3,859

Weston, CT Homes

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  • 103 Steep Hill Rd, Weston, CT 06883
    103 Steep Hill Rd, Weston, CT 06883
    103 Steep Hill Rd, Weston, CT 06883
    /37

    $1,000,000

    Open Sun 11AM - 2PM
    • 4 Beds
    • 3 Baths
    • 3,532 Sq Ft

    103 Steep Hill Rd, Weston, CT 06883

    Welcome to this spacious 4-bedroom, 3-bath Colonial offering 2,700+ square feet of versatile living space in Lower Weston. Set on 2.3 private wooded acres, the home features a flexible floor plan with generous living areas, a finished lower level, and a bright four-season room that provides additional year-round living space. The main level has the convenience of first-floor laundry along with an

    Avery Saitta RE/MAX Heritage

    103 Steep Hill Rd, Weston, CT 06883
  • 102 Ladder Hill Rd N Unit Cottage, Weston, CT 06883
    102 Ladder Hill Rd N Unit Cottage, Weston, CT 06883
    102 Ladder Hill Rd N Unit Cottage, Weston, CT 06883
    /28

    $4,000 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    102 Ladder Hill Rd N Unit Cottage, Weston, CT 06883

    Experience the elegance and tranquility of this exquisite two-bedroom cottage nestled within a picturesque lakeside estate. Bathed in natural light, this like-new home radiates charm and luxury. Revel in the open floor plan with granite kitchen counters and newer appliances, while the spacious bedrooms offer a haven of comfort. Discover quality finishes, high ceilings, and gorgeous hardwood

    Len Schwartz Keller Williams Prestige Prop.

    102 Ladder Hill Rd N Unit Cottage, Weston, CT 06883
  • 30 Cavalry Rd, Westport, CT 06880

    $2,375,000

    Sold Apr 23, 2026

    30 Cavalry Rd, Westport, CT 06880

    • 4 Beds
    • 5 Baths
    • 4,013 Sq Ft
    • Built 1962

    Last Sold Summary

    • 1% Below List Price
    • $592/SF
    • 33 Days On Market

    Current Estimated Value $2,369,806

    Last Listing Agent Hyleri Katzenberg Compass Connecticut, LLC

    30 Cavalry Rd, Westport, CT 06880
    • 83 Lords Hwy, Weston, CT 06883

      Est $584,142

      Not Listed For Sale

      83 Lords Hwy, Weston, CT 06883

      83 Lords Hwy, Weston, CT 06883

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Eva Grant-Rawiszer William Pitt Sotheby's Int'l

  • 11 Hunt Ln, Weston, CT 06883
    11 Hunt Ln, Weston, CT 06883
    11 Hunt Ln, Weston, CT 06883
    /40

    $1,399,995

    • 4 Beds
    • 3.5 Baths
    • 3,506 Sq Ft

    11 Hunt Ln, Weston, CT 06883

    Welcome to 11 Hunt Lane! This charming Colonial delivers lots of space and flexibility while situated at the end of a tranquil double cul-de-sac in Lower Weston, near the Westport line. Perfect for entertaining, the sun-filled, spacious interior boasts excellent flow. Enter a charming two-story foyer flanked by a living room with fireplace and dining room with wet bar and sliders to a beautiful

    Denise Melendez Berkshire Hathaway NE Prop.

