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3 bedsNew construction
5 Bedroom Homes in Winchester, TN
8 listings

5 Bedroom Homes in Winchester, TN

5 Bedroom Homes in Winchester, TN

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8 Listings
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5 Bedroom Homes in Winchester, TN

8 Listings

  1. 130 Peninsula Pt Dr — photo60Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

$1,399,000

5 bd · 4 ba · 3,801 sqft

130 Peninsula Pt Dr, Winchester, TN

Ashley Lynch · Lynch Rigsby Realty & Auction, LLC

  • 3754 Aedc Rd — photo30Active

    $389,000

    5 bd · 3 ba · 3,560 sqft

    3754 Aedc Rd, Winchester, TN

    Adam Brock · Canopy Real Estate

  • listing photo54Active

    $299,000

    5 bd · 2 ba · 1,588 sqft

    Address withheld · Winchester, TN

    Lori Rowton · Keller Williams Nashville-Franklin

  • 171 Cypress Point Dr — photoPrice Reduced63Active

    $975,000

    5 bd · 5 ba · 3,191 sqft

    171 Cypress Point Dr, Winchester, TN

    B. J. Rigsby · Lynch Rigsby Realty & Auction, LLC

  • 1200 Little St — photoPrice Reduced60Active

    $289,000

    5 bd · 2 ba · 1,600 sqft

    1200 Little St, Winchester, TN

    Lori Rowton-Walker · Keller Williams Realty Nashville/Franklin

  • 309 2nd Ave, NW — photoPrice Reduced64Active

    $470,000

    5 bd · 2 ba · 3,922 sqft

    309 2nd Ave, NW, Winchester, TN

    Robert Duncan · eXp Realty

  • 71 David Crockett Hwy — photoPrice Reduced44Active

    $424,999

    5 bd · 3 ba · 2,420 sqft

    71 David Crockett Hwy, Winchester, TN

    Eberley (Ebbie) Holloway · Southern Middle Realty

  • 53 River Watch Way — photo75Active

    $879,900

    5 bd · 5 ba · 3,095 sqft

    53 River Watch Way, Winchester, TN

    John Michael Peck · Century 21 Volunteer Realty

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    L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #338714

    Call Thomas

    Listing data & MLS disclosures

    Greater Chattanooga REALTORS
    IDX information is provided exclusively for consumers’ personal, noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data is deemed reliable but is not guaranteed accurate by the MLS.
    Listing information ©2026 Greater Chattanooga Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-10-22 18:39:06 UTC
    Realtracs
    Based on information submitted to the MLS GRID as of 2026-10-26 15:43:00 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

    September 2026 · This period is still settling

    Winchester 12-month median sale price trend

    Selling at 96.6% of asking price

    Buyers here are paying below asking. MLS · 35 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 29, 2026

    Median sale price
    $554,000$280,000–$1,004,450 typical range
    Price per sq. ft.
    $234
    Sales
    15
    Paid in cash
    40.0%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $464,000
    Homes for sale
    165
    Median days on market
    41 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    65.1%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 10, 2026

    Median home size
    1,752 sq. ft.