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409 Dudley Rd, Lexington
$1,090,000
4 Beds ⋅ 3 Baths ⋅ 26021097 MLS
Set on one of Lexington's most beloved tree-lined streets in the coveted Chevy Chase / Ashland Park area, this 1935 Kentucky limestone Cotswold/Tudor home is a rare blend of storybook character and modern living. From the steeply pitched gables and stone chimney with terracotta chimney pots to the arched red front door and bluestone covered porch, the curb appeal is straight out of a storybook. Timeless and natural materials were chosen throughout to honor the home's original architecture while quietly delivering every modern convenience. Inside, graceful arched doorways and refinished hardwood floors set a warm, inviting tone. A completely renovated open-concept kitchen anchors the main level with custom cabinetry, granite countertops, limestone backsplash, a gas range, and a breakfast-bar peninsula that flows effortlessly into the dining and living spaces — with double pocket doors opening to a light-filled sunroom. A custom travertine-slab fireplace with a herringbone-tile firebox and gas insert serves as a stunning focal point. Original curved ceilings in two of the upstairs bedrooms — a signature of authentic Cotswold design — and distinctive staircase balusters are charming reminders of the home's 1935 pedigree. The 2005 two-story addition expanded the living space with Hardie board siding, solid-wood interior doors with crystal knobs, and a stone skirt around the foundation — some of it original stone reclaimed from the main home. Walls of French doors along the addition open to the backyard, filling the home with natural light and creating a seamless indoor-outdoor flow. Custom built-ins throughout, including a glass-front dining room hutch and a laundry room/pantry with granite and travertine, reflect the same craftsmanship found in every corner. The spa-like primary bath is a true retreat, featuring a freestanding clawfoot soaking tub, a long double vanity with marble countertop, custom cabinetry, a chandelier, penny-tile flooring, and a custom laundry chute. A second-floor secondary bath is equally refined with a new porcelain tile shower and floor, custom cabinetry, and marble countertops. The finished basement is a destination of its own: custom and reclaimed-wood shelving, a bar area with a beverage fridge, a cedar closet, generous storage, and durable LVP flooring — with the adjacent utility area proactively waterproofed to protect the finished space. Outdoors, a generous 17' x 29' patio topped with Pennsylvania bluestone — accessible through multiple sets of French doors — creates an elegant, private setting for entertaining. Out front, professional landscaping and mature trees and hydrangeas, a bluestone covered front porch and walkway, and laurel-stone edging. A rare extra-deep 22' x 26' detached garage with carriage-style doors, coordinating stone front and Hardie board siding was designed to blend seamlessly with the home, and even reuses windows from the original house. Behind its timeless facade, this home offers the best of both worlds: the irreplaceable character of a 1935 Chevy Chase original, paired with thoughtfully updated interiors that honor its heritage down to the smallest detail. Walkable to the shops and restaurants of Chevy Chase and just minutes from the University of Kentucky, downtown, and everything that makes this one of Lexington's most sought-after neighborhoods. Property being sold as is with inspections welcomed.

409 Dudley Rd, Lexington

4199 Cocos Way, Lexington
$749,000
3 Beds ⋅ 4 Baths ⋅ 26021238 MLS
Welcome to The Brownstones at Ethington Heights! Here's your chance to enjoy maintenance-free luxury living at its finest! Situated on the very desirable southwest side of town next to Palomar Hills just a few minutes from the Airport, Keeneland and some of the best Golf Courses around. This 20-unit development has a modern design along with sophisticated finishings. These 3-bedroom townhomes range from approximately 2,250+ sq ft to 2,650 sq ft. With an open floorplan, tons of natural light, hardwood flooring throughout, beautiful cabinetry, high end appliances, large island, gorgeous linear gas fireplace, attached rear entry 2 car garage and first floor primary suite! Also available on certain floor plans - spacious loft with wet bar leading to roof top patio. 4199 Cocos Way has not been built yet. See the 4165 Cocos Way listing for a similar completed townhome. Call/text Tyce or John for viewing arrangements.

