Winchester, KY Homes for Sale

/41
$259,000
- 3 Beds
- 2 Baths
- 2,142 Sq Ft
363 S Main St, Winchester, KY 40391

** Seller is offering a $10,000 credit at close with an acceptable offer!**Welcome to 363 South Main Street in the heart of Winchester, Kentucky! This charming 3-bedroom, 2-bath home offers the perfect blend of timeless character and modern convenience. Built in 1940, the home exudes classic appeal with thoughtful updates that meet today's lifestyle. With 2,142 square feet of living space,

Zachary Otis HomeLand Real Estate Inc

363 S Main St, 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
/49
$635,000
- 6 Beds
- 3.5 Baths
- 5,227 Sq Ft
439 Lynnway Dr, Winchester, KY 40391

Welcome to 439 Lynnway Drive, where a brand new roof was just installed April 2025. The main floor boasts a primary en-suite, office space, and laundry room, while the second floor offers additional bedrooms and a versatile bonus room. The basement offers private bed/bath, custom bar, home theater, and in-home gym. Step outside and prepare to be enchanted by an outdoor oasis. Outdoor kitchen

Reagan Rainey Dream Maker Realty, LLC

439 Lynnway Dr, 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
/34
$235,000
- 3 Beds
- 2 Baths
- 1,680 Sq Ft
37 7th St, Winchester, KY 40391

Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

Andrew Fugitt Coldwell Banker McMahan

37 7th St, Winchester, KY 40391
/62
$272,950
- 3 Beds
- 2 Baths
- 1,247 Sq Ft
3614 Stamper Dr, Winchester, KY 40391

'Fully renovated to perfection, this property features brand-new upgrades throughout. Highlights include newly installed windows, doors, and flooring, complemented by modern appliances and updated cabinetry. A new deck provides an ideal space for outdoor enjoyment, while contemporary fixtures add a touch of elegance. This home is truly a remarkable opportunity and an absolute must-see.'

Darrell Tackett Dream Maker Realty, LLC

3614 Stamper Dr, Winchester, KY 40391
/2
$240,000
- Land
- 12 Acres
- $19,835 per Acre
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 call the listing

Jo Gawthrop Keller Williams Bluegrass Realty

155 Spring Ridge Way, Winchester, KY 40391
/3
$40,000
- Land
- 0.19 Acre
- $210,526 per Acre
113 Mayfair Ct, Winchester, KY 40391

Wowser! Looking for a lot that backs up to greenspace and will NOT have another home on one side? Here it IS! This may be just what you're looking for. Originally, the street was supposed to connect, but due to the changes in grade, this won't be happening! Plus, with the way the lot sits, you can enjoy many beautiful sunsets. It's a hidden gem just waiting for you to find it! The home to

Jo Gawthrop Keller Williams Bluegrass Realty

113 Mayfair Ct, Winchester, KY 40391
/2
$40,000
- Land
- 0.26 Acre
- $153,846 per Acre
105 Bella Ct, Winchester, KY 40391

Vacant Lot in a quiet cul-de-sac

Jo Gawthrop Keller Williams Bluegrass Realty

105 Bella Ct, Winchester, KY 40391
/2
$42,500
- Land
- 0.20 Acre
- $212,500 per Acre
108 Dorset Ln, Winchester, KY 40391

The restictions state that if it is a ranch plan, there is a minimun of 1300 sq ft. It it is a 1 1/2 story or two story then 1800 sq ft will be required. A two car garage must be attached. Developer will need to approve plans before starting construction This lot is ideal for a walkout basement. Perfect setting for watching the sunsets

Jo Gawthrop Keller Williams Bluegrass Realty

108 Dorset Ln, Winchester, KY 40391
/73
$339,900
- 3 Beds
- 2 Baths
- 1,805 Sq Ft
407 Fairholme Way, Winchester, KY 40391

Looking for a newer home in a beautiful, family friendly neighborhood? Look no further than this lovely, low maintenance home in the desirable Fairholme Estates subdivision. Take a step inside and enjoy the sunlight streaming in through the abundant windows in the great room. Gleaming, easy to clean, laminate wood plank flooring spills into the spacious kitchen area which features an oversized

