Winchester, KY homes for sale & real estate

New - 5 hours on Rocket

$10,000 Closing Credit¹

$989,000

3 beds • 3 baths

865 Sugar Ridge Rd, Winchester KY 40391

Listing Office: Century 21 Advantage Realty - Georgetown

view of front of property featuring a garage

New - 5 hours on Rocket

$4,096 Closing Credit¹

$344,900

3 beds • 2 baths

1831 Kiddville Rd, Winchester KY 40391

Listing Office: CENTURY 21 Advantage Realty

Save big

You could save thousands when you partner with Rocket Homes℠ and Rocket Mortgage®

view of front facade featuring a front yard and a garage

New - 15 hours on Rocket

$10,000 Closing Credit¹

$1,375,000

5 beds • 7 baths

6755 Boonesboro Rd, Winchester KY 40391

Listing Office: RE/MAX Elite Lexington

ranch-style house with a porch and a front lawn

unfurnished living room featuring ceiling fan and wood-type flooring

unfurnished living room with lofted ceiling, ceiling fan, and hardwood / wood-style flooring

New - 1 day on Rocket

$3,266 Closing Credit¹

$275,000

3 beds • 2 baths

597 Marseille Blvd, Winchester KY 40391

Listing Office: RE/MAX Creative, Winchester

view of front of house with covered porch

New - 1 day on Rocket

$2,244 Closing Credit¹

$189,000

3 beds • 1 bath

125 Magnolia St, Winchester KY 40391

Listing Office: Dream Maker Realty, LLC

snow covered back of property with cooling unit

New - 2 days on Rocket

$9,203 Closing Credit¹

$775,000

4 beds • 3.5 baths

240 Duclair Dr, Winchester KY 40391

Listing Office: Bluegrass Properties Group

view of front of property featuring central air condition unit

New - 7 days on Rocket

$2,731 Closing Credit¹

$230,000

3 beds • 1.5 baths

42 Park Ave, Winchester KY 40391

Listing Office: Coldwell Banker McMahan

Room to negotiate?

Median Sold Price

$239.9K

Avg. Sale Time

27 Days

Based on our December 2024 Market Report.

