New Listings for Sale in Winchester, KY

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NEW 22 HRS AGO

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Stoney Brook Subdivision! Second time ever offered for sale. Beautiful two story brick home with first and second floor en-suites. Each of the 4 bedrooms has its own walk in closet. Formal family room and dinning rooms, great room with fireplace, breakfast area, all season room with natural lighting, and large flex space located on second floor. All of this setting on . 40 of an acre lot with side entrance 2 car garage. Make your appointment today! 20 minutes to Hamburg Lexington or Richmond, less than 5 minutes from Bypass in Winchester

$550,000

4 beds3.5 baths3,848 sq ft

125 Casa Landa Way, Winchester, KY 40391

Large flex space • All season room • Walk in closet

3D WALKTHROUGH

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Tucked near the cul-de-sac on a dead-end street in the Windridge neighborhood, this 3 bedroom, 3 bath ranch offers easy access to the Bypass and Boone Ave along with a functional, spacious layout. A foyer entry opens to a formal living room featuring a wood-burning fireplace, built-in shelving, and a charming cased opening that provides sightlines into the kitchen and dining area, while a den just off the kitchen offers an additional cozy living space. The den has a full bath and could easily be used as a fourth bedroom. The kitchen includes granite countertops, white cabinetry, bar seating at the peninsula, a shared dining area, and all appliances remain. Hardwood floors span the foyer, ki

$295,000

3 beds3 baths1,738 sq ft

420 Willowbrook Rd, Winchester, KY 40391

Dead-end street • Cul-de-sac • Granite countertops

3D WALKTHROUGH

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
This 3 bedroom, 2 bath home sits on a corner lot with hardwood floors and a two-car detached garage behind the home. Plus, it's walkable to downtown Winchester, the public library, and College Park. Inside, you'll find tall ceilings, a traditional living and dining room, and a unique layout that gives you options for how you use the space. The kitchen opens to the back deck, and a ramp at the back door provides easy access. A partial unfinished basement offers extra storage, and with this great in-town location, the home is priced below a recent appraisal and ready for its new owner to come in and make it their own. Inspections welcomed, selling as-is.

$250,000

3 beds2 baths1,518 sq ft

313 S Burns Ave, Winchester, KY 40391

Tall ceilings • Walkable to downtown • Unique layout

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Step into this 4-bedroom, 2 full bath split-foyer home, perfectly designed for comfortable everyday living. The upper level features three generously sized bedrooms, a full bath, a bright living room, kitchen, and dining area—ideal for gathering with family and friends. Just off the kitchen, enjoy easy access to the covered deck overlooking a spacious backyard. The lower level offers even more living space with a fourth bedroom, full bath, cozy family room with fireplace, and ample storage—perfect for guests, a home office or work out room. With a little personal TLC and your own creative touches, this home is ready to be transformed into a warm and welcoming family home. A won

$270,000

4 beds2 baths2,332 sq ft

35 Cherokee Ct, Winchester, KY 40391

Covered deck • Spacious backyard • Split-foyer home

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
INCREDIBLE! This custom-built home sits on 2.59 acres in a prime location just minutes from I-64 and perfectly positioned between Winchester and Mount Sterling. The main level features a grand formal dining room, a family room with a vaulted coffered ceiling, and an eat-in kitchen open to the living area for easy entertaining. You'll also find the first primary suite plus two additional bedrooms and a full bath on the main floor. Upstairs offers a second primary suite with its own bath and oversized walk-in closet. The finished basement includes a 5th bedroom, two versatile bonus rooms, a full bath, laundry area, unfinished storage, and a single-car garage. Outdoor living is just as impress

