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

Homes with a Pool in Winchester, TN

Homes with a Pool in Winchester, TN

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7 Listings
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Homes with a Pool in Winchester, TN

7 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas
  1. 105 Maple Dr — photo100Active

    $1,100,000

    3 bd · 4 ba · 2,194 sqft

    105 Maple Dr, Winchester, TN

    Alexander Brandau IV · Aperture Global

  2. 204 Homeward Ave — photo77Active

    $350,200

    3 bd · 3 ba · 1,988 sqft

    204 Homeward Ave, Winchester, TN

    Lauren Whittle - THE PREFERRED GROUP · Keller Williams Russell Realty & Auction

  3. 24 Kacey Marie Dr — photoPrice Reduced51Active

    $629,500

    3 bd · 4 ba · 2,977 sqft

    24 Kacey Marie Dr, Winchester, TN

    Ashton Staker · eXp Realty

  4. 368 Chandler Dr — photoPrice Reduced100Active

    $3,475,000

    4 bd · 7 ba · 8,447 sqft

    368 Chandler Dr, Winchester, TN

    Maggie Hargrove · Benchmark Realty, LLC

  5. 44 Houghton Dr — photo45Active

    $399,900

    4 bd · 4 ba · 2,197 sqft

    44 Houghton Dr, Winchester, TN

    Dana Dillinger · RE/MAX 1st Realty

  6. 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

  7. 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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Listing data & MLS disclosures

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Based on information submitted to the MLS GRID as of 2026-11-03 17:07:01 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.
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #338714

    Call Thomas

    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

    October 2026 · This period is still settling

    Selling at 98.4% of asking price

    Buyers here are paying below asking. MLS · 20 sales · as of Oct 28, 2026

    Homes on the market · MLS, as of Oct 18, 2026–Oct 28, 2026

    Median list price
    $446,450
    Homes for sale
    156
    Median days on market
    35 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    1,752 sq. ft.