4199 Cocos Way, Lexington

617 N Broadway, Lexington
$485,000
2 Beds ⋅ 3 Baths ⋅ 26020455 MLS
This charming historical jewel is ready for it's next owner. It's not often you find over 2000 square feet in a house built in the 1910's but this one delivers with an open concept chefs kitchen dining combination that opens to a side patios for outdoor living. There is a large living space with a half bath for guests plus a foyer with character.... Speaking of character, this home has loads of it, exposed brick, decorative fireplaces and amazing lighting. Two spacious bedrooms both with private baths provide plenty of room for everyone to spread out. Finally, the backyard is oversized for the area with room for gardening or entertaining. Walk to all downtown has to offer or to Transylvania University- you don't want to miss making this one your own!

617 N Broadway, Lexington

395 Redding Rd Unit 230, Lexington
$247,500
2 Beds ⋅ 2 Baths ⋅ 26020321 MLS
Welcome home to Unit 230, a top-floor sanctuary offering ultimate privacy, single-level comfort, and tranquil wooded views. Nestled deep within the highly desirable gated community of The Oaks, this premium Eaton floor plan sets itself apart with no overhead neighbors and beautiful nature-filled backdrops. Step inside to a beautifully updated open-concept floor plan accented by luxury vinyl flooring throughout. The kitchen and dining spaces feature elevated-higher ceilings (dated soffits have been completely removed) creating an airy, light-filled atmosphere. At the heart of the home is a bright living room featuring a cozy wood-burning fireplace framed by custom built-in cabinetry. Culinary enthusiasts will love the kitchen's full suite of stainless steel appliances, open breakfast bar, and exceptional storage upgrades. The thoughtful pantry cabinets feature convenient pull-out shelving equipped with integrated electric outlets—perfect for using heavy appliances like a mixer right from the shelf! Relax or entertain in the enclosed sunroom, a versatile bonus living space flooded with natural light and scenic tree views. The large primary suite serves as a true getaway, complete with multiple closets and a private en-suite bathroom. The spacious second bedroom includes a walk-in closet with direct pass-through access to the second full bathroom. A dedicated in-unit laundry room with built in shelving completes the interior layout. Your purchase includes a covered carport space steps from the building entrance, alongside full access to premium community amenities: an inground saltwater pool, tennis courts, a clubhouse, and mature, manicured landscaping. Perfectly situated for enjoying all that Lexington has to offer, The Oaks provides convenient access to Kroger Field for UK football games, Rupp Arena for basketball games and concerts, the University of Kentucky campus, downtown Lexington's restaurants and entertainment, the Arboretum, and The Summit at Fritz Farm for shopping and dining.

395 Redding Rd Unit 230, Lexington

2332 Aristocracy Cir, Lexington
$310,000
2 Beds ⋅ 3 Baths ⋅ 26020289 MLS
Located in the heart of one of Lexington's most popular areas, this home in Hamburg Farms is the oasis you want while having everything you need right outside your doorstep. This rare end unit features spacious living on all of its three floors, a detached two-car garage, a courtyard for relaxation and fresh air, and easy access to the walking trail that leads you to a clubhouse that features a gym and a pool. And no need to worry about mowing, landscaping, snow removal, or exterior repairs: those are all taken care of for you. And speaking of repairs, this home also features a new HVAC system, a new water heater, and a new refrigerator. Just a few more things that will put your mind at ease in your new home. If you're looking for easy access to shopping, dining, entertainment, schools, healthcare and main roads like I-75 and I-64 but still want to feel like you're out of the hustle and bustle, this is the place for you.

2332 Aristocracy Cir, Lexington

109 N Ashland Ave, Lexington
$549,999
3 Beds ⋅ 3 Baths ⋅ 26019969 MLS
Welcome to 109 N. Ashland Avenue, a timeless Craftsman bungalow nestled in one of Lexington's most desirable and walkable neighborhoods. This charming 3-bedroom, 2.5-bath home perfectly blends classic character with modern comfort. Relax on the covered front porch before stepping inside to discover warm hardwood floors, traditional living areas, and an inviting floor plan designed for both everyday living and entertaining. Outside, the deep backyard offers plenty of space to enjoy, while the unbeatable location puts you just steps from local restaurants, coffee shops, parks, and everything that makes the Ashland Park/Bell Court area so special. Whether you're taking an evening stroll through the neighborhood or enjoying nearby Chevy Chase and downtown Lexington, you'll love the convenience and vibrant lifestyle this location provides. Don't miss this rare opportunity to own a classic Lexington bungalow in an exceptional location. This home is being offered AS-IS, inspection welcome. Please note the alleyway includes an easement for this property to access two off road private parking spaces.

