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37398, TN - homes for sale
113 of 113 results displayed
- New
$0Active0 Acres0 Gem Sw, Winchester, TN 37398
MLS# 3244799Listed by: JOHN SMITH JR REALTY AND AUCTION LLC - New
$159,000Active2.19 Acres0 Metcalf Road, Winchester, TN 37398
MLS# 3243837Listed by: LYNCH RIGSBY REALTY & AUCTION, LLC - New
$279,000Active0.8 Acres0 Crestfield Cir, Winchester, TN 37398
MLS# 3241944Listed by: LYNCH RIGSBY REALTY & AUCTION, LLC - New
$150,000Active1.02 Acres0 Bell Dr West, Winchester, TN 37398
MLS# 3232860Listed by: SOUTHERN MIDDLE REALTY 
$195,000Pending0 Acres0 North Jefferson Street, Winchester, TN 37398
MLS# 3232380Listed by: BENCHMARK REALTY, LLC
$349,000Active0.62 Acres0 Agate St, Winchester, TN 37398
MLS# 3230499Listed by: LYNCH RIGSBY REALTY & AUCTION, LLC
$269,000Active0.27 Acres0 Kayak Way, Winchester, TN 37398
MLS# 3229801Listed by: LEADING EDGE REAL ESTATE GROUP
$59,900Active0.29 Acres0 Lookout Dr, Winchester, TN 37398
MLS# 3229580Listed by: GO REALTY, LLC
$199,000Active0 Acres0 Slalom Cir, Winchester, TN 37398
MLS# 3224945Listed by: LYNCH RIGSBY REALTY & AUCTION, LLC
$90,000Active0 Acres0 Turtle Ct, Winchester, TN 37398
MLS# 3225012Listed by: APP REALTY
$144,900Active0.49 Acres0 Cannonball Ct, Winchester, TN 37398
MLS# 3223526Listed by: CENTURY 21 COFFEE COUNTY REALTY & AUCTION
$119,000Active0 Acres0 Latitude Dr, Winchester, TN 37398
MLS# 3223461Listed by: LYNCH RIGSBY REALTY & AUCTION, LLC
$99,999Active0 Acres0 Campfire Ct, Winchester, TN 37398
MLS# 3221516Listed by: SWAFFORDS PROPERTY SHOP
$64,000Pending0.9 Acres0 Meadow Wood Lane, Winchester, TN 37398
MLS# 3218304Listed by: BETTER HOMES & GARDENS REAL ESTATE HERITAGE GROUP
$940,000Active37.6 Acres0 Norwood Creek Rd, Winchester, TN 37398
MLS# 3217363Listed by: LYNCH RIGSBY REALTY & AUCTION, LLC
$69,900Active0.57 Acres0 Mansford Rd, Winchester, TN 37398
MLS# 3217771Listed by: KELLER WILLIAMS REALTY - MURFREESBORO
$99,900Active2.44 Acres0 Sugar Leaf Cir, Winchester, TN 37398
MLS# 3217392Listed by: LYNCH RIGSBY REALTY & AUCTION, LLC
$615,000Active1.13 Acres0 Dry Creek Lane, Winchester, TN 37398
MLS# 3217180Listed by: EXP REALTY
$45,000Active0.2 Acres1512 Clark St, Winchester, TN 37398
MLS# 3216363Listed by: WINTON AUCTION & REALTY CO.
