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609 Portland Dr, Lexington
$339,500
3 Beds ⋅ 3 Baths ⋅ 26022764 MLS
ONLINE ONLY ABSOLUTE AUCTION!!! Online BIDDING ENDS Wednesday, September 23, 2026 at 12:00PM. Terms & Conditions are as follows: As Is/Non-Contingent/10% earnest money deposit/30 day settlement/buyer's premium applies, see terms & conditions for details. Visit www.HalfhillAuctions.com for more information. Kristin Halfhill-Larimore, Principal Auctioneer, 859-333-1855. A Timeless Lexington Charmer Full of Heart & Original Character! Step inside this truly special home and you'll feel the warmth of a place that has been lovingly lived in and cared for for generations. A wonderful example of a home that has retained its original charm, this property is almost like stepping into a time capsule—with vintage details and character you simply can't recreate. The huge front porch immediately sets the tone, offering the perfect spot for morning coffee, visiting with neighbors, or relaxing at the end of the day. Inside, you'll find a home filled with personality, including an adorable original pink bathroom that is sure to make you smile. The kitchen is especially inviting, with large windows that bring in beautiful natural light and look out toward the expansive backyard. Outside, the possibilities continue with a huge backyard, complete with a covered porch that's ideal for gatherings, gardening, or simply enjoying the seasons. The long wrap-around driveway provides plenty of parking and adds to the property's welcoming, tucked-away feel. And the location is hard to beat—inside New Circle Road in the Twin Oaks area, with convenient access to everything Lexington has to offer. This is more than just a house; it's a home with a story. Whether you're looking to make new family memories in a home with room to grow or you're someone who appreciates the charm, quirks, and craftsmanship of an earlier era, this one is truly worth seeing. Come make the next chapter of its story your own!

609 Portland Dr, Lexington

1056 Winding Oak Trl, Lexington
$299,000
3 Beds ⋅ 2 Baths ⋅ 26021752 MLS
There's a lot to love inside this home, but the backyard may steal the show. Backing to the equestrian section of Masterson Station Park, this home offers an uncommon sense of openness and privacy, along with beautiful sunset views and direct backyard access to a park walking trail. An expanded patio gives you even more space to take advantage of the setting. Inside, the updates go well beyond the obvious. Herringbone-pattern LVP flooring runs throughout the home, and thoughtful improvements have been carried from room to room—from updated lighting and plumbing fixtures to coordinated interior hardware, including door handles and hinges. Even the toilets have been replaced. The result is a home that feels fresh, cohesive and exceptionally well finished. The upgraded kitchen features a quartz-topped island, black farmhouse sink with touch faucet, soft-close cabinetry and convenient pull-out drawers. All LG kitchen appliances were replaced in 2024, and the all-in-one washer/dryer conveys. The location also puts shopping, dining and everyday conveniences along the Leestown Road corridor within easy reach. Updated from the finishes you immediately notice to the small details you normally don't, this is a home where much of the work has already been done. And with Masterson Station Park just beyond the backyard, the setting may be the upgrade you appreciate most.

1056 Winding Oak Trl, Lexington

194 Rosemont, Lexington
$347,400
3 Beds ⋅ 2 Baths ⋅ 26022483 MLS
Turnkey and move-in ready! This beautifully renovated and thoughtfully expanded 3-bedroom, 2-bath home offers 1,262 sq. ft. of finished living space with fresh, modern finishes throughout. Extensive updates include a new HVAC system, windows, plumbing, cabinetry, quartz countertops, laminate flooring, tile showers, and updated drywall and ceilings. The newly finished upper level adds valuable living space with an additional bedroom and full bath. From the moment you move in, the work has already been done, simply unpack and enjoy. The bright, refreshed interior offers a functional layout with stylish finishes throughout, while the encapsulated basement features water-management improvements for added peace of mind. Outside, you'll find a newly paved driveway with parking spaces. The fenced in backyard offers plenty of space for entertaining, pets, gardening, or relaxing at home. With three bedrooms, two full baths, a basement, fenced yard, and extensive improvements inside and out, this truly turnkey property offers the opportunity to move in and enjoy your new home from day one!

