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121 Ralston Ln, Winchester
$56,700
3 Beds ⋅ 1 Baths ⋅ 26029234 MLS
INVESTMENT OPPORTUNITY — BUILD YOUR VISION! The existing home is in poor condition and may be suitable for renovation or a tear-down project. The property consists of almost 1/2 Acre (.45 acre) with a newer metal building 20 X 25. An excellent opportunity for investors, builders, or buyers looking to create something new! This could be an excellent place for storing equipment, boats, RVs, or other recreational toys! 1,000-gallon septic system installed in 2023.

121 Ralston Ln, Winchester
12541 Ironworks Rd, Winchester
$70,000
25506465 MLS
Discover the perfect place to build your dream home in Eskippakithiki Overlooks. This beautiful 1.72 acre parcel offers ample space, peaceful surroundings, and stunning natural views. Enjoy the serenity of country living, this land provides an ideal canvas for a custom home or family getaway. Don't miss this opportunity to secure your own piece of paradise.

12541 Ironworks Rd, Winchester
214 Center Dr, Winchester
$197,000
3 Beds ⋅ 1 Baths ⋅ 26028269 MLS
Welcome to 214 Center Drive! Tucked away at the end of a cul-de-sac, this charming 3-bedroom, 1-bath ranch offers a peaceful setting with convenient access to the interstate. Step inside to discover a functional floor plan featuring a spacious living area and an eat-in kitchen. Just off the kitchen, a versatile bonus room offers endless possibilities like a home office. The bathroom features a double vanity, providing extra counter space and convenience. Outside, enjoy a back deck overlooking a tree-lined backyard with neighboring farmland. A freshly paved driveway adds to the home's curb appeal, while the attached storage area, formerly a one-car garage, provides plenty of room for tools, lawn equipment, and more. Some rooms are virtually staged to showcase layout.

214 Center Dr, Winchester
125 Knox Ct, Winchester
$150,000
22024090 MLS
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

125 Knox Ct, Winchester
120 Knox Ct, Winchester
$150,000
22024088 MLS
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

120 Knox Ct, Winchester
100 Duclair Dr, Winchester
$100,000
22024061 MLS
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

100 Duclair Dr, Winchester
250 Duclair Dr, Winchester
$110,000
22024097 MLS
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

250 Duclair Dr, Winchester
260 Duclair Dr, Winchester
$110,000
22024098 MLS
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

260 Duclair Dr, Winchester
115 Jacob Ct, Winchester
$110,000
22024116 MLS
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

115 Jacob Ct, Winchester
139 Jacob Ct, Winchester
$110,000
22024111 MLS
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

139 Jacob Ct, Winchester
520 College St, Winchester
$199,900
3 Beds ⋅ 1 Baths ⋅ 26028060 MLS
Check out this beautifully remodeled 3-bedroom, 1-bath home offering comfortable living and a convenient location within walking distance of the playground! Whether you're looking for your next home or an investment opportunity, this property has plenty of potential. The home is currently tenant-occupied, with the tenant leaving on 11/20/26 A minimum of 48 hours' notice is required for all showings. Please plan accordingly when scheduling your visit. Don't miss the opportunity to see what this property has to offer!

520 College St, Winchester
213 E Broadway St, Winchester
$200,000
3 Beds ⋅ 1 Baths ⋅ 26027397 MLS

213 E Broadway St, Winchester
199 Midway Rd, Winchester
$45,000
26024771 MLS
Discover 5.59 acres in Winchester, offering a peaceful setting with just the right amount of seclusion. With city water and electric available at the road, this property offers plenty of potential—whether you're looking to build your dream home or explore an investment opportunity. Enjoy quiet country surroundings while creating a property that fits your vision.