Josh Wood Freedom Realty & Property Mgt

407 Fairholme Way, Winchester, KY 40391
/21
$149,000
- 2 Beds
- 1 Bath
- 886 Sq Ft
9 Linden Ave, Winchester, KY 40391

Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval, no warranties implied or expressed.Property conveys at

Emily Hacker-Todd CENTURY 21 Advantage Realty

9 Linden Ave, Winchester, KY 40391
/38
$749,000
- 6 Beds
- 4.5 Baths
- 4,021 Sq Ft
4455 Colby Rd, Winchester, KY 40391

Experience country living in this stunning home on 3.56 acres located in a highly desirable area. Minutes from town and a short 15 minute drive to Hamburg. Enjoy beautiful views of the country from the covered front and back porches, perfect for morning coffee or evening gatherings. Open concept living. Spacious bedrooms. Partially finished basement. Beautiful sunroom. Updates throughout. Call

Brian England Keller Williams Bluegrass Realty

4455 Colby Rd, Winchester, KY 40391
/99
$749,000
- 4 Beds
- 4 Baths
- 4,644 Sq Ft
110 Camelot Dr, Winchester, KY 40391

Don't miss this rare opportunity to abide in one of Winchester's finest locations, Camelot Drive. A hidden gem tucked away in the back of Hampton Manor, this home boasts space and privacy on an idyllic cul-de-sac just off Boone Avenue. Details such as crown molding, built-in cabinetry, high ceilings, 2 fireplaces, transom windows, and hardwood floors fill this home with character and charm.

Joyce Ratliff Tom Goebel & Company

110 Camelot Dr, Winchester, KY 40391
/48
$265,000
- 3 Beds
- 2 Baths
- 1,256 Sq Ft
40 N Burns Ave, Winchester, KY 40391

This stunning fully remodeled 3-bedroom, 2-bathroom home is move-in ready with top-to-bottom updates. Every detail has been thoughtfully upgraded, from the modern lighting in every room to the brand-new flooring and fresh paint throughout. The kitchen is a standout with granite countertops, new cabinetry, and brand-new appliances, while the bathrooms boast quartz countertops and elegant tiled

Ernesto Martinez Berkshire Hathaway HomeServices Foster Realtors

40 N Burns Ave, 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 Est Serv

3385 Colby Rd, Winchester, KY 40391
/10
$1,500,000
- Land
- 74 Acres
- $20,322 per Acre
3505 Basin Springs Rd, Winchester, KY 40391

Located in the heart of Clark County this 73+/- acre property has been a part of the family since the 1800s. With its expansive space and fertile land, it offers endless possibilities for agricultural ventures, recreational use or development. Whether you're looking to expand your farming operation or create a private estate, this rare property presents a fantastic opportunity to invest in land

Kathryn Cheuvront Coldwell Banker McMahan

3505 Basin Springs Rd, Winchester, KY 40391
/5
$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
/6
$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
/7
$195,000
- Land
- 6 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
/2
$115,000
- Land
- 1.03 Acres
- $111,650 per Acre
210 Hood Ave, Winchester, KY 40391

This is an unique opportunity to own a beautiful acre + building lot in Winchester! Walking distance to downtown, Country Club, College Park & library! The house seat has been graded to accommodate a daylight walk-out basement. City water, sewer, natural gas & electric are available. Currently being resurveyed to include closed alleyway. Minimal restrictions. Owner/agent.

Angie Conley Dixon Dixon Properties

210 Hood Ave, Winchester, KY 40391
/79
$239,900
- 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 Mgt

133 S Burns Ave, Winchester, KY 40391
/6
$49,500
- Land
- 0.98 Acre
- $50,510 per Acre
204 Wigeon Ct, Winchester, KY 40391

Choose your preferred builder to construct your dream home in Mallard Place. Located in a quiet cul-de-sac at the rear of the subdivision. Only a 20 minute drive to Hamburg/Lexington and only a 5 minute drive to the Winchester Bypass. Enjoy the serenity of living in a private setting AND the convenience of being close to schools, shopping and I-64 and I-75.

