Vintage homes for sale & real estate in Winchester, TN

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ABOUT THIS HOME
Vintage Home for sale in Winchester, TN:
Welcome home to 96 Liberty Road — a beautifully updated 3-bedroom, 2-bath home situated on a spacious corner lot just minutes from downtown Winchester. 7 minutes from Twin Creeks Marina on Tim's Ford Lake. Completely renovated in 2018, this property offers modern comfort with timeless charm. Inside, you’ll find an inviting open layout with laminate flooring throughout and custom lighting that adds warmth and character. The kitchen features white cabinetry, stainless steel appliances, and a large island perfect for gathering or meal prep. The oversized utility room provides ample storage and functionality. The primary suite includes a full bath with tub/shower combo, tile floorin

$295,900

3 beds2 baths1,224 sq ft

96 Liberty Rd, Winchester, TN 37398

Updated in 2018 • Laminate flooring • Open layout

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Winchester, TN:
Discover the perfect blend of comfort, space, and potential with this move-in ready home on 4.25 flat, usable acres in the heart of Winchester, TN. Whether you’re dreaming of a peaceful retreat, a place to raise a family, or a future mini-farm, this property offers endless opportunity. Inside, you’ll find a welcoming home ready for you to make your own—move in today and update at your own pace to create your ideal family haven. Outside, enjoy room to roam, garden, or grow—with a functional 2,500 sq. ft. barn, well house, and outbuilding providing ample storage and versatility for hobbies, animals, or small-scale farming. Located just 5 minutes from Devils Step Campgr

$249,999

3 beds1 bath1,040 sq ft

709 Isbell Turn Rd, Winchester, TN 37398

Outdoor recreation • Usable acres • Functional barn

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Winchester, TN:
3 bedroom 2 bath home with new roof, new Hvac, water heater, new siding in back, new vanity in hall bath , detached 24 x 24 garage with extra garage connected in the back, nice fenced in backyard, fire pit and wraparound driveway- walk to the square or be at the public boat launch in less than two minutes right around the corner.

$279,900

3 beds2 baths1,466 sq ft

132 Highland Dr, Winchester, TN 37398

New vanity • New siding • New hvac

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Winchester, TN:
Welcome to this delightful brick home nestled on a generous corner lot surrounded by mature shade trees. Full of character and timeless appeal, this home features gleaming original hardwood floors that add warmth and authenticity throughout. Perfectly situated close to town and just minutes from Tims Ford Lake. This combines peaceful living with everyday convenience. Replacement windows throughout the home. Home selling "AS IS"

$254,900

3 beds1.5 baths1,333 sq ft

205 8th Ave NW, Winchester, TN 37398

Close to town • Brick home • Mature shade trees

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Winchester, TN:
Great Starter home or Investment Property, Convenient to downtown Winchester, close to Bass Club & Twin Creeks Mariana on Tims Ford Lake. 1 car carport. 3 BR/1BA, Replacement Windows, Metal Roof less than 10 years old, Concrete Driveway, Eat in Kitchen, Kitchen Appliances, Selling "AS IS".

$197,500

3 beds1 bath1,086 sq ft

706 N Vine St, Winchester, TN 37398

Kitchen appliances • Close to bass club • Eat in kitchen

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 1506 Old Cowan Rd, Winchester, TN 37398, 2 beds, 1 bath

$205,000

2 beds1 bath996 sq ft

1506 Old Cowan 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

$289,000

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

$207,000

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 407 Girton St, Winchester, TN 37398, 3 beds, 2 baths

$309,000

3 beds2 baths1,575 sq ft

407 Girton St, 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

$205,000

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 Winchester, TN:
Charming 3-bedroom, 1-bath, 1,332 SQ FT ranch on 3 peaceful acres. Enjoy abundant wildlife, a fenced backyard, storage shed, and an updated deck for relaxing outdoors. Recent improvements include a new roof and new hot water heater. Well-kept home offering true country living with plenty of space to roam.

$244,900

3 beds1 bath1,332 sq ft

2692 Marble Hill Rd, Belvidere, TN 37306

Updated deck • New hot water heater • Storage shed

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Winchester, TN:
This property delivers a pair of well-built, updated living spaces in Lynchburg TN. The main residence offers approximately 2900 square feet under air, with an additional walkout basement of roughly 1140 square feet. Exterior construction blends white cypress siding on the first level with hardy board on the second level. Custom hog wire and wrought iron railings frame the wraparound upper deck, and the roof was replaced in 2018. Inside, the home features spray foam insulation within 6-inch walls and a full finish of Northern Lights Barnwood pine sourced from Duluth MN. Floors are White Oak from the Boulder Mountain Series by Shaw. Custom black iron curtain rods, insulated drapery, LED ret

