+1(860) 966-1834 taylorshurtleffhomes@gmail.com
  • Home
  • Buy
    1. All Listings
    2. Featured Listings
    3. Sold Listings
  • Sell
    1. Sell My Home
    2. Home Valuation
  • About
    1. About Me
    2. Reviews
  • Taylor Shurtleff
  • Market Snapshot
  • Blogs
  • Calculator
    • Register
    • /
    • Sign In
    Filters Reset
    1 Filter
    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
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    Baths
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    • Any
    • 1
    • 2
    • 3
    • 4
    • 5
    Reset
    1 Filter
    1 Filter Applied

    Days On Site
    Advanced
    Less Than
    Days
    Unit Level

    SqFt
    Switch to Acre
    Sqft
    Sqft
    Lot Size
    Switch to Acre
    Sqft
    Sqft
    Price per Sqft
    Monthly HOA Fee
    Year Built
    Stories
    Kitchens
    Acres
    Full Bathrooms
    Half Bathrooms
    Frontage
    Tax Amount
    Land Lease Fee
    Keyword
    Maintenance Fee
    Assessed Value

    Fireplace Number

    Parking Space
    Garage Space
    Carport Spaces

    Open House
    Has Picture
    New
    Hot
    Virtual Tour
    Price Reduced
    Save Search (2)
    Save your search to get Alerts
    59 Properties
    Map

    59 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
    171 Reaching Hill Road, Winchester, CT 06098
    Open Sun 1PM-3PM

