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$445,000
6 Beds ⋅ 2 Baths ⋅ 26024385 MLS
Turnkey investment opportunity in the heart of Lexington's highly desirable Kenwick neighborhood in 40502! This fully occupied duplex offers immediate rental income with both units currently leased and tenants paying all utilities. The downstairs unit rents for $1,500/month with a lease through 2/28/2027, while the upstairs unit rents for $1,580/month with a lease through 1/31/2027—providing $3,080 in combined monthly rent and $36,960 in annual gross rental income. Located just minutes from the University of Kentucky, downtown Lexington, Chevy Chase, shopping, dining and entertainment, this property offers an outstanding location with strong long-term rental appeal. Whether you're looking to expand your portfolio or secure a multifamily property in one of Lexington's most sought-after areas, 270 Sherman Avenue deserves a serious look. Schedule your showing today!

270 Sherman Ave, Lexington
$1,340,000
26023843 MLS
Rare opportunity to acquire a turnkey luxury auto dealership and established business along E New Circle Road. The offering includes two parcels totaling 0.652 acres, a modern, beautifully renovated freestanding 2,400 SF office/showroom, and the Paradise Motorsports business, which has successfully operated at this location for 23 years. The property offers excellent visibility and accessibility with 18,398 VPD and includes existing furniture, fixtures, and equipment. With new auto dealership licenses restricted due to zoning and regulatory requirements, this is a unique opportunity to take over an established dealership location with an existing customer base and strong reputation, including a 4.6-star Google rating, 4.9 KBB.com Dealer Rating, and A+ BBB rating.

435 E New Circle Rd, Lexington
$275,900
4 Beds ⋅ 2 Baths ⋅ 26023397 MLS
1840 Chatsworth Drive - Lexington, KY Excellent investment opportunity in Lexington! This fully occupied duplex offers 4 bedrooms and 2 full bathrooms total, with each unit featuring a comfortable 2-bedroom, 1-bath layout. Both sides are currently rented, providing immediate income for the new owner. One unit rents for $1,095 per month, while the other is occupied by long-term tenants at $760 per month, which is significantly below current market rent and offers excellent potential for future rental income growth. With established tenants already in place and the opportunity to increase rents over time, this property is a great addition to an existing rental portfolio or an excellent entry into multifamily investing. Please do not disturb tenants. Showings by appointment only, 48 hour notice required.

1840 Chatsworth Dr, Lexington
$1,060,000
26023392 MLS
Exceptional opportunity to own a versatile commercial property featuring two separate buildings in a highly convenient Lexington location. The sellers spared no expense in constructing the dedicated office building, creating a professional and well-appointed space complete with three private offices, a full conference room, bathroom, and kitchenette area. Just steps away is an impressive approximately 6,000-square-foot warehouse and office facility designed to accommodate a wide variety of business operations. The front lobby features a sales counter/reception area, along with five designated offices, two bathrooms, and a spacious employee break area offering separate sitting, dining, and kitchen spaces. The warehouse includes two separate workshop areas. The first measures approximately 38'11" x 57'11" with impressive 17-foot ceilings, providing excellent flexibility for equipment, storage, production, or service operations. The second workshop measures approximately 59' x 26' and features a loading dock with an 8-foot dock door, plus an additional 8-foot garage door with drive-in access. Steps lead to an additional 1,363-square-foot mezzanine (not included in the 6,000 sq ft), providing additional space for storage or operational needs. Location is another standout feature. Situated just off Leestown Road, the property offers outstanding connectivity throughout Lexington and the surrounding region—approximately 0.4 miles from New Circle Road, 1.5 miles from Downtown Lexington, 2 miles from Frankfort Pike, and 2.5 miles from I-75. With its combination of professional office space, expansive warehouse and workshop areas, loading and drive-in access, generous ceiling heights, and exceptional proximity to Lexington's major transportation corridors, this property offers the space, functionality, and accessibility to accommodate a wide range of commercial uses and growing businesses.

2408 Merchant St, Lexington
$400,000
26022687 MLS

635 N Broadway, Lexington
$375,000
3 Beds ⋅ 2 Baths ⋅ 26021589 MLS
This property is offered as part of a residential rental portfolio with 309 Squires Road and 3532 Brookewind Way. Asking price for the entire portfolio is $979,000.

