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$459,000
6 Beds 2 Baths 26019619 MLS
Don't miss this versatile duplex located in one of Lexington's most desirable areas. Whether you're an investor looking to add a strong income-producing property to your portfolio or a buyer hoping to live in one unit while offsetting your mortgage by renting the other, this property offers outstanding flexibility and potential. Situated just minutes from the University of Kentucky, downtown Lexington, Chevy Chase, and local shopping and dining, this duplex is well-positioned for consistent rental demand. Each unit offers its own private living space, making it an attractive option for both tenants and owner-occupants. Whether you're looking to generate immediate rental income, build long-term equity, or take advantage of the benefits of owner-occupied investing, 270 Sherman Avenue is an opportunity you won't want to miss.

270 Sherman Ave, 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

$800,000
4 Beds 2 Baths 26018201 MLS
Turnkey income portfolio featuring two single-family homes and one all-brick duplex across desirable Lexington locations. 1104 Liggett Street offers 1,406 sq ft, 3BR/1.5BA in a trendy downtown-adjacent location minutes from the Distillery District and Rupp Arena, leased at $1,750/mo. 1693 Prairie Circle offers 1,466 sq ft, 2BR/2BA with a covered carport and an oversized layout, leased month-to-month at $1,500/mo with room to grow. 1503 Roanoke Road is an all-brick duplex with hardwood floors throughout, ~950 sq ft per side, 2BR/1BA each — Side A leased long-term at $1,050/mo, Side B is leased at $1,195. Well-maintained throughout with minimal deferred maintenance. A rare chance to acquire diversified, cash-flowing assets across multiple Lexington submarkets in a single transaction. Sold as a package.

1503 Roanoke Rd, 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

$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

$375,000
4 Beds 2 Baths 26013381 MLS
Rare opportunity to own a beautifully restored 19th-century duplex in the heart of downtown Lexington. Originally built in the late 1800s and thoughtfully renovated while preserving its historic character, this fully occupied property offers two spacious 2-bedroom, 1-bath units with tall ceilings, restored hardwood floors, updated kitchens and baths, and off-street parking. Recipient of a Historic Preservation Award, the property blends timeless architecture with modern functionality and dependable income potential. Situated just moments from downtown restaurants, entertainment, and local attractions, this is a standout investment in one of Lexington's most desirable and walkable neighborhoods. The neighboring sister duplex at 148 E Fourth Street is also available, creating a rare opportunity to acquire two side-by-side historic duplexes in a premier downtown location.

152 E Fourth St, Lexington

$1,895,000
26015715 MLS
Renovated in 2018, 250 E. Short Street offers modern interior finishes in a great downtown location. The entry way is a split level with glass and wood beams. The space has beautiful hardwood flooring, tall ceilings and large windows which provides ample natural lighting. Investment Opportunity - Downtown Lexington: Located in the heart of downtown Lexington, 250 East Short Street presents an exceptional opportunity for investors seeking a high-quality, income-producing asset in a premier location. The building underwent a complete renovation in 2018 by the current owner and stands as one of the most attractive and well-maintained properties in the downtown market. Over the past year, portions of the building have been further improved and customized to accommodate the specific needs of its three current tenants, enhancing both functionality and tenant satisfaction. The property also features a dedicated parking lot on the west side of the building, providing nine reserved parking spaces for tenants and their clients—a valuable amenity in the downtown area. Currently fully occupied by three tenants, this multi-tenant investment offers stable cash flow and delivers an attractive 6.7% capitalization rate, making it an outstanding opportunity for investors seeking strong returns and long-term value appreciation. Property Highlights: -This building offers prime Downtown Lexington location -Fully renovated in 2018, with some additional tenant-specific improvements completed within the past year -With three established tenants, this investment generates income from day one -Nine reserved on-site parking spaces -Well-maintained, turnkey investment opportunity with a 6.7% CAP Rate

