Downtown Homes with Interior Entry Basement

Downtown Homes with Interior Entry Basement

Welcome to Downtown, a vibrant and dynamic subdivision nestled in the heart of Kentucky! This charming neighborhood combines the rich history of the Bluegrass State with modern amenities, making it an ideal place for families, young professionals, and retirees alike. With its picturesque streets lined with quaint shops, trendy cafes, and delightful parks, Downtown offers a unique blend of urban convenience and small-town charm.

One of the standout features of homes in this area is the presence of interior entry basements. These versatile spaces provide additional square footage that can be transformed into anything your heart desires—whether it’s a cozy family room, a home gym, or an entertaining haven for friends and family. The convenience of having direct access from inside the home adds an extra layer of functionality, making these properties not just houses, but true homes.

The Downtown subdivision is also known for its strong sense of community. Neighbors gather for seasonal events, farmers' markets, and outdoor concerts, fostering an inviting atmosphere that makes everyone feel at home. The local schools are highly regarded, and the nearby recreational facilities cater to all ages, ensuring that there’s always something to do.

If you’re looking for a place where history meets modern living, Downtown in Kentucky is the perfect choice. With homes featuring interior entry basements, you’ll find the ideal blend of space and style, ready for you to create lasting memories. Come explore Downtown and discover your dream home today!

Newest Downtown Homes with Interior Entry Basement

111 Woodland Ave Unit 705, Lexington
$1,400,000
2 Beds ⋅ 3 Baths ⋅ 26026896 MLS
Enjoy elevated city living from the seventh floor of The Woodlands, with sweeping views of downtown Lexington and the University of Kentucky campus. A gracious entry hall with paneled wainscoting opens to a thoughtfully designed interior featuring hardwood floors, detailed millwork and abundant custom storage. The den offers a coffered ceiling, fireplace, built-ins and a wet bar. A separate living room features a second fireplace framed by arched built-ins, while oversized windows fill the living and dining areas with natural light. The formal dining room is distinguished by a hand-painted ceiling dome and decorative lighting. The well-appointed kitchen includes custom cabinetry, stone countertops, a farmhouse sink, double ovens, a warming drawer, glass-front display cabinets, a striking tile backsplash and adjoining pantry storage. Two spacious bedrooms include generous built-ins, and the updated baths feature custom vanities and glass-enclosed showers. A dedicated laundry room and an office with custom built-ins add convenience. The residence includes two first-level spaces in the secured garage, along with multiple private storage closet. Residents enjoy 24-hour security, a fitness center, sauna, hot tub, outdoor pool, game room, catering kitchen, formal gathering spaces, grilling area, covered patio and a ninth-floor terrace with panoramic city and sunset views. Guest parking is conveniently located near the building's inviting front fountain.

111 Woodland Ave Unit 705, Lexington
508 W Maple St Unit A-B, Nicholasville
$245,000
2 Beds ⋅ 2 Baths ⋅ 26026560 MLS
Great opportunity for investors! This duplex at 508 West Maple Street sits on a great lot with plenty of space and lots of potential. The property offers the opportunity to renovate and make it your own, with endless possibilities for someone looking to add value. A new roof was installed in 2025, and the windows were replaced in 2018. Whether you're an investor looking for your next project or someone looking for a property with room to grow, this one is worth taking a look at. Very large lot, tons of space, and so much potential! (Note: the seller also has 408 W Maple Street listed for sale. If you're interested in purchasing both properties, the seller would consider selling them together.)