194 Rosemont, Lexington

525 Patterson St, Lexington
$299,000
3 Beds ⋅ 1 Baths ⋅ 26022649 MLS
Welcome to 525 Patterson Street, a move-in-ready home perfectly positioned in the heart of downtown Lexington! This updated property features 3 bedrooms and 1 bathroom, offering a comfortable and functional layout with modern updates throughout. Location is the standout here—you're within walking distance of the University of Kentucky campus, downtown Lexington, Rupp Arena, Gatton Park, and some of the city's best dining, entertainment, and attractions. Outside, the home sits on a rare double lot, providing extra outdoor space and added possibilities that are hard to find this close to downtown. Whether you're looking for a primary residence or an investment opportunity, 525 Patterson Street combines an unbeatable location, move-in-ready condition, and exceptional lot size—all in one property.

525 Patterson St, Lexington

384 Stone Creek Dr, Lexington
$299,000
3 Beds ⋅ 2 Baths ⋅ 26022341 MLS
Welcome home to Stone Creek, one of Lexington's most sought-after neighborhoods. This adorable 3-bedroom, 2-bath home sits on a corner lot with 0.225 acres, giving you extra privacy and room to spread out. Inside, an open floor plan and vaulted ceilings create a bright, airy feel, while tasteful neutral decor makes it easy to move in and make it your own. A stone fireplace serves as the centerpiece of the living room, and the kitchen, living room, and separate dining room all flow together, ideal for entertaining. The primary suite features double closets and a walk-in tile shower in the primary bath. A large laundry room offers plenty of extra storage space. The 2-car side entry garage keeps curb appeal front and center and comes equipped with an electric car charger, ready for your EV. Out back, enjoy a concrete patio and fenced yard, perfect for pets, play, or relaxing outside. Built in 1990 and just under 1,526 square feet, this home offers a comfortable, low-maintenance layout in a corner-lot setting, all within the Stone Creek community. Zoned for Stonewall Elementary, Jessie Clark Middle School, and Lafayette High School. Schedule your showing today!

384 Stone Creek Dr, Lexington

1748 Brook Park Dr, Lexington
$329,900
3 Beds ⋅ 3 Baths ⋅ 26022539 MLS
PRICED AT APPRAISAL! Squire Oak! What a hidden gem! 2-story situated on a tree-lined court with a huge yard with wild flowers and more backing to a farm. This 3-bedroom features 2.5 baths on a full, partially finished basement. The first floor has nice dining area, a front-to-back large living space with doors that open to the wonderful backyard with patio seating area and double trellises. You will feel as though you are visiting the arboretum. Large kitchen with seating area and built-ins, also a walkout to the backyard. The basement area has a family room with built-ins, a recreation area, and a utility storage room. Also includes a 1-car garage. Updates to the home, bathrooms updated 5 years ago, and windows replaced 8 years ago.

1748 Brook Park Dr, Lexington

1121 Parliament Way, Lexington
$255,000
2 Beds ⋅ 2 Baths ⋅ 26022390 MLS
Welcome to 1121 Parliament Way! This charming 2 bedroom, 2 full bath home offers 1,088 square feet of comfortable, easy-to-maintain living space in a convenient Lexington location. The functional layout provides plenty of flexibility, with two full bathrooms making the home ideal for a variety of living arrangements. Step outside to enjoy the fenced-in backyard, offering a private space for relaxing, entertaining, pets, or outdoor activities. Conveniently located near shopping, dining, and everyday necessities, this home puts much of Lexington within easy reach. Whether you're a first-time buyer, downsizing, or simply looking for a low-maintenance home in a great location, this home is one you'll want to see!