    11 Hunt Ln, Weston, CT 06883
  • 69 Lyons Plain Rd, Weston, CT 06883

    $1,780,000

    Sold Jun 08, 2026

    69 Lyons Plain Rd, Weston, CT 06883

    • 5 Beds
    • 3.5 Baths
    • 3,648 Sq Ft
    • Built 1950

    Last Sold Summary

    • 11% Above List Price
    • $488/SF
    • 5 Days On Market

    Current Estimated Value $1,729,071

    Last Listing Agent Lori Elkins William Raveis Real Estate

    69 Lyons Plain Rd, Weston, CT 06883
    • 178 Davis Hill Rd, Weston, CT 06883

      Est $1,251,643

      Not Listed For Sale

      178 Davis Hill Rd, Weston, CT 06883

      • 5 Beds
      • 2.5 Baths
      • 4,066 Sq Ft
      • Built 1968
      178 Davis Hill Rd, Weston, CT 06883

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Matthew Hyde William Raveis Real Estate

  • 123 Lyons Plain Rd, Weston, CT 06883
    123 Lyons Plain Rd, Weston, CT 06883
    123 Lyons Plain Rd, Weston, CT 06883
    /38

    $1,049,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,392 Sq Ft

    123 Lyons Plain Rd, Weston, CT 06883

    Perched atop a private, sun-drenched hill in the heart of Lower Weston, 123 Lyons Plain Road is a masterclass in charm and character. This home strikes the rare balance between secluded retreat and total convenience, located just minutes from the vibrant shopping and dining of Westport, local beaches, and easy commuting via the Merritt Parkway or Metro-North. Once inside the home, the

    Karen Hagen Compass Connecticut, LLC

    123 Lyons Plain Rd, Weston, CT 06883
  • 17 Grays Farm Rd, Weston, CT 06883

    $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 $1,517,838

    Last Listing Agent Mary Palmieri Gai Berkshire Hathaway NE Prop.

    17 Grays Farm Rd, Weston, CT 06883
    • 27 Blue Spruce Cir, Weston, CT 06883

      Est $1,216,402

      Not Listed For Sale

      27 Blue Spruce Cir, Weston, CT 06883

      • 3 Beds
      • 3.5 Baths
      • 3,158 Sq Ft
      • Built 2005
      27 Blue Spruce Cir, Weston, CT 06883

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Jenny Walsh Coldwell Banker Realty

  • 11 Judges Hollow Rd, Fairfield, CT 06824
    11 Judges Hollow Rd, Fairfield, CT 06824
    11 Judges Hollow Rd, Fairfield, CT 06824
    /10

    $925,000

    • 2 Beds
    • 2 Baths
    • 1,135 Sq Ft

    11 Judges Hollow Rd, Fairfield, CT 06824

    This rare private inholding offers a hilltop property defined by raw beauty and seclusion. The 1930s rustic hunting cabin sits on 1.6 wooded acres at the end of a private drive, surrounded by the 186-acre Brett Woods Conservation Area. The property provides a perfect balance of mature trees, rolling hills, and 18th-century stone walls-all located just eight minutes from Main Street Westport. With

    Lisa Hartmann William Pitt Sotheby's Int'l

    11 Judges Hollow Rd, Fairfield, CT 06824
  • 5 Walker Ln, Weston, CT 06883

    $1,150,000

    Sold Dec 08, 2025

    5 Walker Ln, Weston, CT 06883

    • 4 Beds
    • 3.5 Baths
    • 4,792 Sq Ft
    • Built 1986

    Last Sold Summary

    • 16% Below List Price
    • $240/SF
    • 84 Days On Market

    Current Estimated Value $1,263,065

    Last Listing Agent Ryan Loechner William Pitt Sotheby's Int'l

    5 Walker Ln, Weston, CT 06883
    • 81 Blue Spruce Cir, Weston, CT 06883

      Est $908,312

      Not Listed For Sale

      81 Blue Spruce Cir, Weston, CT 06883

      • 4 Beds
      • 2.5 Baths
      • 1,456 Sq Ft
      • Built 1968
      81 Blue Spruce Cir, Weston, CT 06883

      Last Sold Summary

      • 77 Days On Market

      Last Listing Agent Juan Garcia Sunbelt Sales & Development

  • 32 Silver Ridge Common, Weston, CT 06883
    32 Silver Ridge Common, Weston, CT 06883
    32 Silver Ridge Common, Weston, CT 06883
    /39

