Westport, CT Homes

• 

  Est $3,298,908

  Not Listed For Sale

  2 Bermuda Rd, Westport, CT 06880

  • 5 Beds
  • 3.5 Baths
  • 4,048 Sq Ft
  • Built 2003

  2 Bermuda Rd, Westport, CT 06880

  Last Sold Summary

  • 122 Days On Market
• 

  

  

  /39

  $2,425,000

  Under Contract

  • 4 Beds
  • 3 Baths
  • 2,959 Sq Ft

  9 Marsh Rd, Westport, CT 06880

  Don't miss this rare opportunity to wake up every day to the serenity of breathtaking water views & the charm of coastal living at 9 Marsh Rd, nestled in the coveted Saugatuck Shores of Westport. Perfectly positioned on a private 0.23-acre lot within a tranquil waterfront community, this FEMA-compliant home has been meticulously remodeled to offer modern elegance & everyday comfort. Step inside

  Veronica Monahan Compass Connecticut, LLC

  9 Marsh Rd, Westport, CT 06880
• 

  $2,625,000

  Sold Mar 04, 2026

  19A Darbrook Rd, Westport, CT 06880

  • 6 Beds
  • 8 Baths
  • 7,354 Sq Ft
  • Built 1987

  Last Sold Summary

  • 11% Below List Price
  • $357/SF
  • 178 Days On Market

  Current Estimated Value $3,071,524

  Last Listing Agent Nanci Lewis William Pitt Sotheby's Int'l

  19A Darbrook Rd, Westport, CT 06880
• 

  Est $2,206,148

  Not Listed For Sale

  5 Deerwood Rd, Westport, CT 06880

  • 4 Beds
  • 2.5 Baths
  • 3,182 Sq Ft
  • Built 1967

  5 Deerwood Rd, Westport, CT 06880

  Last Sold Summary

  • 7 Days On Market
• 

  

  

  /35

  $1,000,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft

  4 Davenport Ave, Westport, CT 06880

  Built in 1892, this designer-owned Victorian has been thoughtfully reimagined for modern living while preserving its original character and architectural integrity. Rooted in Westport's early history, the home reflects a seamless balance between timeless craftsmanship and refined contemporary design. Influenced by Scandinavian simplicity with subtle Japanese sensibility, the interiors are

  Susan Vanech Compass Connecticut, LLC

  4 Davenport Ave, Westport, CT 06880
• 

  $1,395,000

  Sold Sep 19, 2025

  33 Pumpkin Hill Rd, Westport, CT 06880

  • 4 Beds
  • 3 Baths
  • 2,128 Sq Ft
  • Built 1963

  Last Sold Summary

  • 7% Below List Price
  • $656/SF
  • 85 Days On Market

  Current Estimated Value $1,464,738

  Last Listing Agent Fred DeMatteo William Raveis Real Estate

  33 Pumpkin Hill Rd, Westport, CT 06880
• 

  Est $1,912,409

  Not Listed For Sale

  35 Old Rd, Westport, CT 06880

  • 5 Beds
  • 4.5 Baths
  • 3,844 Sq Ft
  • Built 1941

  35 Old Rd, Westport, CT 06880

  Last Sold Summary

  • 28 Days On Market
• 

  

  /40

  $5,599,000

  • 6 Beds
  • 9 Baths
  • 9,394 Sq Ft

  5 W Branch Rd, Westport, CT 06880

  Carefully crafted Connecticut modern farmhouse by award-winning Heine Development, this exceptional 6-bedroom residence blends timeless architecture with refined contemporary living amongst 4 finished levels on 2 private, level acres in one of Westport's most convenient luxury locations. Designed with perfection in symmetry, detail, and craftsmanship, the home pairs classic farmhouse inspiration

  Linda Skolnick Coldwell Banker Realty

  5 W Branch Rd, Westport, CT 06880
• 

  $1,925,000

  Sold Feb 12, 2026

  9 Victoria Ln, Westport, CT 06880

  • 5 Beds
  • 3.5 Baths
  • 3,228 Sq Ft
  • Built 1967

  Last Sold Summary

  • 1% Above List Price
  • $596/SF
  • 27 Days On Market

  Current Estimated Value $1,957,541

  Last Listing Agent Fredda Takacs Higgins Group Real Estate

  9 Victoria Ln, Westport, CT 06880
• 

  Est $3,276,649

  Not Listed For Sale

  64 Bayberry Ln, Westport, CT 06880

  • 4 Beds
  • 7 Baths
  • 6,678 Sq Ft
  • Built 2004

  64 Bayberry Ln, Westport, CT 06880

  Last Sold Summary

  • 32 Days On Market
• 

  

  /40

  $1,050,000

  Open Sun 1PM - 3PM

  • 4 Beds
  • 4 Baths
  • 2,724 Sq Ft

  2 Quarter Mile Rd, Westport, CT 06880

  Set on just over an acre in a convenient Westport location, 2 Quarter Mile Road combines comfortable living, modern updates, and outdoor spaces designed to be enjoyed throughout every season. Professionally landscaped grounds showcase mature specimen and evergreen trees, perennial gardens, and expansive lawn areas that create both beauty and privacy. Inside, natural light fills the home,

  Shannon Drury Berkshire Hathaway NE Prop.

