New Listings for Sale in Winchester, KY

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LISTED BY REDFIN 13 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Welcome home to this meticulously maintained 4-bedroom, 2.5-bathroom residence, where classic charm meets modern luxury. From the moment you step inside, you'll be greeted by the warmth of brand-new laminate hardwood flooring that flows seamlessly throughout the entire home. The spacious split-level layout offers the perfect balance of privacy and togetherness. With four generous bedrooms, there is ample space for a home office, guest quarters, or a growing family. Step outside to your own private oasis: a sprawling, well-kept lot featuring a stunning custom gazebo, perfect for morning coffee or evening entertaining in the fresh air. Located close to the heart of downtown Winchester, you a

$299,500

4 beds2.5 baths2,136 sq ft

402 Mcdowell Dr, Winchester, KY 40391

0.24 acre lot • 2 garage spots • Built 1986

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Welcome to your own slice of paradise! This 2022 doublewide sits on an impressive 39.5 acres of rolling countryside in Winchester, offering the perfect blend of modern comfort, privacy, and wide-open space. Step outside and take in the beautiful pastures, ideal for horses, cattle, or hobby farming, all complemented by a peaceful creek that winds through the property—perfect for relaxing evenings and enjoying nature at its best. Whether you're dreaming of a mini-farm, recreational retreat, or simply room to roam, this land delivers endless possibilities. The home itself is move-in ready and thoughtfully designed, featuring a spacious, open layout that's perfect for everyday living and

$440,000

3 beds2 baths1,568 sq ft

870 Pilot View Rd, Winchester, KY 40391

39.5 acres • Beautiful pastures • Peaceful creek

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Welcome to this quad plex income producing property. It is a large lot and the property sits back on the lot away from the road. There are 4 units, each with 3 beds and 1 bath. The whole building has a total of bedrooms of 12 beds and 4 baths. Each unit has its own kitchen. The pictures are of the only vacant unit on the bottom left. The two lower units rent for $950 and $925. The upper units rent for $800 and $875. The two upper units have had the same tenants for a number of years. There is ample parking for tenants and guests.

$290,000

12 beds4 baths4,010 sq ft

149 Winn Ave, Winchester, KY 40391

Ample parking • Own kitchen • Large lot

$425,000

3 beds2 baths1,512 sq ft

4305 Old Boonesboro Rd, Winchester, KY 40391

2.04 acre lot • Built 2023

NEW 25 HRS AGO

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
The Abigail Floor Plan offers an award-winning design created for flexible living, working, and relaxing. With exterior options including Farmhouse, French Country, or Cottage, the Abigail lets you choose a look that perfectly fits your style. Inside, a spacious flex room welcomes you at the entry-ideal as a formal dining room, home office, or creative space. The open kitchen features a large center island and stainless steel appliances, designed for both everyday living and entertaining. An optional morning room expands the kitchen and living area, filling the space with natural light and creating a cozy breakfast or gathering area. The main level also includes a generous living room, a fl

