2,634

Staples Homes

Section Image
  • 5 Lehn Farm Rd, Westport, CT 06880
    5 Lehn Farm Rd, Westport, CT 06880
    5 Lehn Farm Rd, Westport, CT 06880
    /30

    $1,299,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    5 Lehn Farm Rd, Westport, CT 06880

    In the owners' words... We moved to this home looking for an escape from city life and a place to grow our family. It has offered us all of that and more. Every inch of the home serves a purpose, creating a space that feels intentional and complete. The thoughtful size and open layout means we are never far from one another. We can prepare meals in the kitchen while watching our little ones play

    Lynne Nolan Compass Connecticut, LLC

    5 Lehn Farm Rd, Westport, CT 06880
  • 10 Fernwood Rd, Westport, CT 06880
    10 Fernwood Rd, Westport, CT 06880
    10 Fernwood Rd, Westport, CT 06880
    /17

    $11,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 4,029 Sq Ft
    • House for Rent

    10 Fernwood Rd, Westport, CT 06880

    An exceptional opportunity to rent a luxury home in the heart of Westport and be settled in before the school year begins. Tucked away at the end of a peaceful cul-de-sac, this exceptional five-bedroom Colonial offers the rare combination of privacy, expansive living spaces, and an unbeatable in-town location. Set on 1.5+ beautifully landscaped acres, this custom home was thoughtfully rebuilt in

    Kim Harizman Compass Connecticut, LLC

    10 Fernwood Rd, Westport, CT 06880
  • 785 Post Rd E Unit 302, Westport, CT 06880

    $1,420,000

    Sold Apr 24, 2026

    785 Post Rd E Unit 302, Westport, CT 06880

    • 2 Beds
    • 2.5 Baths
    • 1,300 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Above List Price
    • $1,092/SF
    • 70 Days On Market

    Last Listing Agent Todd Gibbons Boost Real Estate Group

    785 Post Rd E Unit 302, Westport, CT 06880
    • 19 Woody Ln, Westport, CT 06880

      Est $4,003,076

      Not Listed For Sale

      19 Woody Ln, Westport, CT 06880

      • 6 Beds
      • 9 Baths
      • 8,928 Sq Ft
      • Built 1997
      19 Woody Ln, Westport, CT 06880

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Linda Skolnick Coldwell Banker Realty

  • 783 Post Rd E Unit 204, Westport, CT 06880
    783 Post Rd E Unit 204, Westport, CT 06880
    783 Post Rd E Unit 204, Westport, CT 06880
    /40

    $1,535,000

    New Construction Pending
    • 2 Beds
    • 2.5 Baths
    • 1,416 Sq Ft

    783 Post Rd E Unit 204, 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 204, Westport, CT 06880
  • 23 Turkey Hill Rd N, Westport, CT 06880
    23 Turkey Hill Rd N, Westport, CT 06880
    23 Turkey Hill Rd N, Westport, CT 06880
    /39

    $7,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,940 Sq Ft
    • House for Rent

    23 Turkey Hill Rd N, Westport, CT 06880

    Beautifully kept and updated Antique Colonial with the Charm of Yesteryear-adapted to today's lifestyle. Fenced in back yard with additional party deck, sited in the heart of Westport. Convenient to town, schools, shopping, restaurants and train. Hardwood Floors, arched doorways, lovely living room with fireplace, formal dining room, Study/Office and library. Newer, updated white kitchen with

    Robert Grodman The Riverside Realty Group

    23 Turkey Hill Rd N, Westport, CT 06880
  • 114 Cross Hwy, Westport, CT 06880

    $2,550,000

    Sold Aug 06, 2026

    114 Cross Hwy, Westport, CT 06880

    • 5 Beds
    • 4.5 Baths
    • 4,179 Sq Ft
    • Built 1964

    Last Sold Summary

    • 6% Below List Price
    • $610/SF
    • 36 Days On Market

    Current Estimated Value $2,635,106

    Last Listing Agent Robert Appell Coldwell Banker Realty

    114 Cross Hwy, Westport, CT 06880
    • 184 Cross Hwy, Westport, CT 06880

      Est $3,464,950

      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

      • 15 Days On Market

      Last Listing Agent Annette Coplit Coldwell Banker Realty

  • 22 Dawn Dr, Westport, CT 06880
    22 Dawn Dr, Westport, CT 06880
    22 Dawn Dr, Westport, CT 06880
    /22