250 E Short St, Lexington

$1,750,000
26008596 MLS
We are pleased to present an exceptional opportunity to purchase or lease a premier creative office building in the heart of Downtown Lexington. Located at 146 E. Third Street, this property showcases a remarkable historic renovation that blends timeless architectural character with modern design and functionality. Originally constructed in 1840, the two-story building offers appx. 6,848 SF above grade plus an additional 410 SF of finished lower-level space, ideal for storage or supplemental workspace. Upon entry, the first floor greets visitors with original hardwood floors, exposed brick, and contemporary finishes. Highlights include a distinguished boardroom with folding privacy doors, granite counters, and a fireplace that flows seamlessly into a spacious library featuring custom maple cabinetry and quartz countertops. A tiled kitchenette with dishwasher, two restrooms (including a full bath with shower), and direct access to a flexible garage space with a drive-in door further enhance the main level. An elevator and steel-wrapped open stairwell with expansive windows provide convenience and natural light throughout. The second floor is equally impressive, offering vaulted ceilings with exposed joists, generous open work areas with hardwood floors, and abundant daylight. A private sundeck with custom railing offers striking views of the Lexington skyline. Meticulously renovated in 2015, the property features a new roof, HVAC systems, windows, elevator, and porous concrete parking surface. On-site parking includes six dedicated spaces, with ample additional surface parking available nearby. This one-of-a-kind office environment combines historic charm, modern amenities, and a prime location--an unparalleled opportunity for businesses seeking a distinctive Downtown Lexington address. Layout: The first floor offers warm reception space leading into open conference room with large attached library/seating area, large bathroom with shower and expansive flex warehouse that could be easily converted to additional office space. The second floor offers large open workspaces, additional bathroom, and wonderfully lit breezeway leading to the rooftop deck. Meticulously Remodeled: The building underwent a complete renovation in 2015, adding modern touches while preserving many of the original architectural finishes. Upgrades include all new mechanical systems, a new roof, new windows, new rear staircase and an elevator. Move-In Ready: The building is suitable for a number of professional users and is move in ready. The workable layout also offers flexibility for minor modifications if needed. Location: The property is located in the heart of Downtown Lexington surrounded by an abundance of retail, restaurants, and more

146 E Third St, Lexington

$850,000
26014210 MLS
Position your business for long-term success with this rare opportunity to acquire an entire top-floor office portfolio at 300 East Main in the heart of downtown Lexington. Consisting of 9,717 square feet, the offering includes multiple office suites that can function seamlessly as a single headquarters for an owner-occupant or be divided into individual suites for investment or multi-tenant use. This portfolio offers privacy, flexibility, and expansive downtown views, creating an ideal environment for professional offices, medical users, creative firms, or regional headquarters. The adaptable layout allows buyers to customize the space to meet operational needs while also providing the potential for additional income through leasing individual suites or potential growth. Situated within walking distance to downtown restaurants, government offices, banking, and entertainment, this property combines convenience, visibility, and flexibility in one of Lexington's most established business corridors. Opportunities to control an entire floor in downtown Lexington are increasingly limited, making this a compelling option for both investors and owner-users seeking a strategic long-term asset. Located in the core of Downtown Lexington, 300 East Main offers immediate access to the city's central business district, government offices, financial institutions, restaurants, hotels, and entertainment venues. Positioned along East Main Street, Lexington's primary downtown corridor, the property benefits from excellent visibility, convenient connectivity, and a highly walkable urban environment. The location provides quick access to New Circle Road, Interstate 75, and Interstate 64, allowing efficient travel throughout Lexington and the surrounding Central Kentucky region. Nearby amenities include the Lexington Convention Center, Rupp Arena, and the growing collection of downtown dining, retail, and hospitality destinations that continue to drive investment and activity within the urban core. -Rare opportunity to acquire an entire top floor of office space in Downtown Lexington, KY offering a flexible floor plan. -8 parking spaces (3 covered and 5 surface spaces) with 4 additional visitor parking spaces. -20 private offices, large conference room, 2 kitchenettes, large private meeting room, and two large open workspaces.