ranch-style house featuring a front yard

view of front of property featuring a front lawn

rear view of house with a deck and central AC

Backup offers

$2,136 Closing Credit¹

$179,900

3 beds • 2 baths

514 Hidden Hls, Winchester KY 40391

Listing Office: Bridgewater Real Estate

$2,672 Closing Credit¹

$225,000

3 beds • 1 bath

28 Stefanie Ct, Winchester KY 40391

Listing Office: Calumet Realty

$5,461 Closing Credit¹

$459,900

4 beds • 3.5 baths

210 College St, Winchester KY 40391

Listing Office: Dixon Properties

view of front of property featuring a yard and a porch

view of front of house featuring a porch and a front lawn

view of front of property featuring covered porch and a front yard

$9,441 Closing Credit¹

$795,000

4 beds • 2.5 baths

280 Penny Ln, Winchester KY 40391

Listing Office: Keller Williams Commonwealth

front facade with a front lawn and a garage

view of front property with a garage and a front lawn

view of front property featuring a garage and a front lawn

$3,479 Closing Credit¹

$293,000

3 beds • 2.5 baths

216 Prescott Ln, Winchester KY 40391

Listing Office: National Real Estate

ranch-style house with covered porch, a garage, and a front yard

view of front of home featuring a garage and covered porch

back of house with a lawn, central AC, ceiling fan, and a patio area

Backup offers

$3,432 Closing Credit¹

$289,000

3 beds • 2 baths

318 Hanover Dr, Winchester KY 40391

Listing Office: RE/MAX Elite Lexington

french country home featuring a front yard and french doors

french country style house featuring a front lawn

$9,322 Closing Credit¹

$785,000

4 beds • 2.5 baths

425 Alexis Way, Winchester KY 40391

Listing Office: Keller Williams Commonwealth

view of front of house with central AC and a porch

exterior space featuring a lawn and a porch

$2,078 Closing Credit¹

$175,000

2 beds • 1.5 baths

224 3rd St, Winchester KY 40391

Listing Office: Keller Williams Bluegrass Realty

view of front facade with central AC, a front lawn, and a garage

view of front of property featuring cooling unit, a garage, and a front lawn

view of front of property featuring a front yard

$3,432 Closing Credit¹

$289,000

3 beds • 2.5 baths

328 Newcastle Ln, Winchester KY 40391

Listing Office: Kentucky Residential Real Estate, LLC

view of front facade featuring a front lawn

$2,725 Closing Credit¹

$229,500

3 beds • 1 bath

4 Pocahontas Trl, Winchester KY 40391

Listing Office: Keller Williams Commonwealth

view of front of home featuring a porch, central AC unit, and a front yard

$6,994 Closing Credit¹

$589,000

5 beds • 3 baths

10 French Ave, Winchester KY 40391

Listing Office: Keller Williams Bluegrass Realty

ranch-style house with a garage and a front lawn

living room with wooden walls, hardwood / wood-style floors, and ceiling fan

$3,076 Closing Credit¹

$259,000

3 beds • 2 baths

59 Hillcrest Dr, Winchester KY 40391

Listing Office: The Agency

view of front of house with a porch and a front yard

bungalow featuring a porch and a front lawn

$2,849 Closing Credit¹

$239,900

3 beds • 2 baths

213 Short St, Winchester KY 40391

Listing Office: Dream Maker Realty, LLC

view of front of home featuring central AC unit, a garage, and a front lawn

$3,622 Closing Credit¹

$305,000

3 beds • 3 baths

421 Skylark Dr, Winchester KY 40391

Listing Office: Coldwell Banker McMahan

ranch-style home featuring solar panels, central air condition unit, and a front yard

