Vintage homes for sale & real estate in 40391, KY

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ABOUT THIS HOME
Vintage Home for sale in 40391, KY:
ABSOLUTE AUCTION — SELLS TO THE HIGHEST BIDDER REGARDLESS OF PRICE! Offered at Live On-Site Absolute Auction with Simulcast Internet Bidding. Auction is on Thursday, October 15, 2026 at 6:00 PM (EST). Buyers premium will be added to the final bid price and non-refundable earnest money required. Property sells AS-IS, WHERE-IS with no contingencies. 3 Bedrooms, 1 Bathroom with separate dining room, standalone kitchen, and living room featuring a fireplace. Full unfinished basement with ample potential for storage or expansion. Investment Potential: Major DIY/fixer-upper opportunity—ideal for investors or buyers looking to customize and add value

$225,000

3 beds1 bath2,244 sq ft

326 W Lexington Ave, Winchester, KY 40391

Separate dining room • Standalone kitchen • 9,583 sq ft lot

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 40391, KY:
Timeless character, thoughtful updates, and a walkable downtown location define this distinctive Winchester residence. From the original front door to the beautifully preserved architectural details within, 107 S Burns Avenue reflects the craftsmanship of an earlier era, with original hardwood floors, cherry wood wainscoting, coffered ceilings, custom brick fireplaces and mantels, and original built-ins throughout. Offering four bedrooms and two full baths, the home has been carefully updated while preserving the details that make it unique. The fully renovated upper level provides a private fourth bedroom, full bath, built-in workspace, generous knee-wall storage, and a dedicated heating a

$367,700

4 beds2 baths2,352 sq ft

107 S Burns Ave, Winchester, KY 40391

Coffered ceilings • Original front door • Garage

NEW 1 DAY AGO

$200,000

3 beds1 bath1,453 sq ft

213 E Broadway St, Winchester, KY 40391

7,405 sq ft lot • Garage • Built 1960

ABOUT THIS HOME
Vintage Home for sale in 40391, KY:
Welcome home to 19 Victory Ave in Winchester's! This single-family residence offers 1,780 sq ft of flexible living space, featuring 3 bedrooms, 2 bathrooms, and handsome hardwood flooring. Enjoy cooking and entertaining with the included kitchen appliances, and take advantage of the detached garage and off-street parking. Situated on a spacious lot under half an acre, this property provides convenient access to local Winchester dining, shopping, and everything this city has to offer!

$285,000

3 beds2 baths1,780 sq ft

19 Victory Ave, Winchester, KY 40391

Hardwood flooring • Kitchen appliances • Convenient access

ABOUT THIS HOME
Vintage Home for sale in 40391, KY:
Welcome to 600 College Street! Offering over 1,700 square feet, this versatile Winchester home features 3 bedrooms, 2 full bathrooms, plus an additional room ideal for a 4th bedroom, home office, or flex space. Inside, you'll find a spacious living room and a dining room with plenty of room to create additional living or entertaining space. The kitchen offers a walk-in pantry and conveniently located laundry area. An unfinished basement provides ample storage and walkout access, while the attached one-car garage adds everyday convenience. Outside, enjoy a covered front porch and a peaceful back porch surrounded by mature trees for added privacy. Conveniently located near Downtown Winchester