$95,000Active2.5 Acres0 Kasserman Switch Rd, Belvidere, TN 37306
MLS# 3215733Listed by: SYNERGY REALTY NETWORK, LLC
$65,000Active1 Acres0 Kasserman Switch Rd, Belvidere, TN 37306
MLS# 3215734Listed by: SYNERGY REALTY NETWORK, LLC
$99,000Active0 Acres0 Golf Shores Dr, Winchester, TN 37398
MLS# 3208495Listed by: LYNCH RIGSBY REALTY & AUCTION, LLC
$475,000Active1.27 Acres0 2nd Ave Se, Winchester, TN 37398
MLS# 3206894Listed by: EXP REALTY
$199,000Active0.91 Acres0 River Watch Way, Winchester, TN 37398
MLS# 3205208Listed by: ONWARD REAL ESTATE
$105,000Active0 Acres0 River Watch Way, Winchester, TN 37398
MLS# 3205200Listed by: ONWARD REAL ESTATE
$135,000Active0.66 Acres0 River Watch Way, Winchester, TN 37398
MLS# 3205204Listed by: ONWARD REAL ESTATE
$69,900Active0 Acres0 Why Worry Lane, Winchester, TN 37398
MLS# 3193828Listed by: THE SAPPHIRE GROUP REAL ESTATE
$104,900Active0 Acres0 Why Worry Lane, Winchester, TN 37398
MLS# 3193010Listed by: BENCHMARK REALTY, LLC
$95,000Active5.34 Acres0 Haddon Lane, Winchester, TN 37398
MLS# 3190742Listed by: JOHN SMITH JR REALTY AND AUCTION LLC
$99,900Active0.32 Acres0 Why Worry Lane, Winchester, TN 37398
MLS# 3186713Listed by: ZEITLIN SOTHEBY'S INTERNATIONAL REALTY
$89,900Active0.34 Acres0 Kayak Way, Winchester, TN 37398
MLS# 3185666Listed by: TEAM GEORGE WEEKS REAL ESTATE, LLC
$79,900Active0.95 Acres5468 Old Tullahoma Rd, Winchester, TN 37398
MLS# 3184476Listed by: FRIDRICH & CLARK REALTY
$125,000Active1.26 Acres0 Cascade Dr, Winchester, TN 37398
MLS# 3183859Listed by: ONWARD REAL ESTATE
$79,000Active0.52 Acres0 Old Holders Cove Rd, Winchester, TN 37398
MLS# 3186328Listed by: SWAFFORDS PROPERTY SHOP
$119,900Active2.32 Acres0 Old Estill Springs Rd, Winchester, TN 37398
MLS# 3180497Listed by: RELIANT REALTY ERA POWERED
$89,999Active0 Acres0 Suntan Ct, Winchester, TN 37398
MLS# 3179843Listed by: LEADING EDGE REAL ESTATE GROUP
$129,000Active1.1 Acres0 Aedc Rd, Winchester, TN 37398
MLS# 3177893Listed by: LYNCH RIGSBY REALTY & AUCTION, LLC
$149,900Active0.36 Acres0 Paddleboard Ct, Winchester, TN 37398
MLS# 3173129Listed by: ZACH TAYLOR REAL ESTATE
$275,000Active9.42 Acres0 Tullahoma Hwy, Winchester, TN 37398
MLS# 3171237Listed by: FREEDOM REALTY GROUP
$125,000Active0.44 Acres0 Shady Cove Ln, Winchester, TN 37398
MLS# 3170070Listed by: ONWARD REAL ESTATE
$250,000Active0.85 Acres0 E Rockcrest Cir, Winchester, TN 37398
MLS# 3170071Listed by: ONWARD REAL ESTATE
$150,000Active0.45 Acres2 Oak St, Winchester, TN 37398
MLS# 3168668Listed by: SIMPLIHOM - THE RESULTS TEAM
$549,000Active2.55 Acres2T Barnes Lane, Lynchburg, TN 37352
MLS# 3168857Listed by: LAKE HOMES REALTY, LLC
$149,957Active45 Acres0 Windjammer Ct, Winchester, TN 37398
MLS# 3168470Listed by: BENCHMARK REALTY, LLC
$97,900Active0.25 Acres0 Turtle Court, Winchester, TN 37398
MLS# 3168309Listed by: BENCHMARK REALTY, LLC
$130,000Active5.17 Acres0 Haddon Ln, Winchester, TN 37398
MLS# 3164418Listed by: TYLER YORK REAL ESTATE BROKERS, LLC
$149,900Active0 Acres0 Kayak Way, Winchester, TN 37398
MLS# 3159700Listed by: BENCHMARK REALTY, LLC
$395,000Active0.33 Acres0 Hickory Pt, Winchester, TN 37398
MLS# 3158940Listed by: FREEDOM REALTY GROUP
$139,000Active0.38 Acres0 Why Worry Lane, Winchester, TN 37398
MLS# 3158573Listed by: LEADING EDGE REAL ESTATE GROUP
$175,000Active1.04 Acres0 Cascade Dr, Winchester, TN 37398
MLS# 3155800Listed by: BEYCOME BROKERAGE REALTY, LLC
$139,000Active0.33 Acres0 Hammock Dr, Winchester, TN 37398
MLS# 3154966Listed by: LAKE HOMES REALTY, LLC
$72,000Active0.91 Acres0 Cooper Ln, Winchester, TN 37398
MLS# 3152479Listed by: SWAFFORDS PROPERTY SHOP
$84,900Pending3 Acres0 Michelle Lane, Winchester, TN 37398
MLS# 3148531Listed by: SOUTHERN MIDDLE REALTY
$165,000Active6.05 Acres0 Box House Rd, Belvidere, TN 37306
MLS# 3137759Listed by: WINTON AUCTION & REALTY CO.
