Bluegrass Sotheby's International Realty
1999 Richmond Road Suite 400, 40502 Lexington (United States)
Listings of the agency
Listings for sale: 1 to 20 / 84
- 33
House Lexington (United States)
Welcome to 944 Winding Oak Trail, a charming ranch-style home in the heart of Masterson Station, offering comfort, simplicity, and easy everyday living. The single-level layout provides an effortless flow for relaxing or gathering, paired with well-proportioned bedrooms and practical storage throughout. All new appliances and upgraded HVAC. Outside, the partially fenced yard creates a potential private space for pets, play, or unwinding at the end of the day. With quick access to Masterson Station Park, neighborhood trails, and the conveniences of Citation and Georgetown Road, this home delivers a balanced lifestyle in one of Lexington's most accessible corridors.
…$279,5003bedrooms2bathroomsland 526m²By Bluegrass Sotheby's International Realty
- 50
House Lexington (United States)
A rare offering in the heart of Ashland Park, this distinguished Colonial Revival residence stands as a testament to the enduring elegance and architectural refinement that defined the style's popularity at the turn of the century. Among the earliest homes constructed on coveted South Ashland Avenue, it enjoys a commanding presence and a rich connection to one of Lexington's most treasured historic neighborhoods. A gracious front porch sets the tone, inviting leisurely afternoons spent greeting neighbors and enjoying the timeless charm of tree-lined South Ashland Avenue. Inside, soaring ceilings, exquisite millwork, and a wide center hall create a sense of grandeur rarely found in today's homes. A remarkable reverse staircase, illuminated by a skylight above, provides access to the second level from the rear of the residence while filling the home's interior with natural light. Throughout, distinctive crown moldings highlight the craftsmanship of a bygone era, while the kitchen's handsome coffered ceiling adds warmth and architectural interest. Designed for both elegant entertaining and comfortable daily living, the first floor features an exceptional collection of gathering spaces, including a formal living room, formal dining room, a richly appointed den, an inviting family room, a spacious kitchen, a bedroom, and a full bath. Each room flows gracefully into the next, creating an atmosphere that is both sophisticated and welcoming. The second level features a spacious primary suite with a cozy sitting area, providing a private retreat at day's end. Two additional bedrooms and a full bath enjoy lovely views of the beautifully landscaped rear grounds. Outdoors, the private backyard serves as a peaceful oasis, with mature landscaping and a deck perfect for al fresco dining and entertaining. The porte cochere provides covered parking and everyday convenience while complementing the home's historic character. Ideally located just steps from the boutiques, cafés, and restaurants of Chevy Chase, this exceptional residence offers the rare opportunity to own a piece of Ashland Park history while enjoying one of Lexington's most desirable and walkable neighborhoods.
…$1,499,0004bedrooms3bathroomsland 1,372m²By Bluegrass Sotheby's International Realty
- 50
House Midway (United States)
Minutes from the charming town of Midway and conveniently positioned for easy access to the Kentucky Horse Park, this 34-acre equine facility — complete with a custom five-bedroom home, a 19-stall barn and both indoor and outdoor arenas — is built for the serious equestrian. The farm infrastructure is extensive and well-appointed. The barn is finished to a high standard with quality stalls, a heated tack room and bathroom, and indoor and outdoor wash bays. The outdoor arena was completely rebuilt in 2025 with upgraded footing for exceptional performance in any weather, and the indoor arena is equipped with premium Trutek footing and designed to ride comfortably year-round. Six paddocks each have individual automatic waterers. Additional support facilities include a run-in shed, an oversized equipment barn with water and electric, and a full RV hookup. The custom home is designed for livability, with the primary suite, two additional bedrooms with a jack-and-jill bath, and a dedicated office all on the main floor. The lower level can function as a fully independent suite with its own living area, full kitchen, bedroom suite, home theater, and walk-out access — ideal for farm management, extended family, or guest accommodations. The home and farm are on separate utilities for easy management.
…$2,590,000599m²5bedrooms5bathroomsland 13.9haBy Bluegrass Sotheby's International Realty
- 50
House Richmond (United States)
A well-kept ranch on more than a half-acre in the middle of Richmond doesn't come to market often. 113 Longview Drive sits on a double lot a short distance from EKU, downtown, I-75, and the dining and shopping at Richmond Centre. The main floor holds three sizable bedrooms and two full baths, light-filled open living and dining, and a generous kitchen with a double oven and newer appliances. The rear screened porch is a perfect spot for morning coffee or an evening drink overlooking a large private backyard. Downstairs adds more finished square footage with a TV room, home office, a potential fourth bedroom or craft room, along with plenty of storage and interior access to the attached two-car garage. This 1960s ranch has been well upgraded, including replaced insulated windows. Discover this rare offering of in-town convenience and space!