321 Squires Rd, Lexington
$375,000
3 Beds ⋅ 2 Baths ⋅ 26021585 MLS
This property is offered as part of a residential rental portfolio with 3532 Brookewind Way and 321 Squires Road. Asking price for the entire portfolio is $979,000.

309 Squires Rd, Lexington
$249,900
4 Beds ⋅ 2 Baths ⋅ 26021218 MLS
This offering includes both sides of the duplex at 414 and 414½ Morrison Avenue. Each unit features two bedrooms and one full bathroom. Both units are currently rented for $625 per month, providing a combined gross monthly income of $1,250. Estimated market rents in the property's current condition are approximately $1,100 to $1,300 per unit, offering significant income-growth potential. The 414 Morrison Avenue unit was updated in 2014, while the 414½ unit has not been updated and offers an opportunity for future improvements and additional value. Neither side has a lease; both tenants currently occupy on a month-to-month basis. This is a solid opportunity for an investor seeking immediate rental income with substantial upside potential near downtown Lexington.

414 Morrison Ave, Lexington
$120,000
26020518 MLS
Whether you are looking for a primary residence, a game-day getaway, or, or housing close to UK and the medical district, this condo offers an unbeatable combination of location, convenience and low-maintenance living. Your monthly HOA fee covers everything except personal electric. The building offers a lovely outdoor pool, an elevator and controlled access for peace of mind. Appraised at $135,000. The HOA fee us $346/month

342 Waller Ave Unit 6K, Lexington
$119,500
26020517 MLS
Welcome to 342 Waller place, enjoy the convenience and peace mind in this secure six-story building with controlled access requiring a key and electronic for entry. Residents have access to a refreshing outdoor swimming pool. Perfect for relaxing on warm summer days. The HOA fee offers exceptional value by covering the water, sewer, trash, heating and cooling, all except your personal electric, making monthly budgeting simple and predictable while minimizing the unexpected. Recently appraised for $135,000! There are a total of 3 units available for sale. The residents are all on a month to month lease.

342 Waller Ave Unit 4J, 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
$3,195,000
26009768 MLS
This is a rare opportunity to own a building in one of Lexington's most desirable corridors. It is situated on 2.2 acres in a premier , highly visible location. Conveniently located on Nicholasville Rd. near Southland Dr, and minutes from UK Healthcare and Baptist Hospital. The traffic count is 40,000 + - cars per day. The expansive lot provides ample, on-site parking for employees and clients, making this an ideal option for medical, professional and administrative use.

2134 Nicholasville Rd, Lexington
$1,050,000
18 Beds ⋅ 18 Baths ⋅ 26006527 MLS
Nine units with 2 bedrooms, 1.5 bath each. Roughly $7909/mo gross income when full. Tenants pay their own water and electric. 6 out of the 9 units have been renovated within the last 2 years with the 3 being renovated within the past 5. The layout is pretty open with big family room that opens into the kitchen. Location is terrific, minutes from the mall, short drive to UK, and much more!

189 Donabrook Ct, 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
$350,000
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
$919,900
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
$2,950,000
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 $2,950,000, 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
$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
$725,000
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
$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
$500,000
26007924 MLS
FABULOUS PRIME LOCATION!!!! Southland Dr is owned and ready for you to take over the franchise or make it your own! Wing Zone is an exciting and rapidly growing franchise that specializes in delivering bold, flavorful wings, along with a variety of sauces and sides. With a focus on fast-casual take-out, delivery, and catering services! If you're passionate about food and looking for a business opportunity with a proven brand, Wing Zone offers an exceptional franchise model that combines strong operational support, a scalable menu, and a unique market niche. All equipment included! Call now for this profitable opportunity!

351 Southland Dr, Lexington
$575,000
26016158 MLS
MOTIVATED SELLER! Commercial Mixed-Use Opportunity! Conveniently located near St. Joseph Hospital and Office Park on Harrodsburg Road, this mixed-use property offers a unique blend of professional functionality and charm. Originally a lovely older home, it features beautiful hardwood floors, character throughout, a welcoming reception area with waiting room, multiple private offices, a conference room, and flexible workspace to accommodate a variety of professional uses. The finished basement provides additional usable space, including lab/work areas and generous storage. Ideal for medical, professional, counseling, administrative, or other office-related businesses seeking a distinctive location with excellent accessibility. Property is being sold AS IS. Buyer to verify zoning and intended use. All offers will be considered.

1618 Harrodsburg Rd, Lexington