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

$365,000
3 Beds ⋅ 3 Baths ⋅ 26019889 MLS
Find peace in Gainesway, one of South Lexington's most established and desirable neighborhoods. Tucked away on a quiet dead-end street surrounded by mature trees, this beautifully updated home offers the perfect blend of privacy, comfort, and convenience. Inside, you'll find a renovated kitchen with quartz countertops, stainless steel appliances, and an inviting dining area. Spacious bedrooms, a versatile flex room, and a bright sunroom with remote-controlled skylight shades provide flexible living spaces filled with natural light. The primary suite features an updated bath with dual vanities, while a new HVAC system and newer roof offer added peace of mind. Step outside to a private patio overlooking the partially fenced, tree-lined backyard. Ideally located just minutes from New Circle Road, the University of Kentucky, shopping, dining, and parks, this move-in-ready home delivers the lifestyle buyers are looking for in the heart of South Lexington.

3512 Winding Dr, Lexington
$325,000
4 Beds ⋅ 2 Baths ⋅ 26019755 MLS
Tucked away on a quiet cul-de-sac in the established Gainesway neighborhood, 3279 Waterford Park is a warm and welcoming four-bedroom, two-bath brick home filled with character, flexible living space, and an exceptional backyard designed to be enjoyed. From the memorable red front door to the mature trees surrounding the property, this is a home that feels comfortable and familiar from the moment you arrive. Step inside to a bright interior featuring hardwood floors, detailed trim, crown molding, and a traditional floor plan that provides plenty of room for everyday living without sacrificing the charm of defined spaces. The spacious front living area features built-in shelving and offers the flexibility to serve as a second sitting room, home office, library, playroom, music room, or creative space. Large windows bring in natural light, while the easy connection to the nearby dining room allows the front of the home to feel open and inviting. The formal dining room provides a natural setting for everything from quiet weeknight meals to holidays and gatherings with friends. It connects easily to the kitchen, creating a comfortable flow through the center of the home. Exceptionally well maintained and fully functional, the kitchen offers abundant cabinetry, generous workspace, stainless steel appliances, and a center island with seating for casual meals, conversation, or morning coffee. At the back of the home, the family room becomes the true heart of the house. A substantial stone fireplace and built-in shelving create a warm focal point and give the room the kind of character that makes you want to settle in and stay awhile. Whether it is a quiet evening by the fire, a movie night, or time spent entertaining, this space feels comfortable, inviting, and connected to the rest of the home. French doors open directly from the family room onto the expansive covered porch, creating a seamless connection between the indoor and outdoor living spaces. More than simply a place to step outside, the porch feels like an additional living room. There is plenty of space to relax with a cup of coffee, host a weekend cookout, enjoy the sound of a summer rain, or unwind at the end of the day while looking out over the backyard. The outdoor space is one of the property's most memorable features. The large, fully fenced yard is framed by mature shade trees and established landscaping, offering a sense of privacy along with an impressive amount of usable space. There is room to entertain, garden, play, or simply enjoy the outdoors without feeling crowded. A built-in firepit creates a second gathering area for cool evenings and long conversations, while the broad lawn provides endless possibilities for recreation or future outdoor projects. A large storage shed adds valuable space for tools, lawn equipment, bicycles, and seasonal belongings without taking away from the beauty or function of the yard. Inside, four bedrooms and multiple flexible living areas provide options for guests, work, hobbies, or changing needs. The spacious primary bedroom features hardwood flooring, crown molding, multiple windows, and enough room for substantial furniture without feeling crowded. A dedicated laundry area and additional versatile spaces add everyday convenience while preserving the welcoming personality found throughout the home. Important recent improvements offer added peace of mind, including a new roof installed in June 2026, a new water heater in 2026, and an air-conditioning system replaced in 2024. The heating system has been regularly serviced and inspected and is in good working order. Comfortable, well cared for, and full of warmth, 3279 Waterford Park is more than a collection of rooms. It is a home with inviting spaces, a fireplace that draws people together, a covered porch that encourages you to slow down, and a backyard that gives you every reason to stay awhile.

