Recently Sold Homes in Winchester, KY

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SOLD SEP 18, 2025

ABOUT THIS HOME
Recently Sold Home in Winchester, KY:
This beautifully 4-bedroom, 2-bath home sits on a spacious corner lot on a peaceful street near Lexington Avenue. This brick ranch style home is move in ready, and waiting for you. This home offers a great location to downtown Winchester and for all your shopping needs. Multiple fruit trees located on the property! Call and schedule your showing today!

$244,000 Last sold price

4 beds2 baths1,800 sq ft

314 Carolina Ave, Winchester, KY 40391

SOLD SEP 19, 2025

ABOUT THIS HOME
Recently Sold Home in Winchester, KY:
Welcome to this beautifully maintained 3-bedroom, 2-bath home offering 1,530 sq. ft. of comfortable living space! Step inside to find a move-in ready property featuring newer kitchen appliances and a recently replaced roof for peace of mind. Enjoy outdoor living on the spacious deck overlooking a fantastic flat backyard—perfect for gatherings or play. The oversized 2-car garage provides ample storage and convenience. This home has been very well cared for and is in excellent condition—don't miss your chance to make it yours!

$247,000 Last sold price

3 beds2 baths1,530 sq ft

3588 Stamper Dr, Winchester, KY 40391

SOLD SEP 5, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Winchester, KY:
Beautifully updated 1,397 sq ft ranch-style home with modern upgrades throughout! This move-in ready property features a new roof, HVAC, water heater, gutters, and fresh landscaping. The exterior has been freshly painted, including the back deck, and the driveway and sidewalk have been pressure washed. Inside, you'll find all-new flooring and fresh paint throughout. The kitchen features updated countertops and freshly painted cabinets with new cabinet hardware. Both the full and half baths have been updated, including tile floors and a tiled shower in the full bath. A full wood privacy fence surrounds the backyard, offering the perfect space for pets, play, or entertaining. Blending classic

$263,000 Last sold price

3 beds1.5 baths1,397 sq ft

2 Chickadee Ln, Winchester, KY 40391

SOLD SEP 3, 2025

ABOUT THIS HOME
Recently Sold Home in Winchester, KY:
This beautiful 5 acre property is a rare find! Located on a quiet cul-de-sac just minutes from I-64, Winchester and Bourbon County, this home offers the perfect blend of tranquility and convenience. The home includes 4 bedrooms, 2.5 baths with a mostly finished basement providing additional living space and storage. There are 2 wood burning fireplaces, perfect for cozy evenings. Additionally, there is a 12 X 20 storage building in the backyard. The kitchen features oak cabinetry, tile countertops, double oven and stainless appliances, while all bathrooms have been updated. Enjoy amazing views of the countryside with numerous fruit trees, grape vines and blackberry bushes on the back part o

$370,000 Last sold price

4 beds2.5 baths3,078 sq ft

220 Spring Valley Dr, Winchester, KY 40391

SOLD NOV 17, 2025

ABOUT THIS HOME
Recently Sold Home in Winchester, KY:
Unbelievable, tastefully updated and meticulously maintained with the utmost attention to detail. Bruce flooring, copper flashing, true brass, plantation shutters, 40 yr roof, 2 kitchens-main level has custom cherry and downstairs kitchen is full service and beautiful as well. , extra insulation, newer HVACS and water heaters and so much more! Inspections welcome but sold AS-IS

