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$219,900
26016689 MLS
Discover the possibilities with this unique dual-property offering at 3686 & 3688 Crowe Ridge Road. Enjoy the peace and privacy of a beautiful country setting with room to spread out and endless potential. Whether you're looking for a primary residence with additional living space, an investment opportunity, or housing for extended family, this property offers versatility that's hard to find. Conveniently located just minutes from Winchester off the Mountain Parkway, exit 10, and an easy commute to Lexington.

3686 Crowe Ridge Rd, Winchester
$134,900
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
$1,200,000
25502866 MLS
 Prime I-1 Zoned Industrial Property - Winchester, KY Unlock the potential of this exceptional 3.9-acre parcel located in the heart of Winchester's thriving industrial corridor. Zoned I-1 (Clean Industrial), this property offers flexibility for a wide range of uses—from manufacturing and warehousing to logistics and tech operations. Property Highlights: * 3.9 Acres of flat, usable land * 7,800 Sq Ft Building with high ceilings and open layout * Power Garage Doors for easy access and loading * Utility-Ready with ample power supply * Strategic Location with quick access to major highways and local infrastructure Whether you're expanding your business, launching a new venture, or investing in a high-potential asset, this property delivers the space, zoning, and location to make it happen. The possibilities are endless—don't let this opportunity pass you by!

101 Jefferson St, Winchester
$189,000
26009146 MLS
Escape to your own private retreat with this stunning 41.6± acre wooded tract nestled in the scenic countryside of Winchester, Kentucky. This expansive property offers a rare opportunity to own a secluded slice of nature, perfect for a private estate, recreational getaway, or hunting retreat. With rich with mature timber, this land presents a lot of natural beauty. A network of cleared trails and old roadbeds provides easy access throughout the property, making it ideal for exploring, hiking, or ATV use. Whether you're looking to build your dream home tucked among the trees or create a peaceful weekend escape, this property delivers the privacy and tranquility you've been searching for. A small barn adds utility, while the location offers convenient access to the Mountain Parkway, making travel to Winchester and surrounding areas simple and efficient. Don't miss this opportunity to own a versatile piece of Kentucky land with endless possibilities—recreation, investment, or your future homesite all in one.

2697 Pine Ridge Rd, 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
$325,000
5 Beds ⋅ 4 Baths ⋅ 26012369 MLS
*****PRICED BELOW APPRAISAL & MOTIVATED SELLERS***** Whether you're looking for a large residential home, investment opportunity, business potential, or a combination of uses, this property is ready to fit your vision. Featuring 5 bedrooms, 4 baths, soaring 10 foot ceilings, and a welcoming front porch, this unique property blends character, space and versatility. Generous room sizes, timeless charm, and flexible living spaces make it ideal for multi-generational living, rental income opportunities, or for a great work setup. Opportunity with unlimited potential.

410 W Lexington Ave, Winchester
$165,000
4 Beds ⋅ 3 Baths ⋅ 26008701 MLS
Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

229 S Highland St, Winchester
$225,000
26005737 MLS
Wonderful 24 acre retreat with gentle sloping land, and a creek bed running thru part of the front portion of the lots (6.1 acre parcel & 18.4 acre parcel at the rear). Build your dream home or just use as recreational or farm land until you do. 1 1/2 miles to the first exit on the Mountain Parkway exit #10. 12 miles to I-64 at Winchester. See attached pictures & plat/overhead pictures.

3934 Trapp-Goffs Corner Rd, Winchester
$575,000
23015571 MLS
Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and Catalent Pharmaceuticals. Second Row Lots conveniently located along residential density while being visible from the Bypass. Conceptual Plans have been created which display potential uses of up to 22,800 SF as retail box. Would be a great location for retail, office, storage, and mixed use development. Conceptual Development Plan: https://www.kcrea.com/files/property/6900000/6902843/25814078_2020___Conceptual_Development_Plan_Lots_3.pdf

529 Bullion Blvd Unit 3B, Winchester
$316,900
3 Beds ⋅ 3 Baths ⋅ 26008021 MLS
Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full bath and nice walk in closet. Picture hosting your social events on the expansive two-level decks located at the back of your new home. If that is not enough this home is perfectly located within waking distance to Kroger & Walmart, shopping and dining. Come be the first to see this one or your likely to regret it. This home has never flooded but as of 2025 it does require flood insurance. The current owner has the flood insuance through ( The Hartford ) insurance company at a cost of $100 a month. Owner is offering to pay $1200 for the new owners first year of flood insurance.

