Winchester, KY Homes

/33
$179,900
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
307 Blair Ave, Winchester, KY 40391

This charming 3-bedroom, 1-bath ranch offers fresh updates throughout, including brand new flooring and interior paint. The inviting side porch features a ramp for easy accessibility and leads to a spacious patio—perfect for relaxing or entertaining. A detached two-car garage adds great storage and functionality. Located just minutes from downtown Winchester and I-64, this move-in-ready home

Brooke Otis-Mull RO&CO Real Estate

307 Blair Ave, Winchester, KY 40391
/41
$650,000 Sold Jun 23, 2025
- 3,007 Sq Ft
- $216/SF
- 15 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2002
357 Wades Mill Rd, Winchester, KY 40391

Privacy, tranquil setting, & spectacular views mark this immaculate custom build, one owner, 4 bedroom, 4 bath, story and half brick on 5-manicured acres in Clark County. Centrally located minutes from I-64 with easy access to Lexington & surrounding communities, this well-planned home offers first floor primary suite & walk-in closets, 10 ft ceilings (most), crown moldings first floor, brick

Emily Belcher Rector Hayden Realtors

357 Wades Mill Rd, Winchester, KY 40391

/21
Est $226,350 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,301 Sq Ft
121 Summerhill Way, Winchester, KY 40391

121 Summerhill Way, Winchester, KY 40391

/15
$145,000
- 4 Beds
- 2 Baths
- 2,928 Sq Ft
108 W Hickman St, Winchester, KY 40391

This Duplex is a fixer-upper!! Perfect for the BRRRR strategy for long term hold! Property needs full rehab. Viewings allowed only after Hold Harmless agreement has been signed. Bring your offers this will go fast!

David Espinosa Bluegrass Realty Pros, Inc

108 W Hickman St, Winchester, KY 40391
/24
$185,000 Sold Jun 23, 2025
- 1,044 Sq Ft
- $177/SF
- 23 Days On Market
- 3 Beds
- 1 Bath
- Built 1990
605 Dixiana Dr, Winchester, KY 40391

This nice brick ranch will make someone a great home. New flooring throughout. Roof and water heater just 2 years old. Home is located close to downtown Winchester and the new Bypass. Schedule a tour before this beauty is gone.

Dale Hatton Dream Maker Realty, LLC

605 Dixiana Dr, Winchester, KY 40391

/30
Est $246,712 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,462 Sq Ft
304 Salem Ave, Winchester, KY 40391

304 Salem Ave, Winchester, KY 40391

/9
$102,000
- 2 Beds
- 1 Bath
- 552 Sq Ft
39 S Highland St, Winchester, KY 40391

Here's your chance to own a nice investment property. This Single Family home has 2 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

39 S Highland St, Winchester, KY 40391
/43
$485,000 Sold Jun 23, 2025
- 2,414 Sq Ft
- $201/SF
- 55 Days On Market
- 3 Beds
- 2 Baths
- Built 2017
430 Fairholme Way, Winchester, KY 40391

Nestled in the serene landscape of Kentucky, is this stunning 1 1/2 story brick home. It offers the perfect blend of elegance and modern comfort. This inviting home offers a timeless appeal that harmonizes beautifully with the tranquil surroundings. It's located on the outskirts of town, in a quiet neighborhood, making it the perfect retreat from the hustle and bustle of life. It's perfect

Robyn Bradley Woods Realty Group

430 Fairholme Way, Winchester, KY 40391

/41
Est $242,732 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,296 Sq Ft
109 Eastridge Dr, Winchester, KY 40391

109 Eastridge Dr, Winchester, KY 40391

/3
$146,000
- 3 Beds
- 1 Bath
- 1,020 Sq Ft
228 Jackson St, Winchester, KY 40391

Here's your chance to own a nice investment property. This single family home has a 3 bed 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

228 Jackson St, Winchester, KY 40391
/26
$239,900 Sold Jun 23, 2025
- 1,878 Sq Ft
- $128/SF
- 74 Days On Market
- 3 Beds
- 2 Baths
- Built 1920
134 Boone Ave, Winchester, KY 40391

Step into this inviting home at 134 Boone Avenue, where timeless charm and thoughtful details create a warm and welcoming atmosphere. The classic front porch sets the tone, while inside, vintage wood floors, beautiful foyer, and large windows flood each room with natural light. The spacious living room has a cozy, intimate feel, perfect for family gatherings or quiet nights in. A delightful

steven lindsey Heart of KY Real Estate

134 Boone Ave, Winchester, KY 40391

/28
Est $301,634 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,588 Sq Ft
317 Fern Ct, Winchester, KY 40391

317 Fern Ct, Winchester, KY 40391

/12
$144,000
- 3 Beds
- 1 Bath
- 805 Sq Ft
150 Cook Ave, Winchester, KY 40391

Here's your chance to own a nice investment property. This has a single family has 3 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

150 Cook Ave, Winchester, KY 40391
/23
$184,900 Sold Jun 20, 2025
- 1,056 Sq Ft
- $175/SF
- 2 Days On Market
- 2 Beds
- 1.5 Baths
- Built 2000
324 Essex Ct, Winchester, KY 40391

