Vintage homes for sale & real estate in 37398, TN

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ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
Second chance opportunity! This property is back on the market after a temporary tenant situation and is now ready for new ownership. Reintroduced at a new price and positioned to sell, 219 Old Mill Rd offers excellent value for today’s buyer. Ideal for owner-occupants or investors looking for a well-located property with strong potential. Buyer and/or Buyers agent to verify all important information. Commercially listed also - MLS 3067446

$499,000

3 beds2 baths3,050 sq ft

219 Old Mill Rd, Winchester, TN 37398

1.05 acre lot • Built 1900

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
Fantastic opportunity for starter home or investment. This 2 bedroom home is just minutes away from Twin Creeks Marina and historic Winchester Square. This home is a great location features hardwood floors, spacious bedrooms, fenced yard, nice deck and covered front porch along with a storage building. With just a little TLC this could be a great home.

$175,000

2 beds1 bath1,092 sq ft

716 N Cedar St, Winchester, TN 37398

Covered front porch • Fenced yard • Nice deck

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
ONLINE ONLY ESTATE AUCTION! BID NOW UNTIL MONDAY, JANUARY 12TH AT 6PM. PREVIEW/ INSPECTION: SUNDAY, JANUARY 11TH 2-4PM OR BY APPOINTMENT. Tract 1: This 3 bedroom 1 bathroom house is conveniently located within walking distance to both downtown Winchester and Twin Creeks Marina! It is a move in ready house and features a covered carport w/ shop, living room, eat-in kitchen, central HVAC, city water, sewer, trash service, and natural gas. The location of this property makes it a fantastic rental prospect or a place for you to call your own! (Also selling adjoining building lot which will be sold separately MLS# 3060759. All appliances and personal property will also be sold at online auctio

Unknown

3 beds1 bath1,008 sq ft

506 6th Ave NW, Winchester, TN 37398

Central hvac • Covered carport • Living room

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
Step into the charm of Winchester living with this beautifully updated 2-bed, 1-bath cottage just minutes from the historic town square. The home offers a bright, welcoming layout with a cozy front porch and a level yard that’s simple to maintain. Enjoy quick access to local shops, restaurants, and community events, along with a short drive to Tims Ford Lake for boating and weekend relaxation. Recent improvements—including new flooring, fresh paint, an updated bathroom, and a newer HVAC system—make this home move-in ready and an excellent choice for first-time buyers, downsizers, or investors.

$199,000

2 beds1 bath936 sq ft

815 N High St, Winchester, TN 37398

Level yard • New flooring • Updated cottage

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
Charming updated one-level home offering 3 bedrooms and 2 bathrooms, plus a possible 4th bedroom that could also serve as a bonus room, playroom, office, or separate living space. The spacious kitchen features granite countertops, ample cabinetry, and an eat-in area that opens to a formal dining space. Hardwood floors and stylish updates flow throughout, creating a warm and inviting atmosphere. A screened-in porch overlooks the park-like backyard, perfect for relaxing or entertaining. Additional highlights include updated bathrooms, a carport, and a well-maintained exterior. Conveniently located just 4 miles from Nissan in Decherd, 3 miles from Twin Creek Marina, and only a 15-minute drive

$374,900

3 beds2 baths2,172 sq ft

120 Dogwood Ln, Winchester, TN 37398

Park-like backyard • Screened-in porch • Spacious kitchen

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 96 Liberty Rd, Winchester, TN 37398, 3 beds, 2 baths

$290,900

3 beds2 baths1,224 sq ft

96 Liberty Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 709 Isbell Turn Rd, Winchester, TN 37398, 3 beds, 1 bath

$237,499

3 beds1 bath1,040 sq ft

709 Isbell Turn Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 132 Highland Dr, Winchester, TN 37398, 3 beds, 2 baths

$279,900

3 beds2 baths1,466 sq ft

132 Highland Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 205 8th Ave NW, Winchester, TN 37398, 3 beds, 1.5 baths

$244,900

3 beds1.5 baths1,333 sq ft

205 8th Ave NW, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 706 N Vine St, Winchester, TN 37398, 3 beds, 1 bath