109 N Ashland Ave, Lexington

726 Spring Meadows Dr, Lexington
$179,500
2 Beds ⋅ 2 Baths ⋅ 26019502 MLS
Low-maintenance living in an unbeatable location! Welcome to 726 Spring Meadows Drive in the desirable Harrods Park community. This well-maintained townhouse offers 2 bedrooms, 2 full baths, and approximately 1,000 square feet of comfortable living space with dedicated parking and a maintenance-free exterior for easy, worry-free ownership. Ideally located just off Harrodsburg Road, you'll enjoy quick access to New Circle Road, downtown Lexington, the University of Kentucky, Baptist Health, UK HealthCare, St. Joseph Hospital, shopping, restaurants, and entertainment. Whether you're a first-time homebuyer, downsizing, a UK employee, or a medical professional, you'll appreciate the convenience of this central location. For investors, this property has an impressive track record, serving as a successful rental for the past 10 years. Whether you're looking for a place to call home or a turnkey investment opportunity, this townhouse offers exceptional value, location, and convenience.

726 Spring Meadows Dr, Lexington

262 S Ashland Ave, Lexington
$1,395,000
4 Beds ⋅ 3 Baths ⋅ 26019454 MLS
A rare offering in the heart of Ashland Park, this distinguished Colonial Revival residence stands as a testament to the enduring elegance and architectural refinement that defined the style's popularity at the turn of the century. Among the earliest homes constructed on coveted South Ashland Avenue, it enjoys a commanding presence and a rich connection to one of Lexington's most treasured historic neighborhoods. A gracious front porch sets the tone, inviting leisurely afternoons spent greeting neighbors and enjoying the timeless charm of tree-lined South Ashland Avenue. Inside, soaring ceilings, exquisite millwork, and a wide center hall create a sense of grandeur rarely found in today's homes. A remarkable reverse staircase, illuminated by a skylight above, provides access to the second level from the rear of the residence while filling the home's interior with natural light. Throughout, distinctive crown moldings highlight the craftsmanship of a bygone era, while the kitchen's handsome coffered ceiling adds warmth and architectural interest. Designed for both elegant entertaining and comfortable daily living, the first floor features an exceptional collection of gathering spaces, including a formal living room, formal dining room, a richly appointed den, an inviting family room, a spacious kitchen, a bedroom, and a full bath. Each room flows gracefully into the next, creating an atmosphere that is both sophisticated and welcoming. The second level features a spacious primary suite with a cozy sitting area, providing a private retreat at day's end. Two additional bedrooms and a full bath enjoy lovely views of the beautifully landscaped rear grounds. Outdoors, the private backyard serves as a peaceful oasis, with mature landscaping and a deck perfect for al fresco dining and entertaining. The porte cochere provides covered parking and everyday convenience while complementing the home's historic character. Ideally located just steps from the boutiques, cafés, and restaurants of Chevy Chase, this exceptional residence offers the rare opportunity to own a piece of Ashland Park history while enjoying one of Lexington's most desirable and walkable neighborhoods.