$139,900Active0.92 Acres0 Sharp Springs Rd, Winchester, TN 37398
MLS# 3134214Listed by: SWAFFORDS PROPERTY SHOP
$94,900Active0 Acres0 River Watch Way, Winchester, TN 37398
MLS# 3134024Listed by: BENCHMARK REALTY, LLC
$85,000Active0 Acres0 Dry Fork Dr, Winchester, TN 37398
MLS# 3131827Listed by: SIMPLIHOM
$159,900Active5.01 Acres0 Lynchburg Road, Winchester, TN 37398
MLS# 3129662Listed by: PARKS AUCTION & REALTY
$99,900Active0 Acres0 Pontoon Pl, Winchester, TN 37398
MLS# 3129038Listed by: LYNCH RIGSBY REALTY & AUCTION, LLC
$89,000Active0.31 Acres109 7th Ave Ne, Winchester, TN 37398
MLS# 3124575Listed by: WINTON AUCTION & REALTY CO.
$89,000Active0.27 Acres612 N Jefferson St, Winchester, TN 37398
MLS# 3124566Listed by: WINTON AUCTION & REALTY CO.
$597,000Active0.43 Acres0 Peninsula Point Dr, Winchester, TN 37398
MLS# 3123795Listed by: SAM HATFIELD REALTY, INC.
$61,500Active0 Acres0 Dry Fork, Winchester, TN 37398
MLS# 3121620Listed by: SOUTHERN MIDDLE REALTY
$79,900Active0 Acres0 Campfire Ct, Winchester, TN 37398
MLS# 3111135Listed by: SOUTHERN MIDDLE REALTY
$140,000Active0.31 Acres0 Suntan Court, Winchester, TN 37398
MLS# 3078602Listed by: BENCHMARK REALTY, LLC
$79,900Active0.15 Acres0 River Watch Way, Winchester, TN 37398
MLS# 3042948Listed by: MARCOMA REALTY, INC.
$84,900Active0 Acres0 Why Worry Ln, Winchester, TN 37398
MLS# 3062133Listed by: LYNCH RIGSBY REALTY & AUCTION, LLC
$1,500,000Active19.58 Acres405 Sharp Springs Rd, Winchester, TN 37398
MLS# 3056561Listed by: WINTON AUCTION & REALTY CO.
$230,000Active0.25 Acres0 Kayak Way W, Winchester, TN 37398
MLS# 3033545Listed by: LEADING EDGE REAL ESTATE GROUP
$100,000Active1.71 Acres0 Old Clark Rd, Winchester, TN 37398
MLS# 3041395Listed by: SOUTHERN MIDDLE REALTY
$134,900Active5.16 Acres0 Haddon Ln, Winchester, TN 37398
MLS# 3181711Listed by: EXP REALTY
$225,000Active3 Acres0 Spring Hill Dr Off, Winchester, TN 37398
MLS# 3014968Listed by: NOBLE REAL ESTATE
$139,900Pending2.67 Acres0 Maple Bend Rd, Winchester, TN 37398
MLS# 3003166Listed by: JOHN SMITH JR REALTY AND AUCTION LLC
$1,800,000Active25.15 Acres3819 Tullahoma Hwy, Winchester, TN 37398
MLS# 3000595Listed by: HORIZON REALTY GROUP DBA KELLER WILLIAMS HORIZON
$166,000Active0.7 Acres0 Cascade Dr, Winchester, TN 37398
MLS# 2987667Listed by: WEICHERT, REALTORS JOE ORR & ASSOCIATES
$166,000Active0.7 Acres0 Stone Field De, Winchester, TN 37398
MLS# 2987669Listed by: WEICHERT, REALTORS JOE ORR & ASSOCIATES
$74,900Active0.24 Acres443 Canoe Ct, Winchester, TN 37398
MLS# 2986802Listed by: BENCHMARK REALTY, LLC
$109,900Active0.21 Acres0 Kayak Way, Winchester, TN 37398
MLS# 3213420Listed by: CENTURY 21 COFFEE COUNTY REALTY & AUCTION
$509,450Active22.15 Acres0 Haddon Lane, Winchester, TN 37398
MLS# 2946006Listed by: CENTURY 21 COFFEE COUNTY REALTY & AUCTION
$160,000Active0 Acres0 Dry Fork Drive, Winchester, TN 37398
MLS# 2946010Listed by: ANDERSON REALTY SERVICES
$89,900Active0.64 Acres0 S College St, Winchester, TN 37398
MLS# 2942332Listed by: LUXSMART REALTY
$145,000Active0.26 Acres0 Wakeboard Way, Winchester, TN 37398
MLS# 2941097Listed by: SOUTHERN MIDDLE REALTY
$74,899Active0 Acres0 Lake Life Ct, Winchester, TN 37398
MLS# 2937046Listed by: ORCHARD BROKERAGE, LLC
$110,000Active0.93 Acres5 Summer Lake, Winchester, TN 37398
MLS# 2936775Listed by: PARKS AUCTION & REALTY
$150,000Active0.95 Acres7 Summer Lake, Winchester, TN 37398
MLS# 2936777Listed by: PARKS AUCTION & REALTY
$110,000Active0.93 Acres13 Summer Lake Ct, Winchester, TN 37398
MLS# 2936779Listed by: PARKS AUCTION & REALTY
$250,000Active1.24 Acres9 Summer Lake Ct, Winchester, TN 37398
MLS# 2936780Listed by: PARKS AUCTION & REALTY
$150,000Active0.95 Acres11 Summer Lake Ct, Winchester, TN 37398
MLS# 2936781Listed by: PARKS AUCTION & REALTY
$110,000Active0.77 Acres3 Summer Lake Ct, Winchester, TN 37398
MLS# 2936782Listed by: PARKS AUCTION & REALTY
$114,900Active0.6 Acres0 Lakeview Way, Winchester, TN 37398
MLS# 2936664Listed by: WINTON AUCTION & REALTY CO.
