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$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

$2,200,000
5 Beds 7 Baths 26007066 MLS
Experience unparalleled luxury in this exquisite English Manor, a Schaefer Homes masterpiece in the prestigious, gated Hartland Estates. The grand two-story entry, featuring a curved staircase and stone-with-wood-inlay flooring, sets a stately tone that continues throughout. While the home retains its magnificent original woodwork—including mahogany and knotty pine cabinetry, beams, and trusses—it has been thoughtfully elevated with a completely reimagined gourmet kitchen and a stunningly updated primary retreat. The lavish first-floor primary suite now boasts a modern, spa-like bath and vaulted sitting room with fireplace. The expansive floor plan includes six fireplaces, a walk-out basement with a pub-style bar, home theatre, and gym, all situated on a lush .67-acre lot. Modern efficiencies like geothermal HVAC and a 4-car garage complete this one-of-a-kind estate.

4848 Chelmsbury Ln, Lexington

$1,750,000
23021742 MLS
101 S. Main Street is a fully-restored historic Opera House in the heart of Downtown Winchester. Now functioning in a multiple use capacity, including gallery space, 7-years-running successful restaurant space, wedding event and reception space, and office space. No detail was overlooked in this extensive renovation, now inclusive of multiple commercial kitchens, interior elevator, gracious entertainment spaces, and an abundance of old-world charm through hardwood floors, large windows, exposed brick, and functioning fireplaces. In fact, the Opera House renovations earned the Clyde Carpenter Adaptive Reuse Award from the Bluegrass Trust Historic Preservation Comm. This offering is extremely flexible in that a new owner can step in and operate the same uses already in place, including Lease Back potential from Loma's which is owner occupied, or use the flexible layouts for its own preferences. It is also in the Opportunity Zone, and Downtown Winchester KY offers numerous grants for both renovations and business development should a buyer wish to participate. *Business purchase is not included in the real estate offering. Property Highlights: -Home of the successful and delicious Loma's at the Opera House restaurant and bar, and The Winchester Opera House Ballroom -Ideally located in the heart of Downtown Winchester -The property benefits from the City of Winchester's investment in neighboring High Side Improvement Project with included $5.5 million invested in new angled parking, new sidewalks and added ramps, making the downtown area more accessible as well as 13 new high-end apartments with 10 more in development.

101 S Main, Winchester

$2,795,000
3 Beds 5 Baths 26013315 MLS
Welcome to 1368 Keene South Elkhorn Road, a rare opportunity to own a truly turn key 20 acre horse farm! Conveniently located near Versailles and Lexington, it has been home to multiple stakes winners and Arkansas and Kentucky Derby contenders! Located at the end of a quiet country lane, you'll appreciate the curb appeal of the home from the second you drive up. Step on to the wrap around porch and enter in to the airy two story foyer. To your left, you'll find the poplar paneled study with built-ins and fireplace. To your right, the spacious formal living room opens to the formal dining room. The kitchen boasts reclaimed hardwood floors from Hamburg Place, two refrigerators, walk in pantry, two sinks, breakfast nook, massive center island with cooktop and an Aga stove. A lovely screened porch, half bath and laundry room are off the kitchen. The first floor primary suite is generously sized and offers an en-suite bath and walk-in closet. Upstairs, you will find two large bedrooms, each with en-suite bathrooms and walk-in closets. The lower level features a bar area, theater room, sauna, guest quarters, spa like bathroom, home gym, office and plenty of storage space. The two car detached garage is at the rear of the home and has a staircase leading to storage above. There is also a 16x16 heated and cooled dog kennel building behind the garage. The 12 stall Amish built metal barn with 40x40 arena offers a tack room, tankless water heater, 2 wash/grooming stalls, hay loft and covered concrete pad for equipment storage. Other outdoor features include 7 paddocks, new 4 board fencing, recently paved driveway, Varnan waterers, and a small vineyard with multiple fruit trees including apple, pear, pawpaw, peaches, figs, apricots and plums. You'll love the location, just minutes from grocery stores, restaurants and Keeneland, and close to prestigious farms like Darley, Shadwell and Mill Ridge.