262 S Ashland Ave, Lexington

558 Central Ave, Lexington
$1,600,000
5 Beds ⋅ 5 Baths ⋅ 26019143 MLS
Discover exceptional craftsmanship and thoughtful design throughout this stunning townhome. The welcoming main level features a gracious entry, a dining room complete with a fireplace and custom built-ins, and a private home office with its own full bathroom. The chef-inspired kitchen showcases designer finishes, exposed wood beams and a spacious island, flowing seamlessly through a butler's pantry into the fireplace-warmed family room. A convenient half bath, an enclosed breezeway leading to a private courtyard, and an oversized two-car garage complete this level. Upstairs, the luxurious primary suite awaits with a generous walk-in closet and a spa-like bathroom boasting heated floors and a steam shower. Two additional bedrooms, a full bathroom, and a dedicated laundry room round out the second floor, while the third level offers two more bedrooms and an additional full bath — ideal for family or guests. The lower level adds even more living space with a versatile recreation room, perfect as a media room or entertainment retreat. This exceptional home is loaded with premium amenities, including a fully owned solar panel system, tankless water heaters, central vacuum, two gas vent-free fireplaces, a security system, an irrigation system, and abundant storage throughout. NO HOA FEE!

558 Central Ave, Lexington

101 S Hanover Ave Unit 2M, Lexington
$344,900
2 Beds ⋅ 2 Baths ⋅ 26019062 MLS
Just a stone's throw from downtown, Hanover Towers is understandably in high demand. It rests within lovely historic Ashland Park, at the corner of Hanover and East Main. Within a short walk are Woodland Park, Henry Clay and Chevy Chase. Hop a bike and its 5 minutes to Rupp, the farmer's market, Gatton Park or the distillery district. Or stay right at home and catch spectacular views of downtown Lex. and the sun setting over the bluegrass on the Hanover Towers rooftop. The complex has covered parking for owners, guest parking, public spaces, basement storage, a laundry facility and a workout room. Most impressive, whether you are coming or going, a doorman will greet you and assist you at the front of the building daily through 6 pm. This lovely 2nd floor corner unit in Hanover Towers was remodeled in 2022 and in pristine condition. The standard clunky Hanover towers glass partitioning in the living room was removed, opening up that space to the amazing morning sunrises through the oaks. The kitchen was gutted, re-configured, opened up to the living room and remodeled. All new. The baths too were renovated, including new vanities and fixtures, new tile and glass. All flooring was replaced, as well. Vacant and move-in ready. Furnishings are negotiable.

101 S Hanover Ave Unit 2M, Lexington

1147 Athenia Dr, Lexington
$499,900
4 Beds ⋅ 3 Baths ⋅ 26017388 MLS
A completely remodeled, move-in ready 4-bedroom, 2.5-bath sitting on a level half-acre lot, the kind of space Beaumont Park is known for, just minutes from the park itself, Keeneland, Blue Grass Airport, and downtown Lexington. Step inside and the kitchen makes the case for staying home more often. Custom soft-close cabinetry, granite counters, new stainless steel appliances, and updated lighting come together for a space built for real life, whether that's a Tuesday night dinner or a Saturday with friends over. Hardwood floors, fresh paint, and new lighting carry that same clean feel through the rest of the home. The layout gives everyone their own space. Three bedrooms and a full bath share one level, while the primary suite takes an entire level for itself, complete with an en suite bath and a walkout rooftop patio that feels like a private escape at the end of the day. Downstairs, the walkout basement adds a family room built around a cozy gas fireplace, plus a laundry room and half bath. This isn't a finished basement in name only. It's real, livable space that flexes with whatever life needs it for. Outside, the level half-acre backyard opens up room to garden, entertain, or just spread out. The extra-deep garage gives you space for a workshop, storage, or longer vehicles, and the attached carport doubles as a covered patio. A brand-new extended driveway means plenty of parking when family and friends come over. The big-ticket items are already handled too, with a new roof in 2021 and updated heating and cooling in 2024. So the home isn't just beautiful, it's worry-free. A true top-to-bottom renovation in one of Lexington's most established neighborhoods, this Beaumont Park home brings modern living together with the space and location this area is known for. Come see it for yourself.

1147 Athenia Dr, Lexington

355 S Broadway Unit 604, Lexington
$375,000
2 Beds ⋅ 2 Baths ⋅ 26018057 MLS
Modern luxury abounds in this 6th floor condo with private balcony that has been reconfigured and opened up for easy entertaining! Located in the gated building of Centre City Condominiums, this 2 bedroom 2 full bath has been been renovated including updated bathrooms as well as new flooring throughout. The kitchen has been moved to center of living space and features a huge island and stainless appliances with french door refrigerator. Amenities of the building include a rooftop saltwater pool, community/party area, and workout room. Excellent location right next to Lex Live and easy access to Rupp Arena for basketball games, concerts, and other events. Short walking distance to many restaurants and shops as well! Two parking spaces included in the secure garage. Don't miss your opportunity to own this beautiful condo in the heart of downtown Lexington!