    $1,750,000

    • 4 Beds
    • 5 Baths
    • 4,234 Sq Ft

    32 Silver Ridge Common, Weston, CT 06883

    Tucked away on a coveted lower Weston cul-de-sac, this beautifully renovated colonial offers the rare combination of privacy, style, and resort-inspired living. Thoughtfully updated by the current owner, the home is truly turnkey and ready for its next chapter. Sun-filled interiors showcase sophisticated finishes and an effortless flow for both everyday living and entertaining. The renovated

    Kim Harizman Compass Connecticut, LLC

    32 Silver Ridge Common, Weston, CT 06883
  • 12 Mountain View Dr, Weston, CT 06883

    $1,213,000

    Sold Jun 15, 2026

    12 Mountain View Dr, Weston, CT 06883

    • 5 Beds
    • 2.5 Baths
    • 4,092 Sq Ft
    • Built 1970

    Last Sold Summary

    • 5% Above List Price
    • $296/SF
    • 2 Days On Market

    Current Estimated Value $1,219,396

    Last Listing Agent Jenny Walsh Coldwell Banker Realty

    12 Mountain View Dr, Weston, CT 06883
    • 68 Blue Spruce Cir, Weston, CT 06883

      Est $1,018,368

      Not Listed For Sale

      68 Blue Spruce Cir, Weston, CT 06883

      • 4 Beds
      • 2.5 Baths
      • 2,888 Sq Ft
      • Built 1968
      68 Blue Spruce Cir, Weston, CT 06883

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Alan Hamilton William Raveis Real Estate

  • 25 Lords Hwy E, Weston, CT 06883
    25 Lords Hwy E, Weston, CT 06883
    25 Lords Hwy E, Weston, CT 06883
    /23

    $519,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 2,184 Sq Ft

    25 Lords Hwy E, Weston, CT 06883

    Beautiful 2 acre location in Weston. This is a 3 bedroom ranch with garage and barn. House is "AS IS" and has in ground oil tank. The septic updated in 1995-plan on MLS. New well pump in 2024. House is currently occupied. Perfect for builder or remodeler. Condition of this property may not qualify for mortgage. Seller asking for highest & best Monday June 22 at 5PM

    Barbara Snyder Coldwell Banker Realty

    25 Lords Hwy E, Weston, CT 06883
  • 195 Steep Hill Rd, Weston, CT 06883

    $1,170,000

    Sold Aug 15, 2026

    195 Steep Hill Rd, Weston, CT 06883

    • 5 Beds
    • 4 Baths
    • 4,344 Sq Ft
    • Built 1975

    Last Sold Summary

    • 6% Below List Price
    • $269/SF
    • 42 Days On Market

    Current Estimated Value $1,240,279

    Last Listing Agent Jenny Walsh Coldwell Banker Realty

    195 Steep Hill Rd, Weston, CT 06883
    • 21 Cavalry Rd, Weston, CT 06883

      Est $1,489,925

      Not Listed For Sale

      21 Cavalry Rd, Weston, CT 06883

      • 4 Beds
      • 3.5 Baths
      • 3,366 Sq Ft
      • Built 1963
      21 Cavalry Rd, Weston, CT 06883

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Michelle Genovesi William Raveis Real Estate

  • 338 Good Hill Rd, Weston, CT 06883
    338 Good Hill Rd, Weston, CT 06883
    338 Good Hill Rd, Weston, CT 06883
    /3

    $900,000

    Open Sun 1PM - 3PM
    • Land
    • 2 Acres
    • $450,000 per Acre

    338 Good Hill Rd, Weston, CT 06883

    Rare opportunity to build your dream home in one of Weston's most desirable locations. Situated on a private 2-acre lot at the end of a quiet cul-de-sac, 338 Good Hill Road is being offered with full town approvals and complete engineering plans already in place, allowing you to begin construction without the lengthy approval process. The approved plans feature a stunning 5-bedroom, 6-bathroom

