Winchester, KY Homes

/49
$645,000
- 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
/17
$390,000 Sold Apr 16, 2025
- 1,854 Sq Ft
- $210/SF
- 73 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1983
3750 Becknerville Rd, Winchester, KY 40391

Are you longing for a quiet country home? A place to have a few farm animals, raise a garden and enjoy the peacefulness of living away from town. Presenting to you 3750 Becknerville Road. It checks all of the boxes! This lovely 5.5 acre mini farm is situated between Winchester and Lexington on a gorgeous, partially fenced tract, with amazing mature trees. With roughly 1850 square feet of living

Holly Goeing The Agency

3750 Becknerville Rd, Winchester, KY 40391

/25
Est $169,615 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,168 Sq Ft
5 2nd St, Winchester, KY 40391

5 2nd St, 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
/17
$278,000 Sold Apr 15, 2025
- 1,292 Sq Ft
- $215/SF
- 7 Days On Market
- 3 Beds
- 2 Baths
- Built 2005
218 Bracken Ct, Winchester, KY 40391

Since warm weather is near you will love the updated huge back deck with new railing overlooking a large, fenced backyard. This spacious turnkey open concept 3-bedroom 2-bath home sitting on a .29-acre lot has been completely updated and ready for you to move in and enjoy. Since it is located in a cul-de-sac no worries regarding busy traffic. This budget friendly home has a newer roof less than

Tonya Skeens RE/MAX Elite Lexington

218 Bracken Ct, Winchester, KY 40391

/35
Est $285,323 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,800 Sq Ft
328 S Main St, Winchester, KY 40391

328 S Main St, 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
/16
$240,000 Sold Apr 15, 2025
- 1,350 Sq Ft
- $178/SF
- 4 Days On Market
- 3 Beds
- 2 Baths
- Built 1980
13385 Ironworks Rd, Winchester, KY 40391

Charming and move-in ready, this 3-bedroom, 2-bath ranch home on 1 acre offers the perfect blend of space, comfort, and convenience. The low-maintenance vinyl siding allows for easy upkeep, while the freshly painted interior creates a bright and inviting atmosphere. The large 10x20 covered rear porch provides the perfect spot to relax or entertain, with the potential to be converted into a

Joshua Davis The Agency

13385 Ironworks Rd, Winchester, KY 40391

/18
Est $264,447 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,596 Sq Ft
384 Boone Ave, Winchester, KY 40391

384 Boone Ave, Winchester, KY 40391

/62
$275,950
- 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
/24
$179,500 Sold Apr 11, 2025
- 1,050 Sq Ft
- $171/SF
- 44 Days On Market
- 2 Beds
- 1 Bath
- Built 1945
606 College St, Winchester, KY 40391

Imagine yourself in this stunning home, where classic charm blends seamlessly with modern sophistication. This lovely, remodeled ranch home is ready for you to make your own. As you step inside, you'll be greeted by an open concept living area, complete with a beautiful fireplace and built-ins that add warmth and character. The newly renovated kitchen is a culinary dream, boasting crisp white

Angelica Hebert Lifstyl Real Estate

606 College St, Winchester, KY 40391

/39
Est $343,630 Not Listed For Sale
- 4 Beds
- 2 Baths
- 980 Sq Ft
352 Boone Ave, Winchester, KY 40391

352 Boone Ave, 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
/16
$221,000 Sold Apr 10, 2025
- 1,053 Sq Ft
- $210/SF
- 0 Days On Market
- 3 Beds
- 2 Baths
- Built 1970
717 Estes Dr, Winchester, KY 40391

Cozy 3 Bed, 2 Bath ranch in Winchester, KY. This delightful home offers a perfect blend of comfort and convenience, located just minutes from shopping and only 25 minutes from Lexington. Ideal for anyone looking to enjoy the tranquility of suburban living while being close to city amenities. Enjoy the beauty of hardwood floors throughout the main living areas and bedrooms and plenty of extra

Rebecca Worth Redfin

717 Estes Dr, Winchester, KY 40391

/32
Est $198,774 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,740 Sq Ft
540 S Maple St, Winchester, KY 40391

540 S Maple St, 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
/62
$384,000 Sold Apr 10, 2025
- 1,425 Sq Ft
- $269/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1965
890 Miller Hunt Rd, Winchester, KY 40391