    $495,000

    171 Reaching Hill Road, Winchester, CT 06098

    3 Beds2 Baths2,700 SqFt

    Listed by Kelly Sullivan of Sullivan Real Estate Inc

    355 West Lake Street, Winchester, CT 06098
    Open Mon 1PM-3PM

    $979,000

    355 West Lake Street, Winchester, CT 06098

    5 Beds4 Baths3,216 SqFt

    Listed by David Sartirana of Northwest CT Realty

    19 Center Street #1R, Winchester, CT 06098
    New

    $1,595

    19 Center Street #1R, Winchester, CT 06098

    3 Beds1 Bath900 SqFt

    Listed by Amanda Balaski of Northwest CT Realty

    98 Spencer Street #4N, Winchester, CT 06098
    New

    $1,595

    98 Spencer Street #4N, Winchester, CT 06098

    4 Beds1 Bath1,000 SqFt

    Listed by Amanda Balaski of Northwest CT Realty

    51 Hinsdale Avenue, Winchester, CT 06098
    New

    $2,150

    51 Hinsdale Avenue, Winchester, CT 06098

    3 Beds2 Baths1,600 SqFt

    Listed by Suzie Larson of Turning Point Realty, LLC

    174 Main Street #C, Winchester, CT 06098
    Active

    $1,150

    174 Main Street #C, Winchester, CT 06098

    1 Bed1 Bath700 SqFt

    Listed by Amanda Balaski of Northwest CT Realty

    150 Mathew Road, Winchester, CT 06098
    Active

    $349,000

    150 Mathew Road, Winchester, CT 06098

    3 Beds2 Baths1,480 SqFt

    Listed by Josh Dionne of Commercial Services Realty

    469 Platt Hill Road, Winchester, CT 06098
    Active

    $995,000

    469 Platt Hill Road, Winchester, CT 06098

    4 Beds2 Baths3,088 SqFt

    Listed by Marshall Cohen of Cohen Agency

    9 John Street, Winchester, CT 06098
    Active

    $158,000

    9 John Street, Winchester, CT 06098

    1 Bed2 Baths1,172 SqFt

    Listed by Michelle Grant of Coldwell Banker Premier Real Estate

    9 Loomis Street, Winchester, CT 06098
    Under Contract

    $165,000

    9 Loomis Street, Winchester, CT 06098

    3 Beds2 Baths1,768 SqFt

    Listed by Kristen Duchene of Litchfield County Real Estate

    323 East Wakefield Boulevard, Winchester, CT 06098
    Under Contract

    $375,000

    323 East Wakefield Boulevard, Winchester, CT 06098

    3 Beds3 Baths1,426 SqFt

    Listed by Heather Crabtree of Coldwell Banker Realty

    144 Marshall Street, Winchester, CT 06098
    Active

    $579,999

    144 Marshall Street, Winchester, CT 06098

    3 Beds2 Baths1,744 SqFt

    Listed by Monica Palmerie of RE/MAX RISE

    155 Mathew Road, Winchester, CT 06098
    Under Contract

    $299,900

    155 Mathew Road, Winchester, CT 06098

    2 Beds2 Baths1,536 SqFt

    Listed by Austin Brochu of Sullivan Real Estate Inc

    421 Unity Place, Winchester, CT 06098
    Under Contract

    $286,000

    421 Unity Place, Winchester, CT 06098

    3 Beds2 Baths1,440 SqFt

    Listed by Michelle Lorenzetti of Premier Re Group LLC

    39 South Main Street, Winchester, CT 06098
    Active

    $749,900

    39 South Main Street, Winchester, CT 06098

    7 Beds3 Baths3,486 SqFt

    Listed by Ryan Horvay of Smith & DeGroat Real Estate

    56 Lakeview Road, Winchester, CT 06098
    Under Contract

    $239,900

    56 Lakeview Road, Winchester, CT 06098

    3 Beds1 Bath1,101 SqFt

    Listed by Anthony Gioia of The Washington Agency

    110 Rugg Brook Road, Winchester, CT 06098
    Under Contract

    $400,000

    110 Rugg Brook Road, Winchester, CT 06098

    3 Beds3 Baths2,209 SqFt

    Listed by Michelle Grant of Coldwell Banker Premier Real Estate

    154 Wallens Street, Winchester, CT 06098
    Under Contract

    $204,000

    154 Wallens Street, Winchester, CT 06098

    4 Beds2 Baths1,848 SqFt

    Listed by Adam Devine of Dorrance Realty

    10 Maple Street #2, Winchester, CT 06098
    Under Contract

    $1,495

    10 Maple Street #2, Winchester, CT 06098

    3 Beds1 Bath881 SqFt

    Listed by Amanda Balaski of Northwest CT Realty

    25 Center Street, Winchester, CT 06098
    Active

    $269,900

    25 Center Street, Winchester, CT 06098

    3 Beds1 Bath2,754 SqFt

    Listed by Jessica Lopez of Our Home Realty Advisors

    47 Moore Avenue, Winchester, CT 06098
    Under Contract

    $295,000

    47 Moore Avenue, Winchester, CT 06098

    4 Beds2 Baths1,509 SqFt

    Listed by Suzie Larson of Turning Point Realty, LLC

    150 Meadow Street, Winchester, CT 06098
    Under Contract

    $249,900

    150 Meadow Street, Winchester, CT 06098

    4 Beds2 Baths2,094 SqFt

    Listed by David Sartirana of Northwest CT Realty

    39 Orchard Street, Winchester, CT 06098
    Active

    $230,000

    39 Orchard Street, Winchester, CT 06098

    3 Beds2 Baths1,200 SqFt

    Listed by Michael Flaherty Jr of Sullivan Real Estate Inc

    173 Torringford Street, Winchester, CT 06098
    Under Contract

    $370,000

    173 Torringford Street, Winchester, CT 06098

    3 Beds2 Baths2,239 SqFt

    Listed by Sandra Fehrs of Lamacchia Realty

    • 1
    • 2
    • 3

    explore listings in Winchester

    • Open House
    • Price Reduced
    • Virtual Tour
    • 3D Tour
    site logo
      • Home
        About
        1. About Me
        2. Reviews
        Calculator
      • Buy
        1. All Listings
        2. Featured Listings
        3. Sold Listings
        Market Snapshot
      • Sell
        1. Sell My Home
        2. Home Valuation
        Blogs
    Taylor Shurtleff
    Taylor Shurtleff

    +1(860) 966-1834 taylorshurtleffhomes@gmail.com

    100 Pearl St, 14th fl., Hartford, 06103, USA

    Get My App

    Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

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

    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.
    site logo
      • Home
        About
        1. About Me
        2. Reviews
        Calculator
      • Buy
        1. All Listings
        2. Featured Listings
        3. Sold Listings
        Market Snapshot
      • Sell
        1. Sell My Home
        2. Home Valuation
        Blogs
    Taylor Shurtleff
    Taylor Shurtleff

    +1(860) 966-1834 taylorshurtleffhomes@gmail.com

    100 Pearl St, 14th fl., Hartford, 06103, USA

    Get My App

    Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

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

    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.