200 Dubuy Dr, Winchester
$1,595,000
3 Beds ⋅ 3 Baths ⋅ 26011538 MLS
NEW PRICE!!! Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points in Clark County, where you can see the panoramic views stretching all the way to the dormitories at EKU in Richmond and the mountains near Berea, KY. Relax by the newly lined in-ground pool with a new cover, and unwind in the hot tub while taking in the beautiful sunrise and sunset views — perfect for family gatherings or quiet evenings under the stars. The property features a two-level barn with horse stalls, a tack room, and a spacious open arena — ideal for equestrian enthusiasts. The upper level of the barn provides versatile space for auto storage or a workshop, while the fenced pastures and horse ring make it ready for boarding or training horses. This property also includes a stocked pond, adding to the tranquil landscape, and 2 gated driveways with a security system for peace of mind. The land features mature trees, including fig, pear, and apple. This is the first property on Colby Road out of Winchester with agricultural zoning, a very private estate, and the first time in 40 years this remarkable property has been for sale. Conveniently located just one mile to Kroger, Lowe's, and Walmart, and approximately 20 min. from Man O War via Todds Rd. Lexington. This property offers both peaceful seclusion and easy access to amenities. With potential for income from horse boarding and a rental home on the property, this exceptional farm is more than a home- it's a lifestyle, an investment, and a place to create lasting memories for generations to come.

3166 Colby Rd, Winchester
$78,500
26011488 MLS
NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build your New Kentucky Home. The developer is currently finalizing the restrictions so they are not available for distribution. New restrictions will incorporate the following: 80% brick/stone exterior, Roof pitch requirements, Minimum 1,600 sq ft for a ranch, 1800 for a One-Half Level, 2100 Two Story. Development lot sizes require minimum lot is 9000 sq ft and current development plan has the smallest lot at 9600 sqft. Positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 future single-family homes, and additional acreage available for 8 duplexes and 48 townhomes, meeting the region's demand for quality and attainable housing. Phase Two and Three begin in December with 34 buildable lots expected completion by Spring 2026 Approved development plan in place with Clark County. Additional Phases continuously following with additional buildable lots. Located within 20 miles to Lexington's Hamburg area, Deerlawn sits at the center of Clark County's growth corridor. With $100M in infrastructure improvements completed and the EPA Consent Decree lifted in 2024, the path is clear for accelerated residential and economic expansion.

Lot 4 Plantations, Winchester
$128,800
26008587 MLS
This exceptional 2.3 acre homesite offers the perfect canvas to bring your vision to life. With ample space, a prime cul-de-sac setting, and stunning surroundings, it's an ideal opportunity to create the custom home you've always wanted. Located in The Reserve, one of Winchester's premier subdivisions, this property boasts scenic daytime views and unforgettable sunsets each evening. Enjoy the perfect blend of privacy and convenience with quick access to shopping, dining, schools, and I-64. Don't miss your chance to own the largest lot in the neighborhood. Schedule your visit today!

110 Knox Ct, Winchester
$340,000
4 Beds ⋅ 5 Baths ⋅ 26010324 MLS
Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 3 half baths. Laundry hook-ups in all 3 units! Basement for extra storage room with freight elevator. Two new HVAC units and a new roof within the last 2 years! Approximately 16 parking spaces.