…$359,0003bedrooms2bathroomsland 2,432m²By Bluegrass Sotheby's International Realty
- 50
House with garden and terrace Lexington (United States)
Welcome to this stunning 5-bedroom, 3-full-bath Chilesburg home filled with natural light and impressive details. The two-story foyer and great room feature a curved overlook balcony, soaring bay windows with electronic blinds, a wood-burning fireplace with floor-to-ceiling stone surround, and built-in bookshelves. The main level also offers a formal dining room, office with French doors, guest suite with full bath, and spacious kitchen with granite countertops, abundant cabinetry, large island, and walk-in pantry. Upstairs, the expansive primary suite includes a sitting area, dual walk-in closets with custom systems, dual vanities, soaking tub, and fully tiled walk-in shower, plus three additional bedrooms and a full bath. Enjoy the fenced backyard with mature landscaping, greenspace/farm views, hot tub, and a partially covered patio with ceiling fan and mounted TV, completed in 2024. A beautiful home with exceptional space, character, and indoor-outdoor living!
…$609,900317m²5bedrooms3bathroomsland 688m²By Bluegrass Sotheby's International Realty
- 48
House with garden and terrace Lexington (United States)
Super sharp Craftsman style 3 Br, 2 bath ranch in the desirable Bell CT area within walking distance to National Avenue, UK, downtown, restaurants, parks, shopping and more. A multi windowed sun porch welcomes you into the open great room and completely renovated kitchen, 3 large bedrooms and 2 full baths complete the 1st level. The 1320 sf unfinished basement is an excellent storage and flex space. There is a large 2 car detached garage with a spacious 1 BR, 1 bath apartment above. Great for rental, office or guests! Combined square footage of main house (1696sf) and apartment (576sf) is 2272 SF. Other features include new roof, side patio, large parking pad and ample fenced yard. Rare opportunity in a great and convenient location!
…$519,9004bedrooms3bathroomsland 757m²By Bluegrass Sotheby's International Realty
- 50
House Lexington (United States)
Enjoy the perfect home, near schools, right in the heart of Glendover! This spacious two-story house has 5 bedrooms and 4 full bathrooms. The large eat-in kitchen with high end appliances and a spacious pantry is truly the heart of the house. The den area off the kitchen makes for a perfect family room, and with a closet and full bathroom, could easily be converted into a 6th bedroom and in-law suite. Upstairs you'll find 3 large bedrooms, including a recently updated primary suite with 2 closets. The sunroom and back patio are perfect for relaxing and hosting guests, and the fully fenced back yard with an electric driveway gate gives peace of mind for letting kids and pets play freely. A two-car detached garage with a workshop area and attic storage provides additional convenience. Recent updates include a top-of-the-line tankless water heater, poured concrete front porch, and electrical upgrades to support a whole-home backup generator. Walk to UK Football games or the Arboretum and enjoy living in one of Lexington's most charming and convenient neighborhoods.
…$639,9005bedrooms4bathroomsland 1,182m²By Bluegrass Sotheby's International Realty
- 23
House Lexington (United States)
Beautifully Renovated Ranch with Private Backyard & Modern Updates. Classic charm. Modern comfort. Move-in ready. Welcome to 3475 Greentree Road, where timeless character meets today's style and convenience. This beautifully renovated 3-bedroom, 2-bath ranch offers all the warmth of an established neighborhood with the fresh feel of a nearly new home. Step inside to discover fresh interior paint, gorgeous new flooring, updated lighting, modern fixtures, and modern finishes throughout. Every detail has been thoughtfully updated, creating a home that's ready to enjoy from day one. The spacious floor plan offers comfortable living and effortless entertaining. Enjoy a bright formal living room, dedicated dining area, and an impressive atrium-style family room with library walls, where abundant natural light creates an inviting gathering space unlike any other. The private primary suite—an uncommon feature in many homes of this era—includes its own full bath, while two additional bedrooms provide flexible space for family, guests, or a home office. Peace of mind included, major improvements mean you can simply move in and enjoy: New flooring throughout, fresh interior paint, new light fixtures & ceiling fans, new faucets, updated energy-efficient windows, newer HVAC system, recent roof replacement, updated kitchen with new stainless-steel appliances, Your own backyard retreat. Outside, you'll find a beautifully landscaped, fully fenced backyard offering privacy, mature trees, and plenty of room for entertaining, gardening, pets, or simply relaxing. It's the kind of outdoor space that established neighborhoods are known for—and difficult to find in newer developments. An outstanding Lexington location. Located in the desirable Gainesway neighborhood, you'll enjoy convenient access to: Chinoe Shopping Center, restaurants and everyday shopping, parks and recreation, high school, downtown Lexington and major commuter routes. Property highlights: 3 bedrooms, 2 full bathrooms, 1,574 square feet, one-level ranch living, spacious atrium-style family room with library walls, formal dining room, private primary suite, beautifully renovated kitchen, attached two-car garage with additional storage, beautifully landscaped, fully fenced backyard, established neighborhood, move-in ready.