300 E Main St Unit 510-560, Lexington

$949,900
26003675 MLS
**Prime ±0.40-acre B-1 zoned commercial redevelopment opportunity in the core of Lexington's established Winchester Road corridor. The site offers approximately 150 feet of frontage along Winchester Road with an additional ±125 feet of highly visible corner exposure, positioned on one of the area's most heavily traveled retail arterials with traffic counts of ±32,000 vehicles per day. Immediate access to New Circle Road and I-75 provides exceptional local and regional connectivity. The property benefits from a previously approved Conditional Use Permit for a drive-through facility (LFUCG Board of Adjustment Case PLN-BOA-23-00006), significantly reducing entitlement timelines and creating a clear path for restaurant, coffee, banking, pharmacy, medical, or other drive-through users. Its efficient rectangular configuration (approximately 150' × 125') allows for highly functional site planning and is ideally suited for a single-tenant net-lease pad, build-to-suit opportunity, or neighborhood retail concept. Environmental remediation is state-managed and actively progressing through a defined regulatory pathway toward a No Further Action (NFA) determination. The site is located within a dense in-town trade area with more than 96,000 residents within a 3-mile radius and over 211,000 residents within 5 miles and is surrounded by a strong mix of national and regional retailers that generate consistent daily traffic and consumer draw.

1209 Winchester Rd, Lexington

$3,100,000
25503131 MLS
Excellent owner-occupant or investment opportunity in Lexington's desirable Beaumont Centre. 1020 Monarch Street is a well-maintained three-story professional office building containing approximately 22,536 square feet with elevator service and ample surface parking. The first floor is fully leased to two professional tenants providing stable income. The second floor features a large training room, open area for cubicles or workstations, three private offices, a large conference room, and a spacious break room. The third floor (7,632 RSF) offers 22 private offices, large and small conference rooms, two public restrooms plus one private restroom, a large break room, and a dedicated storage room. Located in the heart of Beaumont Centre near Harrodsburg Road, New Circle Road, and Man O' War Boulevard, the property is surrounded by restaurants, retail, and professional services. Offered at $3,100,000, this property provides flexibility for an owner-occupant to occupy the upper floors while benefiting from existing rental income on the first floor

1020 Monarch St, Lexington

$3,500,000
25505468 MLS
Turnkey Greenhouse Operation in Central Kentucky. Exceptional 28.96-acre agricultural property featuring 225,400± sq. ft. of modern greenhouses designed for high-efficiency and year-round cultivation. A premier opportunity for commercial vegetable, flower or specialty crop hydroponic/aquaponic producers, this property is fully equipped and ready for immediate operation. The sale includes all equipment, infrastructure, and environmental systems, providing a complete turnkey solution for consistent, high-quality production. Fertile Central Kentucky soils, ample water resources including a high volume well, and a favorable growing climate create an ideal foundation for sustained yields and long-term success. Whether expanding an existing enterprise or launching a new controlled-environment agriculture venture, this property offers the perfect combination of scale, technology, and proven productivity in one of Kentucky's most desirable growing regions.

4610 Hamilton Ln, Lexington

$650,000
25507333 MLS
Multi-Tenant building for SALE on high visibility location of Lane Allen Rd., across the street from Home Depot and close to the Broadway/Harrodsburg Rd intersection. Two private tenant entrances with street level and upper level SF, approx. 1327 SF on both sides. Total of 2654 SF above grade + an additional 1830 SF below grade space (2 spaces approx 915 SF each), currently used as a meeting area in one below grade space and storage/contractor space in the other. 765: Currently owner occupied and used as a contractor office with reception area, private offices and kitchen. (Basic conference space and storage of contractor items, ladders... in below grade SF spaces). 763: Tenant occupied as a salon space for many years. B-1 zoned for an array of Uses. Perfect for an Owner Occupant with income from other Tenant(s). Recent Upgrades: * Complete renovation of interior spaces including new paint, flooring, smooth ceilings * Repairs and painting of Exterior * New Fence and newly painted * Enlarged parking lot with new paving and stripes * Solar panels installed on roof * Two new staircases at back entrances *New AC unit in 763 Lane Allen side