If you've been searching for a place that just feels right—whether it's your first home or time to simplify—324 Essex Ct might be exactly what you've been waiting for. Tucked at the end of a quiet cul-de-sac, this home offers comfort, charm, and a layout that makes everyday life easy.Inside, the main level welcomes you with updated flooring, a cozy living area, and a bright eat-in kitchen

Kymberly Clem EXP Realty, LLC

324 Essex Ct, Winchester, KY 40391

/14
Est $225,668 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,092 Sq Ft
126 Spring Ridge Way, Winchester, KY 40391

126 Spring Ridge Way, Winchester, KY 40391

/6
$388,000
- 5 Beds
- 3 Baths
- 2,762 Sq Ft
101 E Lexington Ave, Winchester, KY 40391

Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

101 E Lexington Ave, Winchester, KY 40391
/25
$216,000 Sold Jun 20, 2025
- 1,350 Sq Ft
- $160/SF
- 17 Days On Market
- 3 Beds
- 2 Baths
- Built 2024
138 Linden Ave, Winchester, KY 40391

Adorable and affordable — this brand-new construction home in downtown Winchester is the perfect blend of style, comfort, and convenience. Featuring an open-concept layout that seamlessly connects the living, dining, and kitchen areas, this home offers 3 bedrooms and 2 full bathrooms, making it ideal for a variety of lifestyles. The kitchen is complete with sleek granite countertops, stainless

Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

138 Linden Ave, Winchester, KY 40391

/13
Est $172,896 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,330 Sq Ft
4 Burton Ave, Winchester, KY 40391

4 Burton Ave, Winchester, KY 40391

/4
$650,000
- 8 Beds
- 5 Baths
- 3,834 Sq Ft
202 S Maple St, Winchester, KY 40391

Here's your chance to own a nice investment property. This 5-unit has 3 - 2 bed 1 bath units,1 - 1 bed 1 bath unit and a studio. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

202 S Maple St, Winchester, KY 40391
/21
$219,500 Sold Jun 20, 2025
- 1,480 Sq Ft
- $148/SF
- 6 Days On Market
- 4 Beds
- 2 Baths
- Built 2002
523 Acadia Way, Winchester, KY 40391

This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of AMI for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

Tyler I Back The Brokerage

523 Acadia Way, Winchester, KY 40391

/40
Est $230,167 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,451 Sq Ft
84 Brink Ave, Winchester, KY 40391

84 Brink Ave, Winchester, KY 40391

/2
$255,000
- 4 Beds
- 2 Baths
- 2,732 Sq Ft
206 S Maple St, Winchester, KY 40391

Here's your chance to own a nice investment property. This duplex has a 2 bed 1 bath unit and a 2 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

206 S Maple St, Winchester, KY 40391
/41
$325,000 Sold Jun 20, 2025
- 1,890 Sq Ft
- $172/SF
- 7 Days On Market
- 3 Beds
- 2 Baths
- Built 1980
525 Lasalle Ct, Winchester, KY 40391

Don't miss this charming ranch on a walkout basement nestled in one of the most desirable neighborhoods in Winchester. This open floor plan home offers a first floor primary with two additional bedrooms on the main floor. A spacious kitchen is the heart of the home with room to cook and converse with guests. The basement offers the best of both worlds with another living area and a flex space

Lindsay Barsotti ERA Select Real Estate

525 Lasalle Ct, Winchester, KY 40391

/16
Est $179,605 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,122 Sq Ft
141 Alabama St, Winchester, KY 40391

141 Alabama St, Winchester, KY 40391

/12
$295,000
- 6 Beds
- 4 Baths
- 3,035 Sq Ft
117 Linden Ave, Winchester, KY 40391

Here's your chance to own a nice investment property. This duplex has a 3 bed 2 bath unit and a 3 bed 2 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

117 Linden Ave, Winchester, KY 40391
/65
$380,000 Sold Jun 19, 2025
- 4,572 Sq Ft
- $83/SF
- 3 Days On Market
- 3 Beds
- 4 Baths
- Built 1976
399 Stonecrest Rd, Winchester, KY 40391

Tucked away near the end of a private road in Clark County, this custom-built mid-century modern home sits on 2.9 acres stretching to Old Stone Church Rd, with a wooded backyard offering privacy and natural beauty. Just 10 minutes from I-75 and 10 minutes from I-64, the location is ideal for peaceful living with convenient access. Built in 1976 and updated with a new roof (2025), some new windows

ROBIN TRIMBLE HomeFirst Real Estate

399 Stonecrest Rd, Winchester, KY 40391

/16
Est $351,857 Not Listed For Sale
- 4 Beds
- 2 Baths
- 4,176 Sq Ft
122 French Ave, Winchester, KY 40391

122 French Ave, Winchester, KY 40391

/14
$292,000
- 6 Beds
- 2 Baths
- 3,196 Sq Ft
124 S Burns Ave, Winchester, KY 40391

