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$57,500,000
7 Beds 6 Baths 26021823 MLS
What an opportunity as few properties in the Bluegrass carry Castleton Farm's pedigree. Established in 1793, this storied land has been shaped by generations of Kentucky's great horsemen — from a U.S. Senator's original breeding operation to the Castleman family's 1840 Greek Revival mansion, which still stands as a landmark of the farm today. Over two centuries, Castleton bred and stood champions across three breeds — Thoroughbreds, Standardbreds, and Saddlebreds — cementing its place among the Bluegrass's most storied nurseries. Today, the farm spans 951 acres and offers an unmatched scale of infrastructure: 16 barns ranging from intimate 4-stall setups to a substantial 30-stall facility, totaling 268 stalls. Ten homes across the property — including several managers' houses — provide ample accommodation for staff, making Castleton as functional as it is historic. This is more than a horse farm; it's a self-sufficient equine operation with two centuries of pedigree behind it, offered for the first time in 25 years to a new steward.

2469 Iron Works Pike, Lexington

$18,900,000
5 Beds 6 Baths 26021280 MLS
We are honored to present historic Payson Stud available for purchase. This legendary farm property consists of 142 acres along the famed Paris Pike in Lexington, Kentucky and is the epicenter of the Central Kentucky Bluegrass region. Anchored by the iconic 1850 John McMurty built Greek Revival Mansion, featuring 2 ½ stories and 8200 square feet that are currently undergoing a total renovation while thoughtfully preserving the unique history of the property and outbuildings. Included in the 10 acre curtilage surrounding the Mansion is a beautifully restored 1550 sqft 2 story brick residence (c.1850) with additions, and The Cottage, an elegantly renovated 1600 sqft brick residence- a favorite of the former property steward Virginia Kraft Payson. (The 10.7 acres with Main Residence and guest houses may be purchased separately, with inquiries directed to the listing agent.) The 132 acre improved horse farm portion has a secure place in the history of Kentucky's signature horse industry as the former home of champions from several breeds, including Classic and Kentucky Derby winners throughout the years. With 4 excellent barns housing over 77 stalls, 2 large run in sheds, 4 large fields, and 16 paddocks, the property is well designed and equipped for raising top quality horses. This is a generational opportunity to purchase a property steeped in the history of the Thoroughbred and one that has been completely and thoroughly renovated to present a truly unique turn-key opportunity to a discerning new steward.

4400-4434 Paris Pike, Lexington

$1,295,000
5 Beds 4 Baths 26021231 MLS
Tucked away at the end of a long custom gated and paved drive, this stunning contemporary home offers the perfect blend of luxury, privacy, and modern design. Situated on 1.4 beautifully landscaped wooded and open acres, this exceptional property features over 4,200 finished square feet, including 5 bedrooms and 4 full baths. The heart of the home is a spectacular chef's kitchen with waterfall granite countertops, premium KitchenAid stainless steel appliances, two ovens, and an open layout designed for both everyday living and entertaining. Brazilian pecan hardwood floors, soaring vaulted ceilings, and a dramatic custom staircase create an unforgettable first impression. The main-level primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub and separate body shower. A dedicated home theater with immersive 7.1 surround sound and separate bourbon room adds the ultimate entertainment experience. Outdoor living rivals a private resort with expansive decking, a stamped concrete patio, outdoor kitchen, multiple fire pits, pergola, hot tub, sauna, custom rock waterfall, and lush new landscaping. Garden enthusiasts will love the custom greenhouse complete with growing lights and a solar water system. Additional features include a 4-car garage, EV charger hookup, 220V service in the basement, custom front gate, and custom mailbox. Over 900 square feet of unfinished basement space, already roughed in for a full bath, provides endless potential for a guest suite, gym, recreation room, man cave, or workshop. Whatever you can dream up! A rare opportunity to own a private luxury retreat designed for exceptional living, entertaining, and relaxation in the highly desired neighborhood of Stonewall.

