Farms neighborhood. Sun-filled rooms and soaring 91/2-foot ceilings create an open, airy feel throughout the home. The flexible layout includes a bedroom and new full bathroom on the main level, with two additional bedrooms and a full bath upstairs, ideal for guests, a home office, or comfortable family living. The private fenced

  Christine Oleynick Keller Williams Realty

  65 W Parish Rd, Westport, CT 06880
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  /26

  $6,500 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 1,964 Sq Ft
  • House for Rent

  97 Godfrey Rd, Fairfield, CT 06825

  Walking distance to Lake Mohegan, and just 5 minutes from the golf course, library, tennis courts, and Blackrock shopping. This beautiful contemporary ranch offers about 2000 sq ft on the 1st floor and an additional 1,100 sq ft in the lower level, 4 to 5 bedrooms, 3.5 bathrooms, a 2-car garage, full house generator and a private backyard spanning 0.46 acres. On the First Floor, the open kitchen

  Dorothee Ancel Brown Harris Stevens

  97 Godfrey Rd, Fairfield, CT 06825
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  $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

  Current Estimated Value $1,653,475

  Last Listing Agent Susan Vanech Compass Connecticut, LLC

  8 Washington Ave, Westport, CT 06880
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  Est $3,455,038 Not Listed For Sale

  318 Greens Farms Rd, Westport, CT 06880

  • 5 Beds
  • 7 Baths
  • 7,459 Sq Ft
  • Built 1986

  318 Greens Farms Rd, Westport, CT 06880

  Last Sold Summary

  • 23% Above List Price
  • $375/SF
  • 47 Days On Market

  Last Sold Price $2,800,000

  Last Listing Agent Maya Wertheim Coldwell Banker Realty
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  /3

  $3,950,000 Coming Soon

  • 5 Beds
  • 9 Baths
  • 7,040 Sq Ft

  44 Pumpkin Hill Rd, Westport, CT 06880

  Set in one of Westport's most sought-after central neighborhoods, this gracious 5+ bedroom custom Colonial with a stunning gunite pool and spa offers the perfect balance of timeless elegance and modern comfort. Sun-filled interiors and thoughtful design create seamless flow for both entertaining and everyday living. The main level features a private office, elegant dining room with butler's

  Christine Oleynick Keller Williams Realty

  44 Pumpkin Hill Rd, Westport, CT 06880
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  /40

  $10,000 total monthly price

  • 4 Beds
  • 3 Baths
  • 2,027 Sq Ft
  • House for Rent

  1 Otter Trail, Westport, CT 06880

  Tenants have described this charming bungalow as "a thoughtfully-curated 5-star accommodation in a fantastic location". Furnished rentals do not get any better! You can enjoy this sparkling clean and tastefully decorated cottage for 12 to 15 months. WALKABLE TO TRAIN, Saugatuck Center, Levitt Pavilion, our award-winning Westport Library and so much more. Beautiful Compo Beach and Longshore Golf,

  Martha Eidman Coldwell Banker Realty

  1 Otter Trail, Westport, CT 06880
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  $1,705,000 Sold Jun 27, 2025

  6 N Ridge Rd, Westport, CT 06880

  • 5 Beds
  • 3.5 Baths
  • 3,320 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Above List Price
  • $514/SF
  • 11 Days On Market

  Current Estimated Value $1,771,625

  Last Listing Agent Cindy Raney Coldwell Banker Realty

  6 N Ridge Rd, Westport, CT 06880
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  Est $2,285,277 Not Listed For Sale

  17 Harborview Rd, Westport, CT 06880

  • 4 Beds
  • 3.5 Baths
  • 3,921 Sq Ft
  • Built 1986

  17 Harborview Rd, Westport, CT 06880

  Last Sold Summary

  • 17% Above List Price
  • $497/SF
  • 13 Days On Market

  Last Sold Price $1,950,000

  Last Listing Agent Susan Tracy Higgins Group Bedford Square
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  /22

  $879,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,747 Sq Ft

  25 Helen St, Fairfield, CT 06824

  **THANK YOU FOR YOUR INTEREST: SELLER REQUESTS HIGHEST & BEST OFFERS BY 6PM SUNDAY FEBRUARY 8TH** Welcome to 25 Helen Street, ideally located in the heart of Fairfield-just a short walk to town, the train, shops, and dining. This charming home blends classic character with thoughtful updates, offering hardwood floors throughout and a warm, inviting feel from the moment you step inside. The main

  Clyde Wauchope Coldwell Banker Realty

  25 Helen St, Fairfield, CT 06824
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  /40

  $37,000 total monthly price

  • 5 Beds
  • 11 Baths
  • 8,361 Sq Ft
  • House for Rent

  345 Governors Ln, Fairfield, CT 06824

  Available August 1- September 5: Fully Furnished. You'll never want to leave 'Splendido Manor', an iconic estate perfect for the sophisticated and active lifestyle. This sprawling 4-acre compound nestled in the heart of Greenfield Hill has all of the amenities of an idyllic retreat. With 5 bedrooms, a separate one-bedroom guest cottage, a lighted Sport/Tennis Court, a 1900 SF Indoor/Outdoor Pool

  Laura Kottler Compass Connecticut, LLC

  345 Governors Ln, Fairfield, CT 06824
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  $1,425,000 Sold Jun 20, 2025

  3 Donald Dr, Westport, CT 06880

  • 3 Beds
  • 2.5 Baths
  • 2,714 Sq Ft
  • Built 1983

  Last Sold Summary

  • 19% Above List Price
  • $525/SF
  • 11 Days On Market

  Current Estimated Value $1,424,252

  Last Listing Agent Nikunj Gandhi Equity Capital Real Estate

  3 Donald Dr, Westport, CT 06880
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  Est $1,245,168 Not Listed For Sale

  3 Concord Ln, Westport, CT 06880

  • 2 Beds
  • 2.5 Baths
  • 1,769 Sq Ft
  • Built 1986

  3 Concord Ln, Westport, CT 06880

  Last Sold Summary

  • 7% Above List Price
  • $659/SF
  • 84 Days On Market

  Last Sold Price $1,165,000

  Last Listing Agent Lainie Floyd William Pitt

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