Southport, CT Homes

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  /37

  $1,399,000 Pending

  • 4 Beds
  • 3 Baths
  • 4,057 Sq Ft

  88 Overhill Rd, Fairfield, CT 06824

  Please submit highest and best by 5PM Monday, October 6th. Classic Lines. Creative Soul. Located on one of Sasco Hill's most beloved streets, this classic Colonial offers timeless curb appeal and a highly walkable lifestyle. Inside, thoughtful architectural details - arched doorways, original built-ins, and natural light throughout - create a warm, character-rich feel. The main level begins with

  Cindy Raney Coldwell Banker Realty

  88 Overhill Rd, Fairfield, CT 06824
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  /16

  $3,000 total monthly price

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

  2 Oak St Unit upper, Westport, CT 06880

  Sun-filled rental in a charming farmhouse just north of downtown Westport! With a sparkling recently added new kitchen and gorgeous restored antique floors, this sun-filled second floor rental is a stylish and happy place to be. With central air AND a garage, this checks all the boxes. Set in lovely neighborhood close to town, this spacious 980SF rental comprises the entire second floor of this

  Lisa Rowan William Pitt Sotheby's Int'l

  2 Oak St Unit upper, Westport, CT 06880
• 

  $4,250,000 Sold Jul 24, 2025

  3113 Bronson Rd, Fairfield, CT 06824

  • 5 Beds
  • 6 Baths
  • 8,004 Sq Ft
  • Built 1840

  Last Sold Summary

  • 15% Below List Price
  • $531/SF
  • 41 Days On Market

  Last Listing Agent Andrew Whiteley Brown Harris Stevens

  3113 Bronson Rd, Fairfield, CT 06824
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  Est $1,127,533 Not Listed For Sale

  220 Riverside Ave Unit 8, Westport, CT 06880

  • 2 Beds
  • 2.5 Baths
  • 1,291 Sq Ft
  • Built 2005

  220 Riverside Ave Unit 8, Westport, CT 06880

  Last Sold Summary

  • 3% Below List Price
  • $902/SF
  • 7 Days On Market

  Last Sold Price $1,165,000

  Last Listing Agent Debra Shaughnessy Coldwell Banker Realty
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  $2,495,000

  • 2 Beds
  • 2.5 Baths
  • 1,760 Sq Ft

  41 Richmondville Ave Unit Duplex 2, Westport, CT 06880

  IMMEDIATE OCCUPANCY! The FInal opportunity to own at The Mill Westport! This impressive home has floor-to-ceiling windows, wood floors and a linear gas fireplace. The kitchen has an oversized island, high-end appliances, and is complete with custom cabinetry. The 2 bedrooms are on opposites sides of the home for maximum privacy. The primary suite has a generous walk-in closet and a luxurious

  Ashlei De Souza Serhant LLC

  41 Richmondville Ave Unit Duplex 2, Westport, CT 06880
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  /14

  $2,200 total monthly price

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

  450 Poplar St, Bridgeport, CT 06605

  Bright & Spacious 3BR/1BA – 3rd Floor Unit in Quiet Neighborhood Near Fairfield BorderMove-in ready 3-bedroom, 1-bath apartment located on the 3rd floor in a clean and well-maintained property. This bright and spacious unit features large rooms, abundant natural sunlight, and a comfortable, functional layout.Conveniently situated near the Fairfield border with easy access to

  450 Poplar St, Bridgeport, CT 06605
• 

  $1,600,000 Sold Apr 04, 2025

  1242 Old Academy Rd, Fairfield, CT 06824

  • 3 Beds
  • 4 Baths
  • 3,225 Sq Ft
  • Built 1946

  Last Sold Summary

  • 23% Above List Price
  • $496/SF
  • 9 Days On Market

  Last Listing Agent Denise Walsh William Raveis Real Estate

  1242 Old Academy Rd, Fairfield, CT 06824
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  Est $1,116,226 Not Listed For Sale