3279 Waterford Park, Lexington
$399,000
4 Beds ⋅ 2 Baths ⋅ 26019645 MLS
Welcome to 3337 Crown Crest Road, a beautifully updated 4-bedroom, 2-bath brick ranch that rests on a basement. This home offers the perfect blend of classic charm with a modern touch while centrally located in the Gainesway neighborhood on a low traffic street. Inside, you'll find an open concept, hardwood flooring and a beautifully renovated kitchen featuring quartz counters and a sizable butcher block island. A functional layout designed for everyday living and entertaining. Down the hall, you have 2-bedrooms, a full bathroom, and your primary suite with an en suite bedroom. The full finished basement provides flexibility with additional living space, including a fourth room that can serve as a bedroom, office, or workout space. Outside you'll enjoy a welcoming front porch, spacious backyard, and a covered back deck perfect for relaxing or entertaining. The attached rear-entry garage enhances curb appeal while providing added convenience. Ideally situated less than five minutes from New Circle Road, Tates Creek Golf Course, Lansdowne Shoppes, Kroger, and more. Don't miss your opportunity to make this centrally located gem your own!

3337 Crown Crest Rd, Lexington
$182,000
2 Beds ⋅ 2 Baths ⋅ 26019529 MLS
Seller has loved this townhome for 26 years. Wonderful easy living community with HOA of only $87 a month includes a swimming pool, clubhouse, snow removal, and mowing. Downstairs features a living room, dining area, kitchen and half bathroom. Seller has installed beautiful built-in custom cabinetry in the dining and living areas. Upstairs there are two spacious bedrooms and a full bathroom. Small enclosed patio off the back with professional landscaping designed to route any water away from the home. Roof was installed in 2025. Come check it out!

3462 Sutherland Dr, Lexington
$375,000
4 Beds ⋅ 2 Baths ⋅ 26019457 MLS
Welcome to 1288 Gainesway Drive! This spacious 4-bedroom, 2-full-bath home offers 2,750+ sq. ft. of finished living space in the heart of Southeast Lexington. Step inside to find rich hardwood flooring, a welcoming entrance foyer, and a cozy living room featuring one of two masonry fireplaces. The light-filled main level flows seamlessly into a well-appointed kitchen equipped with a range, dishwasher, and refrigerator. Downstairs, the finished walk-out basement doubles your entertaining options with a secondary living space, wet bar, and a second fireplace - perfect for movie nights or hosting guests. Outside, enjoy a lush, tree-lined yard from your choice of the covered porch, deck, or patio. Complete with an attached garage and carport, this move-in-ready home sits just minutes from local parks, pools, Chinoe Kroger and Tates Creek schools. Schedule your private showing today!

1288 Gainesway Dr, Lexington
$340,000
2 Beds ⋅ 2 Baths ⋅ 26019329 MLS
Beautifully updated brick ranch with private primary suite with attached primary bath, a flexible floor plan, and a backyard oasis. This move-in ready home offers comfort, versatility, and effortless living in one of Lexington's most convenient locations!

3527 Greentree Rd, Lexington
$349,900
3 Beds ⋅ 2 Baths ⋅ 26018650 MLS
Gainesway subdivision is one of the most sought after in Lexington! 3475 Greentree Road is located close to all you need with grocery stores, schools, restaurants, and recreation close by. One level living in a newly remodeled home with 3 brs, 2 full baths, Large kitchen with new appliances, the versatility of this ranch allows a family to live together in many ways: formal living area, spacious dining room that opens to a side exterior patio and a large family room for the kids to play. Good size two car garage that opens to the kitchen. You'll love all aspects of how you can live in this ranch home!

3475 Greentree Rd, Lexington
$419,900
3 Beds ⋅ 3 Baths ⋅ 26017097 MLS
Don't miss this beautifully remodeled home in the heart of Lexington! Gorgeous hardwood floors welcome you into a home that perfectly blends timeless charm with modern style. The stunning kitchen features quartz countertops, stainless steel appliances, and opens to the spacious yet cozy family room with a wood-burning fireplace and an abundance of natural light. The primary suite is a true retreat, complete with a beautifully updated ensuite featuring a tiled glass shower, double vanity, and a walk-in closet. Two additional bedrooms and a bright, updated full bath complete the main level. Need extra space? The finished basement offers endless possibilities with a large flex area and its own full bathroom, ideal for a home office, recreation room, gym, or guest space. The outdoor living is just as impressive! Relax year-round in the oversized three-season room, or step outside to enjoy the private, fenced backyard that feels like your own peaceful retreat. Schedule your private showing today! OPEN HOUSE: Sunday 07/26 from 2PM-4PM.