916 Bravington Way, Lexington

$2,300,000
2 Beds 4 Baths 26021023 MLS
Located in the highly coveted Lakewood neighborhood, this beautifully updated ranch offers refined living with a peaceful water backdrop and over 4,400 sq. ft. of finished space with 2-3 bedrooms and 3 and a half baths. Architectural elegance defines the home from the moment you arrive. Lavish woodwork, elaborate trim details, and abundant custom cabinetry complement gleaming hardwood floors and timeless millwork throughout. A gracious foyer with fanlight transoms and elegant archways introduces the formal living room and handsome wood-paneled library with fireplace. French doors extend the living space to an elevated brick terrace overlooking the manicured grounds and serene pond. The gourmet kitchen impresses with vaulted ceilings, exposed beams, two large islands, and designer finishes, opening seamlessly into a stunning hearth room framed by floor-to-ceiling windows, skylights, and a striking stone fireplace. The private primary suite evokes spa-like luxury with marble flooring, a freestanding soaking tub, an expansive glass shower, dual vanities, and sunlit windows that capture the tranquil setting. The finished walk-out lower level expands the home's versatility with a spacious family room, custom built-ins, an office nook, a convenient kitchenette, possible 3rd bedroom suite, and French doors leading to a screened porch perfectly positioned to enjoy pond views. Professional landscaping, a stack-stone wall, and multiple outdoor living areas enhance the property's beauty and livability. With three fireplaces, premium craftsmanship, and a location among Lexington's most desirable addresses, this home offers a rare blend of timeless elegance and everyday comfort—an exceptional Lakewood opportunity.

1785 Mooreland Dr, Lexington

$3,850,000
4 Beds 3 Baths 26020901 MLS
A unique boutique farm in the heart of Lexington horse country, this beautifully renovated four bedroom home on 14 pristine acres is completely turn key and ready for you and your two legged and four legged family. Nestled among some of the most beautiful aged trees you will find in this area, including the one of the oldest Bur Oak trees, you will find equestrian paradise. Secluded among trees and opening into pastures you can see your horses in from all views, the quiet of farm life exists just minutes to all the necessities. The completely renovated home features 5800 square feet under air with flexible spaces for many options for staff and/or a home business. Key features include a whole house generator running off a 1000 gallon buried propane tank, separate staff apartment in the walk out basement with private entrance, new fencing in 2025 on entire property, 3 RV hookups at the barn and arena. The fully steel 125 x 250 covered arena features a 3' concrete ribbon wall and screen curtains throughout. Complete gutter system empties into a cistern for reusable water. Six stall barn features Lucas doors, rubber pavers and mat systems, tack room, feed room, and hot/cold wash rack and storage loft. No detail has gone unnoticed on this meticulously maintained exquisite equestrian estate. Just 15 min to downtown Lexington and Paris, Bluegrass Airport, and Keeneland, as well as two world class veterinary clinics and the Kentucky Horse Park.

2830 2830 Old Lemons Mill Rd Rd, Lexington

$2,295,000
4 Beds 5 Baths 26020802 MLS
Rare opportunity to own a completely renovated home on Richmond Road. located on the corner of Richmond Rd. and Bassett Avenue directly across from the Henry Clay estate; this 1923 colonial home has been gutted down to the studs and meticulously renovated by Wooddale Partners. Every inch of the interior is brand new. Enter through the front door into a bright and inviting living room with full high window and fireplace looking into the formal dining room with a large triple window and full height window. The large family room is open to the kitchen that has custom handmade inlay cabinetry with built in fridge and dishwasher, 48? gas range, direct ventilation range hood, and large 48? workstation sink looking out onto the covered lanai that features a large gas fireplace, built in grill and fridge. The main level also features a breakfast nook, office, and mud/ laundry room. The primary bedroom has a large walk-in closet with custom built ins and island, sitting room, and beautifully designed bathroom. 3 guest bedrooms are all on suite with built in closets. The property sits on a 1/3 of an acre with a large yard, completely fenced in with room for an in ground pool. The detached 3 car garage is accessed off Bassett avenue with a driveway that fits 9 cars. Book your showing today to see all the fabulous hand selected finishes in person.