$383,900

5 beds4.5 baths2,263 sq ft

Abigail Plan, Winchester, KY 40391

Large center island • Private patio • Flex room

Listing provided by Zillow

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

$452,500

3 beds2.5 baths2,961 sq ft

42 Mockingbird Valley Rd, Winchester, KY 40391

Property at Martha Plan, Winchester, KY 40391, 3 beds, 2 baths

$334,900

3 beds2 baths1,580 sq ft

Martha Plan, Winchester, KY 40391

Listing provided by Zillow

Property at 113 Mimosa Dr, Winchester, KY 40391, 3 beds, 2 baths

$95,000

3 beds2 baths750 sq ft

113 Mimosa Dr, Winchester, KY 40391

Property at Barbara Plan, Winchester, KY 40391, 3 beds, 2 baths

$356,900

3 beds2 baths1,770 sq ft

Barbara Plan, Winchester, KY 40391

Listing provided by Zillow

Property at 120 Sunset Hts, Winchester, KY 40391, 3 beds, 2 baths

$275,000

3 beds2 baths1,440 sq ft

120 Sunset Hts, Winchester, KY 40391

Property at Elizabeth Plan, Winchester, KY 40391, 4 beds, 2.5 baths

$349,900

4 beds2.5 baths2,100 sq ft

Elizabeth Plan, Winchester, KY 40391

Listing provided by Zillow

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

$129,900

2 beds1 bath876 sq ft

122 Callaway Street SE Callaway St, Winchester, KY 40391

Property at 345 Providence Ln, Winchester, KY 40391

$1,250,000

— beds— baths— sq ft

345 Providence Ln, Winchester, KY 40391

Property at Grace Plan, Winchester, KY 40391, 3 beds, 2.5 baths

$346,900

3 beds2.5 baths1,828 sq ft

Grace Plan, Winchester, KY 40391

Listing provided by Zillow

Property at Eleanor Plan, Winchester, KY 40391, 3 beds, 2.5 baths

$414,900

3 beds2.5 baths2,722 sq ft

Eleanor Plan, Winchester, KY 40391

Listing provided by Zillow

Property at Lucy Plan, Winchester, KY 40391, 3 beds, 2 baths

$329,900

3 beds2 baths1,424 sq ft

Lucy Plan, Winchester, KY 40391

Listing provided by Zillow

Property at Jackie Plan, Winchester, KY 40391, 3 beds, 2.5 baths

$392,900

3 beds2.5 baths2,570 sq ft

Jackie Plan, Winchester, KY 40391

Listing provided by Zillow

Property at Nancy Plan, Winchester, KY 40391, 3 beds, 2.5 baths

$364,900

3 beds2.5 baths2,098 sq ft

Nancy Plan, Winchester, KY 40391

Listing provided by Zillow

Property at 446 Tremont Ln, Winchester, KY 40391, 4 beds, 2.5 baths

$367,000

4 beds2.5 baths2,811 sq ft

446 Tremont Ln, Winchester, KY 40391

Property at 146 W Lexington Ave, Winchester, KY 40391, 7 beds, 3 baths

$269,900

7 beds3 baths3,393 sq ft

146 W Lexington Ave, Winchester, KY 40391

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Nearby homes that match your criteria

NEW 24 HRS AGO

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
2.56 +/- Acres with Manufactured Home and Barn! The Home is a 2 Bedroom, 2 Bath that's not in livable condition.

$49,000

2 beds2 baths980 sq ft

140 Scott Stephens Ln, Jeffersonville, KY 40337

2.56 acre lot • Built 1992

OPEN SAT, 1PM TO 3PM

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Welcome to unparalleled space and sophistication in this fully remodeled, custom 5-bedroom, 5-bathroom estate, perfectly situated on just over an acre. This is the definition of a move-in-ready dream home, meticulously designed for today's lifestyle, including seamless multi-generational living. Enjoy grand scale Living with 5 bedrooms and 5 bathrooms, every resident enjoys privacy and comfort. The generous floor plan offers expansive common areas perfect for large family gatherings and entertaining. Step into your gourmet showcase kitchen in the heart of the home with brand-new, high-end stainless steel appliances, gleaming granite countertops, and custom cabinetry. The fully finished base

$885,500

5 beds4.5 baths5,301 sq ft

2055 Powhatan Trl, Richmond, KY 40475

Fully remodeled • Attached garage • Walk out entrance

NEW 28 HRS AGO

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Wow!! This property has so much to offer! An Immaculate Home with Concrete Front & Side Porches, a 35 x 50 Barn with Workshop with Electric & Water, 288+/- sq. ft. Shed with Electric, 2+ Car Garage and 3 Car Carport. Home has high end upgrades including Flooring, Baths, Kitchen, New Siding, New Doors, Upgraded Shingles and more. Offering an Open Living Room, Beautiful Kitchen with appliances plus washer & dryer, Dining area, 3 Bedrooms, 2 Full Bathrooms and utility room. This 7+/- Acres is cleared and level only minutes from Mt. Sterling. The Barn was refurbished in 2011. All other structures were built in 2018 and 2019.

$379,000

3 beds2 baths1,344 sq ft

739 Old Hwy 11, Jeffersonville, KY 40337

Open living room • Utility room • Shed with electric

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
This one-owner brick ranch on just over an acre lot with scenic views and solid bones is ready for YOU to call it HOME! This 3-bedroom, 2-bath home offers a spacious layout featuring a split bedroom plan, perfect for privacy, a large living room, formal dining area adjacent to the functional kitchen along with a sizable great room with vaulted ceilings and a cozy wood burning fireplace, making it ideal for everyday living and entertaining. The primary bedroom is generously sized and also features vaulted ceilings, creating a comfortable retreat not to mention a large walk-in closet and attached primary bath. Just off the great room, an 11' x 14' sunroom provides additional space to enjo

$299,000

3 beds2 baths1,745 sq ft

843 Three Forks Rd, Richmond, KY 40475

1.02 acre lot • 2 garage spots • Built 1992

NEW 33 HRS AGO

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
Affordable opportunity in Estill County! This single-wide manufactured home sits on a spacious lot with a peaceful rural setting just minutes from Irvine. The home offers a functional layout with a living room, eat-in kitchen, and multiple bedrooms, providing plenty of potential for customization or improvement. Outside, enjoy open yard space, room for parking, and scenic surroundings. Property is being sold as-is and presents a great option for investors, renovators, or buyers looking for a budget-friendly home with land. Convenient access to town amenities while still offering privacy and country charm.