1368 Keene South Elkhorn Rd, Nicholasville

$2,175,000
4 Beds 6 Baths 26013347 MLS
Experience elevated living in this custom-built home, completed in 2025 and thoughtfully designed from top to bottom. Offering approximately 4,953 square feet, this four-bedroom residence includes four full bathrooms and two half baths, with each bedroom featuring its own private full bath for added comfort and convenience. The all-brick and Hardie board exterior sets a timeless tone, while the interior showcases carefully selected finishes throughout. Two fireplaces, including a wood-burning option outdoors, create warm and inviting gathering spaces. The primary suite includes a walk-in closet with a dedicated space for a stackable washer and dryer, adding everyday functionality. The home is also equipped with a whole-house Generac generator and is wired for Sonos surround sound. The finished basement is designed for versatility and entertainment, featuring a kitchenette, a recreation room wired for televisions, and a dedicated fitness space with rubber flooring. A reinforced storm room with 12-inch concrete walls adds an extra layer of security. Two sump pumps, including one with a backup battery, provide additional peace of mind. Step outside to a covered back porch designed for entertaining and relaxation. The outdoor living space offers a seamless extension of the home's interior. A detached three-car garage includes epoxy flooring, with additional finished space above that has been floored and drywalled. Four additional driveway spaces ensure ample room for guests. Located in the 40502 area, this home offers convenient proximity to dining, shopping, and everyday amenities. Schedule your private showing to experience the craftsmanship, space, and thoughtful design this property has to offer.

1267 Scoville Rd, Lexington

$415,000
3 Beds 2 Baths 26012300 MLS
Now an additional lot included! See photos for approximate boundaries. Rare doesn't even begin to cover it. Welcome to 513 Edgewood Drive where you get a full acre of flat, usable land and a massive 30x40 shop with electric, all tucked inside Nicholasville city limits. Properties like this simply don't come around often. Inside, the home has been thoughtfully refreshed with all new flooring and fresh paint throughout, giving you that move-in-ready feel without the new-construction price tag. The spacious, functional layout offers three bedrooms and two full baths with plenty of room for everyday living, entertaining, or working from home. But let's talk about that shop! Whether you're a contractor, hobbyist, car enthusiast, or simply someone who needs serious storage and workspace, the 60x40 outbuilding with electric is a game changer. Most buyers spend years searching for a setup like this and here it's already waiting for you. A full acre in the middle of town means room to breathe, space to grow, and the kind of privacy that's nearly impossible to find at this price point. No long commutes. No sacrificing convenience for space. You get both. Opportunities like 513 Edgewood don't sit on the market. Schedule your private showing today.

513 Edgewood Dr, Nicholasville

$265,000
26011270 MLS
GARDEN LOT 6: Welcome to The Sanctuary Garden Lots, a thoughtfully designed new construction community in Lexington offering a new standard of living centered around luxury, convenience, and natural beauty. These garden homes are the perfect blend of traditional homeownership with the benefits of maintenance-free, community-focused living. They're ideal for those who love having their own outdoor space, with each home including a charming yard and an optional private pool. Plus, you get easy access to all our community features. The Sanctuary will feature a unique mix of luxury townhomes, garden homes, and spacious estate lots with built-to-suit opportunities available. At the heart of the development will be The Sanctuary Gardens, featuring walking paths, lush green space, water features, and peaceful gathering areas designed for relaxation and connection. Enjoy the rare combination of serene surroundings and prime convenience, located just 8 miles from Rupp Arena, 3 miles from Brannon Crossing, and 4.5 miles from The Summit at Fritz Farm. The development is situated across both Fayette County and Jessamine County lines, with portions located within each county jurisdiction. Neighborhood plat, design guidelines and deed restrictions available upon request.

5447 Tates Creek Road Gdn Unit Garden Lot 6, Nicholasville

$99,900
2 Beds 1 Baths 26010949 MLS
Cave Run Lake Cabin for Sale! LOCATION, LOCATION, LOCATION! Rustic Fishing/Lake Cabin located 1 mile from Banger Boat Ramp, 4 miles to Longbow and Scott's Creek Marina! This cabin would make a wonderful home, short term rental, long term rental, air B&B, or vacation getaway!. No HOA, NO RESTRICTIONS! If you are looking for privacy, this 2 bedroom 1 bath piece of paradise that sits on 2.86 plus/minus acres is for you! You are within walking distance to Banger boat ramp, it is perfect for an air bb and/or transient rentals, has plenty of room to park multiple boats and trailers. Would make an excelent fishing cabin, and boast beautiful woodland views from the wrap around deck that is on three sides. You will not find more gorgeous wooded acreage and cabin so close to the lake Bonus! you are 45 minutes to the Red Rive Gorge, 25 minutes to Morehead! This Cabin is vacant and ready for your private showing today!