Jim Woodrum RE/MAX Creative, Winchester

204 Wigeon Ct, Winchester, KY 40391
/4
$70,000
- Land
- 1.92 Acres
- $36,458 per Acre
12569 Ironworks Rd, Winchester, KY 40391

Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! This lot containing 1.919 acres, offer unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential!

Kathryn Cheuvront Coldwell Banker McMahan

12569 Ironworks Rd, Winchester, KY 40391
/3
$70,000
- Land
- 2.04 Acres
- $34,314 per Acre
150 Spencer Ln, Winchester, KY 40391

Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! This lot totaling 2.041 acres, offer unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential!

Kathryn Cheuvront Coldwell Banker McMahan

150 Spencer Ln, Winchester, KY 40391
/26
$339,900
- 3 Beds
- 2.5 Baths
- 2,065 Sq Ft
118 Sturbridge Ln, Winchester, KY 40391

Nestled right in the heart of town, lies this charming 2 story home that embodies the essence of rustic glam. This cozy retreat offers a convenient escape from the hustle and bustle of life. The first floor offers ample space to host friends and family gatherings. Upstairs, the bedrooms serve as serene sanctuaries. Each room offers the perfect balance of the rustic charm. The backyard boasts

A. Rebecca Woods Woods Realty Group

118 Sturbridge Ln, Winchester, KY 40391
/2
$135,000
- 3 Beds
- 1 Bath
- 1,046 Sq Ft
175 Magnolia St, Winchester, KY 40391

Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Both units are currently used as investment property. Both homes need extensive repair. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is

A. Rebecca Woods Woods Realty Group

175 Magnolia St, Winchester, KY 40391
/15
$187,500
- Land
- 7 Acres
- $25,202 per Acre
7575 Irvine Rd, Winchester, KY 40391

Amazing 7.44 acre country building lot / mini farm / homestead with views! Established driveway leads a nice 38' x 50' pole barn that would serve as a nice shop / garage! Partially fenced with gated entrance. Perfect spot to potentially build a pond. Water meter base and electricity pole already in place.

Jason Townsend Kentucky Residential Real Estate, LLC

7575 Irvine Rd, Winchester, KY 40391
/3
$93,500
- 2 Beds
- 1 Bath
- 825 Sq Ft
1860 Ford Rd, Winchester, KY 40391

AS IS property!This unique property, located near the beautiful Kentucky River, offers incredible potential for those seeking a rewarding project. The 825 square foot mobile home is ready for renovation, providing an excellent opportunity for flipping or customization to suit your vision. Alongside the home, you'll find a massive 1792 square foot detached garage, perfect for storage, a

Omar Shalash Tru Life Real Estate

1860 Ford Rd, Winchester, KY 40391
/13
$146,400
- Land
- 2.30 Acres
- $63,652 per Acre
110 Knox Ct, Winchester, KY 40391

The largest and most desirable lot in The Reserve is now available! Nestled in a cul-de-sac, this 2.3 acre tract offers exceptional views of Bluegrass farmland. Build your custom dream home and watch the sun set over the pond, right from your porch. Located in one of Winchester's newest luxury subdivisions, featuring carefully crafted guidelines to preserve the community's character. All of this

Jarran Thomas The Agency

110 Knox Ct, Winchester, KY 40391
/71
$950,000
- 4 Beds
- 2.5 Baths
- 5,290 Sq Ft
186 Chardonnay Ct, Winchester, KY 40391

Step into a world of both comfort and convenience with this beautiful 3/4 bedroom, two and one half bath, perfectly designed for relaxation and entertainment. Key features of this property include outdoor spaces to enjoy morning coffee or quiet evening chats. The cozy back porch extends your living space, ideal for dining and enjoying the tranquil surroundings, The beautifully designed patio