  220 Riverside Ave Unit 7, Westport, CT 06880

  • 2 Beds
  • 2.5 Baths
  • 1,291 Sq Ft
  • Built 2005

  220 Riverside Ave Unit 7, Westport, CT 06880

  Last Sold Summary

  • 14% Above List Price
  • $755/SF
  • 21 Days On Market

  Last Sold Price $975,000

  Last Listing Agent Debra Shaughnessy Coldwell Banker Realty
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  /35

  $1,750,000 Pending

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

  785 Post Rd E Unit 303, 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

  785 Post Rd E Unit 303, Westport, CT 06880
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  /21

  $26,000 total monthly price

  • 4 Beds
  • 3 Baths
  • 3,420 Sq Ft
  • House for Rent

  2 Valley Rd, Westport, CT 06880

  Family retreat with in ground pool and outdoor entertaining and cooking area is available for your summer getaway. Bike to the beach from this 4 bedroom 4 full bath cozy home with welcoming front porch, playroom and full bath on every level. Primary suite is private and features a full bath, and balcony for your morning coffee. Huge new deck off kitchen. Three family bedrooms with full bath, open

  Lisa Neufeld William Raveis Real Estate

  2 Valley Rd, Westport, CT 06880
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  $4,200,000 Sold Jul 10, 2025

  11 Gault Park Dr, Westport, CT 06880

  • 7 Beds
  • 9 Baths
  • 6,898 Sq Ft
  • Built 2008

  Last Sold Summary

  • 5% Above List Price
  • $609/SF
  • 58 Days On Market

  Current Estimated Value $4,166,539

  Last Listing Agent Imke Lohs Compass Connecticut, LLC

  11 Gault Park Dr, Westport, CT 06880
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  Est $2,822,969 Not Listed For Sale

  4A Woodhill Rd, Westport, CT 06880

  • 5 Beds
  • 5 Baths
  • 4,733 Sq Ft
  • Built 2006

  4A Woodhill Rd, Westport, CT 06880

  Last Sold Summary

  • 12% Above List Price
  • $534/SF
  • 26 Days On Market

  Last Sold Price $2,527,500

  Last Listing Agent Cindy Raney Coldwell Banker Realty
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  /39

  $1,385,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,300 Sq Ft

  785 Post Rd E Unit 302, Westport, CT 06880

  Nearly completed this residential flat offers the best of first floor living. Situated in a prime location in the heart of Westport, this development by RPM Home features a limited collection of eight luxury townhomes and five flats, designed for convenient in-town living. This particular unit offers desirable single-level living and is filled with natural light thanks to expansive Marvin windows

  Todd Gibbons Boost Real Estate Group

  785 Post Rd E Unit 302, Westport, CT 06880
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  $1,950 total monthly price

  • 1 Bed
  • 1 Bath
  • 676 Sq Ft
  • Condo for Rent

  255 Fairfield Woods Rd Unit 2, Fairfield, CT 06825

  255 Fairfield Woods Rd Unit 2, Fairfield, CT 06825
• 

  $1,940,000 Sold Nov 06, 2025

  93 Millspaugh Dr, Fairfield, CT 06824

  • 5 Beds
  • 5 Baths
  • 4,440 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Above List Price
  • $437/SF
  • 34 Days On Market

  Current Estimated Value $1,871,496

  Last Listing Agent Ken Betza Higgins Group Real Estate

  93 Millspaugh Dr, Fairfield, CT 06824
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  Est $4,601,235 Not Listed For Sale

  25 Flower Farm Cir, Westport, CT 06880

  • 5 Beds
  • 7.5 Baths
  • 6,404 Sq Ft
  • Built 2007

  25 Flower Farm Cir, Westport, CT 06880

  Last Sold Summary

  • 5% Above List Price
  • $687/SF
  • 85 Days On Market

  Last Sold Price $4,400,000

  Last Listing Agent Robert Appell Coldwell Banker Realty
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  /12

  $630,000 Pending

  • 9 Beds
  • 3 Baths
  • 3,047 Sq Ft

  203 Lenox Ave Unit 205, Bridgeport, CT 06605

  Three family mainly occupied as the third floor was recently renovated. Owners are ready to pass the baton to the next owner. Take a look and present your best offer. AS IS SALE.