199 Midway Rd, Winchester
209 E Washington St, Winchester
$159,000
3 Beds ⋅ 1 Baths ⋅ 26024016 MLS
Conveniently located in Winchester, this one-story home offers three bedrooms, one bath, and plenty of potential for a first-time buyer or investment property. Inside, you'll find laminate and vinyl flooring throughout, a spacious kitchen, and a separate laundry room. The bathroom received new fixtures in 2025, while the roof is approximately 1.5 years old, taking care of two worthwhile updates for the next owner. Gas freestanding heaters provide heat, and the home does not currently have central air. Outside, there's a covered front porch and a nice-sized backyard with an alley running behind the property. Whether you're looking for an affordable place to call your own or an addition to your rental portfolio, this home is ready for its next chapter.

209 E Washington St, Winchester
3208 Ford Hampton Rd, Winchester
$135,000
2 Beds ⋅ 1 Baths ⋅ 26023193 MLS
Set on a half-acre in a rural Winchester setting, this 2-bedroom, 1-bath home offers an efficient one-level layout with approximately 807 square feet of living space. The eat-in kitchen provides a comfortable spot for everyday meals, while main-level laundry hookups add convenience. Front and rear porches extend the living space outdoors and offer places to enjoy the surrounding trees, countryside, and views. A metal roof adds practicality, and the property's location near the Kentucky River provides easy access to one of the area's notable natural features. Whether you're looking for a primary residence, weekend getaway, or a smaller property with a little room around it, 3208 Ford Hampton Road offers a straightforward home in a scenic rural setting.

3208 Ford Hampton Rd, Winchester
24 Spring St, Winchester
$160,000
3 Beds ⋅ 1 Baths ⋅ 26022678 MLS
Lovely one story home located minutes from downtown Winchester with large detached garage ans shed! This home as three bedrooms and one bath with covered porch and walled patio outside. The garage is equipped with large ares for parking and storage and also has its own kitchen. Don't let this one pass by. Come see TODAY!!! Note: This is an auction property. Please call agent for more info Buyer to verify all information including schools

24 Spring St, Winchester
16 Denny Ave, Winchester
$58,500
3 Beds ⋅ 1 Baths ⋅ 26022585 MLS
Well priced and well located, 16 Denny Avenue is conveniently located near Eugene Gay Splash Park, downtown Winchester, shopping and schools. Home features 1152 sq ft with 3 bedrooms, 1 full bath, eat in kitchen and living room. Enclosed porch is located on front of house. Upgrades include laminate flooring, ductless heating and cooling and roof. Property has been tenant occupied and is sold as is. No repairs.

16 Denny Ave, Winchester
606 College St, Winchester
$199,900
2 Beds ⋅ 1 Baths ⋅ 26021605 MLS
606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom faucets were all added in 2025. The living room fireplace and original trim add so much character, while the enclosed laundry and mudroom gives you useful extra space. Downstairs, the full unfinished walk-up basement offers more than 1,000 square feet for storage, hobbies, or future possibilities. Outside, you'll find a fenced backyard, detached one-car garage, storage shed, and welcoming front porch. The seller reports the roof and HVAC are both under six years old. A wonderful home with charm, practical space, and a great Winchester location!

606 College St, Winchester
546 Constitution Dr, Winchester
$65,000
2 Beds ⋅ 2 Baths ⋅ 26020744 MLS
This 2 bedroom 2 bath home is perfect for an investor or a family looking for a nice home. All new flooring throughout. New bathroom sinks and commodes. The home backs up to the community park. It is located just minutes from Hamburg or the Winchester Bypass.

546 Constitution Dr, Winchester
6699 Boonesboro Rd, Winchester
$195,000
25000480 MLS
For all sales related communications please contact Jenny Ray, 859-221-6961. For all offers please send via Dotloop to jennyraysells@gmail.com READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

6699 Boonesboro Rd, Winchester
2395 Paris Rd Unit LOT 7, Winchester
$100,000
26018712 MLS
Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family homes, 48 duplex units and 8 townhomes, creating one of Clark County's largest new residential communities. Homesites include city water and sewer, KU electric and Columbia Gas, with additional estate-style lots scheduled in upcoming stages through year-end 2026. Deed restrictions are designed to maintain architectural consistency and include 80% brick and/or stone exteriors, roof-pitch requirements, and minimum heated living areas of 1,600 SF for ranch homes, 1,800 SF for 1½-story homes, and 2,100 SF for two-story homes. Located near I-64 Exit 96, approximately 10 miles from Lexington's Hamburg area, with convenient access to downtown Winchester, Lexington, Paris and Richmond. Shopping, dining, healthcare and major employment centers are within easy reach while maintaining the space and setting of Winchester living. Choose your homesite, choose your builder, and build in Deerlawn. Additional development plans, plats, restrictions and lot information available upon request.