…$334,9003bedrooms2bathroomsland 801m²By Bluegrass Sotheby's International Realty
- 34
House Frankfort (United States)
Discover downtown living at 103 Watson Court. Tucked away on a peaceful street, this stunning 2-bedroom, 2.5-bath home showcases hardwood flooring throughout, tasteful updates, and timeless finishes. Designed with both comfort and functionality in mind, this home offers an inviting atmosphere perfect for families or anyone looking to enjoy the charm of downtown Frankfort. Enjoy being just a short walk from your favorite local restaurants, shops, and the Kentucky State Capitol, while still coming home to the quiet comfort of this desirable location.
…$259,0002bedrooms3bathroomsland 526m²By Bluegrass Sotheby's International Realty
- 50
House with pool and garden Lexington (United States)
On an established lot in the heart of Lansdowne Merrick, 2985 Montavesta Road is an offering that rewards vision. This property carries the space, structure, and setting that are increasingly hard to find at this price point and location, and it is ready for a new owner to bring it fully back to life. At 4,240 square feet, the floor plan lives large, with four bedrooms, four full baths, and two half baths. Generous formal and everyday living spaces flow across the main part of the home, and an updated primary bathroom is already complete. A separate section of the home could easily become a second residence complete with its own family room, kitchen and laundry well suited to extended family or guests. Outside, a fenced rear yard offers real privacy, anchored by an in-ground pool and mature landscaping that give the grounds a quiet, resort-like feel with the right attention. This home is remarkably convenient to so much - just a short distance from the University of Kentucky, the Arboretum, neighborhood parks, and the shops and restaurants of Chevy Chase, in one of Lexington's most durable established corridors. The property is offered as part of an estate, sold as-is, and a pre-listing inspection is already completed. This is a genuine opportunity to restore a substantial home in a fantastic location. Bring your vision and make it your own.
…$495,000448m²4bedrooms6bathroomsland 1,299m²By Bluegrass Sotheby's International Realty
- 50
House Lexington (United States)
Beautifully remodeled and well maintained 4 bedroom (2 primary suites) 3.5 bathroom home on a half acre lot in one of Lexington's most desirable neighborhoods. With a most sensible, effortless layout, the home has a cozy, comfortable feel all on one level. One feels immediately at home. Cindy Blair Way offers both a formal living and dining room, with beautiful crown moldings throughout. The beautiful hardwood floors were redone in 2023, with LVP added in the Great Room and the office/4th bedroom. In addition, a wonderful eat-in kitchen with all new stainless steel appliances and quartz countertops were installed in 2023. The kitchen flows seamlessly into the family room with a gorgeous fireplace surrounded by wall high bookcases. This home is heated and cooled with 2 heat pumps, installed in 2023 and 2026, zoned for maximum comfort with a back up steam heating system powered by gas for extremely cold days in winter. The large front porch is welcoming to neighbors and friends in addition to a privacy fence enclosed brick patio perfect for entertaining and relaxation.
…$629,9004bedrooms4bathroomsland 2,104m²By Bluegrass Sotheby's International Realty
- 42
House Frankfort (United States)
The best of both worlds! This beautifully updated 3-bedroom, 2-bath brick ranch offers the privacy and peaceful feel of country living with the convenience of being just minutes from downtown Frankfort, Georgetown, Midway, Lexington, and I-64. Thoughtfully updated with modern finishes and major system improvements, this move-in ready home also features a covered deck, oversized 2-car garage, detached carport, and storage shed. Homes that combine this much privacy, space, and convenience don't come around often.