    $4,995,700

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 4,000 Sq Ft

    22 Dawn Dr, Westport, CT 06880

    Come walk this stunning 1.5 acre lot with me - totally private, tucked at the end of a cul de sac in Long Lots. Peace, quiet, and the highest quality custom home spec'd to your wishlist by Coastal Luxury Homes is yours at 22 Dawn Drive. Go bigger/smaller, add an in-law suite or extra bedroom, an art studio, include a pool/spa, pickle court... let's discuss all the possibilities. Square footage

    Jaclyn Picarillo Higgins Group Bedford Square

    22 Dawn Dr, Westport, CT 06880
  • 26 Hitchcock Rd, Westport, CT 06880

    $2,700,000

    Sold Jan 26, 2026

    26 Hitchcock Rd, Westport, CT 06880

    • 5 Beds
    • 5 Baths
    • 4,549 Sq Ft
    • Built 2025

    Last Sold Summary

    • $594/SF
    • 224 Days On Market

    Current Estimated Value $2,693,891

    Last Listing Agent Mar Jennings Higgins Group Bedford Square

    26 Hitchcock Rd, Westport, CT 06880
    • 5 High Point Rd, Westport, CT 06880

      Est $4,521,656

      Not Listed For Sale

      5 High Point Rd, Westport, CT 06880

      • 5 Beds
      • 7 Baths
      • 8,835 Sq Ft
      • Built 2007
      5 High Point Rd, Westport, CT 06880

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Amy Swanson William Raveis Real Estate

  • 32 Morningside Dr N, Westport, CT 06880
    32 Morningside Dr N, Westport, CT 06880
    32 Morningside Dr N, Westport, CT 06880
    /17

    $1,275,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,270 Sq Ft

    32 Morningside Dr N, Westport, CT 06880

    4 Bedroom 3 Bath Farmhouse in the heart of Westport set on a picturesque level .5 acre. Full of potential, this home awaits your creative vision. Flat, pretty property with city water and sewer available nearby. Detached one car garage. Ideally located in the coveted Long Lots neighborhood, minutes to the train, restaurants, schools, shops, Burying Hill Beach, Sherwood Island Park, Compo Beach,

    Patricia Shea Coldwell Banker Realty

    32 Morningside Dr N, Westport, CT 06880
  • 119 Long Lots Rd, Westport, CT 06880

    $3,352,000

    Sold Jun 19, 2026

    119 Long Lots Rd, Westport, CT 06880

    • 5 Beds
    • 4.5 Baths
    • 5,616 Sq Ft
    • Built 1964

    Last Sold Summary

    • 3% Above List Price
    • $597/SF
    • 13 Days On Market

    Current Estimated Value $3,213,629

    Last Listing Agent Cyd Hamer William Pitt Sotheby's Int'l

    119 Long Lots Rd, Westport, CT 06880
    • 9 Windy Hill Rd, Westport, CT 06880

      Est $3,971,845

      Not Listed For Sale

      9 Windy Hill Rd, Westport, CT 06880

      • 5 Beds
      • 6 Baths
      • 6,560 Sq Ft
      • Built 2002
      9 Windy Hill Rd, Westport, CT 06880

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Elizabeth Steffen Higgins Group Bedford Square

  • 5 Baldwin Place, Westport, CT 06880
    5 Baldwin Place, Westport, CT 06880
    5 Baldwin Place, Westport, CT 06880
    /20

    $6,495,000

    New Construction
    • 6 Beds
    • 8 Baths
    • 9,062 Sq Ft

    5 Baldwin Place, Westport, CT 06880

    Rarely does a new construction home and property like this come on the market in Westport. Set at the end of a cul-de-sac, in the coveted Long Lots neighborhood, this 2.3-acre, flat property offers a rare combination of privacy and convenience to town. The property features a resort-style, saltwater pool w/spa and automatic safety cover, expansive covered and open-air patios, and a fully equipped

    Lori Popkin Coldwell Banker Realty

    5 Baldwin Place, Westport, CT 06880
  • 10 Wakenor Rd, Westport, CT 06880

    $2,630,000

    Sold Apr 01, 2026

    10 Wakenor Rd, Westport, CT 06880

    • 5 Beds
    • 5.5 Baths
    • 5,008 Sq Ft
    • Built 2026

    Last Sold Summary

    • 1% Above List Price
    • $525/SF
    • 41 Days On Market

    Current Estimated Value $2,260,136

    Last Listing Agent Julie Haroun Westport Residential, LLC.