$110,000Active0.81 Acres1 Summer Lake Ct, Winchester, TN 37398
MLS# 2936666Listed by: PARKS AUCTION & REALTY
$2,990,000Active63.93 Acres0 Tullahoma Highway, Estill Springs, TN 37330
MLS# 2929042Listed by: WINTON AUCTION & REALTY CO.
$55,000Active0.5 Acres1533 Rowe Gap Rd, Winchester, TN 37398
MLS# 2929003Listed by: WINTON AUCTION & REALTY CO.
$69,000Active2.05 Acres1533 Rowe Gap Rd, Winchester, TN 37398
MLS# 2929005Listed by: WINTON AUCTION & REALTY CO.
$177,000Active3.16 Acres5 Anderton Branch Road, Winchester, TN 37398
MLS# 2925123Listed by: BENCHMARK REALTY, LLC
$119,000Active2.13 Acres4 Anderton Branch Road, Winchester, TN 37398
MLS# 2925121Listed by: BENCHMARK REALTY, LLC
$99,900Active0.9 Acres0 Owl Hollow Lane, Winchester, TN 37398
MLS# 2821723Listed by: WEICHERT, REALTORS JOE ORR & ASSOCIATES
$94,900Active0 Acres0 Driftwood Ct, Winchester, TN 37398
MLS# 3129033Listed by: LYNCH RIGSBY REALTY & AUCTION, LLC
$64,900Active0.28 Acres67 Edgefield Ct, Winchester, TN 37398
MLS# 2792697Listed by: SWAFFORDS PROPERTY SHOP
$64,900Active0.55 Acres66 Edgefield Ct, Winchester, TN 37398
MLS# 2792698Listed by: SWAFFORDS PROPERTY SHOP
$195,000Active1.35 Acres16 Cascade Drive, Winchester, TN 37398
MLS# 2786623Listed by: 1ST CHOICE REALTOR
$139,900Active0 Acres0 Dry Fork Dr, Winchester, TN 37398
MLS# 2754013Listed by: LEADING EDGE REAL ESTATE GROUP
$999,999Active25.75 Acres0 Honey Ln, Winchester, TN 37398
MLS# 2689137Listed by: CENTURY 21 COFFEE COUNTY REALTY & AUCTION
$149,900Active0.29 Acres0 Twin Creeks Drive, Winchester, TN 37398
MLS# 2685254Listed by: WEICHERT, REALTORS JOE ORR & ASSOCIATES
$115,000Active0.35 Acres0 Driftwood Ct, Winchester, TN 37398
MLS# 2985981Listed by: BARLOW REALTY LLC
$49,500Active0.33 Acres0 Sherry Street, Winchester, TN 37398
MLS# 2670574Listed by: SOUTHERN MIDDLE REALTY
$84,900Active0.18 Acres0 Kayak Way, Winchester, TN 37398
MLS# 2648864Listed by: SAM HATFIELD REALTY, INC.
$730,000Active1.3 Acres0 Rocky Hollow Road, Winchester, TN 37398
MLS# 2624341Listed by: SIMMONS REALTY
$140,000Active0 Acres0 Slalom Circle, Winchester, TN 37398
MLS# 2618426Listed by: LEADING EDGE REAL ESTATE GROUP
$149,900Active0.31 Acres0 Cannonball Ct, Winchester, TN 37398
MLS# 2568563Listed by: WINTON AUCTION & REALTY CO.
$250,000Active0.31 Acres0 Cypress Point Drive, Winchester, TN 37398
MLS# 2559824Listed by: WEICHERT, REALTORS JOE ORR & ASSOCIATES
$154,900Active0.5 Acres0 River Watch Way, Winchester, TN 37398
MLS# 3039225Listed by: FRANKLIN COUNTY REALTY
$90,000Active0.24 Acres443 Canoe Ct, Winchester, TN 37398
MLS# 2398144Listed by: HODGES AND FOOSHEE REALTY INC.
Local realty services provided by:CENTURY 21 Premier
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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.