1501 Richmond Rd, Lexington

$1,414,900
4 Beds 6 Baths 26020773 MLS
Nestled in the highly sought-after Ellerslie at Delong, this beautifully appointed home showcases timeless design, exceptional craftsmanship, and thoughtfully curated upgrades throughout. The main level welcomes you with elegant wainscoting, tiered ceilings with designer lighting, and extensive 6-inch crown molding. At the heart of the home is a chef's kitchen featuring premium appliances, a spacious walk-in pantry, and an open layout that flows seamlessly into the inviting great room with custom built-ins, a fireplace, and picturesque views of the greenspace beyond. Enjoy indoor-outdoor living with screened porches on both the main and lower levels overlooking the fully fenced backyard. Upstairs, three generously sized bedrooms each offer en suite baths, providing comfort and privacy for family or guests. The finished walkout basement is designed for entertaining, complete with a full bar, billiards area, digital home theater with whole-home audio zones, a full bath, and a dedicated fitness space that could easily serve as a fifth bedroom. Combining luxury finishes, flexible living spaces, and an unbeatable neighborhood setting, this home offers an exceptional lifestyle in one of Lexington's most desirable communities.

201 Kelburn Ct, Lexington

$1,750,000
6 Beds 7 Baths 26020527 MLS
Welcome to Sahalee, a lovely gated community of ten-acre estates that perfectly captures timeless Southern charm. Defined by classic columned entryways, elegant Palladian windows, and four-plank horse fencing, this property offers sophisticated living at its finest. Step inside to a grand foyer featuring soaring two-story ceilings and gleaming hardwood floors. To the left sits a spacious formal dining room detailed with lavish woodwork, while a cozy, wood-paneled library/office rests to the right. Directly ahead, the expansive living room serves as the heart of the home, showcasing built-in shelving, a warm fireplace, and dramatic two-story views, and leads to an inviting Sunroom. Designed for everyday living and entertaining, the open-concept kitchen features light cherry cabinetry, quartzite countertops, and newly updated sink fixtures. The main-level primary suite offers a private retreat, complete with a spa-like bath featuring heated floors and a tiled walk-in shower. Upstairs, you'll find a second primary suite, two additional bedrooms with a full bath, and a dedicated cedar closet. The fully finished basement adds exceptional living space, featuring a recreation room with a wet bar, a cozy TV area with a fireplace, two additional bedrooms, and a full bath. This home has been meticulously maintained with significant recent capital improvements, including three new Amana HVAC systems and two new 75-gallon water heaters added in 2026. A Vantage custom lighting system featuring two motorized chandeliers was installed in 2025, alongside additional high-end systems like a natural gas generator, an Aqua Chill purified water system, and an automated irrigation system. The outdoor space is a private paradise designed for relaxed luxury. Enjoy an inviting in-ground heated pool—complete with a fresh liner and new pump—and a poolside pavilion equipped with cable TV access. The expansive patio is built for outdoor entertaining, boasting a chef's kitchen outfitted with premium Fire Magic appliances. A side-entry three-car garage rounds out this exceptionally livable, turnkey estate.

