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Winchester, TN Homes for Sale — Page 6 | Realty.com

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3 beds New construction

Homes for Sale in Winchester, TN

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24 of 176 Listings

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24 of 176 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

100Active
$3,499,000
4 bd · 7 ba · 8,447 sqft
368 Chandler Dr, Winchester, TN
Maggie Hargrove · Benchmark Realty, LLC
25Active
$469,900
3 bd · 2 ba · 1,817 sqft
172 Lookout Dr, Winchester, TN
Renee Delbridge · Benchmark Realty, LLC
Price Reduced27Active
$349,999
3 bd · 2 ba · 1,548 sqft
131 Charlotte Dr, Winchester, TN
Landon Keller · Century 21 Volunteer Realty

Price Reduced62Active
$525,000
3 bd · 3 ba · 2,494 sqft
92 Freeman Ct, Winchester, TN
Misty Guzman · Century 21 Wright Realty
Price Reduced58Active
$464,000
3 bd · 4 ba · 4,244 sqft
466 Willow Oak Dr, Winchester, TN
Angie Miller · John Smith Jr Realty and Auction LLC
57Active
$775,000
4 bd · 3 ba · 3,104 sqft
22 Hammock Dr, Winchester, TN
Lauren Bailey · Swaffords Property Shop
Price Reduced81Active
$460,000
3 bd · 3 ba · 2,543 sqft
201 Lookout Dr, Winchester, TN
Mena Shaker · Dream Homes Realty
72Active
$774,900
4 bd · 5 ba · 3,090 sqft
210 Cascade Dr, Winchester, TN
MITCHELL BOWMAN · simpliHOM - The Results Team
Price Reduced49Active
$425,000
3 bd · 2 ba · 1,814 sqft
84 Meadowood Ln, Winchester, TN
Hunter Forsythe · Southern Elite Realty
Price Reduced29Active
$350,000
3 bd · 2 ba · 1,886 sqft
67 Lake Ln, Winchester, TN
Brandy Michelle Scott · Winton Auction & Realty Co.
29Active
$489,900
3 bd · 2 ba · 2,116 sqft
647 Golf Shores Dr, Winchester, TN
Chris Hawkersmith · Lynch Rigsby Realty & Auction, LLC
Price Reduced75Active
$474,900
4 bd · 4 ba · 2,260 sqft
805 N Jefferson St, Winchester, TN
Shelia Lunsford · Benchmark Realty, LLC
75Active
$740,000
3 bd · 3 ba · 2,075 sqft
59 Walnut Dr, Winchester, TN
Alyssa Roland / The Haven Group · Southern Middle Realty
Price Reduced42Active
$359,000
3 bd · 2 ba · 1,972 sqft
6606 Old Tullahoma Rd, Winchester, TN
Ashley Lynch · Lynch Rigsby Realty & Auction, LLC
Price Reduced17Active
$295,999
3 bd · 2 ba · 1,213 sqft
99 N Shephard St, Winchester, TN
Ashley W. Nelson · Franklin County Realty
Price Reduced15Active
$354,500
3 bd · 2 ba · 1,797 sqft
145 Murray Lake Dr, Winchester, TN
Chris Hawkersmith · Lynch Rigsby Realty & Auction, LLC
Price Reduced57Active
$840,900
4 bd · 3 ba · 3,484 sqft
282 Owl Hollow Ln, Winchester, TN
Sam Hatfield · Sam Hatfield Realty, Inc.
45Active
$399,900
4 bd · 4 ba · 2,197 sqft
44 Houghton Dr, Winchester, TN
Dana Dillinger · RE/MAX 1st Realty
Price 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
Price Reduced13Active
$299,000
3 bd · 3 ba · 2,047 sqft
173 Country Club Ter, Winchester, TN
Sharon Swafford · Swaffords Property Shop
56Active
$1,399,900
6 bd · 6 ba · 6,176 sqft
61 Joy Cir, Winchester, TN
Mike Winton · Mike Winton Realty & Auction
Price Reduced41Active
$745,000
3 bd · 3 ba · 2,592 sqft
25 Dry Fork Dr, Winchester, TN
Dena Abbott · SimpliHOM
Price Reduced38Active
$344,900
3 bd · 2 ba · 1,300 sqft
253 Brookfield Cir, Winchester, TN
Jackson Lynch · Lynch Rigsby Realty & Auction, LLC
70Active
$450,000
3 bd · 3 ba · 2,629 sqft
314 4th Ave, NW, Winchester, TN
Sharon Swafford · Swaffords Property Shop

1…5 6 7 8

Listing data & MLS disclosures

Realtracs: Based on information submitted to the MLS GRID as of 2026-10-01 12:26:00 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

July 2026 · This period is still settling

Selling at 97.0% of asking price

Buyers here are paying below asking. MLS · 26 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 10, 2026

Median sale price: $407,500$268,000–$606,250 typical range
Sales: 12
Paid in cash: 50.0%

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

Median list price: $480,000
Homes for sale: 159
Median days on market: 47 days

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

Year-over-year: 14.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 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

Explore Winchester homes

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3 Bedroom Homes
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Nearby areas

ZIP codes

37398 (175)
37388 (172)
37160 (170)
37355 (118)
37330 (49)
37387 (48)
37356 (38)
37352 (30)

Cities

Tullahoma (172)
Shelbyville (170)
Manchester (118)
Estill Springs (49)
Tracy City (48)
Monteagle (38)
Lynchburg (30)
Fayetteville (23)

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 2026-10-01 12:26:00 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

37398 (175)
37388 (172)
37160 (170)
37355 (118)
37330 (49)
37387 (48)
37356 (38)
37352 (30)

Cities

Tullahoma (172)
Shelbyville (170)
Manchester (118)
Estill Springs (49)
Tracy City (48)
Monteagle (38)
Lynchburg (30)
Fayetteville (23)

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

July 2026 · This period is still settling

Selling at 97.0% of asking price

Buyers here are paying below asking. MLS · 26 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 10, 2026

Median sale price: $407,500$268,000–$606,250 typical range
Sales: 12
Paid in cash: 50.0%

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

Median list price: $480,000
Homes for sale: 159
Median days on market: 47 days

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

Year-over-year: 14.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Median home size: 1,752 sq. ft.