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- $ 800,000
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- $ 1,000,000
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450 Properties Available In Winchester
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$ 949,900
105 Cannonball Ct, Winchester, TN 37398
Single Family Home
Listed by Angela Privett of Benchmark Realty, LLC


$ 949,900
105 Cannonball Ct, Winchester, TN 37398
Single Family Home
Listed by Angela Privett of Benchmark Realty, LLC

$ 524,900
201 Lookout Dr, Winchester, TN 37398
Single Family Home
Listed by Mena Shaker of Dream Homes Realty


$ 524,900
201 Lookout Dr, Winchester, TN 37398
Single Family Home
Listed by Mena Shaker of Dream Homes Realty

$ 519,900
67 Summerset Dr, Winchester, TN 37398
Single Family Home
Listed by Mena Shaker of Dream Homes Realty

$ 1,499,900
314 N Porter St, Winchester, TN 37398
Single Family Home
Listed by Angela Privett of Benchmark Realty, LLC


$ 1,499,900
314 N Porter St, Winchester, TN 37398
Single Family Home
Listed by Angela Privett of Benchmark Realty, LLC

$ 999,999
101 Cypress Point Dr, Winchester, TN 37398
Single Family Home
Listed by Emily Montgomery of simpliHOM


$ 999,999
101 Cypress Point Dr, Winchester, TN 37398
Single Family Home
Listed by Emily Montgomery of simpliHOM

$ 769,900
0 Ridgecrest, Winchester, TN 37398
Single Family Home
Listed by Angela Privett of Benchmark Realty, LLC


$ 769,900
0 Ridgecrest, Winchester, TN 37398
Single Family Home
Listed by Angela Privett of Benchmark Realty, LLC

$ 759,900
35 Cedar Ln, Winchester, TN 37398
Single Family Home
Listed by Carl Thomas of RE/MAX Unlimited


$ 1,200
105 Hillcrest Dr, Winchester, TN 37398
Single Family Home
Listed by Benjamin Allen Merrill of Lynch Rigsby Realty & Auction, LLC


$ 1,200
105 Hillcrest Dr, Winchester, TN 37398
Single Family Home
Listed by Benjamin Allen Merrill of Lynch Rigsby Realty & Auction, LLC

$ 294,000
4025 David Crockett Pkwy #W, Winchester, TN 37398
Single Family Home
Listed by Angie Miller of John Smith Jr Realty and Auction LLC


$ 294,000
4025 David Crockett Pkwy #W, Winchester, TN 37398
Single Family Home
Listed by Angie Miller of John Smith Jr Realty and Auction LLC

$ 359,900
655 Clark Rd, Winchester, TN 37398
Single Family Home
Listed by Shawna Kay Denby of 1st Choice REALTOR

$ 450,000
44 Rocky Hollow Dr, Winchester, TN 37398
Single Family Home
Listed by Tim Crabtree of Benchmark Realty, LLC

$ 1,650,000
86 Simmons Circle, Winchester, TN 37398
Single Family Home
Listed by Mikayla Abraham of Legacy South Brokerage

$ 1,650,000
86 Simmons Circle, Winchester, TN 37398
Single Family Home
Listed by Mikayla Abraham of Legacy South Brokerage


$ 1,295,000
732 Fanning Bend Dr, Winchester, TN 37398
Single Family Home
Listed by Mikayla Abraham of Legacy South Brokerage


$ 1,295,000
732 Fanning Bend Dr, Winchester, TN 37398
Single Family Home
Listed by Mikayla Abraham of Legacy South Brokerage

$ 365,000
906 N High St, Winchester, TN 37398
Single Family Home
Listed by Patsy Truslow of Sewanee Realty


$ 1,125,000
62 Abby Cir, Winchester, TN 37398
Single Family Home
Listed by Grey Smotherman / 615-542-4657 of Reliant Realty ERA Powered