355 S Broadway Unit 604, Lexington

565 W Second St, Lexington
$1,050,000
3 Beds ⋅ 3 Baths ⋅ 26016794 MLS
Experience the timeless character of this beautifully restored downtown Lexington home, where historic charm meets thoughtfully updated modern living. Ideally located within walking distance of downtown restaurants, shopping, Central Bank Center, and the new Gatton Park on the Town Branch, this home offers exceptional convenience in the heart of the city. Extensive improvements include updated sewer and plumbing lines, electrical, HVAC, insulation, appliances, and more, providing peace of mind while preserving the home's original character. Hardwood flooring flows throughout the interior, complemented by a beautifully restored staircase that serves as a striking architectural centerpiece. The main level features an open-concept kitchen and family room anchored by a natural gas linear fireplace and bar area, creating an inviting space for both everyday living and entertaining. The kitchen opens directly to the rear deck and patio, extending the living space outdoors. A separate living room and formal dining room provide additional flexibility for gatherings and special occasions. Upstairs, you'll find three bedrooms, two full bathrooms, and a conveniently located laundry room. The spacious primary suite includes a large walk-in closet and an updated ensuite bathroom. The third floor offers a versatile office or flex space with hardwood flooring, while the finished basement provides additional living space ideal for a media room, recreation area, or entertaining, along with unfinished storage. Step outside to a private backyard retreat featuring a deck, patio, and hot tub, creating a rare outdoor oasis in downtown Lexington. Whether enjoying a quiet evening or hosting family and friends, this space is designed to be enjoyed year-round. With its exceptional restoration, modern updates, versatile living spaces, and premier downtown location, this home offers a unique opportunity to enjoy the best of historic Lexington living. Schedule your private showing to experience everything this remarkable property has to offer.

565 W Second St, Lexington

322 W 3rd St, Lexington
$649,000
3 Beds ⋅ 2 Baths ⋅ 26011135 MLS
Historic Thomas January office renovated and rebuilt from foundation up offers modern amenities including tankless water heater, marble kitchen and bathrooms, new heat and air, plumbing, electrical, appliances and salvaged hardwood floors. Property is income producing as Airbnb and VRBO but could be used as single family dwelling. House includes a charming and private courtyard with neighboring Gratz Park and Transylvania University close by. Walking distance to restaurants, Opera House, Rupp Arena, and all downtown has to offer. Three designated parking spaces behind the house and on street parking in front of the house. Opportunity to own one of Lexinton's most unique properties. House being sold AS IS. Inspections welcome.

322 W 3rd St, Lexington

2051 Bridgeport Dr, Lexington
$769,000
4 Beds ⋅ 3 Baths ⋅ 25506627 MLS
Welcome to 2051 Bridgeport Drive, a beautifully maintained brick ranch located in the sought-after Lakeview Estates neighborhood of Lexington. Set on nearly half an acre, this spacious one-story home offers over 4,200 sq. ft. of refined living space, including four bedrooms, three full bathrooms, and a partially finished basement. Inside, the home features a warm and inviting layout with hardwood floors, plush carpeting, and a cozy family room centered around a fireplace. The well-appointed eat-in kitchen includes modern appliances and flows naturally into the formal dining and living areas—perfect for gatherings and everyday living. Large windows throughout the home bring in abundant natural light and provide views of the mature landscaping surrounding the property. Outdoors, the expansive lot offers privacy and plenty of room for relaxation or outdoor activities, complete with a patio and fenced yard. Located near many Lexington amenities, this exceptional home combines classic charm, generous space, and an outstanding location.

