Gainesway Real Estate

Gainesway Real Estate

Welcome to Gainesway, a prestigious subdivision nestled in the heart of Lexington, Fayette County, Kentucky. Known for its picturesque surroundings and upscale living, Gainesway offers an unparalleled lifestyle for those seeking tranquility and luxury.

Located in the vibrant city of Lexington, Gainesway provides residents with easy access to a wide array of amenities, including top-rated schools, shopping centers, dining options, and entertainment venues. The community is also renowned for its well-maintained streets, lush green spaces, and friendly atmosphere, making it an ideal place to call home.

Gainesway is a haven for nature lovers, with beautiful parks, walking trails, and scenic views right at your doorstep. Whether you enjoy a leisurely stroll through the neighborhood or prefer to relax in the comfort of your own backyard, Gainesway offers something for everyone.

With its convenient location, upscale amenities, and serene atmosphere, Gainesway is the perfect place to settle down and create lasting memories. Come and experience the charm and elegance of Gainesway – where luxury meets tranquility in the heart of Lexington, Kentucky.

Newest Listings in Gainesway

1026 Claiborne Way, Lexington
$395,000
4 Beds ⋅ 2 Baths ⋅ 26028444 MLS
Welcome to 1026 Claiborne Way! This charming 1.5-story brick Cape Cod in popular Gainesway offers plenty of finished living space that is packed with several updates! Come inside to find a welcoming entry foyer, hardwood flooring, and cozy wood-burning fireplaces in both the living room and lower level. The main floor features convenient bedroom accommodations and a full bathroom, while upstairs boasts two additional bedrooms and a beautifully remodeled full bathroom (2026). The kitchen comes equipped with a new dishwasher (2024) and opens directly out to a newly replaced deck platform, which leads down to a custom stone patio (2024) and a generous, fenced backyard—ideal for outdoor entertaining! Additional peace of mind comes from a replaced HVAC system (2023) and new gutters (2022). Downstairs, the basement provides a flexible second living area, laundry, dedicated unfinished storage, and a rear-entry 1-car garage. All located just minutes from Tates Creek Road, parks, shopping, and New Circle Road. Schedule your private showing today!

1026 Claiborne Way, Lexington
1009 Castleton Way, Lexington
$419,900
3 Beds ⋅ 3 Baths ⋅ 26027719 MLS
Classic Colonial Living in the Heart of Lexington A rare opportunity in the established Gainesway neighborhood, this classic two-story Colonial offers timeless design, stately features, and an exceptional Lexington location. Ideally positioned just steps from New Circle Road access and convenient to shopping, schools, restaurants, parks, UK, the Arboretum, and downtown, this home puts the best of Lexington within easy reach. Inside, classic architectural details and traditional character create a strong foundation for a new owner to make the home uniquely their own. The spacious two-story design offers the versatility and scale today's buyers appreciate, while the established setting provides the mature neighborhood atmosphere that is increasingly difficult to find. Whether you're drawn to its classic Colonial character, convenient location, or the opportunity to bring your own vision to a well-established home, this is a property worth seeing. A rare chance to own in Gainesway and create something truly your own in the heart of Lexington.

1009 Castleton Way, Lexington
1046 Elmendorf Dr, Lexington
$379,900
3 Beds ⋅ 3 Baths ⋅ 26027723 MLS
Welcome home to this beautifully updated 3-bedroom, 2.5-bath home, offering plenty of space and thoughtful features throughout! The spacious kitchen is a standout, featuring an abundance of cabinet space, tile backsplash, and stainless steel appliances. The comfortable primary suite includes a private bath, while two additional generously sized bedrooms provide plenty of room for family, guests, or a home office. The home also features a gorgeous tile walk-in shower. The partially finished basement offers even more versatility, with an additional room that could easily serve as a 4th bedroom, home office, playroom, or flex space. The large garage is a true bonus, featuring a separate workshop area complete with cabinets, along with additional unfinished storage space for all your organizational needs. Inside, the inviting living room offers a cozy fireplace with gas logs and a convenient remote for easy operation. Outside, you'll love the large, fully fenced lot, providing plenty of space for entertaining, relaxing, or letting the pets play. Speaking of pets, the home also features a convenient dog wash, which could easily be converted back to a utility sink if desired. Best of all, this home is move-in ready with major updates already taken care of. The roof, furnace, and water heater are all less than a year old, giving you added peace of mind from day one. With its spacious layout, updated features, flexible living spaces, large garage, and expansive fenced yard, this home truly has so much to offer. Schedule your private showing today before it is gone! Special financing available through the Neighborhood Housing Program for this property!