$609,900

5 beds4 baths4,515 sq ft

6595 Mt Sterling Rd, Winchester, KY 40391

First primary suite • Custom-built home • 2.59 acres

Property at 455 Davis Ln, Winchester, KY 40391, 2 beds, 1.5 baths

$825,000

2 beds1.5 baths2,361 sq ft

455 Davis Ln, Winchester, KY 40391

Property at 233 Cunningham Ln, Winchester, KY 40391, 3 beds, 2.5 baths

$450,000

3 beds2.5 baths2,258 sq ft

233 Cunningham Ln, Winchester, KY 40391

Property at 217 S Highland St, Winchester, KY 40391, 4 beds, 2 baths

$259,900

4 beds2 baths2,683 sq ft

217 S Highland St, Winchester, KY 40391

Property at 204 Jett Dr, Winchester, KY 40391, 3 beds, 2 baths

$369,900

3 beds2 baths1,558 sq ft

204 Jett Dr, Winchester, KY 40391

Property at 33-41 Winn Ave, Winchester, KY 40391

$550,000

— beds— baths— sq ft

33-41 Winn Ave, Winchester, KY 40391

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NEW 10 HRS AGO

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Enjoy the perfect balance of peaceful rural living and everyday convenience with this inviting 3 bedroom 2 full bath home. This home has a very functional lay out with upgraded farm house charm. Did someone say soak tub!?! The front deck and covered back porch just add to the relaxing scene and coziness of this home. Less than 10 minutes to "town" and only 5 minutes to the Mountain Parkway, makes for convenient and quiet country living all rolled into one place! Not to mention the shed for all your extra storage room! Call today for your private showing!

$199,000

3 beds2 baths1,456 sq ft

113 Summer Ridge Rd, Mt Sterling, KY 40353

Front deck • Shed • Soak tub

NEW CONSTRUCTION

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
The Castleton II is SO much bang for your buck & all of the luxury home features you expect! This home is over 1400 sqft on the main level w/ large BRs (WICs), tiled walk in shower in the master w/ double sinks, open concept, main level laundry room, pantry, stainless appliances, granite in the kitchen + tiled back splash, kitchen breakfast bar + dining area. Downstairs you'll find an over sized 2 car garage (25' deep. .. store your boat), family room, 2 more bedrooms & a full bathroom. Purchase with confidence and discover the distinctive quality of Payne Homes. With over 30 years of building experience in Madison County, Payne Homes are renowned for their award-winning functio

$429,900

4 beds3 baths2,306 sq ft

136 Ivy Creek Dr, Richmond, KY 40475

Double sinks • Tiled walk in shower • Stainless appliances

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Well-maintained ranch home situated on a spacious 1-acre lot, partially fenced for added privacy and flexibility. This 3-bedroom, 2-bath home features an open floor plan that seamlessly connects the kitchen, dining, and living areas—perfect for everyday living and entertaining. The split bedroom layout offers a private primary suite separate from the additional bedrooms. Enjoy the convenience of easy access to I-75, with just minutes to Lexington or Richmond, while still appreciating the peace of a country-style setting

$315,000

3 beds2 baths1,606 sq ft

420 Hunters Run Dr, Richmond, KY 40475

Ranch home • Open floor plan • Partially fenced

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Modern Farmhouse Living: Country Privacy, City Convenience! Escape to your own private country oasis without sacrificing convenience. This beautifully renovated 3-bedroom home offers the perfect blend of rural tranquility and modern luxury, located just minutes from town. Step inside to discover a spacious, open-concept interior anchored by a designer kitchen—the heart of the home—featuring premium finishes and ample prep space for the home chef. Durable new luxury vinyl plank flooring flows seamlessly throughout, marrying style with country-living practicality. Move in with total peace of mind: this is a truly turnkey property. Beyond the cosmetic beauty, the home features exte