This charming 3-bedroom, 2-bathroom brick home offers everything you need for country living, along with plenty of room to grow. Situated on 31.5 acres of beautiful farmland, this property is perfect for anyone looking to start a dream farm or invest in land for future potential.Key Features:•3 Bedrooms & 2 Full Bathrooms•Full Basement - perfect for additional storage or living space with

Daniel Mullins ERA Select Real Estate

890 Miller Hunt Rd, Winchester, KY 40391

/37
Est $243,365 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,783 Sq Ft
17 Short St, Winchester, KY 40391

17 Short St, 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
/42
$394,000 Sold Apr 10, 2025
- 2,325 Sq Ft
- $169/SF
- 118 Days On Market
- 4 Beds
- 3 Baths
- Built 2024
432 Fairholme Way, Winchester, KY 40391

Hot New Price Improvement!! We couldn't wait another minute to share it with you! Have you been looking for a four bedroom ranch home? on a large lot? quiet street? walking distance to the Winchester Country Club? or maybe you want to ride your golf cart to hit a bucket of balls! New Construction and we're about three weeks from completion! Professional pictures as soon as we have the light

Jo Gawthrop Keller Williams Bluegrass Realty

432 Fairholme Way, Winchester, KY 40391

/36
Est $318,605 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,870 Sq Ft
204 Boone Ave, Winchester, KY 40391

204 Boone Ave, 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
/3
$140,000 Sold Apr 09, 2025
- Land
- 7 Acres
- $20,378 per Acre
- 18 Days On Market
895 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 are sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 6.8 acres of unrestricted land and your own private pond. Schedule your showing today!

Holly Goeing The Agency

895 Gay Evans Rd, Winchester, KY 40391

/13
Est $184,729 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,453 Sq Ft
219 Boone Ave, Winchester, KY 40391

219 Boone Ave, Winchester, KY 40391

/32
$290,000
- 3 Beds
- 2.5 Baths
- 1,690 Sq Ft
602 Laura Dr, Winchester, KY 40391

MOTIVATED SELLERS. Find peace in this updated all-brick ranch that's made for summer fun and year-round comfort — complete with an in-ground pool, walk-out basement, and a backyard that's calling for your next BBQ. Tucked in a quiet neighborhood just over the Fayette County line, you're only 10 minutes from Hamburg, giving you the best of both convenience and calm.Inside, this 3 bedroom, 2.5 bath

Ryan O'Gara Real Broker, LLC

602 Laura Dr, Winchester, KY 40391
/56
$241,000 Sold Mar 25, 2025
- 2,160 Sq Ft
- $112/SF
- 3 Days On Market
- 3 Beds
- 2 Baths
- Built 1970
725 Estes Dr, Winchester, KY 40391

The location of this property offers a major plus for commuters and those who travel frequently with reduced travel time and increased convenience to interstates, shopping areas, restaurants, and parks.With a blend of classic as well as updated features, including original hardwood flooring that has been lovingly protected through the years, adding character to the home, a smart thermostat

Brenda Sipes WEICHERT REALTORS - ABG Properties

725 Estes Dr, Winchester, KY 40391

/22
Est $209,835 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,705 Sq Ft
118 Southern Ct, Winchester, KY 40391

118 Southern Ct, Winchester, KY 40391

/17
$35,000
- Land
- 1.72 Acres
- $20,349 per Acre
12591 Ironworks Rd, Winchester, KY 40391

This 1.722-acre lot presents a fantastic opportunity to design your ideal home in the subdivision of Eskippakithiki Overlooks. Enjoy the lovely views and ample space to unwind and relax. Located just minutes from Bert T. Combs Mountain Parkway, this property offers both convenience and tranquility. Utilities are readily available at the road, allowing you to start planning your new home right

Cathleen Gedeon CENTURY 21 Advantage Realty

12591 Ironworks Rd, Winchester, KY 40391
/20
$243,000 Sold Mar 24, 2025
- 1,540 Sq Ft
- $158/SF
- 56 Days On Market
- 3 Beds
- 2 Baths
- Built 2006
235 Dubuy Dr, Winchester, KY 40391

This beautiful 3 bed/2 bath , 1 car attached garage home is located just minutes from the Interstate and shopping. Fenced in back yard for privacy or pets. This home is located at the end of a cul-de- sac. Come take a look and make this your home. Home is being sold ''AS IS'' Inspections Welcome