508 W Maple St Unit A-B, Nicholasville
305 W Main St, Mt Sterling
$474,900
5 Beds ⋅ 4 Baths ⋅ 26026409 MLS
Stately, spacious, and filled with timeless character, this circa 1915 Colonial brick home is a true downtown Mt. Sterling treasure! Offering an impressive 5 bedrooms, 3 full baths and 1 half bath, this historic home provides an abundance of space both inside and out, all while being filled with beautiful natural light. From the moment you step into the grand and inviting entry foyer—the kind foyers dreams are made of—you'll immediately appreciate the craftsmanship and charm found throughout. The home features a spacious living room, den/study or home office, formal dining room, kitchen with breakfast nook and beautiful cabinetry and counter tops, mudroom, and two laundry areas. Original character shines through with beautiful hardwood flooring, crown molding, intricate door frames and trim work, built-ins, and several fireplaces that add warmth and personality throughout the home. The finished third level offers even more incredible living space with a huge recreation/family room plus an additional bonus room with skylights. This versatile space could even serve as another primary suite with its attached bathroom featuring a relaxing soaking tub. Outside, the home is situated on a generous .60-acre lot right in downtown Mt. Sterling and features a picture-perfect front porch worthy of the cover of a home and garden magazine, a rear patio perfect for entertaining, and a detached garage with additional storage space in the rear. The unfinished basement provides even more room for storage. Recent improvements include a new architectural shingle roof installed in August 2026, along with new guttering and downspouts. As a Mt. Sterling Historic Registered Home, this property offers the history, craftsmanship, space, and character that simply cannot be recreated today. If you've always dreamed of owning a LARGE historic home in the heart of downtown Mt. Sterling, this may be the one you've been waiting for. This remarkable property truly must be seen in person to fully appreciate everything it has to offer!

305 W Main St, Mt Sterling
103 Bennett Ct, Richmond
$100,000
4 Beds ⋅ 2 Baths ⋅ 26026406 MLS
Auction Live or Online October 24 at 10 AM. Welcome to this spacious 4-bedroom, 2-bath home conveniently located in downtown Richmond! Offering approximately 2,500 square feet of living space plus a basement, this property provides plenty of room for comfortable living, entertaining, and storage. The home's central location puts you close to downtown shopping, dining, local businesses, and other Richmond amenities. With four bedrooms, two full baths, generous living space, and the added versatility of a basement, this property offers a great opportunity for homeowners or investors looking for space and convenience in the heart of Richmond. Don't miss the opportunity to make this downtown property your next home or investment! Sale terms: If you bid online you must submit a letter of good standing from your bank at least 24 hours prior to auction. Selling by the deed. Call Auctioneer Ken DeGrant license # 281879 www.highpointky.com

103 Bennett Ct, Richmond
1136 Rayburn Dr, Olive Hill
$275,000
4 Beds ⋅ 2 Baths ⋅ 26026376 MLS
Welcome to the desirable Eastwood Addition! This recently remodeled 4-bedroom, 2-bath home offers a great combination of updated finishes, generous living space and outdoor amenities. The entire main level features beautiful hardwood flooring through the living space and bedrooms, both bathrooms are finished with tile and the upstairs bedroom has easy-care laminate flooring. The exterior offers attractive cedar siding across the front with low-maintenance vinyl siding on the remaining three sides, along with a new roof, new gutters and new windows. A convenient ground-level entrance through the dining room provides easy access to the main living area. The basement adds an incredible amount of usable space, including a 1,020-square-foot garage plus approximately 1,000 square feet of wide-open living space, giving you plenty of room for a family room, recreation area, home gym, hobbies or whatever fits your lifestyle. Upstairs is finished into a bedroom with plenty of closet and storage space and even space to install a bathroom! Outside, you'll find a swimming pool and screened porch, creating the perfect setup for relaxing or entertaining during the warmer months. All kitchen appliances, as well as the washer and dryer, remain with the home. The garage is equipped with two brand-new garage doors installed last year, featuring both app-controlled operation and keyless entry. With its recent remodeling, major exterior updates, abundant living and garage space and inviting outdoor areas, this Eastwood Addition home is ready for its next owner.