1700 Sahalee Dr, Lexington

$1,359,999
4 Beds 6 Baths 26020505 MLS
New Construction in Prestigious Beaumont Reserve! Experience refined luxury in this exceptional custom-built home, ideally situated in Beaumont Reserve, one of West Lexington's most prestigious and sought-after communities. Offering the rare opportunity to own a brand-new home in an established neighborhood, this residence blends timeless elegance with modern sophistication. Positioned on a spacious corner lot, the home features soaring ceilings, abundant natural light, and thoughtfully designed living spaces throughout. The oversized three-car garage provides generous parking and storage. At the heart of the home is a spectacular chef's kitchen, beautifully appointed with premium appliances, custom-crafted cabinetry, an expansive island, and an open-concept design that flows effortlessly into the inviting great room—perfect for everyday living and elegant entertaining. The main level also offers a private office or study and a spacious laundry room. Upstairs, all four generously sized bedrooms feature their own en-suite full bathrooms, providing exceptional comfort and privacy. The luxurious primary suite serves as a retreat, complete with its own private covered deck. The finished basement offers many possibilities for future customization, additional living space, recreation, or storage. Step outside to the large, covered patio, a perfect setting for outdoor entertaining, relaxing, or creating the outdoor kitchen of your dreams. This remarkable new construction offers the perfect combination of contemporary design, exceptional craftsmanship, and an unbeatable Beaumont location. Don't miss this rare opportunity to own one of Lexington's finest luxury homes. Original house was completely distorted in a house fire Dec 2020 - It is completely rebuilt on new foundation in 2025/26. Schedule your private showing today.

2269 Savannah Ln, Lexington

$12,000,000
7 Beds 6 Baths 26020118 MLS
The premier Broodmare & Stallion complex of Shadwell Farm, including 90 world-class stalls. Opportunities to acquire a farm of this caliber, with this provenance, come once in a lifetime. If you've ever dreamed of owning a true diamond in the Bluegrass, now is your chance. Established in the heart of the Bluegrass more than four decades ago, Shadwell Farm quickly rose to become one of the most respected breeding and racing operations in the world. From its iconic teal-and-white silks to the countless champions that have called these rolling Central Kentucky pastures home, Shadwell has left an indelible mark on the Thoroughbred industry. Notable highlights from Shadwell Farm's extraordinary legacy include: Home to two-time Horse of the Year and leading sire Invasor (Argentine Triple Crown winner and Breeders' Cup Classic victor). Broodmare band that produced international superstars such as Nashwan (English Derby & King George VI and Queen Elizabeth Stakes), Sakhee, Haafhd, Ghanaati, Muhaarar, and Baaeed. Multiple Eclipse Award winners and champions raised and developed on the property. Consistently ranked among North America's leading breeders by earnings and stakes winners. A state-of-the-art facility that has set the standard for stallion stations, foaling barns, and yearling preparation in the region. For over 40 years, Shadwell Farm has been far more than a commercial operation--it has been a cornerstone of Lexington's equine community, a place where tradition meets excellence, and where generations of horsemen and women have walked the same lanes as some of the greatest Thoroughbreds of our time. My goal is simple: to find the next steward who understands and cherishes what Shadwell represents -- not just as one of the finest horse farms in Kentucky, but as a living piece of Thoroughbred nostalgia that deserves to be preserved, respected, and carried forward into its next chapter.

