Winchester, KY Homes

/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

/8
Est $474,756 Not Listed For Sale
- 4 Beds
- 3 Baths
- 4,447 Sq Ft
419 Fairholme Way, Winchester, KY 40391

419 Fairholme Way, Winchester, KY 40391

/8
$129,000
- 2 Beds
- 1 Bath
- 637 Sq Ft
109 Spring St, Winchester, KY 40391

Investment opportunity in Winchester! This 2-bedroom, 1-bath home at 109 Spring St is currently tenant-occupied and leased at $900/month. Functional layout with a spacious kitchen and separate living area. Conveniently located near downtown, schools, and local amenities. Whether you're expanding your portfolio or looking for a starter investment, this property offers steady rental income from day

Shari Frasure Keller Williams Commonwealth

109 Spring 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

/20
Est $364,336 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,487 Sq Ft
307 Gallahadion Ct, Winchester, KY 40391

307 Gallahadion Ct, Winchester, KY 40391

/5
$29,000
- Land
- 0.46 Acre
- $63,043 per Acre
102 Augusta Dr, Winchester, KY 40391

This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

Dale Hatton Dream Maker Realty, LLC

102 Augusta Dr, 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

/33
Est $298,005 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,475 Sq Ft
305 Gallahadion Ct, Winchester, KY 40391

305 Gallahadion Ct, Winchester, KY 40391

/14
$650,000
- Land
- 3 Acres
- $216,667 per Acre
205 Codella Dr, Winchester, KY 40391

Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

Greg Leveridge Block + Lot Real Estate

205 Codella Dr, 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

/67
Est $380,631 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,674 Sq Ft
401 Fairholme Way, Winchester, KY 40391

401 Fairholme Way, Winchester, KY 40391

/13
$400,000
- Land
- 2.19 Acres
- $182,648 per Acre
145 Codella Dr, Winchester, KY 40391

Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

Greg Leveridge Block + Lot Real Estate

145 Codella Dr, 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

/25
Est $137,088 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,057 Sq Ft
416 Country Club Dr, Winchester, KY 40391

416 Country Club Dr, Winchester, KY 40391

/2
$240,000
155 Spring Ridge Way, Winchester, KY 40391

Great opportunity to develop/ build on 12+ acres. The property has three street stubs adjoining it. Three different concepts are included under documents. They are-R-1E, 4000 sq. Ft lots for 80 lotsR-4- 14 Duplexes and 6 4plexes for 52 units R-1D - 6000 sq. Ft. Lots for 41 lots. Utilities are to the property and sewer availability should not be an issue. Please feel free to

Jo Gawthrop Keller Williams Bluegrass Realty

155 Spring Ridge Way, 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

/31
Est $167,782 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,513 Sq Ft
414 Country Club Dr, Winchester, KY 40391

414 Country Club Dr, Winchester, KY 40391

/6
$200,000
- Land
- 0.81 Acre
- $246,914 per Acre
550 Bullion Blvd, Winchester, KY 40391

Rarely available Bypass frontage lot for sale! Exciting opportunity to locate alongside a new Chipotle that is soon to be under construction. Retention in place, leaving approximately 1/2-acre developable. Perfect location for a national retailer.Ideally located along the heart of Bypass Road in Winchester, Kentucky between Kroger and Walmart shopping centers.Winchester, Kentucky

Greg Leveridge Block + Lot Real Estate

550 Bullion Blvd, 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

/25
Est $171,152 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
413 Country Club Dr, Winchester, KY 40391

413 Country Club Dr, Winchester, KY 40391

/2
$150,000
- Land
- 2.77 Acres
- $54,152 per Acre
3385 Colby Rd, Winchester, KY 40391

Small acreage lot on Colby Road! Accessed by easement from neighbors driveway.

Steve Adams Steven D Adams Real Estate Services, LLC

3385 Colby Rd, 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

/38
Est $282,365 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
2020 Two Mile Rd, Winchester, KY 40391

2020 Two Mile Rd, Winchester, KY 40391

/6
$110,000
- Land
- 2.06 Acres
- $53,398 per Acre
1185 Craig Crossing Rd, Winchester, KY 40391

Lot # 30 contains 2.058 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

Keith Wilson Coldwell Banker McMahan

1185 Craig Crossing Rd, Winchester, KY 40391
/18
$99,000 Sold Jun 17, 2025
- 1,242 Sq Ft
- $80/SF
- 8 Days On Market
- 2 Beds
- 2 Baths
- Built 1940
27 Oliver St, Winchester, KY 40391

Who's looking for their next Home? 27 Oliver Street located in downtown Winchester should definitely be on your list to see! This 2 Bedroom and 2 full Bathroom ranch home offers foyer, living room, dining room & kitchen. Hardwood floors in the home + gas logs in fireplace. There is an unfinished basement for extra storage options! This would be a great option for a handy person owner occupant or

Daniel Ellis Metro Max Realty

27 Oliver St, Winchester, KY 40391

/13
Est $180,827 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,330 Sq Ft
4 Burton Ave, Winchester, KY 40391

4 Burton Ave, Winchester, KY 40391

/7
$180,000
- Land
- 4.45 Acres
- $40,449 per Acre
1030 Craig Crossing Rd, Winchester, KY 40391

Lot # 14 contains 4.450 acres of gently rolling land with small stream perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

Keith Wilson Coldwell Banker McMahan

1030 Craig Crossing Rd, Winchester, KY 40391
/12
$75,000 Sold Jun 17, 2025
- Land
- 0.55 Acre
- $136,364 per Acre
- 210 Days On Market
120 Jacob Ct, Winchester, KY 40391

HUGE PRICE REDUCTION!!! Prime Reserve building lot in the new luxury subdivision located on the West side of Winchester. This is your opportunity to own one of the prime lots in Mallard Place. Enjoy the peaceful quiet of this subdivision while enjoying the beautiful views.