2395 Paris Rd Unit LOT 7, Winchester
2395 Paris Rd Unit Lot 6, Winchester
$100,000
26018711 MLS
Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family homes, 48 duplex units and 8 townhomes, creating one of Clark County's largest new residential communities. Homesites include city water and sewer, KU electric and Columbia Gas, with additional estate-style lots scheduled in upcoming stages through year-end 2026. Deed restrictions are designed to maintain architectural consistency and include 80% brick and/or stone exteriors, roof-pitch requirements, and minimum heated living areas of 1,600 SF for ranch homes, 1,800 SF for 1½-story homes, and 2,100 SF for two-story homes. Located near I-64 Exit 96, approximately 10 miles from Lexington's Hamburg area, with convenient access to downtown Winchester, Lexington, Paris and Richmond. Shopping, dining, healthcare and major employment centers are within easy reach while maintaining the space and setting of Winchester living. Choose your homesite, choose your builder, and build in Deerlawn. Additional development plans, plats, restrictions and lot information available upon request.

2395 Paris Rd Unit Lot 6, Winchester
2395 Paris Rd Unit Lot 5, Winchester
$100,000
26018710 MLS
Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family homes, 48 duplex units and 8 townhomes, creating one of Clark County's largest new residential communities. Homesites include city water and sewer, KU electric and Columbia Gas, with additional estate-style lots scheduled in upcoming stages through year-end 2026. Deed restrictions are designed to maintain architectural consistency and include 80% brick and/or stone exteriors, roof-pitch requirements, and minimum heated living areas of 1,600 SF for ranch homes, 1,800 SF for 1½-story homes, and 2,100 SF for two-story homes. Located near I-64 Exit 96, approximately 10 miles from Lexington's Hamburg area, with convenient access to downtown Winchester, Lexington, Paris and Richmond. Shopping, dining, healthcare and major employment centers are within easy reach while maintaining the space and setting of Winchester living. Choose your homesite, choose your builder, and build in Deerlawn. Additional development plans, plats, restrictions and lot information available upon request.

2395 Paris Rd Unit Lot 5, Winchester
2395 Paris Rd Unit Lot 3, Winchester
$100,000
26018706 MLS
Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family homes, 48 duplex units and 8 townhomes, creating one of Clark County's largest new residential communities. Homesites include city water and sewer, KU electric and Columbia Gas, with additional estate-style lots scheduled in upcoming stages through year-end 2026. Deed restrictions are designed to maintain architectural consistency and include 80% brick and/or stone exteriors, roof-pitch requirements, and minimum heated living areas of 1,600 SF for ranch homes, 1,800 SF for 1½-story homes, and 2,100 SF for two-story homes. Located near I-64 Exit 96, approximately 10 miles from Lexington's Hamburg area, with convenient access to downtown Winchester, Lexington, Paris and Richmond. Shopping, dining, healthcare and major employment centers are within easy reach while maintaining the space and setting of Winchester living. Choose your homesite, choose your builder, and build in Deerlawn. Additional development plans, plats, restrictions and lot information available upon request.

2395 Paris Rd Unit Lot 3, Winchester
2395 Paris Rd Unit Lot 2, Winchester
$100,000
26018705 MLS
Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family homes, 48 duplex units and 8 townhomes, creating one of Clark County's largest new residential communities. Homesites include city water and sewer, KU electric and Columbia Gas, with additional estate-style lots scheduled in upcoming stages through year-end 2026. Deed restrictions are designed to maintain architectural consistency and include 80% brick and/or stone exteriors, roof-pitch requirements, and minimum heated living areas of 1,600 SF for ranch homes, 1,800 SF for 1½-story homes, and 2,100 SF for two-story homes. Located near I-64 Exit 96, approximately 10 miles from Lexington's Hamburg area, with convenient access to downtown Winchester, Lexington, Paris and Richmond. Shopping, dining, healthcare and major employment centers are within easy reach while maintaining the space and setting of Winchester living. Choose your homesite, choose your builder, and build in Deerlawn. Additional development plans, plats, restrictions and lot information available upon request.