3303 Pimlico Pkwy, Lexington
$299,000
5 Beds ⋅ 2 Baths ⋅ 26015081 MLS
Lovingly cared for and updated by the same family for more than 50 years, this brick ranch on a finished walk-up basement offers a lot of living space and a modern floor plan in convenient and established Gainesway neighborhood. Walls were removed to create the open floorplan Buyers love featuring a spacious kitchen with tons of cabinetry and countertops, and an island that provides perfect prep space for the home chef. Natural light from the replacement windows fills the great room highlighting the original hardwood floors. Three bedrooms on the first floor, including one with added shelving and washer/dryer hookups that could easily serve as a generous laundry room or walk-in closet. The updated full bath features a walk-in shower. Finished walk-up basement expands the living area with two additional bedrooms, full bath, a family room with a wood-burning fireplace insert and a large unfinished workshop perfect for hobbies, projects, or additional storage. The outdoor space offers privacy and a spacious deck overlooking a peaceful, park-like yard with mature trees and established landscaping. 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.

3418 Greentree Rd, Lexington
$399,000
4 Beds ⋅ 3 Baths ⋅ 26013135 MLS
Welcome to 3508 Arden Place, a beautifully remodeled ranch on a walk-out basement in the highly sought-after Gainesway neighborhood. Thoughtfully updated from top to bottom, this home has a trendy, artistic edge while still holding onto its classic charm, blending character with modern designer finishes throughout. The remodeled kitchen features butcher block countertops, a farmhouse sink, stainless steel appliances, a low-profile microwave, and a timeless checkered tile floor. The wall between the kitchen and living room has been opened up, creating a brighter, more connected layout that feels perfect for everyday living and entertaining. The main level offers three bedrooms and a stunning fully remodeled hallway bathroom with floor-to-ceiling 2x4 tile, a white oak double-bowl mitered vanity, two free-mounted mirrors, designer sconces, a soaking tub, a walk-in tile shower, and champagne bronze fixtures. The remodeled half bath adds even more style with a checkered tile floor and a single-bowl mitered vanity. Downstairs, the finished walk-out basement provides incredible additional living space, featuring a spacious recreation room with its own fireplace, an adjacent bedroom or flex room, a full bathroom with a new tile surround, and convenient access to the backyard. The laundry room includes a new tankless water heater. With a newer roof, newer HVAC system, updated finishes, multiple living spaces, and a highly desirable Gainesway location, this home is truly move-in ready. Homes with this level of style and updates do not come along often — do not delay.

3508 Arden Pl, Lexington
$215,000
2 Beds ⋅ 2 Baths ⋅ 26014340 MLS
Welcome home to this well-maintained property in the heart of Lexington! Featuring beautiful luxury vinyl plank flooring and tile throughout, this home offers 2 spacious bedrooms, 1 full bathroom, and 1 half bathroom, providing both comfort and functionality. Enjoy relaxing evenings by the fireplace in the large living room, perfect for entertaining or unwinding after a long day. The eat-in kitchen offers ample dining space and is equipped with a brand-new oven and dishwasher. Several windows and doors have been updated, adding to the home's appeal. Conveniently located near shopping, dining, parks, schools, and major roadways, this home offers easy access to everything Lexington has to offer while being tucked away in an established neighborhood. Don't miss the opportunity to make this charming property your own!

3195 Aqueduct Dr, Lexington
$355,000
4 Beds ⋅ 2 Baths ⋅ 26013703 MLS
Welcome home to this beautifully updated ranch offering space, comfort, and versatility! Featuring 4 bedrooms and 2 full bathrooms, including a desirable first-floor primary suite with a private en-suite bath, this home provides a functional layout designed for everyday living. The heart of the home is the oversized eat-in kitchen, recently updated with beautiful new cabinetry and plenty of space for gathering with family and friends. Gorgeous hardwood floors flow throughout the main level, adding warmth and timeless character. The full walk-out basement provides an abundance of additional living space, featuring a large great room perfect for entertaining, relaxing, or hosting game-day gatherings. An additional finished room offers endless possibilities as a home office, craft room, playroom, fitness space, or hobby room. Step outside and discover your own backyard retreat! A large deck overlooks the expansive, flat, fully fenced backyard, providing the perfect setting for outdoor dining, summer cookouts, and family gatherings. The outdoor brick BBQ grill adds charm and functionality, making this backyard an entertainer's dream. With generous living areas, beautiful hardwood floors, an updated kitchen, flexible basement space, and an incredible outdoor living area, this move-in-ready ranch offers the perfect combination of comfort, convenience, and lifestyle. Don't miss your chance to make this exceptional property your new home! Co-owner is a licensed real estate agent in the state of KY.

3320 High Hope Rd, Lexington
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