…$269,9003bedrooms2bathroomsBy Bluegrass Sotheby's International Realty
- 18
House Lexington (United States)
Great opportunity to renovate a home in the heart of Chevy Chase! This charming brick-and-vinyl 1.5-story home is ready for its next chapter. Offering 4 bedrooms, 2 baths, a living room, dining room, galley kitchen, and a partially finished basement. Walk to shopping and restaurants, with easy access to UK and downtown. Home is being sold as-is and is in need of repairs per LFUCG code enforcement that will have to be satisfied by new purchaser.
…$431,9004bedrooms2bathroomsland 673m²By Bluegrass Sotheby's International Realty
- 38
Property with garden Paris (United States)
The Collins-Evans house is now being offered for sale in North Middletown. This beautiful historic home dates back to 1894. On the historic registry, this treasure has been renovated with great love and taste by its current owner. Sitting on 2 acres, it is a gentleman's farm, but with all the conveniences within a small town. Inside you'll find large Victorian rooms with stunning original woodwork and doors, that includes five bedrooms and three full baths. The current owners have updated the home with new paint throughout and refinished the hardwood floors. Its Victorian charm continues upstairs with its winding staircase and bedrooms, including one that has been transformed into a personal living area. You enter the property through historic stone fencing to find a wraparound porch with easy access to the front and side of the house. Many exterior updates include new box guttering and soffits. A newly built roofed pergola with outdoor kitchen and a screened-in deck are found at the rear of the house. The newly fenced backyard is great for your dogs and includes a refurbished greenhouse. The rear acreage has a fenced orchard, a sizable paddock, and a three bay garage/barn with a large run-in shed and an enclosed horse stall. There is also a self contained workshop as well as a handy covered three sided shed for outdoor storage. You'll love living in peaceful North Middletown, and enjoy all that this property includes, as it has been genuinely and lovingly restored to its current condition. A list of the extensive updates is included within the seller disclosure, showing all that has been completed.
…$499,900284m²5bedrooms3bathroomsland 8,094m²By Bluegrass Sotheby's International Realty
- 50
Property with garden Lexington (United States)
Located in the desirable Firebrook neighborhood, this beautifully updated 4-bedroom, 3.5-bath home offers more than 3,600 square feet with exceptional craftsmanship and thoughtful design throughout. Hardwood floors, detailed ceilings and an open, light-filled floor plan create an inviting main level, anchored by a true chef's kitchen designed and crafted by Chris Russell of Cucina Hand Crafted Kitchens. Custom cabinetry, generous prep space and striking stone surfaces make the kitchen as functional as it is beautiful. The attention to detail continues in the primary suite, where the bath is finished with granite floors, walls and shower, while the second-floor full bath features travertine tile and the main-level powder room is accented by a full marble wall. Custom cabinetry by Cucina Hand Crafted Kitchens is also featured in the second-floor bath and finished basement. Designed with entertaining in mind, the lower level offers expansive living space, porcelain tile flooring, a wet bar and plenty of room to gather. Outdoors, a gorgeous covered patio finished with solid 3/4-inch walnut wood overlooks the spacious backyard, creating a standout extension of the home's living space. From its custom finishes to its generous indoor and outdoor spaces, this Firebrook home offers quality and character at every turn.
…$765,0004bedrooms4bathroomsBy Bluegrass Sotheby's International Realty
- 8
Property Lexington (United States)
A once-in-a-lifetime opportunity to renovate a timeless architecturally unique home in the heart of Ashland Park, one of Lexington's most sought-after neighborhoods. Situated on South Hanover Avenue, one of Lexington's most desirable addresses, this classic 1923 brick two-story home with partially finished basement has been prepared for its next chapter. The owner has removed all kitchen and bathroom cabinetry and fixtures, removed all attic insulation, and completed other partial internal demolition. The property now essentially provides a blank canvas for a complete renovation as you envision. The property was previously configured with a living room, dining room, kitchen, separate breakfast area, sunroom and half bath on the first floor; three bedrooms, two full baths and laundry room on the second floor; and with two windowed bedrooms and full bath in the partially finished basement. The internal layout on all floors is capable of being reconfigured to create newly sized living areas. Exterior renovations including a rear addition and new garage are also possible, subject to Board of Architectural Review approval due to the property being in a historic district. The property is being sold AS-IS, and the seller makes no representations or warranties regarding the property or its condition. The home was occupied by the same family for several decades, with the seller acquiring the property in the fall of 2025. This property offers a rare, if not once in a lifetime, opportunity to create your dream home by renovating this historic Lexington treasure in an exceptional location. Possession and closing date are negotiable. Kitchen and bathroom added to room count but are part of the potential remodel.