502 W Lexington Ave, Winchester
$325,000
26014051 MLS
******PRICED BELOW APPRAISAL & MOTIVATED SELLERS****** Whether you're looking for a large residential home, investment opportunity, business potential, or a combination of uses, this property is ready to fit your vision. Featuring 5 bedrooms, 4 baths, soaring 10 foot ceilings, and a welcoming front porch, this unique property blends character, space and versatility. Generous room sizes, timeless charm, and flexible living spaces make it ideal for multi-generational living, rental income opportunities, or for a great work setup. Opportunity with unlimited potential.

410 W Lexington Ave, Winchester
$355,000
1 Beds ⋅ 2 Baths ⋅ 26012322 MLS
Home listed as one bedroom while unofficially has 3 but 2 of them are interior rooms without windows. ( Owners Now Offering to pay up to $5,000 in closing cost and pre-paids on behalf of buyers). Tired of the honking horns , congested traffic, sirens of town living and dreaming of country living, your own slice of paradise? Maybe raising your own garden , owning chickens , goats, horses , whatever you always dreamed of. Maybe just kicking back on the wrap around porch watching the chickens peck. This really is an amazing property and you will fall in love with all the bells and whistles like the beautiful soaking tub, 2 walk in showers, huge kitchen island, large primary bedroom and bath, stainless steel appliances. It practically a new house , the front portion of the house where the living room , hall, primary bedroom were all built new in 2020 . All the wiring , plumbing , insulation, flooring , drywall has been replaced since 2020. Home is also very conveniently placed just minutes from exit 10 on the Mountain Parkway between, Winchester and Clay City. Dont let anyone beat you to it , this is a real jewel. Porch swing belonged to owners great grandmother and does not convey.

3359 Trapp-Goffs Corner Rd, Winchester
$550,000
3 Beds ⋅ 3 Baths ⋅ 24025578 MLS
Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy maintenance with luxury vinyl plank flooring throughout the home. The heart of the home is the spacious great room, complete with a cozy gas log fireplace, perfect for gathering with loved ones. The well-appointed kitchen features a large island, ideal for both cooking and entertaining. Additional features on the first floor include a full bathroom, a convenient half bath, and a separate laundry room for added convenience. Step outside onto the back patio and enjoy the fresh air and sunshine. Let's build your dream home and make the Winchester Floor Plan yours!

107 Bella Shae Way, Winchester
$699,000
26004697 MLS
Operated for over 20 years as a physician's office this two-story building features a "ready to go" office on the main floor with two large apartments on the second floor with walkup, outside entry. The entire structure is on an unfinished basement perfect for storage and access to the mechanical systems. There is also a detached 3-bay garage for parking and storage as well as an asphalt parking lot with more room for more than 25 vehicles.

218 S Maple St, Winchester
$2,999,000
6 Beds ⋅ 5 Baths ⋅ 25507353 MLS
Some properties are special simply because of the story behind them. This 150 acre farm with 3,168 feet of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function to the farm, while four barns and two storage sheds make it ready for cattle, horses, or anyone wanting a true working farm. There are two homes on the property, offering flexibility for extended family, guests, or farm operations. Whether you dream of continuing its farming legacy, creating a private retreat, or investing in a truly special piece of Kentucky land, this is the kind of place that rarely becomes available. Opportunities like this don't come around often. This farm has been part of one family's story for over two centuries, now it's ready for its next chapter.

3049 Ironworks Rd, Winchester
$78,500
26011487 MLS
NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build your New Kentucky Home. The developer is currently finalizing the restrictions so they are not available for distribution. New restrictions will incorporate the following: 80% brick/stone exterior, Roof pitch requirements, Minimum 1,600 sq ft for a ranch, 1800 for a One-Half Level, 2100 Two Story. Development lot sizes require minimum lot is 9000 sq ft and current development plan has the smallest lot at 9600 sqft. Positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 future single-family homes, and additional acreage available for 8 duplexes and 48 townhomes, meeting the region's demand for quality and attainable housing. Phase Two and Three begin in December with 34 buildable lots expected completion by Spring 2026 Approved development plan in place with Clark County. Additional Phases continuously following with additional buildable lots. Located within 20 miles to Lexington's Hamburg area, Deerlawn sits at the center of Clark County's growth corridor. With $100M in infrastructure improvements completed and the EPA Consent Decree lifted in 2024, the path is clear for accelerated residential and economic expansion.