1046 Elmendorf Dr, Lexington
3475 Greentree Rd, Lexington
$325,000
3 Beds ⋅ 2 Baths ⋅ 26027364 MLS
This stylish 3BR/2BA home has been carefully updated throughout and offers a unique floor plan made for lasting memories. Strong curb appeal draws you in, and the handsome details inside will make you want to stay. Luxury vinyl plank flooring flows from the living room into the open kitchen, which features white cabinetry, updated stainless steel appliances, a farmhouse sink, and a breakfast bar. The kitchen opens to a large dining area and a cozy octagonal den with plush carpet, overlooking the backyard. Tucked away on the opposite side of the home are three bedrooms and two full baths, including a primary suite with a private bath. All bedrooms feature luxury vinyl plank flooring and fresh neutral paint. Outside, a spacious side deck and patio overlook a private, park-like yard with mature trees, established landscaping, and privacy fencing. It's a peaceful retreat in the heart of convenient Gainesway, just minutes from the University of Kentucky, downtown Lexington, Kroger Field, and The Arboretum.

3475 Greentree Rd, Lexington
1044 Elmendorf Dr, Lexington
$312,000
3 Beds ⋅ 2 Baths ⋅ 26026845 MLS
Welcome home to this 3 bedroom, 1.5 bathroom ranch just outside New Circle Road, where everyday convenience meets breathing room. The large covered porch with a swing is ready for morning coffee or chats with neighbors, overlooking welcoming and green landscaping. Step inside to an open layout designed for entertaining. The living area flows easily into the surrounding dining and kitchen spaces, so hosting friends and family feels effortless. Brand-new custom built-in bookcases frame the living room, adding warmth, character, and plenty of space for your books, collections, and favorite décor. A versatile bonus room gives you flexibility to fit your lifestyle: home office, playroom, reading nook, or media lounge. Out back, the spacious lot is a rare find. Plant a vegetable garden, cultivate flower beds, or give pets plenty of room to roam. A brand-new, oversized shed on leveled foundation provides ample storage for tools, lawn equipment, and weekend projects. Sellers are leaving everything you need to make the yard your own - electric wheelbarrow, mower, trimmer, and other yard tools, most are less than one year old. Single-level living and outdoor space to spare, all in a convenient location.

1044 Elmendorf Dr, Lexington
1295 Oaklawn Park, Lexington
$349,000
3 Beds ⋅ 3 Baths ⋅ 26026546 MLS
Nestled on a quiet cul-de-sac, this beautifully updated 3-bedroom, 2.5-bath home perfectly blends comfort, style, and functionality. Fresh updates throughout include new flooring, countertops, appliances, and paint, creating a bright and welcoming space that's ready to call home. The finished basement offers even more room to spread out, featuring a spacious bar area, laundry room, and a versatile bonus room that could serve as a fourth bedroom, home office, or playroom. Step outside to enjoy the beautifully landscaped yard, perfect for relaxing or entertaining. Complete with a huge 2-car garage with workbench and a peaceful cul-de-sac location, this home offers the perfect combination of modern updates, flexible living space, and curb appeal. Schedule your showing today!

1295 Oaklawn Park, Lexington
3486 Sutherland Dr, Lexington
$173,500
3 Beds ⋅ 3 Baths ⋅ 26026335 MLS
Rare Find in Gainesway! This spacious 3-bedroom, 2.5-bath townhome offers comfortable, low-maintenance living in Lexington's established Gainesway neighborhood. Well cared for and move-in ready, the home features an HVAC system and water heater both approximately six years old, along with newer French doors at the back of the home that add both style and functionality. The townhome includes two dedicated parking spaces, and the HOA covers lawn care, snow removal, access to the pool, and clubhouse. Even better, the pool is just steps from the back door, making it incredibly convenient to enjoy during the warmer months. With three bedrooms, two full baths plus a half bath, updated mechanicals, newer French doors, community amenities, and a great location within Gainesway, this townhome is a rare opportunity. **Schedule your showing today!**

3486 Sutherland Dr, Lexington
1011 Castleton Way, Lexington
$398,000
3 Beds ⋅ 3 Baths ⋅ 26026323 MLS
Wonderful opportunity on this 3 bedroom 2.5 bathroom home conveniently located in Gainesway Neighborhood offering incredible curb appeal, inviting floorplan with entry foyer, living room, dining room, Kitchen with island, half bath and large family room with fireplace, the upper level offers 3 bedrooms and full bathroom, the lower level offers den, full bathroom, utility area and garage. Numerous updates and amenities including new roof shingles in 2022 (per-sellers). The rear patio overlooks large, fenced yard. First time offer in over 29 years Don't miss this very special home!!