$2,699,900

3 beds2.5 baths2,900 sq ft

2900 Tanyard Hill Rd, Lynchburg, TN 37352

White cypress siding • White oak floors • 86.51 acre lot

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Winchester, TN:
Cozy 2-bedroom 1 bath starter home offers new kitchen cabinets, fresh paint, new LVP flooring, light fixtures, and more. Situated on a nice size lot just a short walk to Cowan Elementary School. Perfect for a first-time buyer or anyone seeking comfort and convenience. Whether you're starting out, downsizing, or looking for a solid investment, this cozy gem is ready to make you feel right at home. Selling "AS IS"

$152,900

2 beds1 bath700 sq ft

302 Poplar St N, Cowan, TN 37318

Fresh paint • Light fixtures • New kitchen cabinets

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Winchester, TN:
Completely remodeled 3 bedroom 1 bath 1 car carport home with stainless steel appliances and an outbuilding.

$219,900

3 beds1 bath1,112 sq ft

404 Horton St, Decherd, TN 37324

Outbuilding • 0.28 acre lot • Built 1948

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Winchester, TN:
Investor’s Opportunity — 306 College St, Decherd, TN Built in 1943, this 3-bedroom, 2-bath home sits on an expansive 0.95-acre lot offering endless potential. The property is ready for renovation and provides a rare chance to restore classic character while creating modern value. With nearly one acre of land, there’s room to divide and build additional homes — making this an ideal opportunity for a contractor, builder, or investor looking for a high-upside project in the heart of Decherd. The home will require a full remodel and is only eligible for conventional financing or cash purchase. The structure offers good bones and a layout that can be reimagined for today

$179,900

3 beds2 baths1,229 sq ft

306 College St, Decherd, TN 37324

0.95 acre lot • Built 1943

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Winchester, TN:
Newly Remodeled 5BR/2BTH home right in the heart of Cowan TN. with a spacious backyard perfect for kids to play or entertaining family and friends. .Storagebuilding conveys with the property. Located in a quiet neighborhood close to Restaurants local shops. Home does have a 27x14 unfinished basement. That SQFT is not included .

$350,900

5 beds2 baths2,124 sq ft

121 Popular St N, Cowan, TN 37318

Spacious backyard • Unfinished basement • Quiet neighborhood

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 210 Willie Six Rd, Sewanee, TN 37375, 3 beds, 1 bath

$359,900

3 beds1 bath1,390 sq ft

210 Willie Six Rd, Sewanee, TN 37375

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 364B Cook Rd, Tullahoma, TN 37388, 4 beds, 2 baths

$649,000

4 beds2 baths2,903 sq ft

364B Cook Rd, Tullahoma, TN 37388

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 502 E Market St, Decherd, TN 37324, 2 beds, 1 bath

$229,900

2 beds1 bath1,060 sq ft

502 E Market St, Decherd, TN 37324

Listing provided by REALTRACS as Distributed by MLS Grid

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

$173,000

3 beds1 bath1,232 sq ft

313 Tennessee Ave S, Cowan, TN 37318

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 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 501 W Broad St, Decherd, TN 37324, 1 bath

$300,000

0 beds1 bath4,671 sq ft

501 W Broad St, Decherd, TN 37324

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 107 10th Ave N, Decherd, TN 37324, 3 beds, 1 bath

$194,900

3 beds1 bath1,025 sq ft

107 10th Ave N, Decherd, TN 37324

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 103 Cowan St W, Cowan, TN 37318, 3 beds, 2 baths

$349,900

3 beds2 baths2,528 sq ft

103 Cowan St W, Cowan, TN 37318

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 201 Hodges St N, Cowan, TN 37318, 3 beds, 2.5 baths

$199,000

3 beds2.5 baths2,248 sq ft

201 Hodges St N, Cowan, TN 37318

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

Property at 102 Hodges St N, Cowan, TN 37318, 2 beds, 1 bath

$239,900

2 beds1 bath1,120 sq ft

102 Hodges St N, Cowan, TN 37318

Listing provided by REALTRACS as Distributed by MLS Grid

Vintage Homes for Sale in Winchester

There are currently 17 vintage homes for sale in Winchester at a median listing price of $414K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winchester stay on the market for 105 days. Popular neighborhoods include Franklin Hills. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 16 homes have been sold in Winchester. In addition to houses in Winchester, there was also 1 condo, 8 townhouses, and 2 multi-family units for sale in Winchester last month. Find your dream home in Winchester 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 Winchester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winchester. Our Winchester real estate stats and trends will give you more information about home buying and selling trends in Winchester. If you're looking to sell your home in the Winchester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winchester 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 Tue Dec 02 2025. 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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Vintage homes for sale & real estate in Winchester, TN

Vintage Homes for Sale in Winchester

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