  2 Quarter Mile Rd, Westport, CT 06880
• 

  $2,760,500

  Sold Jul 16, 2025

  7 Over Rock Ln, Westport, CT 06880

  • 5 Beds
  • 4 Baths
  • 3,311 Sq Ft
  • Built 1956

  Last Sold Summary

  • 15% Above List Price
  • $834/SF
  • 12 Days On Market

  Current Estimated Value $2,826,345

  Last Listing Agent Angela Benzan Higgins Group Bedford Square

  7 Over Rock Ln, Westport, CT 06880
• 

  Est $633,338

  Not Listed For Sale

  2 Bonnie Brook Rd, Westport, CT 06880

  • 5 Beds
  • 3 Baths
  • 4,257 Sq Ft
  • Built 1960

  2 Bonnie Brook Rd, Westport, CT 06880

  Last Sold Summary

  • 23 Days On Market
• 

  

  /40

  $4,850,000

  • 5 Beds
  • 5 Baths
  • 5,103 Sq Ft

  22 Evergreen Ave, Westport, CT 06880

  Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate

  Valerie Alvarez Serhant Connecticut, LLC

  22 Evergreen Ave, Westport, CT 06880
• 

  $2,025,000

  Sold May 15, 2026

  21 Turkey Hill Rd N, Westport, CT 06880

  • 3 Beds
  • 3.5 Baths
  • 2,883 Sq Ft
  • Built 1936

  Last Sold Summary

  • 21% Above List Price
  • $702/SF
  • 15 Days On Market

  Current Estimated Value $1,682,294

  Last Listing Agent Cindy Raney Coldwell Banker Realty

  21 Turkey Hill Rd N, Westport, CT 06880
• 

  Est $629,537

  Not Listed For Sale

  25 Soundview Dr, Westport, CT 06880

  • 4 Beds
  • 4.5 Baths
  • 3,492 Sq Ft
  • Built 1920

  25 Soundview Dr, Westport, CT 06880

  Last Sold Summary

  • 15 Days On Market
• 

  

  /39

  $2,799,000

  Pending

  • 4 Beds
  • 6 Baths
  • 5,627 Sq Ft

  299 Saugatuck Ave, Westport, CT 06880

  *THANK YOU FOR YOUR INTEREST, SELLER REQUESTS HIGHEST/BEST OFFERS BY 3PM MONDAY 6/1/26*Set on over an acre of park-like, usable property, this stunning Modern home with an oversized gunite pool is a showcase of exhilarating design. In an area known for major watefront properties as well as immediate convenience to the railroad station and all commuting routes, this home blends sophisticated

  Alex Chingas Coldwell Banker Realty

  299 Saugatuck Ave, Westport, CT 06880
• 

  $912,000

  Sold Sep 19, 2025

  3 Parsell Ln, Westport, CT 06880

  • 3 Beds
  • 2.5 Baths
  • 1,404 Sq Ft
  • Built 1958

  Last Sold Summary

  • 4% Below List Price
  • $650/SF
  • 57 Days On Market

  Current Estimated Value $969,253

  Last Listing Agent Sandra Calise Cenatiempo Settlers & Traders

  3 Parsell Ln, Westport, CT 06880
• 

  Est $1,937,372

  Not Listed For Sale

  26 Harbor Rd, Westport, CT 06880

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1981

  26 Harbor Rd, Westport, CT 06880

  Last Sold Summary

  • 20 Days On Market
• 

  

  /39

  $2,100,000

  Under Contract

  • 5 Beds
  • 5.5 Baths
  • 4,135 Sq Ft

  18 River Ln, Westport, CT 06880

  Update: Offers are due at 6pm on Monday June 15th. Set along one of Westport's most coveted stretches of the Saugatuck River, 18 River Lane is a timeless 1939 English Manor offering a rare blend of architectural character, waterfront serenity, and exceptional potential. Privately sited on 1.38 picturesque acres with sweeping river views and mature landscaping, this six-bedroom residence embodies