$595,000 Last sold price

7 beds4 baths4,386 sq ft

304 Winterberry Dr, Winchester, KY 40391

Property at 208 Royal Oak Dr, Winchester, KY 40391, 4 beds, 2.5 baths

$472,500 Last sold price

4 beds2.5 baths2,593 sq ft

208 Royal Oak Dr, Winchester, KY 40391

Property at 130 Winterberry Cir, Winchester, KY 40391, 5 beds, 3.5 baths

$510,000 Last sold price

5 beds3.5 baths3,741 sq ft

130 Winterberry Cir, Winchester, KY 40391

Property at 104 Teakwood Ct, Winchester, KY 40391, 4 beds, 2.5 baths

$320,000 Last sold price

4 beds2.5 baths1,970 sq ft

104 Teakwood Ct, Winchester, KY 40391

Property at 204 Moss Ct, Winchester, KY 40391, 3 beds, 2.5 baths

$246,000 Last sold price

3 beds2.5 baths1,430 sq ft

204 Moss Ct, Winchester, KY 40391

Property at 210 Moss Ct, Winchester, KY 40391, 3 beds, 2 baths

$235,000 Last sold price

3 beds2 baths1,201 sq ft

210 Moss Ct, Winchester, KY 40391

Property at 865 Pretty Run Rd, Winchester, KY 40391, 3 beds, 2 baths

$462,000 Last sold price

3 beds2 baths2,727 sq ft

865 Pretty Run Rd, Winchester, KY 40391

Property at 7875 Bybee Rd, Winchester, KY 40391, 3 beds, 2 baths

$365,000 Last sold price

3 beds2 baths1,616 sq ft

7875 Bybee Rd, Winchester, KY 40391

Property at 946 Pine Ridge Rd, Winchester, KY 40391, 4 beds, 3 baths

$460,000 Last sold price

4 beds3 baths3,523 sq ft

946 Pine Ridge Rd, Winchester, KY 40391

Property at 23 Hillcrest Dr, Winchester, KY 40391, 2 beds, 1 bath

$185,000 Last sold price

2 beds1 bath1,557 sq ft

23 Hillcrest Dr, Winchester, KY 40391

Property at 1831 Kiddville Rd, Winchester, KY 40391, 3 beds, 2 baths

$332,000 Last sold price

3 beds2 baths1,756 sq ft

1831 Kiddville Rd, Winchester, KY 40391

Property at 406 W Washington St, Winchester, KY 40391, 2 beds, 1 bath

$9,000 Last sold price

2 beds1 bath1,428 sq ft

406 W Washington St, Winchester, KY 40391

Property at 76 Clay St, Winchester, KY 40391

$55,000 Last sold price

0 beds— baths— sq ft

76 Clay St, Winchester, KY 40391

Property at 220 Pendleton St, Winchester, KY 40391, 2 beds, 1 bath

$140,000 Last sold price

2 beds1 bath902 sq ft

220 Pendleton St, Winchester, KY 40391

Property at 219 Hampton Ave, Winchester, KY 40391, 4 beds, 2.5 baths

$340,000 Last sold price

4 beds2.5 baths2,929 sq ft

219 Hampton Ave, Winchester, KY 40391

Property at 110 Hampton Ave Exd, Winchester, KY 40391, 4 beds, 3 baths

$380,000 Last sold price

4 beds3 baths2,516 sq ft

110 Hampton Ave Exd, Winchester, KY 40391

Property at 115 Hampton Ave, Winchester, KY 40391, 4 beds, 2.5 baths

$310,900 Last sold price

4 beds2.5 baths3,042 sq ft

115 Hampton Ave, Winchester, KY 40391

Property at 103 Hampton Ave, Winchester, KY 40391, 3 beds, 2.5 baths

$257,400 Last sold price

3 beds2.5 baths1,715 sq ft

103 Hampton Ave, Winchester, KY 40391

Property at 17 Hampton Ave, Winchester, KY 40391, 4 beds, 2 baths

$428,000 Last sold price

4 beds2 baths3,181 sq ft

17 Hampton Ave, Winchester, KY 40391

Property at 35 Mockingbird Valley Rd, Winchester, KY 40391, 3 beds, 2.5 baths

$330,000 Last sold price

3 beds2.5 baths1,735 sq ft

35 Mockingbird Valley Rd, Winchester, KY 40391

Property at 321 S Maple St, Winchester, KY 40391, 6 beds, 4 baths

$270,000 Last sold price

6 beds4 baths4,490 sq ft

321 S Maple St, Winchester, KY 40391