3661 & 3669 Military Pike, Lexington

$1,299,000
5 Beds 5 Baths 26018925 MLS
Luxury, elegance, and thoughtful design come together in this exceptional custom-built home, completed in late 2024, in Lexington's highly sought-after Tuscany community. Offering nearly new construction with timeless architecture and premium finishes throughout, this home was designed to impress at every turn. Step through the grand foyer into light-filled living spaces where wide-plank hardwood flooring with a timeless white oak finish, custom millwork, coffered ceilings, designer lighting, and a stunning gas fireplace create a warm yet sophisticated atmosphere. At the heart of the home, the gourmet kitchen is designed for both everyday living and entertaining, featuring an oversized quartz island, premium KitchenAid appliances, a gas cooktop with pot filler, beverage refrigerator, walk-in pantry, and an open-concept layout that flows seamlessly into the dining and living areas. Designed with flexibility in mind, the home offers two exceptional en suite bedroom retreats. The main-level suite provides the convenience of first-floor living and includes a walk-in closet with washer and dryer hookups, making it ideal for multigenerational living, extended guests, or a luxurious private retreat. The upstairs owner's retreat is truly unforgettable. A grand custom walk-in closet offers exceptional storage, with additional hanging and wardrobe space extending beyond the main dressing area. The closet connects directly to a beautifully finished marble laundry room, while the spectacular primary bathroom is finished in elegant marble and offers a true spa experience with an expansive walk-in shower, freestanding soaking tub, dual vanities, and a stunning open design. The finished walkout basement offers incredible versatility with a kitchenette, spacious guest suite, full bath, bonus room ideal for a theater, fitness room, or home office, a second laundry area, generous storage, and abundant space for entertaining family and friends. Outdoor living is equally inviting with a spacious Trex deck and covered patio, providing the perfect setting for morning coffee, evening gatherings, or simply enjoying the peaceful surroundings. Ideally located just minutes from Hamburg Pavilion, premier shopping, dining, entertainment, and I-75, this extraordinary home combines luxury, comfort, and thoughtful functionality in one remarkable package. A rare opportunity to own a nearly new custom luxury home in one of Lexington's most desirable communities.

2648 Lucca Pl, Lexington

$2,450,000
26019604 MLS
1040-1050 Eastland Drive offers 17,247 SF for lease or is available as an ideal owner occupant/investment sale where a purchaser can occupy its business in the vacancy, while enjoying in place income. The property features 30,488 total SF demised into three high demand sizes for the market creating a diversified asset, has an excellent overall office to warehouse ratio of 13.65% office, concrete block construction ranging between 1970-1974, 1.41 acres zoned I-1, 6 docks, 4 drive-ins, 16' clear height, LED lighting, newer EPDM roofs (2016/2019) with assignable warranties, wet sprinkler system, and much more. 1040-1050 Eastland Drive runs between Loudon Avenue and New Circle Road in the Winchester Road/eastern corridor of Lexington, KY. The property is 0.8 miles from New Circle Road, 2.7 miles from I-75/I-64 and 8.5 miles from Bluegrass International Airport. With an MSA over 645,000, Lexington is the second largest market in the Commonwealth of Kentucky. Central Kentucky provides a strategic location for businesses through access to a highly educated labor force, low startup and operational costs, below average cost of living and its location at the I-75/I-64 intersection providing a 24 hour or less drive to approximately 70% of the United States population. Property Highlights: -High demand size for Lease (17,247 SF) -Great owner-occupant purchase with in place income -Excellent office:warehouse ratio with newly-renovated office space -6 docks/4 drive ins, 16' clear height -Small outside storage for each unit -Newer roofs

1040-1050 Eastland Dr, Lexington

$1,499,000
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

$3,100,000
4 Beds 7 Baths 26019343 MLS
Nestled in the heart of Chevy Chase just off Tates Creek Road, this 4-bedroom, 6.5-bath home is a stunning study in classic elegance minutes from the University of Kentucky, Kroger Field, hospitals, dining, and entertainment. A masterful, complete renovation doubled the original square footage. Reclaimed wood floors sourced from a single Virginia barn run throughout. The eat-in kitchen showcases Imperial Danby countertops and Thermador appliances; an indoor-outdoor patio features a two-way fireplace. The main level adds a full and half bath plus laundry. Upstairs, the expansive primary suite offers two full baths and two walk-in closets, alongside two bedrooms, each with an en-suite bath. The finished lower level includes a home gym, playroom, en-suite bedroom, and ample storage. Outside: a gated drive with porte cochère and a two-car detached garage with finished space above full bath and kitchenette included.

