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3 bedsNew construction
Homes with a Pool in Winchester, TN
4 listings

Homes with a Pool in Winchester, TN

Homes with a Pool in Winchester, TN

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4 Listings
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Homes with a Pool in Winchester, TN

4 Listings

  1. 368 Chandler Dr — photo100Active

    $3,499,000

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

4 bd · 7 ba · 8,447 sqft

368 Chandler Dr, Winchester, TN

Maggie Hargrove · Benchmark Realty, LLC

  • 3539 Liberty Rd — photoPrice Reduced80Active

    $1,775,000

    6 bd · 4 ba · 3,617 sqft

    3539 Liberty Rd, Winchester, TN

    Chesney R Luttrell · John Smith Jr Realty and Auction LLC

  • 1485 Water Tank Rd — photoPrice Reduced86Active

    $1,475,000

    3 bd · 5 ba · 6,300 sqft

    1485 Water Tank Rd, Winchester, TN

    Sharon Swafford · Swaffords Property Shop

  • 1657 Boswell Rd — photo70Active

    $3,800,000

    6 bd · 8 ba · 8,002 sqft

    1657 Boswell Rd, Winchester, TN

    Davey Hackett · Parks Compass

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #338714

    Call Thomas

    Listing data & MLS disclosures

    Realtracs
    Based on information submitted to the MLS GRID as of 2026-09-21 18:45:00 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

    Winchester, TN community profile

    Population
    9,947
    Median income
    $58,811
    Housing units
    4,383
    People per sq. mi.
    83.2
    Area
    119.5 sq. mi.

    Source: HJN community data

    Winchester housing market

    August 2026 · This period is still settling

    Winchester 12-month median sale price trend

    Selling at 98.2% of asking price

    Buyers here are paying below asking. MLS · 16 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 12, 2026

    Median sale price
    $236,600$135,000–$288,000 typical range
    Price per sq. ft.
    $149
    Sales
    13
    Paid in cash
    46.2%

    Homes on the market · MLS, as of Aug 31, 2026

    Median list price
    $480,000
    Homes for sale
    155
    Median days on market
    87 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -12.3%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 12, 2026

    Median home size
    1,752 sq. ft.