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Homes for sale in Winchester

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Winchester

137 homes for sale in Winchester

Showing 73–96 of 137 · as of September 23, 2026 at 11:58 AM CDT

More listings are being added as photos arrive. Looking for something you do not see here? Call 615-265-1000 and we will search the full MLS with you.

368 Chandler Dr1 / 6

$3,499,000

368 Chandler Dr

Winchester, TN, 37398

4 bd 7 ba 8,447 sq ftBuilt 2008

Single Family Residence · Lakefront · Boat dock

“The perfect definition of elevated lake living. Before you even enter the gated driveway…”

85 days on market

Listed by Benchmark Realty, LLC · MLS# 3255695

Active · (615) 809-2323

172 Lookout Dr1 / 6

$469,900

172 Lookout Dr

Winchester, TN, 37398

3 bd 2 ba 1,817 sq ftBuilt 2022

Highlands · Single level · Main-level primary

“Better than new with tons of builder and seller upgrades in a beautiful, gated community!…”

90 days on market

Listed by Benchmark Realty, LLC · MLS# 3189545

Active · (615) 809-2323

210 Cascade Dr1 / 6

$774,900

210 Cascade Dr

Winchester, TN, 37398

4 bd 5 ba 3,090 sq ftBuilt 2026

Stone Field Heights · Finished basement · Main-level primary

“The perfect blend of comfort, space, and functionality in this stunning walkout basement…”

92 days on market

Listed by simpliHOM - The Results Team · MLS# 3248070

Active · (615) 270-3111

805 N Jefferson St↓ $25,0001 / 6

$474,900

805 N Jefferson St

Winchester, TN, 37398

4 bd 4 ba 2,260 sq ftBuilt 2022

Single Family Residence · Waterfront view · Main-level primary

“BIG PRICE ADJUSTMENT! With Tims Ford Lake just across the street, be prepared to love the…”

102 days on market

Listed by Benchmark Realty, LLC · MLS# 3242752

Active · (615) 809-2323

59 Walnut Dr1 / 6

$740,000

59 Walnut Dr

Winchester, TN, 37398

3 bd 3 ba 2,075 sq ftBuilt 1994

Cline Ridge · Lakefront · Boat dock

“Tucked away in the trees of desirable Cline Ridge, this charming cottage-style retreat…”

103 days on market

Listed by Southern Middle Realty · MLS# 3242474

Active · (931) 597-0263

6606 Old Tullahoma Rd↓ $20,0001 / 6

$359,000

6606 Old Tullahoma Rd

Winchester, TN, 37398

3 bd 2 ba 1,972 sq ftBuilt 1929

Single Family Residence · Acreage · Main-level primary

“Charming Farmhouse on 1 Acre – Move-In Ready! Welcome to your peaceful country retreat!…”

104 days on market

Listed by Lynch Rigsby Realty & Auction, LLC · MLS# 3242003

Active · (931) 967-1672

282 Owl Hollow Ln↓ $36,1001 / 6

$840,900

282 Owl Hollow Ln

Winchester, TN, 37398

4 bd 3 ba 3,484 sq ftBuilt 2007

Single Family Residence · Lakefront · Boat dock

“VERY MOTVATED SELLER, Beautiful Lake house perfect for multi families. A cozy fireplace…”

114 days on market

Listed by Sam Hatfield Realty, Inc. · MLS# 3123764

Active · (931) 968-0500

44 Houghton Dr1 / 6

$399,900

44 Houghton Dr

Winchester, TN, 37398

4 bd 4 ba 2,197 sq ftBuilt 1967

Houghton-Hill · Pool · Single level

“Renovations complete! Brick ranch style home with so much space! This 4 Bedroom, brick…”

114 days on market

Listed by RE/MAX 1st Realty · MLS# 3229184

Active · (931) 728-5552

MLS GRID logo slot — approved artwork pending

Listings courtesy of Realtracs as distributed by MLS GRID

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Based on information submitted to the MLS GRID as of September 23, 2026 at 11:58 AM CDT. 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.

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