    10 Wakenor Rd, Westport, CT 06880
    • 5 Country Ln, Westport, CT 06880

      Est $3,805,778

      Not Listed For Sale

      5 Country Ln, Westport, CT 06880

      • 5 Beds
      • 7 Baths
      • 5,955 Sq Ft
      • Built 1951
      5 Country Ln, Westport, CT 06880

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Susan Seath Compass Connecticut, LLC

  • 4 Lantern Hill Rd, Westport, CT 06880
    4 Lantern Hill Rd, Westport, CT 06880
    /2

    $2,650,000

    • Land
    • 1.23 Acres
    • $2,154,472 per Acre

    4 Lantern Hill Rd, Westport, CT 06880

    Rare opportunity to build a custom residence on 1.2 acres in Westport. The previous home has been demolished, and the property is offered with approved architectural plans. Bring your preferred builder and collaborate with the project architect to tailor the design to your vision. Also listed as a to-be-built single-family residence.

    Ian Defronze Serhant Connecticut, LLC

    4 Lantern Hill Rd, Westport, CT 06880
  • 104 Harvest Commons Unit 104, Westport, CT 06880

    $1,400,000

    Sold Jul 31, 2026

    104 Harvest Commons Unit 104, Westport, CT 06880

    • 2 Beds
    • 2.5 Baths
    • 2,161 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $648/SF
    • 70 Days On Market

    Last Listing Agent Patricia Prenderville Higgins Group Real Estate

    104 Harvest Commons Unit 104, Westport, CT 06880
    • 16 Morningside Ln, Westport, CT 06880

      Est $2,586,089

      Not Listed For Sale

      16 Morningside Ln, Westport, CT 06880

      • 4 Beds
      • 4.5 Baths
      • 3,764 Sq Ft
      • Built 2000
      16 Morningside Ln, Westport, CT 06880

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Karen Liss-uomoleale Coldwell Banker Realty

  • 107 Roseville Rd, Westport, CT 06880
    107 Roseville Rd, Westport, CT 06880
    107 Roseville Rd, Westport, CT 06880
    /40

    $1,199,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,572 Sq Ft

    107 Roseville Rd, Westport, CT 06880

    Sweet Cottage with In-Ground Pool on a lovely 1-acre property in Westport. Fabulous location, close to everything! This peaceful 3 Bedroom, 2 1/2 Bath home feels worlds away from the hustle and bustle, while being just minutes to Downtown Westport, Compo Beach, Longshore, and major commuter routes. Enjoy a dip in the pool, then relax on the expansive backyard deck and listen to the birds. You'll

    Lorelei Atwood Higgins Group Real Estate

    107 Roseville Rd, Westport, CT 06880
  • 32 Webb Rd, Westport, CT 06880

    $4,100,000

    Sold Jul 15, 2026

    32 Webb Rd, Westport, CT 06880

    • 8 Beds
    • 9 Baths
    • 8,412 Sq Ft
    • Built 2026

    Last Sold Summary

    • 2% Below List Price
    • $487/SF
    • 47 Days On Market

    Current Estimated Value $4,131,341

    Last Listing Agent Judy Michaelis Coldwell Banker Realty

    32 Webb Rd, Westport, CT 06880
    • 24 Oakview Cir, Westport, CT 06880

      Est $717,145

      Not Listed For Sale

      24 Oakview Cir, Westport, CT 06880

      • 3 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1985
      24 Oakview Cir, Westport, CT 06880

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Carolina Norwick Compass Connecticut, LLC

  • 9 Sturges Hwy, Westport, CT 06880
    9 Sturges Hwy, Westport, CT 06880
    9 Sturges Hwy, Westport, CT 06880
    /15

    $5,474,945

    New Construction $1M PRICE DROP Pending
    • 7 Beds
    • 8 Baths
    • 6,660 Sq Ft

    9 Sturges Hwy, Westport, CT 06880

    Design Your Dream Home with an Award-Winning Builder. Step into a world of elegance and sophistication with a soon-to-be-built 6,660 sq. ft. masterpiece by Coastal Luxury Homes. Known for their innovative designs, sleek modern lines, and unparalleled craftsmanship, Coastal Luxury Homes has earned a reputation for creating some of the most sought-after residences. With a focus on prime location,