$189,500

3 beds1 bath1,086 sq ft

706 N Vine St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 1000 N Vine St, Winchester, TN 37398, 4 beds, 2 baths

$1,600,000

4 beds2 baths2,164 sq ft

1000 N Vine St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 620 Maple Bend Rd, Winchester, TN 37398, 3 beds, 2 baths

$260,000

3 beds2 baths1,632 sq ft

620 Maple Bend Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 4516 Mansford Rd, Winchester, TN 37398, 3 beds, 2 baths

$349,900

3 beds2 baths1,680 sq ft

4516 Mansford Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 1466 Bible Crossing Rd, Winchester, TN 37398, 2 beds, 1 bath

$240,000

2 beds1 bath1,116 sq ft

1466 Bible Crossing Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 621 S Jefferson St, Winchester, TN 37398, 3 beds, 1 bath

$279,000

3 beds1 bath2,236 sq ft

621 S Jefferson St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 114 Allen Dr, Winchester, TN 37398, 3 beds, 2 baths

$245,000

3 beds2 baths1,400 sq ft

114 Allen Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 209 Franklin Park, Winchester, TN 37398, 3 beds, 2 baths

$299,000

3 beds2 baths2,053 sq ft

209 Franklin Park, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 408 Style St, Winchester, TN 37398, 3 beds, 2 baths

$265,000

3 beds2 baths1,584 sq ft

408 Style St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 715 N High St N, Winchester, TN 37398, 3 beds, 2 baths

$199,900

3 beds2 baths1,360 sq ft

715 N High St N, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 713 N Vine St, Winchester, TN 37398, 3 beds, 1 bath

$185,000

3 beds1 bath924 sq ft

713 N Vine St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

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ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
ATTENTION INVESTORS

$380,000

4 beds2 baths3,723 sq ft

9711 Old Alto Hwy, Decherd, TN 37324

3.5 acre lot • Garage • Built 1950

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
Older home, Covered Front Porch 40 X 8 * * Kitchen has been updated with Granite Counter Tops * Main floor features High Ceilings, Nice size Living Room, Formal Dining Rm, Eat-in Kitchen * Master bedroom on main floor * Utility Rm * Extra room downstairs 15 X 12 could be used as a 4th Bedroom, game room, office, Etc. .. 2nd Floor has 2 Bedrooms and a Full Bath * Crawl Space was encapsulated in 2023 and has a dehumidifier. Some windows have been replaced in 2017 * HVAC 2015 * Circuit Breaker Box installed in 2023, Needs some TLC

$199,000

3 beds2.5 baths2,248 sq ft

201 Hodges St N, Cowan, TN 37318

Covered front porch • Eat-in kitchen • Granite counter tops

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
Investor Special – Historic Craftsman in Downtown Flintville! Incredible opportunity for investors or renovators! This 3-bedroom, 2-bath historic Craftsman-style home sits on nearly half an acre just past the beloved Flintville Store in downtown Flintville. Featuring both a charming front porch with swing and a spacious back porch, this home exudes small-town character and offers serious potential. The property includes an outbuilding perfect for storage or a workshop. With strong bones and timeless appeal, this home is ready for your vision and updates. Being sold as-is. No claims are made regarding the functionality of appliances, HVAC, plumbing, or other systems. The owner has rent

$139,900

3 beds2 baths1,356 sq ft

249 Flintville Rd, Flintville, TN 37335

Historic craftsman • Spacious back porch • 0.43 acre lot

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
Motivated Seller! Charming 2-bedroom, 1-bath home located within the heart of Decherd. This property has been completely remodeled inside and out from the bottom to the top. This home offers modern finishes and convenience. The home features a fully enclosed backyard with a privacy fence, providing a secure and relaxing outdoor space. Conveniently located near schools, shopping, and local amenities. Ideal for first-time home buyers, or those looking to downsize, or invest.

