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 area is a perfect blend of urban excitement and suburban tranquility, making it an ideal place for families, young professionals, and retirees alike. With its rich history and modern amenities, Downtown offers a lifestyle that is both convenient and fulfilling.

One of the standout features of homes in Downtown is the presence of interior entry basements. These thoughtfully designed spaces provide additional living areas, perfect for a home office, recreational room, or even a cozy guest suite. The interior entry basements enhance the functionality of the homes while offering a seamless flow between the main living areas and the lower levels. Imagine the possibilities—entertain guests in your spacious basement, create a personal gym, or simply enjoy a quiet retreat away from the hustle and bustle of daily life.

The Downtown area is not just about beautiful homes; it’s also about community. Residents enjoy easy access to an array of local shops, delightful eateries, and cultural attractions that make this neighborhood truly special. Stroll through tree-lined streets, enjoy local art galleries, or unwind in nearby parks—there’s always something to do in Downtown.

Whether you’re looking to invest in your first home or seeking a peaceful place to retire, Downtown in Kentucky offers a unique opportunity. With its combination of stunning homes featuring interior entry basements and a lively community atmosphere, you’ll find the perfect place to call home. Come discover the charm of Downtown—where your dream lifestyle awaits!

Newest Downtown Homes with Interior Entry Basement

128 E Bruen St, Midway
$850,000
5 Beds ⋅ 5 Baths ⋅ 26028882 MLS
Historic Victorian Character in the Heart of Midway Step into Midway history at The Teacherage, a distinctive brick residence dating to 1873. Rich in architectural character, this remarkable property features a Victorian-era flair, a mansard-roofed tower, and an ornate cast-iron porch. Originally known as the Midway Hotel, the property later became known as The Teacherage, serving as a boarding house for faculty of Midway College through approximately 1942. Offering over 4,200 square feet of living space, the home features four bedrooms, including a first-floor primary suite with an ensuite bath. The flexible floor plan also includes a front office that could offer the potential for a fifth bedroom, subject to buyer needs and applicable requirements. Jack-and-Jill-style bathroom arrangements provide connections between additional bedrooms. Outside, enjoy a charming landscaped walkway along the side of the home and a welcoming backyard. A former detached garage has been converted into a workshop, offering additional space for hobbies, creative pursuits, or projects. Located within walking distance of Midway's business district, the property is near the community's restaurants, boutiques, gift shops, and coffee shops. The property is zoned B-2, Central Business District, offering an opportunity to explore its potential within this established commercial area. Buyers should independently verify zoning, permitted uses, building details, and any intended modifications with the appropriate authorities. With its historic significance, distinctive architecture, generous interior space, and location near downtown Midway, The Teacherage presents a unique opportunity to own a memorable piece of local history. A one year 2-10 home warranty is provided by the seller.

128 E Bruen St, Midway
102 First St, Carlisle
$269,900
4 Beds ⋅ 2 Baths ⋅ 26028845 MLS
RARE PACKAGE DEAL IN CARLISLE | Renovated 4-Bedroom Cape Cod + 2 Additional Buildable Lots (~1 Total Acre)! Welcome to the perfect blend of timeless character and modern updates in this beautifully renovated Cape Cod! Situated on app. 1 acre, this move-in-ready home features 4 spacious bedrooms, 2 full bathrooms, and the rare opportunity of two additional buildable lots, offering endless possibilities for expansion. Plenty of room to build a garage, have a large garden or two additional homes. From the moment you arrive, you'll be welcomed by the charming new covered front porch, the perfect place to enjoy your morning coffee or relax at the end of the day. Step inside to find fresh interior paint, new flooring throughout, and beautifully remodeled kitchen complete with brand new appliances. The inviting living room showcases a gorgeous fireplace, creating a warm and cozy gathering space, while the dining room is ideal for hosting family dinners and holiday celebrations. The main level offers two bedrooms and a full bath. The second floor offers two additional bedrooms and another full bathroom, providing flexibility for a growing family or a home office. An unfinished basement provides abundant storage and potential to create additional living space, a recreation room, or workshop. Beautifully updated, full of charm, and offering room to grow, this exceptional property is truly a must see! Schedule your showing today and experience everything this stunning home has to offer!

102 First St, Carlisle
235 Mills Ave, Flemingsburg
$170,000
3 Beds ⋅ 2 Baths ⋅ 26028059 MLS
Don't miss this move-in ready, 3 bedroom, 2 bath home in a great Flemingsburg location! This home boasts many updates and features a large back deck and back yard for your enjoyment! Home is recently renovated with all new paint, flooring, and light fixtures. New gas furnace in 2025. New water heater in 2023.

235 Mills Ave, Flemingsburg
111 Woodland Ave Unit 705, Lexington
$1,400,000
2 Beds ⋅ 3 Baths ⋅ 26026896 MLS
Elevated above one of Lexington's most recognizable addresses, this seventh-floor residence at The Woodlands offers 2,358 square feet of refined living with sweeping views of downtown Lexington and the University of Kentucky. A paneled entry hall introduces hardwood floors, detailed millwork and exceptional custom storage throughout. The coffered-ceiling den features a fireplace, built-ins and wet bar, while the adjoining living and dining spaces are framed by oversized windows, a second fireplace with arched built-ins, and a distinctive hand-painted ceiling dome. The custom kitchen is appointed with granite countertops, a farmhouse sink, double ovens, a warming drawer, glass-front cabinetry, a striking tile backsplash and pantry storage. The spacious primary suite features built-in cabinetry, two walk-in closets and a beautifully updated private bath with a custom vanity and glass-enclosed shower. The guest bedroom offers stunning city views, generous storage and convenient access to an updated guest bath. A dedicated laundry room and private office with built-ins add comfort and flexibility. The residence also includes two first-level spaces in the secured garage and multiple private storage closets. Residents enjoy 24-hour security, a fitness center, sauna, hot tub, outdoor pool, game room, catering kitchen, 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 welcoming 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
$464,900
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
$264,500
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
$284,900
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
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