Here's your chance to own a nice investment property. This duplex has a 3 bed 1 bath unit and a 3 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

124 S Burns Ave, Winchester, KY 40391
/28
$345,000 Sold Jun 19, 2025
- 3,149 Sq Ft
- $110/SF
- 58 Days On Market
- 4 Beds
- 3 Baths
- Built 1950
512 Boone Ave, Winchester, KY 40391

Step into this stunning home that seamlessly blends modern comfort with timeless charm. The spacious living room boasts an open-concept design, complemented by beautiful hardwood floors, an abundance of natural light, and a cozy fireplace. The large kitchen is a chef's dream, featuring ample shelving, stainless steel appliances, and breathtaking views. Step outside to a massive deck overlooking a

Jordan James Lifstyl Real Estate

512 Boone Ave, Winchester, KY 40391

/8
Est $237,803 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,359 Sq Ft
109 Alabama St, Winchester, KY 40391

109 Alabama St, Winchester, KY 40391

/3
$221,000
- 4 Beds
- 2 Baths
- 2,600 Sq Ft
223 W Hickman St, Winchester, KY 40391

Here's your chance to own a nice investment property. This duplex has a 2 bed 1 bath unit and a 2 bed one bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

223 W Hickman St, Winchester, KY 40391
/65
$290,000 Sold Jun 18, 2025
- 1,844 Sq Ft
- $157/SF
- 1 Day On Market
- 3 Beds
- 2 Baths
- Built 1980
13 Robyn Dr, Winchester, KY 40391

It is hard to find a home that has been as meticulously maintained as this one! Nestled in the wonderful neighborhood of Verna Hills, this 3 bedroom, 2 full bath, one level brick home is turn key ready to move in! All of the major expense items have been replaced in the last few years such as the HVAC, water heater, and the metal roof! Out back you will find a lovely covered patio, a storage

Jason Townsend Kentucky Residential Real Estate, LLC

13 Robyn Dr, Winchester, KY 40391

/40
Est $233,888 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,023 Sq Ft
120 Georgia St, Winchester, KY 40391

120 Georgia St, Winchester, KY 40391

/9
$274,000
- 5 Beds
- 3 Baths
- 2,384 Sq Ft
135 Winn Ave, Winchester, KY 40391

Here's your chance to own a nice investment property. This duplex has a 3 bed 2 bath unit and a 2 bed one bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

135 Winn Ave, Winchester, KY 40391
/30
$185,000 Sold Jun 18, 2025
- 1,188 Sq Ft
- $156/SF
- 3 Days On Market
- 2 Beds
- 2.5 Baths
- Built 2000
308 Essex Ct, Winchester, KY 40391

Tucked away on a peaceful cul-de-sac and backing up to a serene tree line, this beautifully maintained home offers privacy and tranquility just minutes from town. The main level offers a spacious living room, eat-in kitchen, half bath, and the utility room that has space for a full size washer and dryer. The upstairs features a nice size primary bedroom with ensuite, a spacious secondary

Lisa Sosa Keller Williams Commonwealth

308 Essex Ct, Winchester, KY 40391

/27
Est $245,735 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,626 Sq Ft
116 Alabama St, Winchester, KY 40391

116 Alabama St, Winchester, KY 40391

/64
$989,000
- 4 Beds
- 2.5 Baths
- 2,670 Sq Ft
1110 Craig Crossing, Winchester, KY 40391

Discover timeless elegance and modern luxury in this newly constructed residence, perfectly situated on over 2.5 acres in Winchester. With 2,670 sq ft of custom designed living space, this 4-bedroom, 2.5-bath home offers craftsmanship, high-end finishes, and exceptional outdoor living. White oak engineered hardwood flooring, moulding throughout, and exquisite details. The spacious great room

Michael Hilario The Agency

1110 Craig Crossing, Winchester, KY 40391
/35
$265,000 Sold Jun 18, 2025
- 2,240 Sq Ft
- $118/SF
- 82 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1974
606 Laura Dr, Winchester, KY 40391

Exceptional value! Now offered at a compelling new price. This charming ranch home with a full finished walkout basement in Verna Hills offers incredible space and comfort. Just minutes from Lexington & Winchester. This spacious ranch home offers 3 bedrooms and 2.5 baths. New vinyl windows throughout (except the front living room). Large kitchen with new appliances that is open and offers

Bradley Morgan The Local Agents

606 Laura Dr, Winchester, KY 40391

/35
Est $294,483 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,769 Sq Ft
8 French Ave, Winchester, KY 40391

8 French Ave, Winchester, KY 40391

/17
$1,350,000
16 Linden Ave, Winchester, KY 40391

Income-Producing 16-Unit Apartment complex in the Heart of WinchesterTurn-key opportunity on North Maple Avenue—just minutes from Downtown Winchester and a quick 20-minute drive to Lexington via I-64. Consisting of sixteen one-bed/one-bath apartments on a 0.34-acre lot with 20 parking spaces, the property has a 2022 new roof, new vinyl siding added in 2023, and several fully

Patrick Doyle National Real Estate

16 Linden Ave, Winchester, KY 40391

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