• Home
  • Buy
    1. All Listings
    2. Featured Listings
  • Sell
    1. Sell My Home
    2. Home Valuation
    3. Recent Sold
  • Rent
    1. Rental Listings
  • About
    1. About Us
    2. Contact Us
    3. Reviews
  • The YlH Real Estate Team
    +1(646) 261-4698
    • Home
    • Buy
      1. All Listings
      2. Featured Listings
    • Sell
      1. Sell My Home
      2. Home Valuation
      3. Recent Sold
    • Rent
      1. Rental Listings
    • About
      1. About Us
      2. Contact Us
      3. Reviews
    • Market Snapshot
    • Register
    • Sign In
    Price
    • Any
    • $ 100,000
    • $ 150,000
    • $ 200,000
    • $ 400,000
    • $ 800,000
    • Any
    • $ 200,000
    • $ 300,000
    • $ 400,000
    • $ 600,000
    • $ 1,000,000
      Beds Tap two numbers to select a range
      Any
      1
      2
      3
      4
      5+
      Baths Tap two numbers to select a range
      Any
      1
      2
      3
      4
      5+
    • List
    • Mixed
    • Map
    City: Winchester, CT
    Listing Status: Active
    Map
    52 Properties Available In Winchester

    52 Properties Available In Winchester

    • Default
    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    CT >Winchester >
    Market Insights
    752 Lake Drive, Winchester, CT 06098
    1/2
    Open Sun 12PM-2PM

    $1,600,000

    4 Beds3 Baths2,129 SqFt

    752 Lake Drive, Winchester, CT 06098

    Listed by Pam Famiglietti of William Raveis Real Estate

    132 East Lake Street, Winchester, CT 06098
    1/36
    Open Sat 11AM-1PM

    $389,900

    3 Beds2 Baths1,820 SqFt

    132 East Lake Street, Winchester, CT 06098

    Listed by Bryan Palladino of Showcase Realty, Inc.

    112 Rockwell Street #2, Winchester, CT 06098
    New

    $1,595

    4 Beds2 Baths900 SqFt

    112 Rockwell Street #2, Winchester, CT 06098

    Listed by Amanda Balaski of Northwest CT Realty

    19 Center Street #1R, Winchester, CT 06098
    1/8
    Active

    $1,695

    3 Beds1 Bath900 SqFt

    19 Center Street #1R, Winchester, CT 06098

    Listed by Amanda Balaski of Northwest CT Realty

    98 Spencer Street #4N, Winchester, CT 06098
    1/7
    Active

    $1,645

    4 Beds1 Bath1,000 SqFt

    98 Spencer Street #4N, Winchester, CT 06098

    Listed by Amanda Balaski of Northwest CT Realty

    43 Wallens Street #1st, Winchester, CT 06098
    1/5
    Active

    $1,300

    1 Bed1 Bath595 SqFt

    43 Wallens Street #1st, Winchester, CT 06098

    Listed by Diane Carroll of The Washington Agency

    380 Main Street, Winchester, CT 06098
    1/16
    Active

    $999,000

    5 Baths6,200 SqFt

    380 Main Street, Winchester, CT 06098

    Listed by Anthony Gioia of The Washington Agency

    103 Cordano Road, Winchester, CT 06098
    1/35
    Active

    $339,900

    3 Beds2 Baths1,442 SqFt

    103 Cordano Road, Winchester, CT 06098

    Listed by David Sartirana of Northwest CT Realty

    237 Wallens Hill Road, Winchester, CT 06098
    1/40
    Price Dropped by $19K

    $579,900

    4 Beds3 Baths2,628 SqFt

    237 Wallens Hill Road, Winchester, CT 06098

    Listed by David Sartirana of Northwest CT Realty

    88 Spencer Street #2, Winchester, CT 06098
    1/3
    Active

    $1,495

    2 Beds1 Bath800 SqFt

    88 Spencer Street #2, Winchester, CT 06098

    Listed by Amanda Balaski of Northwest CT Realty

    205 Old New Hartford Road, Winchester, CT 06098
    1/7
    Active

    $499,900

    6 Beds5 Baths2,864 SqFt

    205 Old New Hartford Road, Winchester, CT 06098

    Listed by TK Krumm of Berkshire Hathaway NE Prop.