1011 Castleton Way, Lexington
3528 Winding Dr, Lexington
$319,900
3 Beds ⋅ 2 Baths ⋅ 26026174 MLS
Charming Gainesway ranch with inviting spaces and thoughtful updates! This 3-bedroom, 2-bath home welcomes you into the foyer with a convenient drop zone. The separate dining area is perfect for gatherings, while the granite kitchen features under-cabinet lighting and plenty of functionality. New carpet in both guest bedrooms adds a fresh touch. Enjoy relaxing or exercising in the sunroom overlooking the backyard, complete with a ceiling fan for added comfort. Step outside to the patio and beautifully mature landscaping, creating a private and enjoyable outdoor setting. A utility room and separate storage room off the back provide excellent everyday convenience, with plenty of space for lawn equipment, tools, or extra storage. A wonderful opportunity to enjoy comfortable one-level living in an established Lexington neighborhood!

3528 Winding Dr, Lexington
3411 Pimlico Pkwy, Lexington
$379,000
4 Beds ⋅ 3 Baths ⋅ 26025823 MLS
Improved price! This inviting home blends classic character with comfortable, everyday living. Thoughtfully designed and lovingly maintained, this home is being offered to the market for the first time in nearly 50 years! Stately double doors welcome you into the heart of the home. The spacious living room features a striking brick fireplace that creates a warm focal point, while large windows bring in plenty of natural light. The living room is large enough to allow for multiple uses like a game room or home office. The kitchen offers an abundance of rich wood cabinetry, generous granite countertops, and a practical layout with a breakfast bar overlooking the adjoining dining space overlooking the large backyard. A first floor bedroom suite and separate laundry room finish of the first floor. Upstairs you will find three large bedrooms, including the primary suite with walk-in closet, and another full bath that is easily accessible from the hallway or adjoining bedroom. The flexible floorplan offers plenty of options for today's lifestyle, including a dedicated dance room with hardwood floors that could easily serve as a home gym, studio, office, playroom, or creative space. Charming details throughout, including traditional millwork, paneled cabinetry, and distinctive finishes, add personality and timeless appeal. With its comfortable living spaces, welcoming atmosphere, and classic style, this home offers a wonderful opportunity to make it your own. Within walking distance to Tates Creek Golf Course and Tates Creek Aquatic Center, this home has it all!

3411 Pimlico Pkwy, Lexington
3187 Aqueduct Dr Unit A & B, Lexington
$300,000
4 Beds ⋅ 4 Baths ⋅ 26025792 MLS
Investment property just outside New Circle Rd. Each side includes 2 bedrooms and 1 1/2 bathrooms. Vaulted ceilings in the living areas. Bedrooms on lower level. Both units occupied. Current rents, unit A: $1,050, unit B: $1,095.

3187 Aqueduct Dr Unit A & B, Lexington
3343 Sutherland Dr, Lexington
$279,900
4 Beds ⋅ 2 Baths ⋅ 26024837 MLS
Back on the market due to previous buyers financing falling through no fault of sellers!! This spacious 4-bed, 1.5 bath home featuring beautiful updates and a functional layout. The newly renovated full bathroom offers double sinks and ample storage, making busy mornings a breeze. Hardwood floors extend throughout the main and second levels, while the recently installed carpet in the lower level creates a warm and inviting family room complete with a cozy fireplace and access to the bright sunroom. The welcoming foyer features a convenient nook for shoes, coats and everyday essentials. Just off the foyer, you'll find a comfortable family room that is adjacent to the large kitchen and dining area. A door leads to an expansive patio-perfect for entertaining, grilling, and enjoying the privacy of the backyard. Natural light fills the home, and the sunroom provides additional living space to relax. Three bedrooms are located on the second level, while the fourth bedroom is situated on the lower level, directly across from the half bath, making it an ideal guest room, home office or private retreat. This well-maintained home offers the prefect combination of comfort, style and space for everyday living and entertaining.

3343 Sutherland Dr, Lexington
Start Your Search

How much is your home worth?

Get instant property value now!