Melissa Combs Sandy Stuart Realty

235 Dubuy Dr, Winchester, KY 40391

/8
Est $331,623 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,562 Sq Ft
14 Western Ave, Winchester, KY 40391

14 Western Ave, Winchester, KY 40391

/19
$40,000
- Land
- 2.34 Acres
- $17,094 per Acre
12651 Ironworks Rd, Winchester, KY 40391

This 2.336-acre lot presents a fantastic opportunity to design your ideal home in the subdivision of Eskippakithiki Overlooks. Enjoy the lovely views and ample space to unwind and relax. Located just minutes from Bert T. Combs Mountain Parkway, this property offers both convenience and tranquility. Utilities are readily available at the road, allowing you to start planning your new home right

Cathleen Gedeon CENTURY 21 Advantage Realty

12651 Ironworks Rd, Winchester, KY 40391
/30
$150,000 Sold Oct 31, 2024
- 1,126 Sq Ft
- $133/SF
- 3 Days On Market
- 2 Beds
- 1 Bath
- Built 1930
370 E Washington St, Winchester, KY 40391

This charming home has been recently updated and ready for you to move in! Features include 2 large bedrooms and 1 full bath (with access from hallway or bedroom) with new updates, such as: new roof, new heat pump, and new vinyl siding all updated in March 2024! New pet/moisture proof vinyl flooring installed in 2023, and a new fresh coat of paint! Ample off-street parking with a 2 car concrete

Tyler McRoberts Story Realty

370 E Washington St, Winchester, KY 40391

/39
Est $337,120 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,660 Sq Ft
14 Euclid Ave, Winchester, KY 40391

14 Euclid Ave, 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
/22
$265,000 Sold Aug 23, 2024
- 1,400 Sq Ft
- $189/SF
- 8 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1975
759 Wayland Dr, Winchester, KY 40391

Wonderful Brick Ranch with beautiful large yard. 2 car detached garage with side workshop. Storage bldg for lawn equipment. Generator is a bonus. Great location minutes from shopping, hospital and interstate. Same owner for 22 years. Sunroom w patio doors and screens. Plenty of room for entertaining or just relaxing, Great home for anyone! Showings begin at the Open house this Saturday August

Michelle Riggs Waldron Properties, LLC

759 Wayland Dr, Winchester, KY 40391

/22
Est $237,159 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,546 Sq Ft
17 Euclid Ave, Winchester, KY 40391

17 Euclid Ave, Winchester, KY 40391

/46
$224,500
- 3 Beds
- 2 Baths
- 1,167 Sq Ft
115 Georgia St, Winchester, KY 40391

✨ ''Warm, inviting, and full of character—your dream home awaits!'' 🔥 ''Cozy up by the fireplace in a home that feels like home!'' 🏡 ''Classic charm meets modern convenience in this Winchester gem!'' 🌳 ''Tranquility meets accessibility—peaceful neighborhood, minutes from downtown!'' 🚗 ''Detached garage = extra storage, workspace, and convenience!'' 💎

Darrell Tackett Dream Maker Realty, LLC

115 Georgia St, Winchester, KY 40391
/72
$460,000 Sold Aug 05, 2024
- 2,800 Sq Ft
- $164/SF
- 60 Days On Market
- 4 Beds
- 3 Baths
- Built 2024
127 Hibiscus Ln, Winchester, KY 40391

This new construction house will be completed soon and ready for you to move in and call home! From the moment you step inside, you'll find stunning features including 9 foot ceilings for an open and airy feel, with hardwood floors throughout. In the kitchen will be granite countertops with white cabinets including an island with bar top seating. New stainless appliances will complete the

Josh Wood Freedom Realty & Property Mgt

127 Hibiscus Ln, Winchester, KY 40391

/24
Est $154,742 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,839 Sq Ft
115 College St, Winchester, KY 40391

115 College St, Winchester, KY 40391

/23
$140,000
- Land
- 5.00 Acres
- $28,000 per Acre
2100 Old Log Lick Rd, Winchester, KY 40391

Dreaming of peaceful country living with a head start on the building process? This beautiful 5-acre tract in the country has everything you need to get started: electric and water already in place, a septic system installed, and a cleared, flat spot just waiting for your dream home. The property features a pond, a gravel driveway, and a small shop with a bathroom and attached carport, perfect

Michelle Blackburn RE/MAX Creative, Winchester

2100 Old Log Lick Rd, Winchester, KY 40391

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