    Derek Heering Property Twins Real Estate

    338 Good Hill Rd, Weston, CT 06883
  • 2 & 4 Old Weston Old Weston Rd, Weston, CT 06883

    $800,000

    Sold Jun 10, 2026

    2 & 4 Old Weston Old Weston Rd, Weston, CT 06883

    • 5 Beds
    • 4 Baths
    • 1,223 Sq Ft
    • Built 1770

    Last Sold Summary

    • 9% Below List Price
    • $654/SF
    • 40 Days On Market

    Last Listing Agent Sandra Calise Cenatiempo Settlers & Traders

    2 & 4 Old Weston Old Weston Rd, Weston, CT 06883
    • 33 W Branch Rd, Weston, CT 06883

      Est $2,179,223

      Not Listed For Sale

      33 W Branch Rd, Weston, CT 06883

      • 5 Beds
      • 4.5 Baths
      • 4,438 Sq Ft
      • Built 1966
      33 W Branch Rd, Weston, CT 06883

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Susan Seath Compass Connecticut, LLC

  • 18 Briar Oak Dr, Weston, CT 06883
    18 Briar Oak Dr, Weston, CT 06883
    18 Briar Oak Dr, Weston, CT 06883
    /8

    $899,000

    Pending
    • 5 Beds
    • 4 Baths
    • 2,444 Sq Ft

    18 Briar Oak Dr, Weston, CT 06883

    Nestled on 2.25 breathtaking hilltop acres, this is one of Lower Weston's beautiful building sites. Set in a picturesque, level meadow w/ mature trees, the property offers exceptional privacy on a coveted cul-de-sac just south of Weston Center, near the Historical Society, & minutes from the Merritt Parkway. Whether you choose to renovate the existing home or create the custom estate you've

    Jenny Walsh Coldwell Banker Realty

    18 Briar Oak Dr, Weston, CT 06883
  • 10 Hyde Ridge Rd, Weston, CT 06883

    $1,620,000

    Sold May 29, 2026

    10 Hyde Ridge Rd, Weston, CT 06883

    • 4 Beds
    • 3.5 Baths
    • 3,310 Sq Ft
    • Built 1963

    Last Sold Summary

    • 16% Above List Price
    • $489/SF
    • 13 Days On Market

    Current Estimated Value $1,574,261

    Last Listing Agent Max Dober Keller Williams Prestige Prop.

    10 Hyde Ridge Rd, Weston, CT 06883
    • 5 Good Hill Rd, Weston, CT 06883

      Est $1,454,802

      Not Listed For Sale

      5 Good Hill Rd, Weston, CT 06883

      • 5 Beds
      • 3.5 Baths
      • 4,100 Sq Ft
      • Built 1940
      5 Good Hill Rd, Weston, CT 06883

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Lynne Nolan Compass Connecticut, LLC

  • 38 Old Redding Rd, Weston, CT 06883
    38 Old Redding Rd, Weston, CT 06883
    38 Old Redding Rd, Weston, CT 06883
    /40

    $1,325,000

    $50K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 3,457 Sq Ft

    38 Old Redding Rd, Weston, CT 06883

    This sun-kissed contemporary captivates with private panoramic views overlooking the forever-green 14th and 15th fairways of Aspetuck Country Club. Designed to fully embrace its striking setting, this home offers a wide deck, large patio, five balconies, and grand windows framing views. Sited on two idyllic acres in bucolic Lower Weston, this premier property is minutes to the amenities and train