1121 Parliament Way, Lexington

2460 Checkerberry Dr, Lexington
$294,900
3 Beds ⋅ 2 Baths ⋅ 26022381 MLS
Move-in ready, beautifully updated, and tucked away in a private setting, this ranch checks all the boxes! Step inside to a bright, welcoming layout designed for comfortable everyday living. The spacious kitchen features quartz countertops, a brand-new dishwasher, and opens seamlessly to the large living room, where an upgraded fireplace creates a warm and inviting gathering space. LVP flooring flows throughout the main living areas and bathrooms, while plush carpet adds comfort to all three generously sized bedrooms. The primary bedroom offers an ensuite bathroom and spacious walk-in closet. Step outside to enjoy the covered back deck overlooking the fully fenced, private backyard. A storage shed and an attached two-car garage offers additional space for all your outdoor essentials. Plus, a new roof and gutters provide added peace of mind. Conveniently located near all that Hamburg has to offer, you'll enjoy easy access to shopping, dining, entertainment, and everyday conveniences.

2460 Checkerberry Dr, Lexington

1401 Yosemite Cir, Lexington
$334,900
4 Beds ⋅ 2 Baths ⋅ 26022311 MLS
Welcome to your private oasis! Situated on a expansive tree lined lot at the end of a quite cul-de-sac, this immaculate 2,400 sq ft home is clean, fresh and ready for its next owner. Step inside to find extensive updates throughout, including fresh paint, newer light fixtures, and granite counter tops. The spacious kitchen flows seamless into the main living areas , while the inviting family room features a cozy fireplace with a classic brick hearth. The generous layout offers four bedrooms and two full bathrooms headlined by a massive fourth bedroom complete with a huge walk in closet. The outdoor living is where the property truly shines: step out to the massive, freshly re-stained deck to take in tranquil views of the private, mature treed backyard. The oversized yard also features a huge detached storage shed, offering endless space for tools, equipment, or hobbies. Spotless from top to bottom with unbelievable privacy and space, this one will not disappoint! Schedule your showing today!

1401 Yosemite Cir, Lexington

2414 Lake Park Rd Unit 1104, Lexington
$224,200
2 Beds ⋅ 2 Baths ⋅ 26022273 MLS
Resort-Style Waterfront Living inside New Circle Road: Experience everyday vacation vibes in one of Lexington's most unique gated communities. This stunning 2-bedroom, 2-bathroom condo perfectly blends low-maintenance luxury with premier waterfront access. Inside, the open layout features elegant countertops and easy access to everyday fun. Step directly outside to your private patio, which leads straight to the sparkling pool and serene lake waters.The community amenities offer an unmatched resort lifestyle. Launch your kayak or canoe from the private community dock, spend sunny afternoons lounging by the pool, or gather with friends around the community fire pit. Located in a prime, highly accessible location inside New Circle Road, this property delivers security, convenience, and a permanent escape from the everyday routine. Schedule an appointment for your showing today.

2414 Lake Park Rd Unit 1104, Lexington

1113 Ashford Ln, Lexington
$280,000
3 Beds ⋅ 3 Baths ⋅ 26022092 MLS
Experience the best of low-maintenance luxury in the heart of Lexington. This stunning 3-bedroom, 2.5-bathroom townhome offers a spacious and thoughtful floor plan designed for both comfort and entertaining. The main level features a massive living room perfect for hosting, flowing seamlessly into a beautifully updated kitchen. You'll love the modern aesthetic, highlighted by elegant granite countertops and premium finishes. The bathrooms have also been fully updated, providing a spa-like retreat throughout the home. Upstairs, you will find generously sized bedrooms that offer plenty of room to unwind. The property includes the convenience of an attached two-car garage, providing ample storage and secure parking. Best of all, enjoy a truly lock-and-leave lifestyle—your HOA takes care of all yard work, giving you more time to enjoy everything Lexington has to offer. Don't miss your chance to own this move-in-ready gem in a prime location!