2395 Paris Rd Unit Lot 2, Winchester
2395 Paris Rd Unit Lot 4, Winchester
$100,000
26018695 MLS
Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family homes, 48 duplex units and 8 townhomes, creating one of Clark County's largest new residential communities. Homesites include city water and sewer, KU electric and Columbia Gas, with additional estate-style lots scheduled in upcoming stages through year-end 2026. Deed restrictions are designed to maintain architectural consistency and include 80% brick and/or stone exteriors, roof-pitch requirements, and minimum heated living areas of 1,600 SF for ranch homes, 1,800 SF for 1½-story homes, and 2,100 SF for two-story homes. Located near I-64 Exit 96, approximately 10 miles from Lexington's Hamburg area, with convenient access to downtown Winchester, Lexington, Paris and Richmond. Shopping, dining, healthcare and major employment centers are within easy reach while maintaining the space and setting of Winchester living. Choose your homesite, choose your builder, and build in Deerlawn. Additional development plans, plats, restrictions and lot information available upon request.

2395 Paris Rd Unit Lot 4, Winchester
2395 Paris Rd Unit Lot 1, Winchester
$100,000
26018697 MLS
Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family homes, 48 duplex units and 8 townhomes, creating one of Clark County's largest new residential communities. Homesites include city water and sewer, KU electric and Columbia Gas, with additional estate-style lots scheduled in upcoming stages through year-end 2026. Deed restrictions are designed to maintain architectural consistency and include 80% brick and/or stone exteriors, roof-pitch requirements, and minimum heated living areas of 1,600 SF for ranch homes, 1,800 SF for 1½-story homes, and 2,100 SF for two-story homes. Located near I-64 Exit 96, approximately 10 miles from Lexington's Hamburg area, with convenient access to downtown Winchester, Lexington, Paris and Richmond. Shopping, dining, healthcare and major employment centers are within easy reach while maintaining the space and setting of Winchester living. Choose your homesite, choose your builder, and build in Deerlawn. Additional development plans, plats, restrictions and lot information available upon request.

2395 Paris Rd Unit Lot 1, Winchester
404 Mount Vernon Dr, Winchester
$124,000
2 Beds ⋅ 2 Baths ⋅ 26005794 MLS
Ready to Stop Renting? Your Opportunity Is Here Step into the comfort and freedom of homeownership with this spacious, well maintained 2-bedroom, 2-bath modular home — and yes, the lot is included. An attached room addition provides even more flexibility, easily adaptable into a third bedroom, home office, hobby room, or bonus space to suit your lifestyle. --- Interior Highlights • 2 full bathrooms • Large walk in shower • Wheelchair ramp for easy accessibility • Generous closet space throughout • Ample kitchen counter space • Clean, comfortable, and truly move in ready --- Exterior Features • Large corner lot offering extra privacy • Parking for up to 4 vehicles • Outbuilding for additional storage • Equipped with a Generac backup generator for peace of mind during outages --- This home offers affordable living without compromise—space, accessibility, convenience, and the security of owning your own land. $149,000

404 Mount Vernon Dr, Winchester
122 Callaway Street Se Callaway Street, Winchester
$124,500
2 Beds ⋅ 1 Baths ⋅ 26000228 MLS
Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless possibilities! Property is AS IS! Bring me a offer.

122 Callaway Street Se Callaway Street, Winchester
175 Magnolia St, Winchester
$169,000
3 Beds ⋅ 1 Baths ⋅ 26008759 MLS
Newly renovated and move-in ready! This charming 3-bedroom, 1-bath home features 1,046 sq. ft. of living space along with a large storage shed in the fenced in backyard.

175 Magnolia St, Winchester

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