  Ruth-Ann Mitchell Larracuente & Johnson Realty, LLC

  203 Lenox Ave Unit 205, Bridgeport, CT 06605
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  /14

  $2,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 882 Sq Ft
  • Apartment for Rent

  168 Alfred St Unit 1, Bridgeport, CT 06605

  Renovated first-floor 2-bedroom apartment located in the desirable Black Rock area. This unit features a modern interior with updated finishes and a bright, functional layout. Enjoy the comfort of central A/C, plus laundry included for added convenience. Off-street parking available. Ideally situated near the train station, bus lines, shopping, dining, and major routes-perfect for commuters.

  Jose Cuahuizo Whitestone Real Estate Group

  168 Alfred St Unit 1, Bridgeport, CT 06605
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  $1,300,000 Sold Mar 10, 2025

  315 Harvest Commons Unit 315, Westport, CT 06880

  • 2 Beds
  • 3 Baths
  • 2,262 Sq Ft
  • Built 1982

  Last Sold Summary

  • 31% Above List Price
  • $575/SF
  • 0 Days On Market

  Last Listing Agent Susan Cassidy Coldwell Banker Realty

  315 Harvest Commons Unit 315, Westport, CT 06880
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  Est $4,607,610 Not Listed For Sale

  6 Pan Handle Ln, Westport, CT 06880

  • 5 Beds
  • 9 Baths
  • 10,471 Sq Ft
  • Built 2007

  6 Pan Handle Ln, Westport, CT 06880

  Last Sold Summary

  • 7% Above List Price
  • $411/SF
  • 81 Days On Market

  Last Sold Price $4,300,000

  Last Listing Agent Mersene Norbom William Pitt
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  /21

  $1,279,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft

  15 Wright St, Westport, CT 06880

  Another opportunity on one of Westport's most desirable streets! This Antique gem has been lovingly cared for by the same family for 31 years. It underwent massive renovations in 2017. Some walls were removed to create a beautiful open gourmet kitchen which opens to a charming Family Room with fireplace. There is also a front living room with pretty builtins. All three full baths have been

  Laurie Morris Compass Connecticut, LLC

  15 Wright St, Westport, CT 06880
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  /15

  $2,450 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,482 Sq Ft
  • Condo for Rent

  96 Seaview Terrace Unit 2, Bridgeport, CT 06605

  MOVE RIGHT IN AND ENJOY ALL BLACK ROCK OFFERS FROM YOUR SPACIOUS 3 BEDROOM 2ND FLOOR APARTMENT FEATURING FORMAL DINING ROOM, EAT IN KITCHEN, OFFICE/DEN, PRIVATE REAR DECK AND OFF STREET PARKING. FRESHLY PAINTED, HARDWOOD FLOORING WITH NATURAL SUNLIGHT THROUGHOUT, ALL STEPS TO ST. MARY'S BY THE SEA, ELLSWORTH PARK, HARBORVIEW MARKET, RESTAURANTS/DINING, METRO NORTH TRAIN STATION WITH EASY ACCESS

  96 Seaview Terrace Unit 2, Bridgeport, CT 06605
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  $2,550,000 Sold Jun 26, 2025

  97 Benson Place, Fairfield, CT 06824

  • 5 Beds
  • 5 Baths
  • 4,347 Sq Ft
  • Built 2016

  Last Sold Summary

  • $587/SF
  • 31 Days On Market

  Current Estimated Value $2,716,270

  Last Listing Agent Patricia Shea Coldwell Banker Realty

  97 Benson Place, Fairfield, CT 06824
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  Est $1,716,049 Not Listed For Sale