299 Igo Rd, Morehead

$195,000
26007887 MLS
Check out this beautiful property, boasting 10.5 acres of prime Kentucky land that offers endless potential! Ideally located just off HWY 460, this exceptional property features cleared, usable pasture land that is currently producing hay! With multiple ideal building sites, this tract is perfect for your dream home, mini farm, or future investment. *Developers take note!* The layout and location offer a RARE opportunity to subdivide into a highly desirable, top-dollar development. Huge potential for a return on investment! Equipped with a large equipment shed on site. The property has been surveyed and offers the freedom of being completely unrestricted, no limitations, yet loads of possibilities! Whether you're looking to build, invest, or expand - this land delivers the flexibility to bring your vision to life. Schedule a time to view and secure this beautiful slice of God's green earth today!

Main St, Jeffersonville

$444,999
4 Beds 3 Baths 26002824 MLS
NEW CONSTRUCTION Move In Ready!! Abigail Elevation-A by James Monroe Homes located in the Eastgate neighborhood in Nicholasville, KY The award-winning Abigail plan offers exceptional flexibility for living, working, and relaxing. Just off the foyer, a spacious flex room provides the perfect setting for a home office, formal dining room, or additional sitting area. The well-appointed kitchen features a center island, double-door pantry closet, and stainless steel appliances. A 4-foot extension enhances the family room, creating even more space for gathering and entertaining. The first floor also includes a floating breakfast area and a convenient powder room. Upstairs, the primary suite boasts a generously sized walk-in closet. Three additional bedrooms, two full baths, and a dedicated laundry room complete the second level, offering both comfort and functionality. Every James Monroe Home includes Connected Living features such as a Ring doorbell and chime, WiFi garage door opener, two smart switches, data hub, and WiFi thermostat. All homes also come with the Build With Confidence Promise.

105 Roland Ct, Nicholasville

$995,000
3 Beds 4 Baths 25000969 MLS
Welcome to The Silks Club of Lexington, an elegant private community designed specifically for the 55 and better age group, conveniently located across from the world renowned Calumet Farm. As you enter the stately iron gates with our custom copper jockey logos, you are greeted by colorful flowers and beautiful mature tree lined streets. The picturesque setting creates a serene ambiance that instantly makes you feel at home. Residents have access to a range of shared amenities such as the historic home converted to a clubhouse, where neighbors can gather and socialize, along with a pool and cabana area for lounging and grilling. The Silks Club features a collection of thoughtfully designed homes that are individually tailored to each home owner. Come tour the new Villa floor plan 'under construction.' This townhome is ready for your complete personal touches. **All photos of townhouses are of current residences to show possible style and finish options. This is a ''new construction'' townhome.

1602 Winners Cir Unit #41, Lexington

$188,900
3 Beds 1 Baths 26015581 MLS
Turnkey brick ranch minutes from Red River Gorge, Natural Bridge and Cave Run Lake, renovated top to bottom and ready for immediate move-in on Half Acre Lot! Move right into this beautifully updated 3-bedroom, 1-bath brick ranch offering modern finishes and peaceful country living. This home features a spacious living room, an all-new kitchen with brand-new cabinets, granite countertops, and stainless steel appliances, a fully remodeled bathroom, laundry room, and a convenient storage room. Recent updates include fresh paint throughout, new luxury vinyl plank flooring, stylish new light fixtures, a brand-new HVAC system (central heat and air), and a new driveway. Situated on a fenced in generous lot, this property offers plenty of outdoor space while providing the comfort and convenience of a completely turnkey home. Schedule your private showing today!