view of front of home featuring a front yard

$3,739 Closing Credit¹

$314,900

3 beds • 2.5 baths

602 Laura Dr, Winchester KY 40391

Listing Office: Real Broker, LLC

view of front of home featuring a garage

view of side of property featuring a lawn

view of home's exterior featuring a lawn

$3,027 Closing Credit¹

$254,900

3 beds • 2 baths

235 Dubuy Dr, Winchester KY 40391

Listing Office: Keller Williams Commonwealth

view of yard with a porch and an outbuilding

$3,491 Closing Credit¹

$294,000

4 beds • 2 baths

705 Oil Springs Rd, Winchester KY 40391

Listing Office: HomeFirst Real Estate

split foyer home with a garage and a front lawn

bi-level home with a front yard, a garage, and central air condition unit

entrance to property featuring a yard and a garage

$3,146 Closing Credit¹

$264,900

3 beds • 2.5 baths

418 Jameson Way, Winchester KY 40391

Listing Office: 5.23 Real Estate

view of side of home featuring a yard and a garage

view of front of home featuring a front yard and a porch

$2,791 Closing Credit¹

$235,000

3 beds • 2 baths

37 7th St, Winchester KY 40391

Listing Office: Coldwell Banker McMahan

106 Bella Shae Way, Winchester KY, 40391, 4 bedrooms, 2.5 baths house for sale

Listing photo 2 for 106 Bella Shae Way, Winchester KY 40391

Listing photo 3 for 106 Bella Shae Way, Winchester KY 40391

$7,659 Closing Credit¹

$645,000

4 beds • 2.5 baths

106 Bella Shae Way, Winchester KY 40391

Listing Office: Keller Williams Commonwealth

view of front of home featuring french doors

$7,956 Closing Credit¹

$670,000

3 beds • 2 baths

113 Bella Shae Way, Winchester KY 40391

Listing Office: Keller Williams Commonwealth

exterior space featuring a garage and a front yard

$9,797 Closing Credit¹

$825,000

3 beds • 2.5 baths

111 Bella Shae Way, Winchester KY 40391

Listing Office: Keller Williams Commonwealth

view of front facade featuring a garage, a front yard, and french doors

view of front of property featuring a garage and a front lawn

$8,313 Closing Credit¹

$700,000

3 beds • 2 baths

415 Alexis Way, Winchester KY 40391

Listing Office: Keller Williams Commonwealth

Backup offers

$8,134 Closing Credit¹

$685,000

3 beds • 2 baths

426 Alexis Way, Winchester KY 40391

Listing Office: Keller Williams Commonwealth

view of front of property with a front lawn

view of front of home featuring a porch and a lawn

$3,561 Closing Credit¹

$299,900

4 beds • 2 baths

217 Morris Rd, Winchester KY 40391

Listing Office: Keller Williams Commonwealth

view of front of home with a carport and a front lawn

ranch-style home featuring a porch and a front lawn

$2,470 Closing Credit¹

$208,000

3 beds • 1 bath

160 Autumn Ct, Winchester KY 40391

Listing Office: Bluegrass Home Group

view of front of home with a garage and a front lawn

Backup offers

$4,274 Closing Credit¹

$359,900

3 beds • 2 baths

213 Ivy Ln, Winchester KY 40391

Listing Office: The Agency

living room featuring hardwood / wood-style floors and a textured ceiling

$2,054 Closing Credit¹

$173,000

3 beds • 1 bath

223 Blair Ave, Winchester KY 40391

Listing Office: Lifstyl Real Estate

view of front of property featuring a wooden deck, a front lawn, an outdoor structure, and a garage

$3,444 Closing Credit¹

$290,000

3 beds • 2 baths

2721 Pretty Run Rd, Winchester KY 40391

Listing Office: RE/MAX Creative, Winchester

view of front facade with covered porch, a front lawn, and a storage shed

bird's eye view with a water view and a rural view

kitchen featuring gray cabinets, dark hardwood / wood-style flooring, sink, and appliances with stainless steel finishes

$7,066 Closing Credit¹

$595,000

4 beds • 3.5 baths

1063 Wades Mill Rd, Winchester KY 40391

Listing Office: Christie's International Real Estate Bluegrass

$5,936 Closing Credit¹

$499,900

3 beds • 2 baths

870 Pilot View Rd, Winchester KY 40391

Listing Office: Woods Realty Group

$3,799 Closing Credit¹

$319,900

4 beds • 2.5 baths

8 Chickadee Ln, Winchester KY 40391

Listing Office: Ensor Real Estate, LLC

view of front facade featuring central AC, a front lawn, and a porch

unfurnished living room featuring a fireplace and dark hardwood / wood-style flooring

spare room with dark hardwood / wood-style flooring

$1,176 Closing Credit¹

$99,000

2 beds • 1 bath

120 E Lexington Ave, Winchester KY 40391

Listing Office: Taylor Real Estate, LLC

Winchester, KY Real Estate Market Overview

Browse 126 homes for sale in Winchester, KY. View properties, photos, nearby real estate with school and housing market information. The number of listings in Winchester, KY increased by 3% between November 2024 and December 2024. While the average time on the market in December 2024 was 27 days, the median list price was $239,916. While more than 5 listings in Winchester, KY in December 2024 were sold above asking price, there were more than 5 listings sold at asking price, and more than 10 were sold below.

From Rocket Homes Real Estate and based on county public records data

Schools near Winchester, KY

Elementary Schools

Conkwright Elementary School
360 Mount Sterling Rd
Public District KG-4
Henry E. Baker Intermediate School
1645 Martin Luther King Jr Dr
Public District 5-6
Strode Station Elementary School
1750 Martin Luther King Jr Dr
Public District KG-4

Middle Schools

Robert D. Campbell Junior High School
620 Boone Ave
Public District 7-8

High Schools

Phoenix Academy
100 Vaught Rd
Public District 6-12

Data provided by Great Schools

Homes for sale in Winchester, KY

Winchester, KY Real Estate Market Overview

What is it like to live in Winchester, KY

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