763-765 Lane Allen Rd, Lexington

$1,250,000
26010653 MLS
We are pleased to present this exceptionally updated and maintained Flex building located in the heart of the highly desirable Manchester Street corridor in Central Lexington. The building size at 11,578 SF on approximately 1 acre is very much in demand in this market, and consistently low in supply. As well, the division of office to warehouse is conducive to many business needs who can step right in and enjoy polished office space, cubicle rooms, multiple conference rooms, interior restrooms on each floor, copy room, and a warehouse space in the rear with loading dock access and lot accessibility that allows for large truck deliveries and pick ups. Other perks include two walk in coolers (455 SF and 375 SF), Kohler diesel back up generator that powers the entire building, 400 amp power, detached warehouse, and detached garage. The property also benefits from a central location in a highly desirable corridor that will appeal to a variety of flex users whether they are a local or regional business, benefiting from proximity to New Circle Road, Downtown Lexington, and interstate access. Additionally, extensive improvements from 2014 and optimal upkeep over the years signal a lack of deferred maintenance providing reassurance to buyers looking for a solid investment for their own preferred use accommodate the time and deal structure necessary for such a pursuit. -Constantly high in demand / low in supply offering -Light Industrial zoning (I-1) with Adaptive Reuse Zoning Overlay -Just under 1 acre with generous access and parking areas for delivery -Central Lexington Location just off Downtown in Lexington's booming Distillery District -Adaptive Reuse Zoning Overlay for added use flexibility -Close proximity to New Circle Road, Downtown, and Interstate access -This property is enrolled in Kentucky's Brownfield Program.

1040 Manchester St, Lexington

$1,250,000
16 Beds 16 Baths 26000503 MLS
1416 Townley Drive is a 16-unit multifamily property in Lexington, KY. Its location offers excellent access to downtown Lexington, major employment centers, universities, public transportation, healthcare centers, and retail corridors. The property, built in 1959, is 5,040 square feet and is situated on .405 acres. Each unit is a 330 square feet studio apartment with hardwood and tile floors and a designated kitchen area with range, oven, and refrigerator. Basement storage is available to Tenants and there is an opportunity to add coin laundry in the basement. The property is ideally located in the popular Meadowthorpe neighborhood near the new Commons development and just off Leestown Road, a main Lexington thoroughfare. The location is a strong demand rental area with low vacancy rates. This property can be sold individually or along with other properties in a 60-unit multifamily portfolio. The 60-unit multifamily portfolio is strategically located in the heart of Central Kentucky. The Central Kentucky area benefits from strong renter demand, low vacancy rates, and a stable market. This is a rare opportunity to acquire a large and stabilized multifamily portfolio in one of Kentucky's most reliable rental markets. The other properties in the portfolio are 200 N. Hill-N-Dale Street in Danville, KY and 115 Delmont Drive in Lexington, KY. Financials available upon request.

1416 Townley Dr, Lexington

$799,000
16 Beds 8 Baths 26014338 MLS
Rare opportunity to acquire two fully renovated four-plexes at 1041 & 1043 Cross Keys Road - sold together only, will not be divided. Eight units total, all currently occupied by long-term tenants with an exceptional payment history. Properties feature hardwood floors throughout, updated kitchens, central HVAC, garage parking with washer/dryer hookups in every unit, and marble window sills. Seller has maintained both buildings meticulously since a complete renovation in 2015, including full electrical rewire, new plumbing fixtures, all new appliances, and central air added to all units. Rents are currently below market, offering immediate upside for a new owner. In close proximity to James Lane Allen Elementary, Wolf Run Park, Kroger, and Gardenside Shopping Center. Do not disturb tenants. All inquiries to listing agent. Each apartment is 882 SQ FT, each building is 3528 SQ FT, total for both buildings is 7056 SQ FT.