6053 W Us 460th Hwy, Means

$219,000
3 Beds 2 Baths 26011961 MLS
Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a beautifully updated kitchen featuring stainless steel appliances, a gas range, pantry, and plenty of space for cooking and entertaining. The home offers a primary suite, two additional bedrooms, an additional full bath, and a large utility room with extra storage and functionality. Outside, the 20x24 detached garage with electric is a rare bonus and ideal for carpentry projects, woodworking, hobbies, a workshop, home gym, storage for recreational equipment, or even the perfect space for car enthusiasts and DIYers. Enjoy small-town charm with quick access to shopping, dining, and interstate travel in this thoughtfully updated property ready for its next owner!

14 Cook Ave, Winchester

$13,500
26006806 MLS
 Four Seasons Resort Lot 80 | Wellington, KY 0.48 Acres | Investment Opportunity Near Cave Run Lake Looking for the perfect spot for your next getaway, investment property, or Airbnb cabin? This 0.48-acre unimproved lot in Four Seasons Resort offers a great opportunity to bring your vision to life. Located off Camp Judy Lane near Cave Run Lake, this property is tucked away in a peaceful setting while still being within a short drive to the world-famous Red River Gorge, making it a prime location for short-term rentals, vacation cabins, or a private retreat.  Property Highlights: 0.48 acres (Lot 80) Ideal for Airbnb cabins or vacation getaway Potential for timber income Peaceful, wooded setting Located off Camp Judy Lane near Cave Run Lake Convenient to Red River Gorge Whether you're looking to build a weekend escape, create an income-producing property, or invest in land with future potential, this property offers the flexibility and location to make it happen.  Opportunities like this don't last — secure your piece of Eastern Kentucky today.  ADDITIONAL LOTS AVAILABLE TO PURCHASE  Call or message for more details.

4 Season Resort Unit Lot 80, Wellington

$1,121,574
5 Beds 4 Baths 26006467 MLS
Current progress photos can be made available upon request. (Update: 9/12/26-This beautiful home and complete and ready for you!). The Rochester offers a great first floor layout with a large family room opening to a spacious kitchen and breakfast area. Five bedrooms and four full baths are possible with this plan. The first floor includes a guest bedroom, full bath and coat closet, conveniently located off the entry hall, as well as a formal dining room. A u-shaped central stairway adds elegance to the plan. A mudroom with optional drop zone and walk-in pantry connects the garage to the kitchen. Upstairs are the primary suite, three bedrooms, a large loft, and utility room with folding counter. The luxurious primary bedroom suite is a spacious retreat, with a sitting area and a very large, divided walk-in closet. The primary bath features separate vanities, a fully tiled shower, and freestanding tub. An optional covered deck off the primary bedroom has been added to extend outdoor living space. Exterior details include a covered front porch, shake siding accents, and a multi-layer hip and gable roof design. Job# 78PB

749 Shady Cv, Lexington

$2,950,000
25503131 MLS
Excellent owner-occupant or investment opportunity in Lexington's desirable Beaumont Centre. 1020 Monarch Street is a well-maintained three-story professional office building containing approximately 22,536 square feet with elevator service and ample surface parking. The first floor is fully leased to two professional tenants providing stable income. The second floor features a large training room, open area for cubicles or workstations, three private offices, a large conference room, and a spacious break room. The third floor (7,632 RSF) offers 22 private offices, large and small conference rooms, two public restrooms plus one private restroom, a large break room, and a dedicated storage room. Located in the heart of Beaumont Centre near Harrodsburg Road, New Circle Road, and Man O' War Boulevard, the property is surrounded by restaurants, retail, and professional services. Offered at $2,950,000, this property provides flexibility for an owner-occupant to occupy the upper floors while benefiting from existing rental income on the first floor