$219,900

2 beds1 bath1,060 sq ft

502 E Market St, Decherd, TN 37324

Completely remodeled • Privacy fence • Modern finishes

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
Calling all savvy investors, first-time homebuyers, and sweat equity seekers - this exceptional fixer-upper opportunity on a prime corner lot delivers incredible value for budget-conscious buyers ready to build instant equity through smart renovations. This solid-bones property sits on a desirable corner lot providing extra yard space, privacy, and future curb appeal potential once your vision comes to life. Major infrastructure advantages set this investment apart from typical fixer-uppers, featuring connected city water and sewer eliminating costly well and septic concerns, plus high-speed internet connectivity making it perfect for modern renters or remote work lifestyle. The updated bre

$95,500

3 beds1 bath1,610 sq ft

102 Cowan St W, Cowan, TN 37318

Sewer • High speed internet • City water

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
Peaceful country living on land totaling 1.1+- acres! This adorable 3-bedroom, 1-bath home has been beautifully converted to an open concept using stunning solid wood beams, adding warmth, character, and a true farmhouse feel. Recent updates include new drywall throughout, fresh interior paint, and brand-new electrical wiring. Major systems are already done for you! The roof, siding, HVAC split system with natural gas heat, and all new ductwork were replaced just 2 years ago. The home also features brand new double-pane, energy-efficient windows and doors, along with new insulation throughout the walls and ceilings for year-round comfort and efficiency. An additional back lot offers an RV h

$210,000

3 beds1 bath924 sq ft

210 Ake St, Estill Springs, TN 37330

New drywall • Open concept • Fresh interior paint

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 202 W Main St, Decherd, TN 37324, 5 beds, 3 baths

$299,999

5 beds3 baths3,667 sq ft

202 W Main St, Decherd, TN 37324

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 2900 Tanyard Hill Rd, Lynchburg, TN 37352, 3 beds, 2.5 baths

$2,699,900

3 beds2.5 baths2,900 sq ft

2900 Tanyard Hill Rd, Lynchburg, TN 37352

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 302 Poplar St N, Cowan, TN 37318, 2 beds, 1 bath

$149,900

2 beds1 bath700 sq ft

302 Poplar St N, Cowan, TN 37318

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 404 Horton St, Decherd, TN 37324, 3 beds, 1 bath

$219,900

3 beds1 bath1,112 sq ft

404 Horton St, Decherd, TN 37324

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 306 College St, Decherd, TN 37324, 3 beds, 2 baths

$179,900

3 beds2 baths1,229 sq ft

306 College St, Decherd, TN 37324

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 121 Popular St N, Cowan, TN 37318, 5 beds, 2 baths

$350,900

5 beds2 baths2,124 sq ft

121 Popular St N, Cowan, TN 37318

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 104 Hodges St N, Cowan, TN 37318, 2 beds, 1 bath

$182,900

2 beds1 bath1,107 sq ft

104 Hodges St N, Cowan, TN 37318

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 106 Tennessee Ave S, Cowan, TN 37318, 3 beds, 2 baths

$799,000

3 beds2 baths5,552 sq ft

106 Tennessee Ave S, Cowan, TN 37318

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 402 England St E, Cowan, TN 37318, 2 beds, 1 bath

$179,000

2 beds1 bath936 sq ft

402 England St E, Cowan, TN 37318

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 364A Cook Rd, Tullahoma, TN 37388, 4 beds, 2 baths

$479,000

4 beds2 baths2,903 sq ft

364A Cook Rd, Tullahoma, TN 37388

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 313 Tennessee Ave S, Cowan, TN 37318, 3 beds, 1 bath

$167,000

3 beds1 bath1,232 sq ft

313 Tennessee Ave S, Cowan, TN 37318

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 994 Bull Run Rd, Lynchburg, TN 37352, 3 beds, 1 bath

$565,000

3 beds1 bath1,560 sq ft

994 Bull Run Rd, Lynchburg, TN 37352

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 107 N West St, Decherd, TN 37324, 2 beds, 2 baths

$199,900

2 beds2 baths1,742 sq ft

107 N West St, Decherd, TN 37324

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 240 Dogwood Dr, Winchester, TN 37398, 5 beds, 3.5 baths

$669,000

5 beds3.5 baths5,474 sq ft

240 Dogwood Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Vintage Homes for Sale in 37398

There are currently 20 vintage homes for sale in 37398 at a median listing price of $400K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 37398 stay on the market for 105 days. This map is refreshed with the newest listings in 37398 every 15 minutes.

In the past month, 17 homes have been sold in 37398. In addition to houses in 37398, there was also 1 condo, 6 townhouses, and 2 multi-family units for sale in 37398 last month. Find your dream home in 37398 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 37398 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 37398. If you're looking to sell your home in the 37398 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 37398 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Based on information submitted to the MLS GRID as of Mon Jan 05 2026. 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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