    Annie Klyver Higgins Group Real Estate

    9 Sturges Hwy, Westport, CT 06880
  • 1 Greystone Farm Ln, Westport, CT 06880

    $4,199,000

    Sold Jun 30, 2026

    1 Greystone Farm Ln, Westport, CT 06880

    • 5 Beds
    • 5.5 Baths
    • 5,182 Sq Ft
    • Built 1998

    Last Sold Summary

    • $810/SF
    • 33 Days On Market

    Current Estimated Value $4,146,195

    Last Listing Agent Lisa Hartmann William Pitt Sotheby's Int'l

    1 Greystone Farm Ln, Westport, CT 06880
    • 28 Crescent Park Rd, Westport, CT 06880

      Est $700,930

      Not Listed For Sale

      28 Crescent Park Rd, Westport, CT 06880

      • 3 Beds
      • 2 Baths
      • 1,152 Sq Ft
      • Built 1986
      28 Crescent Park Rd, Westport, CT 06880

      Last Sold Summary

      • 94 Days On Market

      Last Listing Agent Terence Dominick Exceptional Real Estate LLC

  • 11 Hitchcock Rd, Westport, CT 06880
    11 Hitchcock Rd, Westport, CT 06880
    11 Hitchcock Rd, Westport, CT 06880
    /27

    $1,495,000

    • 1 Bed
    • 1 Bath
    • 1,551 Sq Ft

    11 Hitchcock Rd, Westport, CT 06880

    An exceptional offering on 1.38 private acres in the heart of Westport. Ideally situated just moments from vibrant Main Street, this centrally located property offers convenient access to shopping, dining, parks, tennis courts, beaches, the train, and Westport's award-winning schools. It provides an outstanding foundation for creating a one-of-a-kind estate. At the heart of this property stands

    Kelley Long Thrush Berkshire Hathaway NE Prop.

    11 Hitchcock Rd, Westport, CT 06880
  • 3 Valley Field Rd, Westport, CT 06880

    $2,590,000

    Sold Jul 31, 2026

    3 Valley Field Rd, Westport, CT 06880

    • 4 Beds
    • 2.5 Baths
    • 3,581 Sq Ft
    • Built 1985

    Last Sold Summary

    • 10% Above List Price
    • $723/SF
    • 10 Days On Market

    Current Estimated Value $2,299,521

    Last Listing Agent Melissa Jones Houlihan Lawrence

    3 Valley Field Rd, Westport, CT 06880
    • 113 North Ave, Westport, CT 06880

      Not Listed For Sale

      113 North Ave, Westport, CT 06880

      • 5 Beds
      • 3.5 Baths
      • 3,920 Sq Ft
      • Built 1887
      113 North Ave, Westport, CT 06880

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Kim Harizman Compass Connecticut, LLC

  • 2 Ledgemoor Ln, Westport, CT 06880
    2 Ledgemoor Ln, Westport, CT 06880
    2 Ledgemoor Ln, Westport, CT 06880
    /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
  • 785 Post Rd E Unit 103, Westport, CT 06880

    $1,395,000

    Sold Sep 09, 2025

    785 Post Rd E Unit 103, Westport, CT 06880

    • 2 Beds
    • 2.5 Baths
    • 1,416 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Above List Price
    • $985/SF
    • 52 Days On Market

    Last Listing Agent Todd Gibbons Boost Real Estate Group

    785 Post Rd E Unit 103, Westport, CT 06880
    • 9 Brookside Dr, Westport, CT 06880

      Est $4,780,478

      Not Listed For Sale

      9 Brookside Dr, Westport, CT 06880

      • 6 Beds
      • 11 Baths
      • 9,142 Sq Ft
      • Built 1938
      9 Brookside Dr, Westport, CT 06880

      Last Sold Summary

      • 309 Days On Market

      Last Listing Agent Kim Vartuli Keller Williams Realty

  • 8 Pleasant Valley Ln, Westport, CT 06880
    8 Pleasant Valley Ln, Westport, CT 06880
    8 Pleasant Valley Ln, Westport, CT 06880
    /40

    $5,650,000

    New Construction
    • 7 Beds
    • 9 Baths
    • 8,762 Sq Ft

    8 Pleasant Valley Ln, Westport, CT 06880

    Experience modern luxury in this new SIR SIGNATURE Home by SIR Development, Westport's premier builder. Set on 1.02 private acres on a coveted cul de sac, this home offers a striking approach, 3car garage, and rare backyard privacy, all within walking distance to Bedford Middle, Staples High, Wakeman Fields, and Town Farm. A fresh contemporary aesthetic features a dramatic two story foyer, 10ft