1231 Eldemere Rd, 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

$1,200,000
5 Beds 6 Baths 26018087 MLS
Completely reimagined luxury in the heart of Patchen Wilkes. Built by renowned Jimmy Nash Homes and meticulously renovated from top to bottom, this extraordinary residence offers the rare opportunity to own a home that combines timeless craftsmanship with today's most sought-after finishes. Every detail has been thoughtfully curated, creating a truly move-in ready home that lives like new. The stunning chef's kitchen serves as the centerpiece of the home, showcasing custom cabinetry with glass accents, an oversized island, premium KitchenAid appliances, five-burner gas cooktop, built in microwave and wall oven, farmhouse fireclay sink, granite countertops, under-cabinet lighting, pull-out spice racks, and custom tile backsplash. The adjoining family room is equally impressive with soaring coffered ceilings, extensive custom built-ins, New 3/4 inch thick white oak flooring on first and second floors, plus hardwood stair threads. New Premium PVC Wood Theme flooring in basement, double stack crown molding in formal areas and crown molding throughout the basement and second floors and a beautiful fireplace that creates an inviting gathering space. Designed for modern living, the home features beautifully refinished hardwood flooring, elegant neutral designer paint, extensive custom trim work, updated lighting throughout, renovated bathrooms, and luxurious owner's suite complete with a spa-inspired Schuler shower system, freestanding soaking tub, custom glass shower enclosure, granite vanities, custom mirrors, and an exceptional custom walk-in closet. The thoughtful renovation extends throughout the home with two additional second-floor bathrooms, a converted bonus room offering flexible space as a second primary suite or entertainment room, French doors, custom mudroom, new stair treads and spindles, updated flooring, and countless custom details throughout. Major mechanical updates provide peace of mind, including a new roof (2023), updated HVAC systems, commercial-grade 80-gallon Bradford White water heater, interconnected smoke and CO detectors, security cameras, and enhanced exterior lighting. Outside, enjoy professionally landscaped grounds featuring mature Japanese Red Maple trees, Arborvitae privacy screening, irrigation system, welcoming covered front porch, and an under-deck rain management system creating additional covered outdoor living space below. Located in one of Lexington's most desirable neighborhoods, this exceptional Jimmy Nash home delivers luxury, quality, and extensive renovations rarely found in today's market. Property Highlights Jimmy Nash custom-built home in prestigious Patchen Wilkes Extensively renovated from top to bottom Chef's kitchen with custom cabinetry, oversized island & KitchenAid appliances Coffered ceilings, hardwood floors & custom built-ins Spa-quality primary suite with luxury bath renovation Flexible floor plan with additional second-floor suite/bonus room New roof, updated HVAC, water heater & major mechanical improvements Professional landscaping, irrigation & enhanced outdoor living Truly move-in ready with exceptional attention to detail

1937 General Warfield Way, Lexington

$1,499,000
5 Beds 5 Baths 26018503 MLS
Truly one of a kind, this remarkable home seamlessly blends the timeless character of a historic stone cottage with the comfort and functionality of a thoughtfully renovated ranch home. Envisioned by its creative owners, the home offers 4,891 square feet of beautifully designed and exceptionally livable space, where historic charm and modern updates come together in a truly special setting. The open-concept main living area features a spacious Great Room with an inviting fireplace, a generous Dining Area, and an updated Kitchen complete with new cabinetry, appliances, and a charming built-in dinette with seating. A dramatic wall of windows fills the space with natural light and overlooks the expansive bluestone patio and pergola, peaceful lily pond, and picturesque views of the original stone cottage. The main level offers four Bedrooms, two with en suite full Baths, and an additional full Bath and half Bath. A light-filled hallway lined with large windows leads to a comfortable Family Room, Laundry Room, Utility Room, and Safe Room. The second floor is dedicated to an impressive Primary Suite featuring a fireplace, newly added full Bath, three large walk-in closets, an Exercise Room, and a private Office—creating a spacious and serene retreat. Extensive upgrades include a new metal roof, whole home generator, geothermal heating and cooling, structured wiring and camera system, and dual 100-gallon water heaters. Please see the numerous other updates on the attached list. Additional highlights include a spacious two-car attached Garage and generous attic storage. Rich in character, thoughtfully updated, and designed for everyday living and entertaining, this exceptional property offers a rare opportunity to own a home unlike any other.

