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Winchester, TN Homes for Sale — Page 4 | Realty.com

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3 beds New construction

Homes for Sale in Winchester, TN

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22 of 176 Listings

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22 of 176 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Price Reduced71Active
$451,500
3 bd · 3 ba · 2,228 sqft
270 Wood Bluff Rd, Winchester, TN
Ashley Lynch · Lynch Rigsby Realty & Auction, LLC
94Active
$768,500
3 bd · 2 ba · 1,616 sqft
27 Shady Cove Ln, Winchester, TN
Charlie Gonzales, ABR, SRS, e-PRO | 931-808-5521 · Southern Middle Realty
90Active
$1,499,000
4 bd · 4 ba · 4,035 sqft
136 Bay Cove Trl, Winchester, TN
Ashley Lynch · Lynch Rigsby Realty & Auction, LLC

8Active
$349,900
3 bd · 2 ba · 1,400 sqft
80 Tanya Ter, Winchester, TN
Daniel Prince · John Smith Jr Realty and Auction LLC
Price Reduced16Active
$275,000
3 bd · 2 ba · 1,400 sqft
23 Woods Edge Rd, Winchester, TN
Sharon Swafford · Swaffords Property Shop
Price Reduced57Active
$355,000
3 bd · 2 ba · 1,509 sqft
3896 Lynchburg Rd, Winchester, TN
Melissa K. Stewart · Swaffords Property Shop
Price Reduced81Active
$625,000
4 bd · 3 ba · 3,324 sqft
1136 Bible Crossing Rd, Winchester, TN
Dawn Rigsby · eXp Realty
Price Reduced35Active
$659,000
8 bd · 4 ba · 3,187 sqft
110 S Porter St, Winchester, TN
Jim Brock · Lynch Rigsby Realty & Auction, LLC
Price Reduced28Active
$350,000
3 bd · 3 ba · 3,960 sqft
401 E Petty Lane, Winchester, TN
Wade Trammell · Greater Downtown Realty dba Keller Williams Realty
Price Reduced46Active
$849,900
3 bd · 3 ba · 1,821 sqft
287 Shasteen Bend Dr, Winchester, TN
Sam Hatfield · Sam Hatfield Realty, Inc.
Price Reduced65Active
$350,000
3 bd · 2 ba · 1,700 sqft
1522 Holders Cove Road, Winchester, TN
Wade Trammell · Greater Downtown Realty dba Keller Williams Realty
Price Reduced77Active
$355,000
3 bd · 3 ba · 1,988 sqft
204 Homeward Ave, Winchester, TN
Lauren Whittle - THE PREFERRED GROUP · Keller Williams Russell Realty & Auction
Price Reduced56Active
$490,000
6 bd · 4 ba · 3,158 sqft
109 Carter Farris Lane, Winchester, TN
Wade Trammell · Greater Downtown Realty dba Keller Williams Realty
73Active
$685,700
4 bd · 4 ba · 3,705 sqft
356 Ridgecrest Dr, Winchester, TN
Sean Crabtree · Blue Door Realty Group
13Active
$125,000
3 bd · 1 ba · 1,150 sqft
406 2nd Ave, NW, Winchester, TN
Dustyn Reed · United Real Estate Middle Tennessee
Price Reduced62Active
$449,000
3 bd · 2 ba · 2,355 sqft
262 Crimson Dr, Winchester, TN
Melissa K. Stewart · Swaffords Property Shop
12Active
$644,900
3 bd · 3 ba · 2,729 sqft
90 Pine Bluff Ct, Winchester, TN
Susan Baker, Broker. GRI · BHGRE Baker & Cole
Price Reduced60Active
$488,000
4 bd · 3 ba · 2,116 sqft
218 Charlotte Dr, Winchester, TN
Angie Miller · John Smith Jr Realty and Auction LLC
Price Reduced62Active
$459,000
4 bd · 4 ba · 2,209 sqft
220 Bryan Dr, Winchester, TN
Sharon Swafford · Swaffords Property Shop
50Active
$999,000
2 bd · 2 ba · 1,428 sqft
52 Narrows Dr, Winchester, TN
Kaila Hampton Gentry · BMA Properties
Price Reduced8Active
$179,900
3 bd · 2 ba · 1,755 sqft
207 Melody Ln, Winchester, TN
Amanda Lynch · WEICHERT, REALTORS Joe Orr & Associates
Price Reduced74Active
$749,900
4 bd · 4 ba · 2,886 sqft
309 Campfire Ct, Winchester, TN
Shelia Lunsford · Benchmark Realty, LLC

1…3 4 5…8

Listing data & MLS disclosures

Realtracs: Based on information submitted to the MLS GRID as of 2026-10-05 20:17:00 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

August 2026 · This period is still settling

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.

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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Nearby areas

ZIP codes

37388 (185)
37398 (175)
37160 (165)
37355 (118)
37387 (60)
37380 (55)
37330 (50)
37356 (39)

Cities

Tullahoma (185)
Shelbyville (165)
Manchester (118)
Tracy City (60)
South Pittsburg (55)
Estill Springs (50)
Monteagle (39)
Lynchburg (30)

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 2026-10-05 20:17:00 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 (185)
37398 (175)
37160 (165)
37355 (118)
37387 (60)
37380 (55)
37330 (50)
37356 (39)

Cities

Tullahoma (185)
Shelbyville (165)
Manchester (118)
Tracy City (60)
South Pittsburg (55)
Estill Springs (50)
Monteagle (39)
Lynchburg (30)

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

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.