$124,900

3 beds2 baths1,344 sq ft

114 Iron Works Rd, Irvine, KY 40336

Spacious lot • Room for parking • Open yard space

NEW CONSTRUCTION3D WALKTHROUGH

ABOUT THIS HOME
New Listing for sale in Winchester, KY:
One of a kind new construction home in the popular Home Place subdivision located minutes from Hamburg Pavilion & I-75/64. This property offers a terrific floor plan with room to grow offering a full unfinished basement (rough in plumbing for full bath & wet bar) situated on a nice lot backing to greenspace. The first floor provides a nice cozy plan with an open Great Room w/ Natural Gas Stone Fireplace/Built ins/Coffered ceilings, First Floor Master Suite w/ tile shower/dual vanities/soaking tub/custom WIC, Kitchen w/ island bar/Quartz countertops, formal dining room (could be used as a home office), powder room and mud rm/utility. The 2nd floor boasts a 2nd master bedroom wit

$689,900

5 beds3.5 baths3,235 sq ft

1344 Angus Trl, Lexington, KY 40509

Open great room • 7,333 sq ft lot • 2 garage spots

Property at 1069 Squirrel Nest Ln, Lexington, KY 40509, 3 beds, 2.5 baths

$574,500

3 beds2.5 baths2,420 sq ft

1069 Squirrel Nest Ln, Lexington, KY 40509

Property at 197 Antwerp Ave, Mount Sterling, KY 40353, 3 beds, 2 baths

$223,000

3 beds2 baths1,934 sq ft

197 Antwerp Ave, Mount Sterling, KY 40353

Property at 416 Rivers Trce, Richmond, KY 40475, 2 beds, 2.5 baths

$395,000

2 beds2.5 baths2,200 sq ft

416 Rivers Trce, Richmond, KY 40475

Property at 1301 Rabbit Warren Flt, Lexington, KY 40509, 4 beds, 3 baths

$799,000

4 beds3 baths3,184 sq ft

1301 Rabbit Warren Flt, Lexington, KY 40509

Property at 101 Welsley Way, Mount Sterling, KY 40353, 6 beds, 3.5 baths

$1,900,000

6 beds3.5 baths5,070 sq ft

101 Welsley Way, Mount Sterling, KY 40353

Property at 18 Maysville Ave, Mount Sterling, KY 40353, 4 beds, 2 baths

$200,000

4 beds2 baths2,625 sq ft

18 Maysville Ave, Mount Sterling, KY 40353

Property at 45 Countryside Dr, Mount Sterling, KY 40353, 4 beds, 2.5 baths

$425,000

4 beds2.5 baths2,985 sq ft

45 Countryside Dr, Mount Sterling, KY 40353

Property at 4137 Meadowlark Rd, Lexington, KY 40509, 5 beds, 2.5 baths

$629,000

5 beds2.5 baths2,579 sq ft

4137 Meadowlark Rd, Lexington, KY 40509

Property at 110 Summer Ridge Rd, Mount Sterling, KY 40353, 3 beds, 2 baths

$210,000

3 beds2 baths1,848 sq ft

110 Summer Ridge Rd, Mount Sterling, KY 40353

Property at 117 Bear Run Rd, Richmond, KY 40475, 3 beds, 2.5 baths

$439,000

3 beds2.5 baths2,386 sq ft

117 Bear Run Rd, Richmond, KY 40475

Property at 336 Inverness Trl Trl, Richmond, KY 40475, 5 beds, 3.5 baths

$699,000

5 beds3.5 baths3,630 sq ft

336 Inverness Trl Trl, Richmond, KY 40475

Property at 300 Prestwick Cir, Richmond, KY 40475, 4 beds, 4 baths

$1,150,000

4 beds4 baths5,154 sq ft

300 Prestwick Cir, Richmond, KY 40475

Property at Lot 1 Kentucky River Rd, Richmond, KY 40475

$75,000

— beds— baths— sq ft

Lot 1 Kentucky River Rd, Richmond, KY 40475

Property at 512 Avawam Dr Lot 128, Richmond, KY 40475

$85,000

— beds— baths— sq ft

512 Avawam Dr Lot 128, Richmond, KY 40475

New Listings for Sale in Winchester

There are currently 20 new listings for sale in Winchester at a median listing price of $255K. 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 83 days. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 18 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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