Pending Listings in Winchester, KY

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ABOUT THIS HOME
Pending Listing in Winchester, KY:
The property has a few violations of city ordinances. Rotting facia board that must be replaced and painted or covered. The soffits also need to be painted or covered. The porch needs to be completed. Any broken windows need to be replaced. All repairs need to take place within six months of taking ownership.

$55,000

0 beds— baths— sq ft

76 Clay St, Winchester, KY 40391

3,590 sq ft lot • Car-dependent

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ABOUT THIS HOME
Pending Listing in Winchester, KY:
Stunning all-brick ranch home with a finished basement! This home features an open kitchen, beautiful hardwood floors, and updated bathrooms. The spacious primary suite is located in the basement and includes access to a screened-in porch — perfect for enjoying your morning coffee or relaxing in the evening. The large backyard offers plenty of space for outdoor activities and entertaining. Don't miss this beauty. Schedule a showing today!

$260,000

3 beds2 baths2,127 sq ft

213 Southwind Dr, Winchester, KY 40391

0.31 acre lot • Garage • Car-dependent

CONTINGENT

ABOUT THIS HOME
Pending Listing in Winchester, KY:
Move right in and fall in love with this fully renovated 4-bedroom, 2-bath beauty! The open floor plan, neutral tones, and modern finishes create a bright and welcoming feel. The updated kitchen shines with granite countertops, stainless steel appliances, and plenty of space to gather. Fresh flooring, updated baths, and stylish details throughout make this home truly turnkey!

$229,900

4 beds2 baths1,636 sq ft

204 Crawford Ct, Winchester, KY 40391

9204 acre lot • Car-dependent

CONTINGENT

ABOUT THIS HOME
Pending Listing in Winchester, KY:
For only the second time ever, this remarkable Colonial home is being offered for sale in the coveted Stoney Brook subdivision. From the moment you step into the welcoming entry hall, gleaming hardwood floors and timeless details set the stage for a home filled with warmth, tradition, and charm. The main level is designed for both everyday comfort and memorable gatherings. A gracious primary suite with a large walk-in closet provides the perfect retreat, while the formal living room—complete with a grand piano—and elegant dining room invite you to host in style. The heart of the home is the family room, where a cozy gas log fireplace frames sweeping views of the covered porch an

$545,000

4 beds3.5 baths3,649 sq ft

445 Lynnway Dr, Winchester, KY 40391

0.51 acre lot • $3 HOA • 2 garage spots

CONTINGENT

ABOUT THIS HOME
Pending Listing in Winchester, KY:
Charming Split-Level Home in a Peaceful Winchester Neighborhood Discover this beautiful 3-bedroom, 2 full bath split-level home featuring a cozy finished basement perfect for relaxing or entertaining. Enjoy both front and rear porches, ideal for morning coffee or evening gatherings. The spacious, fenced-in backyard offers privacy and room to play, garden, or unwind. Nestled in a quiet neighborhood just minutes from the Winchester Bypass, this home provides easy access to shopping, dining, and everyday conveniences—making it the perfect blend of comfort and location.