  36 Terra Nova Cir, Westport, CT 06880

  • 3 Beds
  • 3 Baths
  • 3,691 Sq Ft
  • Built 2004

  36 Terra Nova Cir, Westport, CT 06880

  Last Sold Summary

  • 6% Above List Price
  • $440/SF
  • 16 Days On Market

  Last Sold Price $1,625,000

  Last Listing Agent Brandy Hall Higgins Group Real Estate
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  /28

  $899,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 3,257 Sq Ft

  84 Algonquin Rd, Fairfield, CT 06825

  Located on beautiful Brooklawn street, this 10RM,4BR, 4BTH COL combines Classic 1920's architecture with spacious living! HDWD floors & custom picture-frame moldings accent wide entry FOYER opening to Large LR w/fplc & 4-season SUNROOM w/French doors to DECK. Formal DR w/fplc overlooks prvt backyard and leads to Gourmet EIK w/butler's pantry & FULL BTH on main level. Upstairs features Primary

  Carol McCullough Berkshire Hathaway NE Prop.

  84 Algonquin Rd, Fairfield, CT 06825
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  /24

  $5,200 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • House for Rent

  892 Reef Rd, Fairfield, CT 06824

  Summer in "The Sandbox"! Wonderful rental available July and August. Walkable to Penfield Beach, close to downtown and all the amenities that Fairfield has to offer. 3 Bedroom, 2 full baths. Sleep 6. Stylish living and dining area. Fully appointed/equipped kitchen. Inviting family room. Wonderful sunroom with slider steps out to spacious deck overlooking private fenced yard, patio and views of

  Patricia Walker Coldwell Banker Realty

  892 Reef Rd, Fairfield, CT 06824
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  $1,560,000 Sold Jan 13, 2026

  85 Patrick Dr, Fairfield, CT 06824

  • 4 Beds
  • 3.5 Baths
  • 2,944 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Above List Price
  • $530/SF
  • 60 Days On Market

  Current Estimated Value $1,434,776

  Last Listing Agent Jackie Davis William Raveis Real Estate

  85 Patrick Dr, Fairfield, CT 06824
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  Est $1,557,524 Not Listed For Sale

  76 Terra Nova Cir, Westport, CT 06880

  • 3 Beds
  • 2.5 Baths
  • 2,358 Sq Ft
  • Built 2004

  76 Terra Nova Cir, Westport, CT 06880

  Last Sold Summary

  • 3% Below List Price
  • $679/SF
  • 36 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent Alex Chingas Coldwell Banker Realty
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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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  /45

  $2,650 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,014 Sq Ft
  • Condo for Rent

  125 Tunxis Hill Rd Unit 2, Fairfield, CT 06825

  Welcome to your future home! This spacious 2-bedroom, 2-bathroom condo/apartment is available for rent starting 04/01/2026. Nestled in a vibrant community, this residence offers 1,014 sq. ft. of comfort and style, making it a perfect fit for anyone. As a non-smoking property, this residence ensures an inviting and fresh environment at all times. You'll ink a 1-year lease and pay a

  125 Tunxis Hill Rd Unit 2, Fairfield, CT 06825
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  $540,000 Sold Dec 18, 2025

  709 Tunxis Hill Rd, Fairfield, CT 06825

  • 3 Beds
  • 1.5 Baths
  • 1,409 Sq Ft
  • Built 1919

  Last Sold Summary

  • 5% Above List Price
  • $383/SF
  • 30 Days On Market

  Current Estimated Value $523,369

  Last Listing Agent Joseph Muratori Coldwell Banker Realty

  709 Tunxis Hill Rd, Fairfield, CT 06825
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  Est $3,856,529 Not Listed For Sale

  4 Michele Ln, Westport, CT 06880

  • 5 Beds
  • 8 Baths
  • 9,240 Sq Ft
  • Built 2005

  4 Michele Ln, Westport, CT 06880

  Last Sold Summary

  • 6% Above List Price
  • $396/SF
  • 63 Days On Market

  Last Sold Price $3,655,000

  Last Listing Agent Mary Ann Lindwall The Riverside Realty Group
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  /39