Brenda Sipes WEICHERT REALTORS - ABG Properties

186 Chardonnay Ct, Winchester, KY 40391
/3
$109,000
- Land
- 4.02 Acres
- $27,114 per Acre
2010 Athens Boonesboro Rd, Winchester, KY 40391

Prime building lot - 4 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2010 and 2058 approved shared entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on

Megan McCoy Keller Williams Legacy Group

2010 Athens Boonesboro Rd, Winchester, KY 40391
/65
$275,000
- 4 Beds
- 1.5 Baths
- 1,873 Sq Ft
151 Hilltop Dr, Winchester, KY 40391

Lovely ranch on a basement home in a small rural neighborhood. This location is the perfect blend of rural living but very convenient to everything! Less than 1 mile from the eastern bypass that provides fast access to I-64, downtown Winchester, parks, and shopping. Large half acre lot with fenced in backyard and a chicken coop! Large deck on the back for entertaining or just relaxing while

Jason Townsend Kentucky Residential Real Estate, LLC

151 Hilltop Dr, Winchester, KY 40391
/70
$999,900
- 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
/15
$53,000
- Land
- 6 Acres
- $9,481 per Acre
199 Midway Rd, Winchester, KY 40391

Introducing this 5.59 acre property in Central Kentucky! With city water and electric available at the road, this land offers a seamless transition for your dream home or investment project. Located just 15 minutes from Winchester, 30 minutes from Hamburg, and 30 minutes from Mt. Sterling. You will enjoy easy access to city amenities while relishing the peace of rural living. Don't miss the

Skyler Lewis Dream Maker Realty, LLC

199 Midway Rd, Winchester, KY 40391
/4
$139,900
- Land
- 6 Acres
- $24,674 per Acre
1445 Gay Evans Rd, Winchester, KY 40391

Welcome to The Retreat at Juett Farms! Come build your dream home on some of the best land that Clark County has to offer. This peaceful setting with unparalleled views of the countryside, is sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 5 acres of unrestricted land. Schedule your showing today!

Holly Goeing The Agency

1445 Gay Evans Rd, Winchester, KY 40391
/4
$149,900
- Land
- 6 Acres
- $26,768 per Acre
1541 Gay Evans Rd, Winchester, KY 40391

Welcome to The Retreat at Juett Farms! Come build your dream home on some of the best land that Clark County has to offer. This peaceful setting with unparalleled views of the countryside, is sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 5 acres of unrestricted land. Schedule your showing today!

Holly Goeing The Agency

1541 Gay Evans Rd, Winchester, KY 40391
/28
$799,900
- Land
- 13 Acres
- $60,644 per Acre
1600 Ironworks Rd, Winchester, KY 40391

This property has it all! Easy access to Veterans Memorial Bypass, I-64, and downtown Winchester, plus entrances on Ironworks road and clear visibility from the Bypass. This does have sewer and water located on the property. Full of potential possibilities zoned Planned Development and more acreage is available if needed. The property access is a driveway off Ironworks Road across from Center

Josh Wood Freedom Realty & Property Mgt

1600 Ironworks Rd, Winchester, KY 40391
/4
$140,000
- Land
- 3.94 Acres
- $35,533 per Acre
12569 Ironworks Rd, Winchester, KY 40391

Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! These two parcels totaling 3.94 acres, offer unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential!

Kathryn Cheuvront Coldwell Banker McMahan

12569 Ironworks Rd, Winchester, KY 40391
/32
$360,000
- 3 Beds
- 1.5 Baths
- 1,356 Sq Ft
4074 Ironworks Rd, Winchester, KY 40391

Welcome to country living! This newly renovated ranch on 4+ scenic acres offers peaceful living just 10 minutes from town. Inside, the open floor plan seamlessly connects the kitchen, dining, and living areas. The kitchen features granite countertops, new stainless steel appliances, a central island with bar seating, while the living room boasts a cozy fireplace. Durable LVP and tile flooring run

Michelle Blackburn RE/MAX Creative, Winchester

4074 Ironworks Rd, Winchester, KY 40391

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