1113 Ashford Ln, Lexington

3462 Sutherland Dr, Lexington
$180,000
2 Beds ⋅ 2 Baths ⋅ 26022144 MLS
Homeownership made easy! This well-maintained all-brick townhome offers the comfort, convenience's, and low-maintenance lifestyle you've been looking for. Featuring 2 bedrooms with generous closet space, dedicated parking, and a fully fenced private garden patio designed for easy outdoor enjoyment - morning coffee or intimate dinner. Inside, thoughtful custom built-ins add character and functionality, including a dining-area built-in hutch that's perfect for a coffee bar and living-room shelving ideal for books, albums, favorite collections, and additional storage closet. NOTE: All appliances remain for the new owner's convenience. Mechanical room, off the centrally located Powder Room, houses the water heater, panel box and furnace for easy filter change. Major updates include new roof shingles and new water heater in 2024. Lovingly maintained by the same owner for 26 years, the home has benefited from numerous improvements over the years, including updated light fixtures and ceiling fans, custom built-ins, new vanities and sinks, and more. For more details, see the attached thorough list of improvements. The HOA adds even more value with swimming pool, clubhouse, lawn mowing, and snow removal. Conveniently located near Kroger, restaurants, New Circle Road, and University of KY/Kroger Field and multiple hospitals, approximately 3.2 miles away, with Downtown and Rupp Arena approximately 5 miles away. Priced to offer an exceptional opportunity for homeownership while leaving room to add your own personal touches. Come see why this cozy, well-loved townhome could be the perfect place to settle in and make your own.

3462 Sutherland Dr, Lexington

493 Joseph Bryan Way, Lexington
$319,900
3 Beds ⋅ 2 Baths ⋅ 26022095 MLS
Welcome home to this beautifully maintained, move-in-ready property tucked away on a quiet dead-end street and backing to a private tree line! Fresh, clean, and thoughtfully updated, this home offers the perfect combination of comfort, privacy, and inviting spaces for everyday living and entertaining. Step inside to a spacious family room featuring a vaulted ceiling, recessed lighting, and a cozy corner ventless fireplace. The large kitchen offers plenty of room to cook and gather, along with a breakfast area, pantry with added lighting, and great functionality. Updated flooring and fresh paint throughout give the home a bright, refreshed feel. The primary suite features a private bath with a relaxing whirlpool tub. One of the highlights of the home is the screened-in porch—the perfect place to enjoy your morning coffee or unwind while overlooking the peaceful, tree-lined backyard. A gorgeous covered patio provides even more outdoor living and entertaining space. Additional features include an oversized 23-foot-deep garage, a large crawlspace with standing-height clearance offering excellent storage potential, and an HVAC system that's only approximately 3 years old. Located on a quiet street with no through traffic and a private backdrop, this well-cared-for home is ready for its next owner!

493 Joseph Bryan Way, Lexington

2848 Gateway Park Ln, Lexington
$299,900
3 Beds ⋅ 2 Baths ⋅ 26022068 MLS
Step into this charming 3-bedroom, 2-full-bath home in Masterson Station. The front door opens to a large living area with extremely high ceilings providing an open and inviting feel. The living room connects directly to the dining area/kitchen which features a breakfast bar and stainless appliances. Down the hall the private primary retreat includes a full bathroom and attached walk-in closet. The main level also includes a guest bedroom with another full bathroom and a laundry room which leads to the attached garage. Upstairs you'll find the spacious third bedroom. Outside, the back patio overlooks a pleasant backyard, the perfect spot for relaxation and recreation. Conveniently located just of US 421 (Leestown Road) and not far from loads of new shopping and restaurants, this home is tucked away but easily accessible to New Circle Road, Interstates 64 and 75 and the rest of Lexington and Central Kentucky. A rare combination of superb layout and phenomenal location.