$239,000

3 beds1 bath1,232 sq ft

1184 Snow Creek Rd, Clay City, KY 40312

Designer kitchen • Mechanical upgrades • New water heater

NEW CONSTRUCTION

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Unfinished new construction offering a rare opportunity for investors to bring their vision to life. The exterior is fully completed, including a beautifully crafted wraparound porch featuring cedar posts and poplar and oak deck boards, highlighting quality craftsmanship and beautiful natural wood details throughout. The home is fully framed for 5 bedrooms and 2.5 bathrooms, with an open-concept kitchen and family room, mudroom, laundry area, and an upstairs loft providing additional living space. Plumbing is already completed, while electrical and septic remain to be installed, allowing flexibility for customization. Situated on just under 4 acres, this property includes three separate lot

$285,000

5 beds2.5 baths2,400 sq ft

1237 Burton Williams Rd, Irvine, KY 40336

Upstairs loft • Three separate lots • Open-concept kitchen

READY TO BUILD

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Located halfway between Richmond and Lexington, just off I-75 at exit 95, Adams Pointe is surrounded by beautiful farmland and rolling hills in a quiet neighborhood close to shopping, employment and schools.

$89,995

3 beds2 baths1,493 sq ft

Apex (Adams) Plan, Richmond, KY 40475

Listed 5 days

Listing provided by Zillow

Property at 219 Holt Ave, Mount Sterling, KY 40353, 3 beds, 1.5 baths

$270,000

3 beds1.5 baths1,573 sq ft

219 Holt Ave, Mount Sterling, KY 40353

Property at 3096 Bobwhite Trl, Lexington, KY 40509, 4 beds, 4 baths

$1,990,000

4 beds4 baths3,638 sq ft

3096 Bobwhite Trl, Lexington, KY 40509

Property at 131 Wells Rd, Mount Sterling, KY 40353, 8 beds, 7 baths

$1,750,000

8 beds7 baths10,825 sq ft

131 Wells Rd, Mount Sterling, KY 40353

Property at 637 Autumnwood Dr, Richmond, KY 40475, 3 beds, 3 baths

$485,000

3 beds3 baths3,802 sq ft

637 Autumnwood Dr, Richmond, KY 40475

Property at 421 Shallow Ford Rd, Richmond, KY 40475, 3 beds, 2 baths

$225,000

3 beds2 baths1,456 sq ft

421 Shallow Ford Rd, Richmond, KY 40475

Property at 69 Powell Rd, Clay City, KY 40312

$27,500

0 beds— baths— sq ft

69 Powell Rd, Clay City, KY 40312

Property at 172 Avawam Dr, Richmond, KY 40475

$46,000

— beds— baths— sq ft

172 Avawam Dr, Richmond, KY 40475

Property at 1700 Red House Rd Lot 23, Richmond, KY 40475

$250,000

— beds— baths— sq ft

1700 Red House Rd Lot 23, Richmond, KY 40475

Property at 1700 Red House Rd Lot 22, Richmond, KY 40475

$250,000

— beds— baths— sq ft

1700 Red House Rd Lot 22, Richmond, KY 40475

Property at 1700 Red House Rd Unit 210 Acres, Richmond, KY 40475

$2,100,000

— beds— baths— sq ft

1700 Red House Rd Unit 210 Acres, Richmond, KY 40475

Property at 625 Imperial Lakes Blvd, Richmond, KY 40475

$265,000

— beds— baths— sq ft

625 Imperial Lakes Blvd, Richmond, KY 40475

Property at 155 Walnut Grove Rd, Richmond, KY 40475

$59,900

— beds— baths— sq ft

155 Walnut Grove Rd, Richmond, KY 40475

Property at 4175 Ambergy Ct, Lexington, KY 40516

$389,898

— beds— baths— sq ft

4175 Ambergy Ct, Lexington, KY 40516

Property at 105 Otter Creek Rd, Richmond, KY 40475

$24,900

— beds— baths18,295 sq ft

105 Otter Creek Rd, Richmond, KY 40475

New Listings for Sale in Winchester

There are currently 10 new listings for sale in Winchester at a median listing price of $259K. 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 70 days. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 19 homes have been sold in Winchester. In addition to houses in Winchester, there were also 0 condos, 4 townhouses, and 4 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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