Lot 3 Plantations, Winchester
$825,000
3 Beds ⋅ 3 Baths ⋅ 24025579 MLS
Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. The spacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a cozy breakfast nook. The luxurious primary suite offers a private retreat with an ensuite bathroom and a walk-in closet. Every bedroom in this home features a walk-in closet, providing ample storage space for the whole family. Additional features on the first floor include a formal dining room, a dedicated study perfect for working from home, a half bath for guests, and an additional full bathroom. This desirable lot also includes an unfinished walkout basement, offering endless possibilities for expansion or customization. Make the Park Place your dream home. Reach out today to schedule a consultation with our experienced team and bring your vision to life.

111 Bella Shae Way, Winchester
$150,000
26008075 MLS
Parcel 4 in the photos. This 2.774 acre lot is available on Colby Road just 1.5 miles from the Winchester Bypass. No building restrictions other than no manufactured housing and a paved driveway must be completed within a year of finishing a residence.

3385 Colby Rd, Winchester
$670,000
3 Beds ⋅ 2 Baths ⋅ 24025580 MLS
Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen island, and a generous walk-in pantry, along with a convenient butler's pantry for added storage and prep space. Nine-foot ceilings and luxury vinyl plank flooring throughout add a touch of elegance, while the separate utility room offers practicality. The additional two bedrooms also include walk-in closets. With a formal dining room, unfinished walkout basement, and a two-car garage, this home combines stunning curb appeal with modern functionality. Come build your dream home in Mallard Cove neighborhood!

113 Bella Shae Way, Winchester
$110,000
22024065 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 Duclair Dr, Winchester
$137,500
26006848 MLS
Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it grows in value. Offering 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

150 Spencer Ln, Winchester
$1,850,000
20101924 MLS
17.87 Acre farm available for sale. Ideal location for redevelopment. Gently rolling topography. Corner lot with excellent visibility. Water, electric, sewer, gas and telecommunications available. Conveniently located near RD Campbell Junior High School, George Rogers Clark High School & Winchester Country Club. Located 3 miles south of Interstate 64. Signalized corner lot at Boonesboro Rd. & Bypass Rd. Easily accessible to nearby retailers, restaurants & residential. Winchester is the county seat of Clark County, KY. This growing city is part of the Lexington-Fayette, KY MSA. Local employers include Amazon, Ale-8-One, and Alltech.

1509 Boonesboro Rd, Winchester
$1,200,000
16 Beds ⋅ 16 Baths ⋅ 26007993 MLS
You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof replacement in 2022, new siding in 2023, and 6 of the AC units were replaced in the last three years. The main electrical service mast was replaced in 2023, and all 100-amp breakers were replaced in 2025. Most units have been updated with LVP flooring.

16 Linden Ave, Winchester
$42,500
26005419 MLS

105 Bella Ct, Winchester
$110,000
22024114 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 Jacob Ct, Winchester
$139,900
3 Beds ⋅ 1 Baths ⋅ 26007798 MLS
3BR/1BA | Winchester, KY Affordable single-family homes are hard to come by at this price — here's your chance. This cozy 3-bedroom, 1-bath home in Winchester sits on a generous lot with a large backyard, long driveway with plenty of parking, a welcoming covered front porch, and accessible front entry with both steps and a ramp. it's efficient and easy to maintain — and don't let the square footage fool you. A huge walk-in crawl space underneath the home offers exceptional storage that most homes twice the size don't have. The big-ticket items are handled: a brand new roof was installed in 2024, giving you peace of mind for years to come. Currently tenant occupied — ideal for an investor looking for immediate cash flow, or a future owner-occupant planning ahead.

19 3rd St, Winchester