  $2,595,000 Under Contract

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

  1380 Old Academy Rd, Fairfield, CT 06824

  THANK YOU FOR YOUR STRONG INTEREST; SELLER REQUESTS HIGHEST & BEST OFFERS BY 4PM SAT 2/28 . One approaches 1380 Old Academy Road through a stone wall, where a paved drive opens to a gravel courtyard arrival framed by mature trees and open skies. Old Academy is the kind of street where homes feel settled rather than transitional, and where people arrive, put down roots, and tend to stay. Inside,

  Cindy Raney Coldwell Banker Realty

  1380 Old Academy Rd, Fairfield, CT 06824
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  /16

  $3,200 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,179 Sq Ft
  • House for Rent

  349 Marlborough Terrace, Fairfield, CT 06825

  Completely renovated 2nd fl unit located in Fairfield's desirable Tunxis Hill neighborhood. This bright and sunny apt offers 3 bedrooms, 1 full bath, office (flexible space) and beautiful hardwood floors throughout. The fully remodeled kitchen features crisp white cabinetry, quartz countertops, stainless steel appliances, a center island, and the convenience of an in-unit washer and dryer.

  Anthony Cali Preston Gray Real Estate

  349 Marlborough Terrace, Fairfield, CT 06825
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  $415,000 Sold Sep 17, 2025

  84-86 Dewey St, Bridgeport, CT 06605

  • 4 Beds
  • 2 Baths
  • 1,628 Sq Ft
  • Built 1918

  Last Sold Summary

  • 3% Below List Price
  • $255/SF
  • 103 Days On Market

  Last Listing Agent Robert Ganim RE/MAX Heritage

  84-86 Dewey St, Bridgeport, CT 06605
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  Est $3,390,953 Not Listed For Sale

  38 Whitney St, Westport, CT 06880

  • 6 Beds
  • 7.5 Baths
  • 5,417 Sq Ft
  • Built 2004

  38 Whitney St, Westport, CT 06880

  Last Sold Summary

  • 21% Above List Price
  • $518/SF
  • 54 Days On Market

  Last Sold Price $2,805,000

  Last Listing Agent Michelle Genovesi William Raveis Real Estate
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  /35

  $496,500

  • 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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  /23

  $2,450 - $3,250 total monthly price

  • 2 - 4 Beds
  • 1.5 Baths
  • 866 Sq Ft
  • Condo for Rent

  284 Berkeley Rd, Fairfield, CT 06825

  Freshly renovated duplex in a quiet, residential neighborhood. Comes with brand-new appliances and updated finishes throughout. Two rental units available now.Location Highlights:- Short distance to Aldi, Stop & Shop, and Planet Fitness- 10-minute drive to Trumbull Mall- Near local park and pickleball courtDetails:- Parking available- Two-month security deposit

  284 Berkeley Rd, Fairfield, CT 06825
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  $1,475,000 Sold Dec 19, 2025

  259 Wilton Rd, Westport, CT 06880

  • 5 Beds
  • 4.5 Baths
  • 3,589 Sq Ft
  • Built 1940

  Last Sold Summary

  • $411/SF
  • 23 Days On Market

  Current Estimated Value $1,449,889

  Last Listing Agent Inna Agujen Coldwell Banker Realty

  259 Wilton Rd, Westport, CT 06880
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  Est $2,411,678 Not Listed For Sale

  14 Sandy Hill Terrace, Westport, CT 06880

  • 5 Beds
  • 4.5 Baths
  • 5,084 Sq Ft
  • Built 2002

  14 Sandy Hill Terrace, Westport, CT 06880

  Last Sold Summary

  • 2% Above List Price
  • $464/SF
  • 12 Days On Market

  Last Sold Price $2,360,000

  Last Listing Agent Kathleen O'Connell Coldwell Banker Realty

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