Keith Wilson Coldwell Banker McMahan

120 Jacob Ct, Winchester, KY 40391

/26
Est $177,415 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,025 Sq Ft
64 Bond Ct, Winchester, KY 40391

64 Bond Ct, Winchester, KY 40391

/8
$195,000
- Land
- 6.15 Acres
- $31,707 per Acre
990 Craig Crossing Rd, Winchester, KY 40391

Lot # 13 contains 6.153 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

Keith Wilson Coldwell Banker McMahan

990 Craig Crossing Rd, Winchester, KY 40391
/43
$430,000 Sold Jun 16, 2025
- 3,465 Sq Ft
- $124/SF
- 47 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1995
1128 Lafayette Blvd, Winchester, KY 40391

Located in Clark County's sought-after Stoneybrook neighborhood, this move-in-ready Ranch with a finished walk-out basement has been extensively updated. The main floor features fresh paint, new light fixtures, and new hardwood in the primary bedroom. The kitchen boasts new granite countertops, backsplash, and black stainless appliances. The primary bath has a new walk-in shower and tile floors,

Alyssa Ryan Marshall Lane Real Estate - Lexington

1128 Lafayette Blvd, Winchester, KY 40391

/22
Est $178,313 Not Listed For Sale
- 3 Beds
- 1 Bath
- 925 Sq Ft
101 Baldwin Ave, Winchester, KY 40391

101 Baldwin Ave, Winchester, KY 40391

/79
$225,000
- 4 Beds
- 2 Baths
- 3,295 Sq Ft
133 S Burns Ave, Winchester, KY 40391

Beautiful, Old-World style in the heart of Winchester! From the red, domed porch roof to the arched doorways and multiple fireplaces, this home is full of character and class. Being sold as-is, but with many renovations and updates already done to maintain and restore the charm of this old beauty including a new shingle roof (2024), replaced porch boards, and a fresh coat of interior paint. The

Josh Wood Freedom Realty & Property Management

133 S Burns Ave, Winchester, KY 40391
/27
$245,000 Sold Jun 13, 2025
- 1,728 Sq Ft
- $142/SF
- 8 Days On Market
- 3 Beds
- 2 Baths
- Built 1968
8 Seneca Dr, Winchester, KY 40391

This 3 bed, 2 bath home is quietly located within the Lyndale subdivision. Home features spacious living areas, full finished basement with garage, large back yard and so much more. Schedule your showing today!

Michael Hilario The Agency

8 Seneca Dr, Winchester, KY 40391

/40
Est $232,079 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,337 Sq Ft
84 Brink Ave, Winchester, KY 40391

84 Brink Ave, Winchester, KY 40391

/17
$439,000
- 4 Beds
- 2 Baths
- 1,950 Sq Ft
104 Colby Hills Dr, Winchester, KY 40391

Welcome to this beautiful ranch home, located in this desirable Colby Hill subdivision this house has been updated with new interior painting, new flooring, new kitchen cabinets, and tops, new bathrooms, large new lighting, 2 car garage, 2 fireplaces, living room, family room, dinning area, large new deck ,all this on a large corner lot. Owner/Broker

Garry Milton Milton and Associates Real Estate

104 Colby Hills Dr, Winchester, KY 40391
/27
$275,000 Sold Jun 13, 2025
- 1,726 Sq Ft
- $159/SF
- 129 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2008
216 Prescott Ln, Winchester, KY 40391

Conveniently located near shopping centers, schools and 6 minutes from the hospital. This home opens to a large den area which could easily be used for dining or flex space. The kitchen has plenty of room for entertaining with an island that opens to a spacious living room with fireplace. Plenty of room for parking in the attached garage. Upstairs features a separate laundry room, bedrooms and

Brittany Lewis National Real Estate

216 Prescott Ln, Winchester, KY 40391

/25
Est $250,709 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,239 Sq Ft
1291 Muddy Creek Rd, Winchester, KY 40391

1291 Muddy Creek Rd, Winchester, KY 40391

/66
$924,000
- 5 Beds
- 4 Baths
- 4,058 Sq Ft
2447 Clintonville Rd, Winchester, KY 40391

What a great opportunity to own 3 acres just 15 minutes from Man O War and 20 minutes to the Hamburg Shopping Area. The move in ready property features a beautiful brick home built by builder, Michael Childers, to use as his main residence. The property also has a 3 car detached Garage which is deep enough to hold 6 cars and one door is tall for storage of a Recreational Vehicle. It has been

Suzanne Elliott Berkshire Hathaway de Movellan Properties

2447 Clintonville Rd, Winchester, KY 40391
/46
$302,500 Sold Jun 11, 2025
- 1,475 Sq Ft
- $205/SF
- 4 Days On Market
- 3 Beds
- 2 Baths
- Built 2020
1740 Oil Springs Rd, Winchester, KY 40391

5 year old manufactured home with over 5 acres in Clark county. Want rural country living with internet, this is it! They just ran fiber down the street. Close to the Clark county mountain parkway exit. Only 30 minutes to Hamburg. Open floor plan with a big island that seats 4. Updated fixtures and stainless steel appliances. Lots of natural light. Primary on one side of the house and the two

Libby VanMeter Marshall Lane Real Estate - Lexington

1740 Oil Springs Rd, Winchester, KY 40391

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