1136 Rayburn Dr, Olive Hill
38 Johnson Avenue, Mt Sterling
$299,900
4 Beds ⋅ 2 Baths ⋅ 26026358 MLS
Cute, cozy, and charming are the three words that immediately come to mind with this beautiful Craftsman-style bungalow in downtown Mt. Sterling! Fully renovated in 2016 and still in pristine condition, this home perfectly blends classic character with modern updates. Inside, you'll find 4 bedrooms, 2 full baths, a welcoming living room with an electric fireplace, dining area, and a beautiful kitchen featuring an island, pantry, and cozy gas-log fireplace. A convenient utility area adds to the functionality, while the unfinished basement provides plenty of additional storage space. Step outside and enjoy even more! The property offers a detached two-car garage, storage shed, inviting covered front porch, and a rear covered patio overlooking the backyard—the perfect spot to relax, entertain, or enjoy your morning coffee. With its charming style, thoughtful updates, convenient downtown location, and truly move-in-ready condition, this home is just waiting for its next owner to arrive, unpack, and start making memories. This one is sure to please.

38 Johnson Avenue, Mt Sterling
108 Court St, Versailles
$1,799,900
26026295 MLS
Dating to the 1880s, 106-110 Court Street presents a rare turnkey restaurant opportunity in the heart of Historic Downtown Versailles. Formerly home to the Versailles Police Department, the property was reimagined by the current owners beginning in 2021, undergoing an extensive transformation while preserving as much of its historic character and architectural detail as possible. Exposed brick, original elements and carefully selected finishes create a distinctive setting throughout multiple dining areas. The restaurant features two outdoor terraces, an impressive main bar, an upstairs bar with wine cellar, and private rooms ideal for events, meetings or private dining. Offered as a fully functioning turnkey restaurant, the sale includes all restaurant furniture and kitchen equipment, allowing a new owner to step into a beautifully finished and fully equipped operation. Approximately 800 square feet is currently occupied by an insurance office, providing an additional component to the property. Steps from Courthouse Square and surrounded by the shops, restaurants and architecture of Downtown Versailles, this is an exceptional opportunity to continue the story of a truly unique historic property.

108 Court St, Versailles
511 E Walnut St, Danville
$269,000
4 Beds ⋅ 2 Baths ⋅ 26025950 MLS
Welcome to this charming, freshly updated 4-bedroom, 2 bath home. Ideally located just a short walk from historic downtown Danville. From the inviting front porch, once you step inside you will appreciate the pristine condition. Timeless character flows through the home with built in bookcases, crown molding and wainscot chair railing in the kitchen. The main level offers a thoughtful layout with a spacious living room, a primary suite, with a nice sized closet, 2 other bedrooms, a second full bath and a sunny kitchen with all of the appliances. Upstairs is a private 4th bedroom or possible home office or playroom. There is plenty of storage space available with the closets and the unfinished basement. The large den on the back of the home opens onto the long-screened porch. This wonderful porch is ideal for the fall weather; whether you are relaxing with your morning coffee or entertaining friends you will enjoy overlooking a private mostly fenced back yard. This turnkey home features a newer, roof and water heater, offers updated electric and plumbing. Other wonderful features are the new light fixtures, doors, wood trim casings, and fresh neutral paint throughout the home. Consider the benefits of this centrally located property and a walkable lifestyle. Stroll to Ephriam McDowell Regional Medical Center, Centre College, the farmer's market, boutique shops, coffee shops, a variety of restaurants and schools. Enjoy the beauty of small-town living.

511 E Walnut St, Danville
302 N 3rd St, Danville
$389,000
5 Beds ⋅ 2 Baths ⋅ 26025246 MLS
Step back in time with this quintessential American Foursquare, seamlessly blending historic architectural splendor with modern upgrades. The front staircase features rustic, curved stone treads, flanked by built-in planter beds, guiding you to the welcoming front porch, perfect for rocking chairs and a swing. This lovely entrance gives a stately tone from the moment you arrive. Step inside to discover the beautiful, preserved period craftsmanship shining through the original diamond-pane windows, rich oak and poplar hardwood floors, elegant dentil molding, arched doorways and handsome wood trim. The magnificent main staircase features raised- panel detailing and a landing with tall windows. Distinct fireplaces add character to the rooms throughout the home. Imagine hosting fabulous holiday dinners beneath the original dining room chandelier, complete with the historic gas fittings. The main level is designed for daily living and effortless entertaining. The open living room and dining room are bathed in natural light. The butler's pantry hallway is outfitted with two large closets for extra storage space. A thoughtful flex room could serve as a cozy breakfast room; a quiet home office or a playroom and features a cheerful row of windows. The good-sized kitchen offers ample cabinetry. The spacious den opens directly onto the rear, private patio and backyard. Upstairs, a spacious foyer connects the five generous sized bedrooms with ample closet space and two full baths including a primary suite featuring a tiled step- in shower. Outside, the property is framed by a charming stone fence along the side and rear yards, with dual driveways providing convenient off-street parking on both sides of the house. A utility garage provides excellent storage for lawn equipment, bikes and basement access. Peace of mind comes easy thanks to updates including hvac, gutters, a water heater, ceiling fans and light fixtures and roof. Consider living an exciting downtown lifestyle with a scenic short stroll to enjoy unique, boutique shopping, coffee shops to meet with friends, dining at the Main Street restaurants, Centre College and the Norton Center for the Arts, Ephriam McDowell Regional Medical Center, schools, churches and the wonderful public library. This iconic treasure offers rare craftsmanship, comfortable living spaces, and convenience.