2051 Bridgeport Dr, Lexington

4176 Buttermilk Rd, Lexington
$725,000
4 Beds ⋅ 4 Baths ⋅ 26016247 MLS
Two Primary Suites. Two Living Spaces. Two Laundry Areas. One Exceptional Home - Just Steps from the Walking Trail. This beautifully designed new-construction home by Portrait Homes offers an exceptional blend of luxury, flexibility, and everyday functionality. With two private primary en-suites, two distinct living spaces, and two convenient laundry options, this home is thoughtfully designed to accommodate the way modern families actually live. The main level features a private primary suite with a spa-inspired bath, along with an inviting open-concept family room, dining area, and stunning chef's kitchen. The kitchen is finished with ceiling-height, all-wood cabinetry, stone countertops, a large island, and a spacious walk-in pantry. A full laundry room and functional drop zone are conveniently located on the main level. Upstairs, a spacious loft creates a true second living area—perfect for a media room, playroom, home office, or additional gathering space. Three additional bedrooms include a second primary-style en-suite, offering an ideal private retreat for guests, older children, or extended family. An additional full bath serves the remaining bedrooms and loft. A second laundry option, with a stackable washer and dryer, is also located upstairs for added convenience. A covered back porch extends the living space outdoors, creating a comfortable setting for relaxing or entertaining. Additional highlights include 9' ceilings, 8' doors, wide-plank hardwood flooring, designer lighting and trim, covered outdoor living, tankless gas water heater, EV charging hookup, and a smart garage door and camera system. With four bedrooms, four baths, two primary en-suites, two living areas, and two laundry options, this home offers an exceptional level of versatility rarely found in new construction. Every detail has been thoughtfully selected to create a home that feels sophisticated, comfortable, and incredibly livable. Home is currently under construction. Exterior image is an AI-generated rendering intended to illustrate the anticipated finished appearance. Additional photos reflect a previously built Portrait Homes property and are provided for design and finish reference only. Final finishes and selection details may vary.

4176 Buttermilk Rd, Lexington

514 W Short St Unit 101, Lexington
$795,000
2 Beds ⋅ 3 Baths ⋅ 26003648 MLS
One of the finest Condo's in the heart of downtown is capturing the eclectic vibe of the urban area with abundance of living & entertaining spaces just steps from Rupp Arena, the new Gatton Park, Fine Dining and much more! This beautifully updated residence offers inviting covered front entry with remote phantom screen, fabulous custom Chef's Kitchen, living room with soaring ceiling, built-ins w/ fireplace, 1st level Primary suite with laundry, walk in closet and luxury bathroom, half bath and large pantry, the second level offers home office, full custom bath, bedroom w/ loft and storage space, the lower level offers a paneled den with exceptional wine cellar and versatile spaces for storage, craft room & utility area. The large shared rear deck offers optimum space for morning coffee, evening cocktails & grilling. Adjacent climate-controlled garage with reserved space and additional guest parking makes this a desirable location. Don't miss this special opportunity.

514 W Short St Unit 101, Lexington

210 E 7th St, Lexington
$135,000
4 Beds ⋅ 3 Baths ⋅ 26013120 MLS
Calling all investors, flippers. and ambitious homeowners. Skip the heavy lifting and step into a property where some of the hardest work has already been completed. Besides their initial investment, the current owners have paid over $50,000 in materials and labor along with putting in countless hours of their own sweat equity into this home before putting the brakes on this mid construction flip. They cleaned out and demoed part of the original home, framed the upstairs, put on new siding, roof, and windows but unfortunately, sometimes, life just gets in the way. Designed to be a stunning 4 bedroom 2.5 bathroom home, the layout is exceptionally functional with a large entry foyer, first floor primary bedroom with an attached primary bathroom, eat in kitchen with pantry, half bath, and living room. Head upstairs to find the second story completely framed for 3 bedrooms, bonus/flex room, and a full bath. There's still plenty of time to change the floor plan to showcase your vision. There is front street parking and you can easily park a car in the rear yard too. With finished neighborhood comps pulling in the mid $200s and up, there is plenty of margin left for a smart investor or savvy homeowner that wants to finish this flip. Property being sold AS IS.

210 E 7th St, Lexington

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