$225,000

3 beds2 baths1,737 sq ft

600 College St, Winchester, KY 40391

Covered front porch • Peaceful back porch • Unfinished basement

Property at 6 French Ave, Winchester, KY 40391, 4 beds, 2 baths

$319,900

4 beds2 baths1,953 sq ft

6 French Ave, Winchester, KY 40391

Property at 405 Nick Ln, Winchester, KY 40391, 2 beds, 1 bath

$280,000

2 beds1 bath1,344 sq ft

405 Nick Ln, Winchester, KY 40391

Property at 7353 Ironworks Rd, Winchester, KY 40391, 4 beds, 1 bath

$390,000

4 beds1 bath2,063 sq ft

7353 Ironworks Rd, Winchester, KY 40391

Property at 5 S Burns Ave, Winchester, KY 40391, 3 beds, 1 bath

$139,000

3 beds1 bath1,842 sq ft

5 S Burns Ave, Winchester, KY 40391

Property at 54 Locust Dr, Winchester, KY 40391, 3 beds, 2 baths

$244,000

3 beds2 baths1,692 sq ft

54 Locust Dr, Winchester, KY 40391

Property at 3 Nunnelly Ct, Winchester, KY 40391, 3 beds, 2 baths

$215,000

3 beds2 baths1,319 sq ft

3 Nunnelly Ct, Winchester, KY 40391

Property at 11304 Irvine Rd, Winchester, KY 40391, 3 beds, 1 bath

$248,900

3 beds1 bath2,249 sq ft

11304 Irvine Rd, Winchester, KY 40391

Property at 198 Hilltop Dr, Winchester, KY 40391, 4 beds, 2 baths

$275,000

4 beds2 baths1,752 sq ft

198 Hilltop Dr, Winchester, KY 40391

Property at 16 Denny Ave, Winchester, KY 40391, 3 beds, 1 bath

$78,500

3 beds1 bath1,152 sq ft

16 Denny Ave, Winchester, KY 40391

Property at 351 Boone Ave, Winchester, KY 40391, 4 beds, 2 baths

$379,000

4 beds2 baths3,306 sq ft

351 Boone Ave, Winchester, KY 40391

Property at 24 Spring St, Winchester, KY 40391, 3 beds, 1 bath

$160,000

3 beds1 bath1,173 sq ft

24 Spring St, Winchester, KY 40391

Property at 209 E Washington St, Winchester, KY 40391, 3 beds, 1 bath

$165,000

3 beds1 bath1,249 sq ft

209 E Washington St, Winchester, KY 40391

Property at 15 Kittison Dr, Winchester, KY 40391, 3 beds, 2 baths

$265,000

3 beds2 baths1,776 sq ft

15 Kittison Dr, Winchester, KY 40391

Property at 65 Fitch Ave, Winchester, KY 40391, 3 beds, 1.5 baths

$146,900

3 beds1.5 baths1,680 sq ft

65 Fitch Ave, Winchester, KY 40391

Property at 229 S Highland St, Winchester, KY 40391, 4 beds, 3 baths

$165,000

4 beds3 baths3,462 sq ft

229 S Highland St, Winchester, KY 40391

Property at 15 Moundale Ave, Winchester, KY 40391, 3 beds, 2 baths

$359,900

3 beds2 baths2,269 sq ft

15 Moundale Ave, Winchester, KY 40391

Property at 606 College St, Winchester, KY 40391, 2 beds, 1 bath

$205,400

2 beds1 bath1,154 sq ft

606 College St, Winchester, KY 40391

Marshall Lane Real Estate

Property at 32 Jackson St, Winchester, KY 40391, 3 beds, 1 bath

$189,000

3 beds1 bath1,152 sq ft

32 Jackson St, Winchester, KY 40391

Property at 38 Mackay Ave, Winchester, KY 40391, 3 beds, 1 bath

$204,900

3 beds1 bath1,128 sq ft

38 Mackay Ave, Winchester, KY 40391

Property at 108 Franklin Ave, Winchester, KY 40391, 2 beds, 1 bath

$140,000

2 beds1 bath630 sq ft

108 Franklin Ave, Winchester, KY 40391

Property at 443 S Maple St, Winchester, KY 40391, 4 beds, 2 baths

$325,000

4 beds2 baths3,261 sq ft

443 S Maple St, Winchester, KY 40391

Property at 410 W Lexington Ave, Winchester, KY 40391, 5 beds, 4 baths

$325,000

5 beds4 baths4,456 sq ft

410 W Lexington Ave, Winchester, KY 40391

Property at 528 Estes Dr, Winchester, KY 40391, 3 beds, 2 baths

$229,900

3 beds2 baths1,904 sq ft

528 Estes Dr, Winchester, KY 40391

Property at 3166 Colby Rd, Winchester, KY 40391, 3 beds, 2.5 baths

$1,595,000

3 beds2.5 baths4,518 sq ft

3166 Colby Rd, Winchester, KY 40391

Property at 42 Mockingbird Valley Rd, Winchester, KY 40391, 3 beds, 2.5 baths

$445,500

3 beds2.5 baths2,961 sq ft

42 Mockingbird Valley Rd, Winchester, KY 40391

Property at 33 Bon-haven Ave, Winchester, KY 40391, 3 beds, 2 baths

$249,000

3 beds2 baths1,386 sq ft

33 Bon-haven Ave, Winchester, KY 40391

Property at 174 Cook Ave, Winchester, KY 40391, 2 beds, 1 bath

$134,900

2 beds1 bath986 sq ft

174 Cook Ave, Winchester, KY 40391

Property at 1494 Amster Grove Rd. Rd, Winchester, KY 40391, 2 beds, 1.5 baths

$165,000

2 beds1.5 baths1,202 sq ft

1494 Amster Grove Rd. Rd, Winchester, KY 40391

Property at 14 Cook Ave, Winchester, KY 40391, 3 beds, 2 baths

$219,000

3 beds2 baths1,261 sq ft

14 Cook Ave, Winchester, KY 40391

Property at 101 Alabama St, Winchester, KY 40391, 1 bed, 2 baths

$155,900

1 bed2 baths1,056 sq ft

101 Alabama St, Winchester, KY 40391

Property at 122 Callaway Street SE Callaway St, Winchester, KY 40391, 2 beds, 1 bath

$124,500

2 beds1 bath876 sq ft

122 Callaway Street SE Callaway St, Winchester, KY 40391

Property at 175 Magnolia St, Winchester, KY 40391, 3 beds, 1 bath

$169,000

3 beds1 bath1,046 sq ft

175 Magnolia St, Winchester, KY 40391

Property at 1509 Boonesboro Rd, Winchester, KY 40391

$1,850,000

Land17.87 acres (lot)

1509 Boonesboro Rd, Winchester, KY 40391

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Vintage Homes for Sale in 40391

There are currently 38 vintage homes for sale in 40391 at a median listing price of $275K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 40391 stay on the market for 80 days. This map is refreshed with the newest listings in 40391 every 15 minutes.

In the past month, 31 homes have been sold in 40391. In addition to houses in 40391, there was also 1 condo, 3 townhouses, and 6 multi-family units for sale in 40391 last month. Find your dream home in 40391 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 40391 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 40391. If you're looking to sell your home in the 40391 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 40391 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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