302 N 3rd St, Danville
344 W Walnut St, Mount Olivet
$129,000
4 Beds ⋅ 3 Baths ⋅ 26024752 MLS
Welcome to 344 W Walnut Street, Mt. Olivet, KY! Nestled in the heart of this historic city, this beautiful home is ready for its next owners. Situated on a 0.31-acre lot with a large driveway, the property offers plenty of convenient off-street parking. Believed to have been built in the early 1900s, this home is filled with timeless charm and character. Outside, you'll find a beautiful half-wraparound porch and a brand-new shingle roof. Step inside to a welcoming entry hall featuring a striking original wood staircase that showcases the craftsmanship and character of the home. With over 2,500 square feet of living space, the home offers four bedrooms, a bonus room, two full bathrooms, and one half bathroom tucked beneath the staircase. An additional unfinished full bathroom downstairs provides even more potential. The kitchen has been refreshed with newly replaced cabinets and countertops, and the home also features a new water heater. With its spacious layout, historic details, recent updates, and convenient location, this beautiful Mt. Olivet home offers plenty of room to grow while preserving the character that makes older homes so special.

344 W Walnut St, Mount Olivet
525 E Pike St, Cynthiana
$299,900
4 Beds ⋅ 2 Baths ⋅ 26024335 MLS
Built of brick and stone in 1931, this traditional home offers the charm of another era with the space and features today's buyers want. Arched doorways and windows, tongue-and-groove ceilings and walls, and gorgeous fireplaces in both the living room and den give this home a personality all its own. The first floor features a cozy breakfast nook, a window-filled back den, and a convenient bedroom. Upstairs, you'll find three additional spacious bedrooms. Altogether, the home offers four bedrooms, one-and-a-half bathrooms, a partially finished basement, and a new HVAC system to boot! Although it's located right in the city, the large corner lot offers many of the features buyers love about country living—a wood privacy fence, mature trees, covered porches, a new above-ground pool with a deck, a detached garage, and off-street parking. Timeless construction, unforgettable character, and an outdoor space made for enjoying—this is one you'll want to see in person!

525 E Pike St, Cynthiana
522 N Main St, Harlan
$392,000
5 Beds ⋅ 3 Baths ⋅ 26024164 MLS
Have you often dreamed of having a home with the character and room of an old home and a nice large yard in or just outside of downtown Harlan? Often you either have the lot size you want or the beautiful older home that has stood the test of time and has features you just don't see in the newer homes. If you have been looking then you know how hard that is to find both features here. Here you go! This listing has it all!! With 1.77 acre of fenced in yard 5 bedrooms and 3 baths along with a heated and cooled basement this home is a hard to find gem! There is even a cozy 2 bedroom, 1 bath cottage in the side yard that can be used as a guest house! Like to travel and have an RV? No worries there is a place for it too! The property has a second entrance to the back coming off Ivy Hill where you can park the RV and there is already an electric hook up there for it! Someone is going to get a hard to find unique and wonderful property! It should be you! Call today to set up your showing and see this one of a kind property for yourself!!

522 N Main St, Harlan
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