1020 Monarch St, Lexington

$255,000
25016652 MLS
Rare 6.8-Acre Gem on Highway 460, Camargo, KY! Don't miss one of the LAST prime commercial lots in Camargo's vibrant core located at 4110 Camargo Rd. Mt. Sterling, KY 40353. This 6.8-acre (296,000 sq ft) parcel, stretching 750 ft deep, is one of the largest on 460, with nearly 400 ft of frontage and 14,000+ daily cars for unmatched exposure. Mostly flat with gentle rolls, it's perfect for a high-traffic business, mini farm, or stunning estate. Features include a 4 bent tobacco barn, one blacktop entrance, a second entry point, and city sewer on-site. With NO ZONING, the possibilities are endless, launch a business, grow your own food, or build a dream home that turns heads! Located steps from Camargo Elementary, 11 min from the interstate, 45 min from Lexington, 35 min from Cave Run Lake, and 30 min from Red River Gorge, it blends rural charm with easy access to city and outdoor hotspots. This rare lot is a one-in-a-million find in Camargo's heart. Opportunities like this vanish fast in today's market so call today!! Property is sold in 3 separate tracts. Includes a brick building leased by the fire department. Seller is a licensed real estate agent in the state of Kentucky.

4110 Camargo Road Mt, Mt Sterling

$459,000
3 Beds 4 Baths 26014332 MLS
A stunning Queen Anne Victorian nestled in the heart of Lexington's historic Elsmere Park neighborhood. Beautifully restored and thoughtfully renovated, this exceptional residence seamlessly blends timeless architectural character with modern comfort and convenience. Featuring 3 bedrooms, 2.5 baths, and nearly 2,000 square feet of living space, the home showcases soaring 10-foot ceilings, abundant natural light, gorgeous hardwood floors, and preserved original details that honor its historic charm. The spacious first-floor primary suite offers a spa-inspired retreat, while the gourmet kitchen boasts custom cabinetry, generous workspace, and an adjoining pantry and laundry area designed for everyday functionality. Elegant living and dining spaces provide the perfect setting for entertaining, while multiple outdoor living areas, including a porch, patio, and deck, invite you to relax and enjoy the beauty of this unique neighborhood. Situated just minutes from downtown Lexington, local dining, entertainment, parks, and the vibrant cultural scene, this home offers the rare opportunity to own a piece of Lexington history without sacrificing modern amenities. Historic elegance, modern luxury, and an unbeatable location—668 Elsmere Park is truly one of Lexington's most distinctive homes.

668 Elsmere Park, Lexington

$535,000
3 Beds 2 Baths 26014883 MLS
The Charleston is a beautifully designed single-level home that blends comfort, function, and timeless style. Offering lots of square footage with 3 bedrooms and 2 bathrooms, this floor plan is perfect for any buyer, and has the everyday convenience all on one level. The heart of the home features an open-concept layout, creating a seamless flow between the family room, dining area, and kitchen. Whether you're entertaining guests, enjoying family time, or relaxing by the fireplace with gas logs, the Charleston offers a warm and inviting space that feels like home from the moment you walk in. The split-bedroom design gives the primary suite added privacy from children, guests, or a home office setup. The primary bath is designed with comfort in mind, featuring a double vanity and custom tiled shower for a more elevated everyday experience. This plan also includes a mudroom/laundry room off the garage, making busy mornings, rainy days, and everyday routines easier. Covered front and back porches/patio add even more charm, giving you the perfect place to enjoy quiet mornings, evening sunsets, or outdoor entertaining. With its smart layout, luxury touches, and easy single-level living, the Charleston is a wonderful option for any buyer.

4136 Buttermilk Rd, Lexington

$240,000
2 Beds 1 Baths 26011623 MLS
If you are reading this, odds are you are a parent of a UK student, or are a UK student hoping your parents will get you out of the dorm before the fall semester starts. Let's get some basics out of the way: **This is a BARGAIN for a 2 bedroom condo. **It is on the edge of campus so walking to class is easy. **You get one assigned parking spot PLUS one in the general parking lot, saving you the cost and hassle of getting a UK permit. **The $220/month dues covers water, sewer, internet and trash. You only have your personal electric bill. **The building is secure. **Indoor and outdoor bike racks. **Lots of food, entertainment and shops within a 2 minute walk and a 15 minute walk to downtown/Rupp Arena. (Students-if your parents are on the fence about buying a condo for you, let them know they can stay here occasionally for UK games and use your extra parking spot!) Now that we have that out of the way, let's talk about what makes this building so cool. It is a legit loft conversion. This was the Liggett & Myer Tobacco Warehouse. It was built in 1904 and retains much of its OG patina and charisma.

585 S Upper St Unit 147, Lexington