  Kim Harizman Compass Connecticut, LLC

  18 River Ln, Westport, CT 06880
• 

  $525,000

  Sold May 29, 2026

  3 Hills Ln, Westport, CT 06880

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft
  • Built 1974

  Last Sold Summary

  • 12% Below List Price
  • $379/SF
  • 35 Days On Market

  Current Estimated Value $546,526

  Last Listing Agent Mary Ann Lindwall The Riverside Realty Group

  3 Hills Ln, Westport, CT 06880
• 

  Est $2,737,197

  Not Listed For Sale

  58 North Ave, Westport, CT 06880

  • 6 Beds
  • 5.5 Baths
  • 4,210 Sq Ft
  • Built 1879

  58 North Ave, Westport, CT 06880

  Last Sold Summary

  • 25 Days On Market
• 

  

  /34

  $949,000

  Under Contract

  • 4 Beds
  • 3 Baths
  • 2,166 Sq Ft

  7 Lincoln St, Westport, CT 06880

  Nestled in one of Westport's most sought-after in-town neighborhoods, 7 Lincoln Street offers a rare opportunity to own a home that has been lovingly maintained and quietly cherished for more than five decades. Just moments from the Saugatuck River, vibrant Main Street, Saugatuck Village, train to NYC, Compo Beach. Easy access to local schools without a car or bus. This property delivers a

  Georgia Wasserman Coldwell Banker Realty

  7 Lincoln St, Westport, CT 06880
• 

  $3,450,000

  Sold Jul 30, 2025

  5 Elwil Dr, Westport, CT 06880

  • 5 Beds
  • 5.5 Baths
  • 5,887 Sq Ft
  • Built 2006

  Last Sold Summary

  • 9% Below List Price
  • $586/SF
  • 47 Days On Market

  Current Estimated Value $3,451,885

  Last Listing Agent Tanya Sprague Coldwell Banker Realty

  5 Elwil Dr, Westport, CT 06880
• 

  Est $1,589,440

  Not Listed For Sale

  39 Guyer Rd, Westport, CT 06880

  • 5 Beds
  • 5 Baths
  • 4,303 Sq Ft
  • Built 1950

  39 Guyer Rd, Westport, CT 06880

  Last Sold Summary

  • 17 Days On Market
• 

  

  /38

  $3,190,000

  New Construction $110K PRICE DROP Pending

  • 5 Beds
  • 4.5 Baths
  • 5,476 Sq Ft

  19 Horseshoe Ln, Westport, CT 06880

  Located on a quiet cul de sac only one mile from Metro North Train Station/I95 and two miles from Compo Beach, Longshore Country Club and downtown Westport - could your new home be any more convenient? Multiple HOBI award winning builder, CCO Habitats, presents its latest new construction project - a 5 bedroom, 4.5 bath home finished on 4 levels with room for a smaller pool. As always, there are

  Maryann Levanti Higgins Group Bedford Square

  19 Horseshoe Ln, Westport, CT 06880
• 

  $2,780,000

  Sold Jul 18, 2025

  29 Otter Trail, Westport, CT 06880

  • 4 Beds
  • 5 Baths
  • 3,660 Sq Ft
  • Built 2007

  Last Sold Summary

  • 10% Below List Price
  • $760/SF
  • 72 Days On Market

  Current Estimated Value $2,802,276

  Last Listing Agent Leslie Clarke Compass Connecticut, LLC

  29 Otter Trail, Westport, CT 06880
• 

  Est $2,108,957

  Not Listed For Sale

  387 Main St, Westport, CT 06880

  • 4 Beds
  • 4 Baths
  • 3,016 Sq Ft
  • Built 1840

  387 Main St, Westport, CT 06880

  Last Sold Summary

  • 28 Days On Market
• 

  

  /38

  $2,399,000

  Pending

  • 5 Beds
  • 6 Baths
  • 5,739 Sq Ft

  2 Ledgemoor Ln, Westport, CT 06880

  Set on a quiet, private cul-de-sac very close to town and Winslow Park, this custom five-bedroom Colonial offers an exceptional opportunity for a new owner to leave their mark and add significant value. Designed with best-in-class materials and a thoughtfully planned layout, the home retains its gracious scale, natural flow, and exceptional character. Deferred maintenance has created the chance

  Alex Chingas Coldwell Banker Realty

  2 Ledgemoor Ln, Westport, CT 06880
• 

  $4,150,000

  Sold Oct 23, 2025

  5 Boxwood Ln, Westport, CT 06880

  • 6 Beds
  • 11 Baths
  • 10,414 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Below List Price
  • $399/SF
  • 183 Days On Market