    936 Main Street #14, Winchester, CT 06098
    1/9
    Active

    $1,500

    2 Beds2 Baths1,000 SqFt

    936 Main Street #14, Winchester, CT 06098

    Listed by Michael Block of Building Blocks LLC

    9 Loomis Street, Winchester, CT 06098
    1/19
    Active

    $469,900

    3 Beds2 Baths1,768 SqFt

    9 Loomis Street, Winchester, CT 06098

    Listed by Marshall Cohen of Cohen Agency

    147 E. Wakefield Boulevard, Winchester, CT 06098
    1/29
    Price Dropped by $20K

    $279,900

    2 Beds1 Bath702 SqFt

    147 E. Wakefield Boulevard, Winchester, CT 06098

    Listed by Kristin Leblanc of Mary LeBlanc Realty

    624 Wynne Road, Winchester, CT 06098
    1/23
    Price Dropped by $25K

    $174,900

    2 Beds1 Bath672 SqFt

    624 Wynne Road, Winchester, CT 06098

    Listed by AJ Davis of Better Homes and Gardens Real Estate Executive Real Estate

    469 Platt Hill Road, Winchester, CT 06098
    1/40
    Active

    $895,000

    4 Beds2 Baths3,088 SqFt

    469 Platt Hill Road, Winchester, CT 06098

    Listed by Marshall Cohen of Cohen Agency

    267 Rockwell Street #1st fl, Winchester, CT 06098
    1/12
    Active

    $1,300

    1 Bed1 Bath600 SqFt

    267 Rockwell Street #1st fl, Winchester, CT 06098

    Listed by Diane Carroll of The Washington Agency

    29 Center Street, Winchester, CT 06098
    1/26
    Active

    $239,000

    7 Beds3 Baths2,400 SqFt

    29 Center Street, Winchester, CT 06098

    Listed by Frank Berg of Town & Country Real Estate

    150 Oak Street, Winchester, CT 06098
    1/19
    Price Dropped by $30K

    $549,000

    11 Beds6 Baths5,233 SqFt

    150 Oak Street, Winchester, CT 06098

    Listed by Pamela Silvestri of Turning Point Realty, LLC

    277 N. Main Street ##3, Winchester, CT 06098
    1/14
    Active

    $900

    1 Bed1 Bath650 SqFt

    277 N. Main Street ##3, Winchester, CT 06098

    Listed by Ryan Marconi of The Washington Agency

    34 Rock Street, Winchester, CT 06098
    1/22
    Active

    $2,150

    3 Beds1 Bath1,042 SqFt

    34 Rock Street, Winchester, CT 06098

    Listed by Terry Cubeddu of Ameristar Royal Realty LLC

    440 Main Street #B, Winchester, CT 06098
    1/5
    Active

    $1,000

    2 Beds1 Bath4,668 SqFt

    440 Main Street #B, Winchester, CT 06098

    Listed by Linda Ganem of Borla & Associates Real Estate

    121 West Wakefield Boulevard, Winchester, CT 06098
    1/38
    Price Dropped by $20K

    $749,000

    4 Beds4 Baths2,265 SqFt

    121 West Wakefield Boulevard, Winchester, CT 06098

    Listed by Elizabeth Stockwell of Coldwell Banker Realty

    431 West Wakefield Boulevard, Winchester, CT 06098
    1/37
    Active

    $1,850,000

    9 Beds6 Baths7,000 SqFt

    431 West Wakefield Boulevard, Winchester, CT 06098

    Listed by Lisa Ogren of Berkshire Hathaway NE Prop.

    • 1
    • 2
    • 3

    explore listings in Winchester

    • Open House
    • Price Reduced
    • Virtual Tour
    • 3D Tour
    site logo
    The YlH Real Estate Team
    Aileen Yambo
        Home
        Buy
        1. All Listings
        2. Featured Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Rent
        1. Rental Listings
        About
        1. About Us
        2. Contact Us
        3. Reviews
        Market Snapshot
    +1(646) 261-4698
    aileen@theyhteam.com
    4 International Dr, Rye Brook, NY 10573

    Get My App

    Do Not Sell or Share My Personal Data
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    site logo
    The YlH Real Estate Team
    Aileen Yambo
        Home
        Buy
        1. All Listings
        2. Featured Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Rent
        1. Rental Listings
        About
        1. About Us
        2. Contact Us
        3. Reviews
        Market Snapshot
    +1(646) 261-4698
    aileen@theyhteam.com
    4 International Dr, Rye Brook, NY 10573

    Get My App

    Do Not Sell or Share My Personal Data
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.