    Doug Bross Coldwell Banker Realty

    8 Pleasant Valley Ln, Westport, CT 06880
  • 504 Harvest Commons Unit 504, Westport, CT 06880

    $1,500,000

    Sold Sep 26, 2025

    504 Harvest Commons Unit 504, Westport, CT 06880

    • 2 Beds
    • 2.5 Baths
    • 2,774 Sq Ft
    • Built 1982

    Last Sold Summary

    • 6% Below List Price
    • $541/SF
    • 109 Days On Market

    Last Listing Agent Carrie Perkins RE/MAX Heritage

    504 Harvest Commons Unit 504, Westport, CT 06880
    • 25 Crescent Rd, Westport, CT 06880

      Est $1,026,227

      Not Listed For Sale

      25 Crescent Rd, Westport, CT 06880

      • 3 Beds
      • 1 Bath
      • 1,472 Sq Ft
      • Built 1954
      25 Crescent Rd, Westport, CT 06880

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Tara Chlupsa Coldwell Banker Realty

  • 4 Sycamore Dr, Westport, CT 06880
    4 Sycamore Dr, Westport, CT 06880
    4 Sycamore Dr, Westport, CT 06880
    /40

    $5,199,000

    New Construction Under Contract
    • 6 Beds
    • 8 Baths
    • 8,935 Sq Ft

    4 Sycamore Dr, Westport, CT 06880

    Tucked away on a quiet cul de sac in the desirable Hunt Club area of Long Lots in Westport is a new construction lux home from CCO Habitats. 3 levels of finished living space with 10 foot ceilings on the 1st floor give an amazing sense of openness, as well as better functionality than 4 level homes. Think about it. Who really wants to walk up to the third floor every day? That's right; no one.

    Maryann Levanti Higgins Group Bedford Square

    4 Sycamore Dr, Westport, CT 06880
  • 785 Post Rd E Unit 203, Westport, CT 06880

    $1,390,000

    Sold Oct 29, 2025

    785 Post Rd E Unit 203, Westport, CT 06880

    • 2 Beds
    • 2.5 Baths
    • 1,416 Sq Ft
    • Built 2025

    Last Sold Summary

    • $982/SF
    • 51 Days On Market

    Last Listing Agent Todd Gibbons Boost Real Estate Group

    785 Post Rd E Unit 203, Westport, CT 06880
    • 25 Colony Rd, Westport, CT 06880

      Est $2,112,341

      Not Listed For Sale

      25 Colony Rd, Westport, CT 06880

      • 4 Beds
      • 2.5 Baths
      • 3,548 Sq Ft
      • Built 1966
      25 Colony Rd, Westport, CT 06880

      Last Sold Summary

      • 81 Days On Market

      Last Listing Agent Marilyn Heffers Coldwell Banker Realty

  • 4 Heather Hill, Westport, CT 06880
    4 Heather Hill, Westport, CT 06880
    4 Heather Hill, Westport, CT 06880
    /36

    $1,200,000

    Open Sat 11AM - 1PM Under Contract
    • 4 Beds
    • 1.5 Baths
    • 1,567 Sq Ft

    4 Heather Hill, Westport, CT 06880

    Back on the market after receiving multiple offers, here is your second chance to make this beautifully remodeled In-Town Cape your own! Timeless charm meets exceptional craftsmanship in this turnkey 4 bedroom, 2 bath home with a thoughtfully designed open concept floor plan. The stunning designer kitchen is the heart of the home, featuring quartz countertops, a large center island, high end

    Brandy Hall Higgins Group Real Estate

    4 Heather Hill, Westport, CT 06880
  • 125 Old Rd, Westport, CT 06880

    $5,036,000

    Sold Mar 26, 2026

    125 Old Rd, Westport, CT 06880

    • 6 Beds
    • 9 Baths
    • 8,545 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Above List Price
    • $589/SF
    • 33 Days On Market

    Current Estimated Value $5,065,617

    Last Listing Agent Doug Bross Coldwell Banker Realty

    125 Old Rd, Westport, CT 06880

Showing Results 41 - 80, Page 2 of 18

Connecticut Fairfield County Westport

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group