2848 Gateway Park Ln, Lexington

505 Bryanwood Pkwy, Lexington
$335,000
5 Beds ⋅ 3 Baths ⋅ 26020203 MLS
Welcome to this spacious and well-maintained two-story home in the established Kenawood neighborhood of northeast Lexington. Offering 5 bedrooms, 2 full bathrooms, 1 half bath, and over 2,500 square feet of living space, this home provides the flexibility and room today's buyers are looking for. Built in 1965, it combines timeless character with a functional floor plan designed for everyday living and entertaining. The main level features multiple gathering spaces, including a comfortable family room anchored by a beautiful masonry fireplace, a formal dining room, and a spacious eat-in kitchen with a breakfast bar. The kitchen comes complete with a range, refrigerator, dishwasher, microwave, disposal, washer, and dryer, making this home truly move-in ready. Hardwood, tile, and carpet flooring add warmth and character throughout. Step outside to enjoy the large backyard shaded by mature trees, offering plenty of space for gardening, play, or entertaining. The enclosed front porch and backyard patio create inviting spaces to relax, while the storage shed provides additional room for lawn equipment and seasonal storage. A two-car attached garage with an automatic opener adds everyday convenience. Located in northeast Lexington, this home is just minutes from New Circle Road, Interstate 75, downtown Lexington, shopping, restaurants, parks, and the University of Kentucky. The property is located in the Fayette County School District, with Deep Springs Elementary, Bryan Station Middle School, and Bryan Station High School. Whether you're looking for extra space, a convenient location, or a home ready to make your own, this property offers exceptional value in an established neighborhood.

505 Bryanwood Pkwy, Lexington

481 Severn Way, Lexington
$335,000
4 Beds ⋅ 2 Baths ⋅ 26021990 MLS
For the first time since it was built in 1974, this one-owner Open Gates home is ready for its next chapter! Located in one of Lexington's most convenient established neighborhoods, you'll have quick access to Nicholasville Road, Harrodsburg Road, downtown Lexington and the University of Kentucky. The split-foyer design provides comfortable living space across both levels. Upstairs, the living room flows into the dining area, where glass doors extend the space onto the rear deck overlooking the fenced backyard. Three bedrooms and a full bath complete the main level, while downstairs offers a second gathering space anchored by a brick fireplace with gas logs. A fourth bedroom and full bath add flexibility for guests, a home office or additional living space, with the utility room and oversized one-car garage rounding out the lower level. This is a home with the space, layout and location to become something special. Bring your ideas, choose the finishes and make the updates that fit your style rather than paying for someone else's choices. With a fenced backyard, four-bedroom, two-bath layout and a sought-after Open Gates location, the foundation is here. Now it's ready for someone with a vision to make it their own.

481 Severn Way, Lexington

3168 Tiburon Way, Lexington
$324,900
3 Beds ⋅ 3 Baths ⋅ 26021606 MLS
Welcome to your new home, which is move-in ready. You will like the granite countertops in the kitchen and bathrooms on the second floor. The main level features all-LVP flooring, an open-concept kitchen and family room, a pantry closet, and a walk-in storage closet in the kitchen. Additionally, there is a powder room. The upper level includes all three bedrooms, with the primary suite featuring an attached bath and walk-in closet. Another full bathroom shared with two additional bedrooms. The laundry room is conveniently located on the second floor and is a walk-in room, not just a closet. Other enhancements include two separate HVAC systems and a crawl space area that you can actually walk into. The private backyard has unlimited potential to become your evening and weekend activities. The neighborhood is conveniently located near several shopping centers and business opportunities. Kindly schedule your viewing appointment to transform this dream home into a tangible reality.

3168 Tiburon Way, Lexington

3981 Winthrop Dr, Lexington
$339,900
3 Beds ⋅ 3 Baths ⋅ 26021997 MLS
Welcome home to this cute 3 BR/2½ BA home located in popular Willow Bend on a dead-end street next to a farm! The entire home has been freshly painted and new flooring installed on the first level. The two-story entry and family room makes it feel open and airy. The kitchen has a very functional design and includes a nice eat-in area, storage under the stairs and bar top. The primary bedroom upstairs is very spacious and includes an ensuite bath with a walk-in closet. Two other bedrooms share the hall bath. Outside the owners have just installed a brand new 6ft privacy fence. The backyard isn't large, but the side yard allows additional space for pets or kids to play. Sellers are offering a 1-year home warranty for your peace of mind with an acceptable contract. Schedule your showing before it's SOLD! (Sellers have accepted an offer 9/12/26 contingent on 14-day inspection timeframe but agents continue to show.)

3981 Winthrop Dr, Lexington