Vintage homes for sale & real estate in 37398, TN

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ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
3 bed/2 bath home conveniently located near Nissan, downtown Winchester, shopping, dining, and more! Enjoy a fenced-in backyard that's perfect for pets, entertaining, or simply relaxing outdoors. Whether you're a first-time buyer, downsizing, or looking for an investment opportunity, this property is one you'll want to see! Priced below recent appraisal = instant equity! Receive 1% towards closing costs with our preferred lender!

$213,999

3 beds2 baths1,104 sq ft

Fenced-in backyard • 9,583 sq ft lot • Built 1956

1508 Clark St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
--- MOVE IN READY --- 1 Level - FLEX space galore - Fully rehabbed from top to bottom and 100% move-in ready, this solid, single-level ranch offers modern comfort just minutes from Tims Ford Lake and Boiling Fork Creek. Designed with zero stairs and two separate living areas, this highly versatile layout is the perfect setup for a large family, multi-generational living or even a high-yield rental investment. Enjoy absolute peace of mind with premium upgrades throughout, including a brand-new metal roof, siding, windows, and a stunning designer kitchen. Outside, the brand-new back deck overlooks a spacious, level half-acre lot—providing an ideal space for entertaining and plenty of ro

$299,000

5 beds2 baths1,600 sq ft

Fully rehabbed • Zero stairs • Premium upgrades

1200 Little St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
SELLER OFFERING OWNER FINANCING AT 5.75% — An ideal income-producing property just over a block from downtown Winchester, provides a rare opportunity for buyers seeking investment property in Tennessee with flexibility for different uses. Built in 1917, this historic, commercially zoned 5-bedroom, 2-bath residence includes approximately 3,922 sq ft on a . 34-acre lot in the heart of Winchester. The property features original hardwood floors, spacious living areas, and a covered front porch that adds character and tenant appeal. A detached 1-car garage and driveway parking provide additional functionality. Located seconds from the Winchester square and Hwy 41A, the property is convenie

$470,000

5 beds2 baths3,922 sq ft

0.34 acre lot • Garage • Built 1917

309 2nd Ave NW, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
2.3 +/- acres in country like setting just minutes from the square in Winchester.

$325,000

3 beds1 bath1,490 sq ft

2.3 acre lot • 2 garage spots • Built 1951

1400 Holders Cove Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37398, TN:
This picturesque Historic home right off the square in Winchester offers 5 bedrooms 3.5 baths and old world charm. Tons of elegant built ins, gas log FP, an amazing office, Very large bedrooms on the 1st floor, 2 car garage, and much more.

$695,000

8 beds3.5 baths3,187 sq ft

0.62 acre lot • 2 garage spots • Built 1930

110 S Porter St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 401 E Petty Ln, Winchester, TN 37398, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths3,960 sq ft

401 E Petty Ln, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 109 Oak Park, Winchester, TN 37398, 3 beds, 2 baths

$449,000

3 beds2 baths2,157 sq ft

109 Oak Park, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 3754 Aedc Rd, Winchester, TN 37398, 2 beds, 1 bath

$399,000

2 beds1 bath3,560 sq ft

3754 Aedc Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 102 Oak Park, Winchester, TN 37398, 2 beds, 1 bath

$269,900

2 beds1 bath1,373 sq ft

102 Oak Park, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 128 Bel Aire Dr, Winchester, TN 37398, 4 beds, 1.5 baths

$299,900

4 beds1.5 baths1,923 sq ft

128 Bel Aire 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

$205,000

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 1010 N High St, Winchester, TN 37398, 3 beds, 2 baths

$249,900

3 beds2 baths1,866 sq ft

1010 N High St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 314 4th Ave NW, Winchester, TN 37398, 3 beds, 3 baths

$450,000

3 beds3 baths2,629 sq ft

314 4th Ave NW, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 406 2nd Ave NW, Winchester, TN 37398, 3 beds, 1 bath

$125,000

3 beds1 bath1,150 sq ft

406 2nd Ave NW, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 1522 Holders Cove Rd, Winchester, TN 37398, 3 beds, 2 baths

$425,000

3 beds2 baths1,700 sq ft

1522 Holders Cove Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 71 David Crockett Hwy, Winchester, TN 37398, 5 beds, 3 baths

$445,000

5 beds3 baths2,420 sq ft

71 David Crockett Hwy, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 2077 Holders Cove Rd, Winchester, TN 37398, 4 beds, 1 bath

$150,000

4 beds1 bath1,580 sq ft

2077 Holders Cove Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 810 N High St, Winchester, TN 37398, 4 beds, 2 baths

$249,900

4 beds2 baths1,930 sq ft

810 N High St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 903 Old Estill Springs Rd, Winchester, TN 37398

$1,750,000

— beds— baths— sq ft

903 Old Estill Springs Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 6606 Old Tullahoma Rd, Winchester, TN 37398, 3 beds, 2 baths

$359,000

3 beds2 baths1,972 sq ft

6606 Old Tullahoma Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 219 Old Mill Rd, Winchester, TN 37398, 3 beds, 2 baths

$349,000

3 beds2 baths3,050 sq ft

219 Old Mill Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 6933 Winchester Hwy, Winchester, TN 37398, 5 beds, 3 baths

$399,900

5 beds3 baths2,632 sq ft

6933 Winchester Hwy, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

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Vintage Homes for Sale in 37398

There are currently 22 vintage homes for sale in 37398 at a median listing price of $477K. 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 100 days. This map is refreshed with the newest listings in 37398 every 15 minutes.

In the past month, 30 homes have been sold in 37398. In addition to houses in 37398, there was also 1 condo, 5 townhouses, and 3 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 Wed Aug 19 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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