    Lori Elkins William Raveis Real Estate

    38 Old Redding Rd, Weston, CT 06883
  • 260 Lyons Plain Rd, Weston, CT 06883

    $1,200,000

    Sold Dec 05, 2025

    260 Lyons Plain Rd, Weston, CT 06883

    • 3 Beds
    • 3.5 Baths
    • 2,668 Sq Ft
    • Built 1946

    Last Sold Summary

    • 4% Above List Price
    • $450/SF
    • 99 Days On Market

    Current Estimated Value $1,245,489

    Last Listing Agent Rita Kirby William Pitt Sotheby's Int'l

    260 Lyons Plain Rd, Weston, CT 06883
    • 17 Huckleberry Ln, Weston, CT 06883

      Est $1,199,235

      Not Listed For Sale

      17 Huckleberry Ln, Weston, CT 06883

      • 4 Beds
      • 4 Baths
      • 2,758 Sq Ft
      • Built 1936
      17 Huckleberry Ln, Weston, CT 06883

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Sheila Shupack William Raveis Real Estate

  • 59 September Ln, Weston, CT 06883
    59 September Ln, Weston, CT 06883
    59 September Ln, Weston, CT 06883
    /37

    $1,425,000

    Pending
    • 5 Beds
    • 3.5 Baths
    • 4,476 Sq Ft

    59 September Ln, Weston, CT 06883

    Nestled in one of Lower Weston's most desirable locations, this beautifully updated and thoughtfully expanded 5-bedroom, 3.5-bath residence offers the perfect blend of timeless charm and modern living. A bright open floor plan centers around a stunning great room with soaring vaulted ceilings and a dramatic double-sided fireplace that creates a warm connection between the kitchen and family room.

    Cyd Hamer William Pitt Sotheby's Int'l

    59 September Ln, Weston, CT 06883
  • 153 Valley Forge Rd, Weston, CT 06883

    $1,485,000

    Sold Aug 29, 2025

    153 Valley Forge Rd, Weston, CT 06883

    • 4 Beds
    • 3.5 Baths
    • 3,896 Sq Ft
    • Built 2025

    Last Sold Summary

    • 7% Below List Price
    • $381/SF
    • 86 Days On Market

    Last Listing Agent Ian Defronze Serhant Connecticut, LLC

    153 Valley Forge Rd, Weston, CT 06883
    • 23 Huckleberry Ln, Weston, CT 06883

      Est $1,769,843

      Not Listed For Sale

      23 Huckleberry Ln, Weston, CT 06883

      • 3 Beds
      • 2 Baths
      • 2,263 Sq Ft
      • Built 1964
      23 Huckleberry Ln, Weston, CT 06883

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Kristi Law William Pitt Sotheby's Int'l

  • 4 Good Hill Rd, Weston, CT 06883
    4 Good Hill Rd, Weston, CT 06883
    4 Good Hill Rd, Weston, CT 06883
    /40

    $3,500,000

    Pending
    • 3 Beds
    • 3 Baths
    • 8,500 Sq Ft

    4 Good Hill Rd, Weston, CT 06883

    Exquisite 1970 Renovated 3 Bedroom House with Renovated Barn and Private Art Museum in Weston, CT Nestled in the heart of Lower Weston, Connecticut, this exceptional 3.25 acre property offers a unique blend of historic charm and modern luxury. Situated on a meticulously landscaped estate, this renovated 3-bedroom house presents an unparalleled opportunity to experience gracious living alongside

    Kim Harizman Compass Connecticut, LLC

    4 Good Hill Rd, Weston, CT 06883
  • 21 Timber Mill Ln, Weston, CT 06883

    $1,715,000

    Sold Jun 23, 2026

    21 Timber Mill Ln, Weston, CT 06883

    • 4 Beds
    • 3.5 Baths
    • 4,496 Sq Ft
    • Built 1980

    Last Sold Summary

    • 14% Above List Price
    • $381/SF
    • 9 Days On Market

    Current Estimated Value $1,617,550

    Last Listing Agent Karen Hagen Compass Connecticut, LLC

    21 Timber Mill Ln, Weston, CT 06883
    • 12 Graylock Rd, Weston, CT 06883

      Est $1,646,315

      Not Listed For Sale

      12 Graylock Rd, Weston, CT 06883

      • 4 Beds
      • 3.5 Baths
      • 4,376 Sq Ft
      • Built 1961
      12 Graylock Rd, Weston, CT 06883