  Current Estimated Value $4,330,133

  Last Listing Agent Karen Scott Compass Connecticut, LLC

  5 Boxwood Ln, Westport, CT 06880
• 

  Est $1,691,050

  Not Listed For Sale

  69 Red Coat Rd, Westport, CT 06880

  • 6 Beds
  • 7.5 Baths
  • 13,112 Sq Ft
  • Built 2008

  69 Red Coat Rd, Westport, CT 06880

  Last Sold Summary

  • 22 Days On Market
• 

  

  /34

  $4,700,000

  • 6 Beds
  • 6.5 Baths
  • 7,575 Sq Ft

  21 Daniel Ct, Westport, CT 06880

  Nestled at the end of an exceptionally wide, tree-lined cul-de-sac on one of Westport's most picturesque streets, this timeless brick estate offers both elegance and privacy while remaining moments from town, beaches, and commuting conveniences. Set with a paver circular driveway and surrounded by mature landscaping, the property exudes warmth, scale, and classic sophistication at every turn.

  Meredith Cohen Serhant Connecticut, LLC

  21 Daniel Ct, Westport, CT 06880
• 

  $3,210,000

  Sold Oct 23, 2025

  8 Fillow St, Westport, CT 06880

  • 6 Beds
  • 7 Baths
  • 6,610 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $486/SF
  • 26 Days On Market

  Current Estimated Value $606,133

  Last Listing Agent Julie Haroun Westport Residential, LLC.

  8 Fillow St, Westport, CT 06880
• 

  Est $1,784,809

  Not Listed For Sale

  16 Weathervane Hill, Westport, CT 06880

  • 3 Beds
  • 3 Baths
  • 2,905 Sq Ft
  • Built 1957

  16 Weathervane Hill, Westport, CT 06880

  Last Sold Summary

  • 5 Days On Market
• 

  

  /40

  $5,000,000

  Under Contract

  • 6 Beds
  • 7 Baths
  • 8,717 Sq Ft

  6 Twin Circle Dr, Westport, CT 06880

  Nestled on a quiet cul-de-sac in one of Westport's most convenient locations, 6 Twin Circle Drive offers luxury living with exceptional indoor and outdoor spaces. Just moments to Bedford Middle School, Staples High School, downtown Westport, trains, shopping, restaurants, Longshore, and Compo Beach, this property combines privacy, recreation, and convenience. The resort-style backyard features a

  Judy Michaelis Coldwell Banker Realty

  6 Twin Circle Dr, Westport, CT 06880
• 

  $3,400,000

  Sold Jul 11, 2025

  22 Oak Ridge Park, Westport, CT 06880

  • 4 Beds
  • 4.5 Baths
  • 4,739 Sq Ft
  • Built 1969

  Last Sold Summary

  • 13% Above List Price
  • $717/SF
  • 14 Days On Market

  Current Estimated Value $3,607,146

  Last Listing Agent Jolanta Rojek eXp Realty

  22 Oak Ridge Park, Westport, CT 06880
• 

  Est $2,874,519

  Not Listed For Sale

  20 Berndale Dr, Westport, CT 06880

  • 5 Beds
  • 6 Baths
  • 5,000 Sq Ft
  • Built 2023

  20 Berndale Dr, Westport, CT 06880

  Last Sold Summary

  • 193 Days On Market
• 

  

  /14

  $4,375,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,100 Sq Ft

  143 Roseville Rd, Westport, CT 06880

  Nestled in peaceful seclusion yet just moments to town's shops, restaurants and amenities, an extraordinary residence crafted to the highest standards is being imagined to live in harmonious dialogue with the surrounding natural landscape. The proposed new construction masterpiece by Coastal Luxury Homes is thoughtfully designed to honor the property's pristine natural beauty, where a babbling

  Jaclyn Picarillo Higgins Group Bedford Square

  143 Roseville Rd, Westport, CT 06880
• 

  $2,825,000

  Sold Oct 17, 2025

  4 Budner Ln, Westport, CT 06880

  • 4 Beds
  • 3 Baths
  • 3,015 Sq Ft
  • Built 1959

  Last Sold Summary

  • 1% Above List Price
  • $937/SF
  • 15 Days On Market

  Current Estimated Value $2,859,117

  Last Listing Agent Carly Woodard William Pitt Sotheby's Int'l

  4 Budner Ln, Westport, CT 06880
• 

  Est $3,582,443

  Not Listed For Sale

  6 Plover Ln, Westport, CT 06880

  • 4 Beds
  • Built 2026

  6 Plover Ln, Westport, CT 06880

  Last Sold Summary

  • 29 Days On Market

Showing Results 521 - 560, Page 14 of 18