$279,500

3 beds2 baths2,250 sq ft

724 Terry Dr, Winchester, KY 40391

7,840 sq ft lot • Garage • Car-dependent

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

$320,000

4 beds2.5 baths1,970 sq ft

104 Teakwood Ct, Winchester, KY 40391

Property at 356 Boone Ave, Winchester, KY 40391, 4 beds, 3 baths

$354,000

4 beds3 baths3,200 sq ft

356 Boone Ave, Winchester, KY 40391

Property at 205 Chardonnay Ct, Winchester, KY 40391, 4 beds, 2.5 baths

$350,000

4 beds2.5 baths2,179 sq ft

205 Chardonnay Ct, Winchester, KY 40391

Property at 223 Bartram Ct, Winchester, KY 40391, 3 beds, 2.5 baths

$289,000

3 beds2.5 baths1,606 sq ft

223 Bartram Ct, Winchester, KY 40391

Property at 536 S Maple St, Winchester, KY 40391, 3 beds, 3 baths

$352,500

3 beds3 baths1,832 sq ft

536 S Maple St, Winchester, KY 40391

Property at 120 E Lexington Ave, Winchester, KY 40391, 3 beds, 1 bath

$172,500

3 beds1 bath1,332 sq ft

120 E Lexington Ave, Winchester, KY 40391

Property at 3900 (mt) Mount Sterling Rd, Winchester, KY 40391, 6 beds, 4 baths

$769,900

6 beds4 baths4,843 sq ft

3900 (mt) Mount Sterling Rd, Winchester, KY 40391

Property at 5705 Mount Sterling Rd, Winchester, KY 40391, 4 beds, 2.5 baths

$389,000

4 beds2.5 baths2,980 sq ft

5705 Mount Sterling Rd, Winchester, KY 40391

Property at 312 Forest Ave, Winchester, KY 40391, 3 beds, 2 baths

$259,000

3 beds2 baths1,550 sq ft

312 Forest Ave, Winchester, KY 40391

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

$472,000

3 beds2 baths2,727 sq ft

865 Pretty Run Rd, Winchester, KY 40391

Property at 213 Honeysuckle Ln, Winchester, KY 40391, 4 beds, 3 baths

$398,000

4 beds3 baths3,087 sq ft

213 Honeysuckle Ln, Winchester, KY 40391

Property at 118 Windridge Dr, Winchester, KY 40391, 3 beds, 2 baths

$325,000

3 beds2 baths1,617 sq ft

118 Windridge Dr, Winchester, KY 40391

Property at 306 Snowden Dr, Winchester, KY 40391, 4 beds, 2 baths

$252,500

4 beds2 baths1,593 sq ft

306 Snowden Dr, Winchester, KY 40391

Property at 165 Hilltop Dr, Winchester, KY 40391, 3 beds, 2 baths

$274,900

3 beds2 baths1,454 sq ft

165 Hilltop Dr, Winchester, KY 40391

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

$225,000

4 beds2 baths3,295 sq ft

133 S Burns Ave, Winchester, KY 40391

Property at 12 Apache Trl, Winchester, KY 40391, 3 beds, 2 baths

$168,500

3 beds2 baths1,026 sq ft

12 Apache Trl, Winchester, KY 40391

Property at 210 College St, Winchester, KY 40391, 4 beds, 3.5 baths

$399,900

4 beds3.5 baths2,718 sq ft

210 College St, Winchester, KY 40391

Property at 102 Camelot Dr, Winchester, KY 40391, 5 beds, 3.5 baths

$475,000

5 beds3.5 baths3,679 sq ft

102 Camelot Dr, Winchester, KY 40391

Property at 205 Evergreen Dr, Winchester, KY 40391, 3 beds, 2 baths

$395,000

3 beds2 baths1,855 sq ft

205 Evergreen Dr, Winchester, KY 40391

Property at 122 Leann Ln, Winchester, KY 40391, 4 beds, 2.5 baths

$379,000

4 beds2.5 baths2,587 sq ft

122 Leann Ln, Winchester, KY 40391

Property at 700 Nick Ln, Winchester, KY 40391, 3 beds, 2.5 baths

$949,950

3 beds2.5 baths2,400 sq ft

700 Nick Ln, Winchester, KY 40391

Property at 395 Croxton Way, Winchester, KY 40391

$374,900

— beds— baths— sq ft

395 Croxton Way, Winchester, KY 40391

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

$239,000

3 beds2.5 baths1,430 sq ft

204 Moss Ct, Winchester, KY 40391

Property at 3988 Trapp-goffs Corner Rd, Winchester, KY 40391, 5 beds, 3 baths

$340,000

5 beds3 baths2,056 sq ft

3988 Trapp-goffs Corner Rd, Winchester, KY 40391

Property at 1138 Lafayette Blvd, Winchester, KY 40391, 3 beds, 3 baths

$385,000

3 beds3 baths2,300 sq ft

1138 Lafayette Blvd, Winchester, KY 40391

Property at 130 Village Ct, Winchester, KY 40391, 4 beds, 2.5 baths

$270,000

4 beds2.5 baths1,988 sq ft

130 Village Ct, Winchester, KY 40391

Property at 123 Strawberry Ln, Winchester, KY 40391, 3 beds, 2 baths

$305,000

3 beds2 baths1,792 sq ft

123 Strawberry Ln, Winchester, KY 40391

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

$330,000

3 beds2.5 baths1,735 sq ft

35 Mockingbird Valley Rd, Winchester, KY 40391

Property at 291 Log Lick Rd, Winchester, KY 40391, 4 beds, 2.5 baths

$435,000

4 beds2.5 baths2,600 sq ft

291 Log Lick Rd, Winchester, KY 40391

Property at 727 Terry Dr, Winchester, KY 40391, 3 beds, 1.5 baths

$275,000

3 beds1.5 baths1,958 sq ft

727 Terry Dr, Winchester, KY 40391

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

$275,000

3 beds2.5 baths1,715 sq ft

103 Hampton Ave, Winchester, KY 40391

Property at 304 Winterberry Dr, Winchester, KY 40391, 7 beds, 4 baths

$599,999

7 beds4 baths4,386 sq ft

304 Winterberry Dr, Winchester, KY 40391

Property at 203 Inverness Ln, Winchester, KY 40391, 3 beds, 2.5 baths

$245,000

3 beds2.5 baths1,935 sq ft

203 Inverness Ln, Winchester, KY 40391

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

$269,000

3 beds2 baths1,928 sq ft

113 Olde Potomac Ave, Winchester, KY 40391

Property at 37 Lynnway Dr, Winchester, KY 40391, 3 beds, 2.5 baths

$300,000

3 beds2.5 baths3,220 sq ft

37 Lynnway Dr, Winchester, KY 40391

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

$165,000

2 beds1 bath902 sq ft

220 Pendleton St, Winchester, KY 40391

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Pending Listings in Winchester

There are currently 66 pending listings for sale in Winchester at a median listing price of $269K. 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, 27 homes have been sold in Winchester. In addition to houses in Winchester, there were also 0 condos, 6 townhouses, and 13 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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