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Sandra Calise Cenatiempo Settlers & Traders

  • 15 Cannondale Rd, Weston, CT 06883
    15 Cannondale Rd, Weston, CT 06883
    15 Cannondale Rd, Weston, CT 06883
    /5

    $2,299,000

    New Construction
    • 4 Beds
    • 5.5 Baths
    • 5,600 Sq Ft

    15 Cannondale Rd, Weston, CT 06883

    UNDER CONSTRUCTION - Photos are architectural renderings and are intended to illustrate the home's anticipated finished appearance. Actual finishes, materials, features, and landscaping may vary. Be the first to own this exceptional new luxury home in one of Weston's most desirable locations. Situated on approximately 2 private acres, this custom-designed 5,600 SF residence offers 4 bedrooms, 4

    Pilar Rios US Asset Realty

    15 Cannondale Rd, Weston, CT 06883
  • 205 Weston Rd, Weston, CT 06883

    $1,560,000

    Sold May 20, 2026

    205 Weston Rd, Weston, CT 06883

    • 4 Beds
    • 2.5 Baths
    • 3,382 Sq Ft
    • Built 1986

    Last Sold Summary

    • 11% Below List Price
    • $461/SF
    • 65 Days On Market

    Current Estimated Value $1,550,318

    Last Listing Agent Jen Kass Higgins Group Bedford Square

    205 Weston Rd, Weston, CT 06883
    • 118 Weston Rd, Weston, CT 06883

      Est $1,089,694

      Not Listed For Sale

      118 Weston Rd, Weston, CT 06883

      • 4 Beds
      • 2.5 Baths
      • 2,651 Sq Ft
      • Built 1840
      118 Weston Rd, Weston, CT 06883

      Last Sold Summary

      • 266 Days On Market

      Last Listing Agent Sal Spadaccino Gower-Spadaccino Asset Management, LLC

  • 457 Newtown Turnpike, Weston, CT 06883
    457 Newtown Turnpike, Weston, CT 06883
    457 Newtown Turnpike, Weston, CT 06883
    /23

    $549,000

    $41K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 525 Sq Ft

    457 Newtown Turnpike, Weston, CT 06883

    Set in a convenient Weston location, this adorable 2 bedroom ranch offers an inviting opportunity to enjoy one of Fairfield County's most desirable communities. Filled with character and easy living, this home offers a bright and comfortable layout featuring a modern kitchen, lovely living room, 2 bedroom, office nook and a full bath. A dry basement provides excellent storage. Highlights include

    Jennifer Lockwood Coldwell Banker Realty

    457 Newtown Turnpike, Weston, CT 06883
  • 47 Godfrey Rd W, Weston, CT 06883

    $1,125,000

    Sold Oct 16, 2025

    47 Godfrey Rd W, Weston, CT 06883

    • 2 Beds
    • 1.5 Baths
    • 1,859 Sq Ft
    • Built 1841

    Last Sold Summary

    • 5% Above List Price
    • $605/SF
    • 10 Days On Market

    Current Estimated Value $1,181,392

    Last Listing Agent Jeannette Floto Compass Connecticut, LLC

    47 Godfrey Rd W, Weston, CT 06883
    • 17 Timber Mill Ln, Weston, CT 06883

      Est $1,537,558

      Not Listed For Sale

      17 Timber Mill Ln, Weston, CT 06883

      • 4 Beds
      • 3.5 Baths
      • 4,754 Sq Ft
      • Built 1978
      17 Timber Mill Ln, Weston, CT 06883

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Cynde Koritzinsky William Pitt Sotheby's Int'l

Showing Results 41 - 80, Page 2 of 18

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