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Winchester, TN Homes for Sale | Realty.com

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3 beds New construction

Homes for Sale in Winchester, TN

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24 of 169 Listings

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24 of 169 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

66Active
$350,000
3 bd · 2 ba · 1,872 sqft
19 Carol Cir, Winchester, TN
Eberley (Ebbie) Holloway · Southern Middle Realty
New16Active
$209,900
3 bd · 2 ba · 1,700 sqft
205 Sells St, Winchester, TN
Kaydence Transue · Better Homes & Gardens Real Estate Heritage Group
New53Active
$1,175,000
2 bd · 3 ba · 2,460 sqft
645 Wildwood Trce, Winchester, TN
Angie Miller · John Smith Jr Realty and Auction LLC

41Active
$269,900
2 bd · 1 ba · 1,373 sqft
102 Oak Park, Winchester, TN
Shelia Lunsford · Benchmark Realty, LLC
20Active
Price unavailable
3 bd · 2 ba · 1,024 sqft
1306 Old Cowan Rd, Winchester, TN
Robert Boswell · Hanson Realty & Auction Company
19Active
Price unavailable
3 bd · 2 ba · 2,664 sqft
292 Old Holders Cove Rd, Winchester, TN
Thomas Ore · Winton Auction & Realty Co.
53Active
$749,900
3 bd · 3 ba · 2,052 sqft
96 Maple Dr, Winchester, TN
Derrick Foster · Freedom Realty
19Active
Price unavailable
3 bd · 2 ba · 2,664 sqft
292 Old Holders Cove Rd, Winchester, TN
Thomas Ore · Winton Auction & Realty Co.
36Active
$889,000
3 bd · 1 ba · 1,600 sqft
5630 Mansford Rd, Winchester, TN
Sam Hatfield · Sam Hatfield Realty, Inc.
62Active
$1,199,900
4 bd · 4 ba · 3,720 sqft
160 Wakeboard Way, Winchester, TN
Angela Privett · Benchmark Realty, LLC
28Active
$250,000
3 bd · 2 ba · 1,552 sqft
300 Edgewater Dr, Winchester, TN
Erica Paige Howard · Freedom Realty Group
77Active
$350,200
3 bd · 3 ba · 1,988 sqft
204 Homeward Ave, Winchester, TN
Lauren Whittle - THE PREFERRED GROUP · Keller Williams Russell Realty & Auction
60Active
$1,399,000
5 bd · 4 ba · 3,801 sqft
130 Peninsula Pt Dr, Winchester, TN
Ashley Lynch · Lynch Rigsby Realty & Auction, LLC
43Active
$245,000
2 bd · 1 ba · 1,292 sqft
1101 High St, N, Winchester, TN
Cole Hodges · Stones River Property Mgmt and Real Estate Service
1Active
$369,000
3 bd · 2 ba · 1,605 sqft
0 Sisk Rd, Winchester, TN
Angie Miller · John Smith Jr Realty and Auction LLC
98Active
$2,499,000
3 bd · 4 ba · 4,258 sqft
2032 Little Hurricane Rd, Winchester, TN
Melissa K. Stewart · Swaffords Property Shop
25Active
$364,900
3 bd · 2 ba · 1,498 sqft
1579 Rowe Gap Rd, Winchester, TN
Angie Miller · John Smith Jr Realty and Auction LLC
Price Reduced83Active
$495,000
3 bd · 3 ba · 2,478 sqft
451 Bell Dr, W, Winchester, TN
Dawn Rigsby · eXp Realty
74Active
$469,000
3 bd · 3 ba · 2,543 sqft
201 Lookout Dr, Winchester, TN
Nadine Choufani · Keller Williams Realty Mt. Juliet
45Active
$749,000
3 bd · 3 ba · 2,207 sqft
153 Brandi Way, Winchester, TN
Ashley Lynch · Lynch Rigsby Realty & Auction, LLC
46Active
$699,000
4 bd · 3 ba · 1,913 sqft
353 Hammock Dr, Winchester, TN
Heather Boldizsar · Lake Homes Realty, LLC
8Active
$169,900
3 bd · 2 ba · 1,672 sqft
1011 Massengill St, Winchester, TN
Sommer Denby · Southern Elite Realty
3Active
$349,900
3 bd · 2 ba · 1,605 sqft
0 Sisk Rd, Winchester, TN
Angie Miller · John Smith Jr Realty and Auction LLC
30Active
$389,000
5 bd · 3 ba · 3,560 sqft
3754 Aedc Rd, Winchester, TN
Adam Brock · Canopy Real Estate

1 2…8

Listing data & MLS disclosures

Realtracs: Based on information submitted to the MLS GRID as of 2026-10-24 12:25:00 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 housing market

September 2026 · This period is still settling

Selling at 96.6% of asking price

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

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

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.

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

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Nearby areas

ZIP codes

37388 (174)
37160 (173)
37398 (168)
37355 (124)
37330 (54)
37387 (49)
37356 (39)
37352 (29)

Cities

Tullahoma (174)
Shelbyville (173)
Manchester (124)
Estill Springs (54)
Tracy City (49)
Monteagle (39)
Lynchburg (29)
Fayetteville (27)

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

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.

Listing data & MLS disclosures

Realtracs: Based on information submitted to the MLS GRID as of 2026-10-24 12:25:00 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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Nearby areas

ZIP codes

37388 (174)
37160 (173)
37398 (168)
37355 (124)
37330 (54)
37387 (49)
37356 (39)
37352 (29)

Cities

Tullahoma (174)
Shelbyville (173)
Manchester (124)
Estill Springs (54)
Tracy City (49)
Monteagle (39)
Lynchburg (29)
Fayetteville (27)

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

Selling at 96.6% of asking price

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

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

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.