269 Cassidy Ave, Lexington

$1,199,000
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

$3,790,000
26008699 MLS
Highly Visible Downtown Office Space or amazing redevelopment opportunity. Position your brand at the center of it all. This iconic office building offers a rare combination of high-profile visibility and unparalleled convenience in the heart of downtown Lexington.Designed for firms that value both prestige and practicality, this property ensures your team and your clients are always exactly where they need to be. Situated on a high-traffic corridor, the building's striking architecture provides a "billboard effect" for your business, capturing the attention of thousands of commuters and pedestrians daily. Onsite Private Parking: Say goodbye to the downtown "parking hunt." This building features a dedicated onsite parking lot, providing seamless access for employees and a premium, stress-free experience for visiting clients.Walkable Urban Lifestyle: Step out the front door and into Lexington's vibrant core. You are minutes away from the District Courts, City Hall, and the city's finest dining, coffee shops, and banks. Building consists of 24 offices 8 half baths, 2 break areas, 1 training room, Server Room, File room, 2 copy rooms and a reception area. Don't miss the opportunity to occupy one of the most recognizable professional hubs in Central Kentucky. Whether you are a growing tech firm, an established law practice, or a creative agency, this building offers the identity and infrastructure required for your next chapter of growth.

277 E High St, Lexington

$1,650,000
6 Beds 6 Baths 26006604 MLS
If you are looking for a home that offers space to unwind from daily demands—along with room for entertaining, celebrations, hobbies, or even a horse or small animal operation—this property delivers. With abundant indoor and outdoor entertaining areas, the shed-row barn offers flexible use as a horse facility, workshop, "she-shed," hobby space, or storage. Set on 10 acres, this is a property where imagination can truly take hold. The home has been spectacularly remodeled by Creative Kitchen and Bath. Impeccably maintained, it was taken down to the studs and completely renovated from top to bottom. Features include new hardwood floors, detailed moldings, new kitchens on both the main level and the basement, new bathrooms throughout, new windows and doors, high-speed broadband, a central vacuum system, a high-powered security system, and a Bluegrass home movie theatre entertainment system. All bedrooms include walk-in closets with custom-designed wood shelving. The lower level offers a separate entrance, making it ideal for a mother-in-law suite or apartment, complete with a full walkout, multiple French doors, and wall-to-wall windows. The property is being sold furnished, with furnishings included in the current price, and is priced under recent appraisal. The location combines convenience with a true country feel—close to shopping in Hamburg and directly across from Hisle Farm Park. The park spans approximately 280 acres of rolling pastureland located five miles northeast of downtown Lexington at 3601 Briar Hill Road. It features shared-use trails for horseback riding and hiking, including 1- and 2.5-mile loops, a 10-lane target archery range, and is open from dawn until dusk. Pets are welcome but must be leashed. Priced $540,000 below recent appraisal!!!

3600 Briar Hill Rd, Lexington

$2,330,000
14 Beds 21 Baths 26010746 MLS
Exceptional new construction multi-family property in Lexington's established Masterson Station area. 3104 Daly Pl offers modern construction, functional design, and low-maintenance ownership in a high-demand rental corridor with convenient access to downtown Lexington, New Circle Road, I-64/I-75, the University of Kentucky, shopping, dining, and major employers. Designed with long-term value in mind, the property features contemporary finishes, efficient floorplans, and the advantages of newer construction that continue to appeal to today's renters. Investors will appreciate the modern aesthetic, reduced maintenance considerations, and strong location fundamentals within one of Lexington's steadily growing residential markets. Convenient access to everyday amenities and commuter routes further supports tenant demand and long-term income potential. Whether expanding an existing portfolio or adding a newer income-producing asset, this property offers a well-positioned opportunity in a growing area of Lexington.