…$722,450324m²3bedrooms4bathroomsland 834m²By Bluegrass Sotheby's International Realty
- 50
House Lexington (United States)
Craftsman Cottage gem in Lexington's favorite neighborhood within a park-like setting in the heart of Kenwick. Lovingly maintained by the same owner for nearly 40 years, this move-in ready home pairs a beautifully maintained and updated home which includes a new roof, custom chef's kitchen and bath with the timeless character of a 1920s Craftsman home. Period-style replacement windows, gorgeous honey-colored original hardwood floors, tall ceilings, beautiful millwork and wide arched doorways. The renovated eat-in kitchen features a second sink, ideal for the serious chef or entertaining. A spacious dining room with French doors opens to the private deck, and the living room offers a fireplace with cozy gas logs. A sunny bonus room on the first floor makes the perfect home office. Upstairs you'll find a beautifully renovated bath and two bedrooms, including an oversized bedroom with tremendous flexibility and potential. Outside, the oasis-like backyard is filled with mature perennials, a peaceful water feature, potting sink, garden and flower beds to enjoy fresh-cut flowers from spring to fall! Given Avenue is a quiet gateway to the vibrant National Avenue corridor, where dining, shopping and entertainment are just steps away. Enjoy dinner at Epping's, Trivia Night at Mirror Twin, or warm sourdough bread from Wild Lab just to name just a few neighborhood favorites. A bike ride away from Downtown or UK the 2-car garage might just be used for storage because who needs a car?! A rare two-story Craftsman in a neighborhood known for its bungalows, this home is as inviting as it is distinctive, from the welcoming front porch to the beautifully landscaped backyard. Don't miss this opportunity to experience the best of Kenwick living.
…$485,0002bedrooms1bathroomland 409m²By Bluegrass Sotheby's International Realty
- 47Video
Farmhouse Lexington (United States)
What an opportunity as few properties in the Bluegrass carry Castleton Farm's pedigree. Established in 1793, this storied land has been shaped by generations of Kentucky's great horsemen — from a U.S. Senator's original breeding operation to the Castleman family's 1840 Greek Revival mansion, which still stands as a landmark of the farm today. Over two centuries, Castleton bred and stood champions across three breeds — Thoroughbreds, Standardbreds, and Saddlebreds — cementing its place among the Bluegrass's most storied nurseries. Today, the farm spans 951 acres and offers an unmatched scale of infrastructure: 16 barns ranging from intimate 4-stall setups to a substantial 30-stall facility, totaling 268 stalls. Ten homes across the property — including several managers' houses — provide ample accommodation for staff, making Castleton as functional as it is historic. This is more than a horse farm; it's a self-sufficient equine operation with two centuries of pedigree behind it, offered for the first time in 25 years to a new steward.
…$57,500,0007bedrooms6bathroomsland 385.1haBy Bluegrass Sotheby's International Realty
- 31
Apartment Lexington (United States)
Welcome to elevated downtown living at Main & Rose! Unit 307 offers the perfect blend of convenience, style, and lifestyle in one of Lexington's most desirable locations. This beautifully appointed 1 bedroom, 1 bathroom residence features stunning city views, modern finishes, and an unbeatable location just steps from Lexington's best dining, entertainment, shopping, and nightlife. Enjoy amenities rarely found in downtown living, including secure access, fitness facilities, resident spaces, and more. Whether you're looking for a low-maintenance home, a downtown retreat, or a premier investment opportunity, this unit delivers a truly unique living experience in the heart of Lexington.
…$265,0001bedroom1bathroomBy Bluegrass Sotheby's International Realty
- 50
House Lexington (United States)
Rare opportunity to own a beautifully updated triplex in Lexington's highly sought-after Chevy Chase neighborhood. 304-306 Ridgeway Drive features three 1BR/1BA units and is being sold partially furnished. Ideally located just steps from the University of Kentucky, downtown Lexington, UK HealthCare, restaurants, shopping, and entertainment. With thoughtful updates and an unbeatable location, this property offers incredible flexibility and a unique opportunity to own in one of Lexington's most desirable areas.
…$715,0003bedrooms3bathroomsland 696m²By Bluegrass Sotheby's International Realty
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