Property at 113 Olde Potomac Ave, Winchester, KY 40391, 3 beds, 2 baths

$260,000 Last sold price

3 beds2 baths1,928 sq ft

113 Olde Potomac Ave, Winchester, KY 40391

Property at 133 S Burns Ave, Winchester, KY 40391, 4 beds, 2 baths

$204,000 Last sold price

4 beds2 baths3,295 sq ft

133 S Burns Ave, Winchester, KY 40391

Property at 407 Fairholme Way, Winchester, KY 40391, 3 beds, 2 baths

$325,000 Last sold price

3 beds2 baths1,805 sq ft

407 Fairholme Way, Winchester, KY 40391

Property at 309 Gallahadion Ct, Winchester, KY 40391, 3 beds, 2.5 baths

$360,000 Last sold price

3 beds2.5 baths1,920 sq ft

309 Gallahadion Ct, Winchester, KY 40391

Property at 307 Blair Ave, Winchester, KY 40391, 3 beds, 1 bath

$180,000 Last sold price

3 beds1 bath1,000 sq ft

307 Blair Ave, Winchester, KY 40391

Property at 213 Blair Ave, Winchester, KY 40391, 3 beds, 1 bath

$220,000 Last sold price

3 beds1 bath1,025 sq ft

213 Blair Ave, Winchester, KY 40391

Property at 305 Geronimo Ct, Winchester, KY 40391, 3 beds, 2 baths

$210,000 Last sold price

3 beds2 baths1,150 sq ft

305 Geronimo Ct, Winchester, KY 40391

Property at 322 Buffalo Trce, Winchester, KY 40391, 3 beds, 2 baths

$205,000 Last sold price

3 beds2 baths1,110 sq ft

322 Buffalo Trce, Winchester, KY 40391

Property at 110 Colonial Park Dr, Winchester, KY 40391, 3 beds, 1 bath

$201,000 Last sold price

3 beds1 bath1,235 sq ft

110 Colonial Park Dr, Winchester, KY 40391

Property at 511 Acadia Way, Winchester, KY 40391, 4 beds, 2 baths

$217,500 Last sold price

4 beds2 baths1,400 sq ft

511 Acadia Way, Winchester, KY 40391

Property at 231 Leslie Dr, Winchester, KY 40391, 3 beds, 2 baths

$245,000 Last sold price

3 beds2 baths1,438 sq ft

231 Leslie Dr, Winchester, KY 40391

Property at 9 Apache Trl, Winchester, KY 40391, 4 beds, 2 baths

$249,000 Last sold price

4 beds2 baths1,750 sq ft

9 Apache Trl, Winchester, KY 40391

Property at 313 Geronimo Ct, Winchester, KY 40391, 4 beds, 2.5 baths

$258,900 Last sold price

4 beds2.5 baths1,678 sq ft

313 Geronimo Ct, Winchester, KY 40391

Property at 301 Cabin Creek Hts, Winchester, KY 40391, 3 beds, 1 bath

$227,500 Last sold price

3 beds1 bath1,220 sq ft

301 Cabin Creek Hts, Winchester, KY 40391

Property at 7934 Ironworks Rd, Winchester, KY 40391, 3 beds, 1 bath

$260,000 Last sold price

3 beds1 bath1,633 sq ft

7934 Ironworks Rd, Winchester, KY 40391

Property at 44 5th St, Winchester, KY 40391, 3 beds, 1 bath

$173,000 Last sold price

3 beds1 bath1,270 sq ft

44 5th St, Winchester, KY 40391

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Recently Sold Homes in Winchester

There are currently 150 recently sold homes for sale in Winchester at a median listing price of $265K. 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 56 days. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 17 homes have been sold in Winchester. In addition to houses in Winchester, there were also 0 condos, 4 townhouses, and 5 multi-family units for sale in Winchester last month. Winchester is a minimally walkable city in Kentucky with a Walk Score of 36. Winchester is home to approximately 17,893 people and 8,688 jobs. 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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