3104 Daly Pl, Lexington

$1,250,000
2 Beds 3 Baths 26010192 MLS
Experience elevated living at its finest in downtown's newest 36-unit condominium project, The Vine. This collection of one- and two-bedroom residences showcases thoughtfully designed interiors with refined finishes from floor to ceiling, creating a seamless blend of style and comfort. Each residence features a private balcony with city views, while community amenities include a rooftop pool and access to The Vine Club, offering an elevated social and leisure experience. Residents also enjoy concierge services, including a doorman, along with a professionally managed program for short-term rental opportunities. Ideally positioned in the heart of downtown Lexington, The Vine offers close proximity to Rupp Arena, the University of Kentucky, local dining, nightlife, and everyday conveniences. Imagine starting your mornings with coffee at a nearby café and ending your evenings taking in the energy of the city, all just steps from your front door. This is more than a residence; it is a lifestyle.

106 W Vine St Unit 605, Lexington

$1,925,000
3 Beds 3 Baths 26010885 MLS
A Private equestrian estate gives you a rare opportunity to own 27.11 acres in the valuable Bluegrass horse country, 3.25 miles from The Ky Horse Park and situated between horse farms, this quiet setting is ideal for training, relaxing and living your best life! From the 1800s dry stacked stone walls at the entrance, drive down the treelined drive, to your left is the 100 x 230 all weather footing arena, paddocks with run in sheds, and around the bend is the 3 car detached garage and a beautifully designed seven stall barn with a distinctive 3 bedroom, 3 bathroom residence above. Beyond are the remaining acres with run in sheds. The residence has 3 nice size bedrooms and 3 full bathrooms,(1 bedroom and full bathroom on the barn level and other 2 bedrooms/bathrooms are up) wood burning fireplace in living room, custom kitchen cabinetry, granite countertops, hardwood floors, and fabulous decks overlooking the grounds. Tack room, feed room, wash stall and automatic waterers complete this spectacular, one of a kind premium property. Hardi-board siding, standing seam metal roof, rubber matted barn floors. Each paddock has well designed run in sheds, automatic waterers , and board fencing. PDR protected land. This property offers the rare ability to live, train and enjoy your horses on your own private farm while remaining close to Lexingtons equestrian and cultural amenities.

4351 Bethel Rd, Lexington

$1,650,000
6 Beds 6 Baths 26007206 MLS
If you are looking for a home that offers space to unwind from daily demands—along with room for entertaining, celebrations, hobbies, or even a horse or small animal operation—this property delivers. With abundant indoor and outdoor entertaining areas, the shed-row barn offers flexible use as a horse facility, workshop, "she-shed," hobby space, or storage. Set on 10 acres, this is a property where imagination can truly take hold. The home has been spectacularly remodeled by Creative Kitchen and Bath. Impeccably maintained, it was taken down to the studs and completely renovated from top to bottom. Features include new hardwood floors, detailed moldings, new kitchens on both the main level and the basement, new bathrooms throughout, new windows and doors, high-speed broadband, a central vacuum system, a high-powered security system, and a Bluegrass home movie theatre entertainment system. All bedrooms include walk-in closets with custom-designed wood shelving. The lower level offers a separate entrance, making it ideal for a mother-in-law suite or apartment, complete with a full walkout, multiple French doors, and wall-to-wall windows. The property is being sold furnished, with furnishings included in the current price, and is priced under recent appraisal. The location combines convenience with a true country feel—close to shopping in Hamburg and directly across from Hisle Farm Park. The park spans approximately 280 acres of rolling pastureland located five miles northeast of downtown Lexington at 3601 Briar Hill Road. It features shared-use trails for horseback riding and hiking, including 1- and 2.5-mile loops, a 10-lane target archery range, and is open from dawn until dusk. Pets are welcome but must be leashed. Priced $540,000 below recent appraisal!!!

3600 Briar Hill Rd, Lexington