1041-1043 Cross Keys Rd, Lexington

$325,000
26003466 MLS
For SALE or LEASE Very convenient location near I75 and I64 and visible from Man-of-War. Looking for a professional, move in ready office space in one of Lexington's most convenient locations? This office condo is perfect for small businesses, medical/wellness professionals, or anyone ready to elevate their work environment.  Why You'll Love It: • Prime Lexington location with easy access for clients • Professional setting without the high overhead • Great layout for private meetings or focused work • Perfect for owners or tenants looking for a long term home base Whether you're expanding, downsizing, or stepping out of the home office, Unit 55 offers the flexibility and professionalism your business deserves.

513 Darby Creek Rd Unit 55, Lexington

$749,000
8 Beds 4 Baths 26015659 MLS
An exceptional opportunity to acquire a turnkey portfolio of two neighboring, fully occupied historic duplexes in the heart of downtown Lexington. Originally built in the late 1800s and thoughtfully restored while preserving their historic character, these award-winning properties offer a total of four spacious 2-bedroom, 1-bath residences featuring tall ceilings, restored hardwood floors, updated kitchens and baths, and convenient off-street parking. The package includes a shared off-street parking lot serving both buildings, adding convenience for residents while enhancing the long-term value and functionality of the portfolio. Fully occupied and meticulously maintained, these neighboring duplexes seamlessly blend timeless architecture with modern updates and dependable income potential in one of Lexington's most desirable and walkable neighborhoods, just steps from downtown restaurants, entertainment, shopping, and local attractions. Ideal for investors seeking a stabilized, income-producing asset, this portfolio also presents an outstanding opportunity for an owner-occupant. Live in one unit while the remaining residences help offset your mortgage, create a multigenerational living arrangement, or capitalize on future rental upside. Whether maintained as a long-term cash-flow investment, repositioned through future rent optimization, or utilized as a premium house hack, the portfolio offers multiple value-creation strategies. Priced well below its 2025 appraised value, this offering provides the potential for immediate equity in addition to dependable cash flow and long-term appreciation. Opportunities to acquire two adjacent, Historic Preservation Award-winning duplexes with a shared parking lot in such a premier downtown location are exceptionally rare. This is a truly one-of-a-kind chance to own a landmark investment in one of Lexington's most sought-after neighborhoods.

148 152 E Fourth St, Lexington

$594,000
6 Beds 2 Baths 26016208 MLS
ONLINE ONLY ABSOLUTE AUCTION!!! Online BIDDING ENDS Sunday, August 2, 2026 at 6:00PM. Terms & Conditions are as follows: As Is/Non-Contingent/10% earnest money deposit/30 day settlement/buyer's premium applies, see terms & conditions for details. Visit www.HalfhillAuctions.com for more information. Kristin Halfhill-Larimore, Principal Auctioneer, 859-333-1855. Amazing opportunity to bring your vision to life! This property has already been partially demoed, providing a head start on renovations and allowing for maximum design flexibility. Continue its current use as a multi-family property or transform it into a spacious single-family residence—the possibilities are endless. Whether you're an investor or a homeowner looking for a custom renovation project, this property offers exceptional potential. Property has a shared driveway.

33 Mentelle Park, Lexington

$1,650,000
26014906 MLS
160 Prosperous Place is a two story medical office building with a full basement, consisting of approximately 6,840 square feet plus additional basement area. The building was completely renovated in 2021 and converted to its current medical office use, making it ideal for an owner/user or an investor seeking a modern, turnkey healthcare facility. The first floor features a reception and waiting area, two private offices, a nurses 'station/lab, seven exam rooms, and two procedure/xray rooms. The second floor offers multiple private offices, a conference room, a break room, and additional shell space suitable for future expansion or for buildout to generate additional rental income. The full basement is configured as partially finished office space with additional storage and is accessible via an overhead door, providing excellent flexibility for records, equipment, or ancillary services. Additional property features include a backup generator and sinks in four of the exam rooms.

160 Prosperous Pl, Lexington