Vintage homes for sale & real estate in 40544, KY

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3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 40544, KY:
Move in ready Mid-century modern ranch inside New Circle! This unique and fun all-brick home is updated with refinished hardwood floors, newer paint throughout, newer roof and open layout. Just inside you're greeted with a gas fireplace and loads of natural light flowing in. Kitchen overlooks the great room with vaulted ceilings and has views to a den with custom brickwork and woodburning stove. This 3 bedroom and 2.5 bath home is even more spacious than the square footage shows. Outback the yard is privacy fenced and there's a covered back brick patio with mature trees. Attached carport with decorative brick work. Located dangerously close to Dad's Deli, Home Depot, and gardenside Kroger.

$330,000

3 beds2.5 baths1,629 sq ft

895 Lane Allen Rd, Lexington, KY 40504

Gas fireplace • Natural light • Vaulted ceilings

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 40544, KY:
Welcome home to 993 Celia Ln—just minutes from downtown, the University of Kentucky, and some of the city's best dining and entertainment. This beautifully renovated 3-bedroom, 3-bath home blends timeless craftsmanship with modern luxury. The impressive stone exterior offers exceptional curb appeal and complements the large private lot with mature trees and a fire pit, perfect for gatherings or quiet evenings outdoors. Inside, the open-concept layout showcases custom wood accents, refined finishes, and warm contemporary flooring throughout. The living room centers around a sleek modern fireplace, flowing seamlessly into a sophisticated kitchen designed with clean lines and a contempor

$449,000

3 beds3 baths1,930 sq ft

993 Celia Ln, Lexington, KY 40504

Custom wood accents • Large private lot • Fire pit

ABOUT THIS HOME
Vintage Home for sale in 40544, KY:
Boasting over 3,000 square feet of livable space on a half-acre lot, this home is a must-see! The sellers have elegantly remodeled the interior, featuring luxury vinyl flooring, stainless steel appliances, and stunning fixtures. The first floor includes three bedrooms, highlighted by a primary suite, and two beautifully renovated full baths. For ample storage, you'll find an oversized garage, a storage shed, and numerous closets throughout the home. Enjoy the outdoors from the charming covered front porch or the spacious back patio, surrounded by a fenced yard adorned with mature trees. This property is conveniently located near parks, shopping, restaurants, and more. Schedule your showing

$309,900

4 beds3 baths1,770 sq ft

133 Londonderry Dr, Lexington, KY 40504

Remodeled interior • Covered front porch • Fenced yard

ABOUT THIS HOME
Vintage Home for sale in 40544, KY:
Extremely investor-friendly duplex in a desirable location. This well-maintained and fully leased property comprises two well-appointed units, each offering 2 bedrooms and 1 full bath. Both units are occupied by long-term tenants with a strong history of care and reliability, providing immediate and stable income for the next owner. The building has been exceptionally maintained, both structurally and cosmetically, delivering a proven rental history with consistent cash flow—an excellent opportunity for investors seeking a low-maintenance, income-producing asset. The property offers 1,708 square feet of total living space and sits on 0.25 acres, featuring a generous, well-kept grassy

$280,000

4 beds2 baths1,708 sq ft

1653-1655 Maywick View Ln, Lexington, KY 40504

Consistent cash flow • 0.25 acre lot • Built 1959

ABOUT THIS HOME
Vintage Home for sale in 40544, KY:
Looking to buy with the Easy button? Home Inspection has already been completed! Step inside this completely renovated 3-bedroom, 2-bath home and prepare to be surprised by the space, style, and thoughtful updates throughout. Every inch has been refreshed—inside and out—to deliver a move-in-ready home that blends modern comfort with everyday functionality. This home has gone through a total facelift. Improvements include a brand-new roof, HVAC system, light fixtures, interior doors, flooring, plumbing fixtures, and fresh paint throughout. A brand-new bathroom and laundry room have been added, giving the layout a smart, practical flow that suits today's lifestyle. The new deck i

$270,000

3 beds2 baths1,586 sq ft

1680 Brittany Ln, Lexington, KY 40504

6,264 sq ft lot • Built 1960 • Listed 17 days

Property at 1929 Alexandria Dr, Lexington, KY 40504, 3 beds, 2 baths

$325,000

3 beds2 baths1,363 sq ft

1929 Alexandria Dr, Lexington, KY 40504

Property at 944 Maywick Dr, Lexington, KY 40504, 4 beds, 2 baths

$339,900

4 beds2 baths1,924 sq ft

944 Maywick Dr, Lexington, KY 40504

Property at 513 Woodbine Dr, Lexington, KY 40503, 3 beds, 3 baths

$439,900

3 beds3 baths2,195 sq ft

513 Woodbine Dr, Lexington, KY 40503

Property at 1860 Pershing Rd, Lexington, KY 40504, 3 beds, 1 bath

$345,000

3 beds1 bath2,157 sq ft

1860 Pershing Rd, Lexington, KY 40504

Property at 575 Bob O Link Dr, Lexington, KY 40503, 3 beds, 1 bath

$365,000

3 beds1 bath2,580 sq ft

575 Bob O Link Dr, Lexington, KY 40503

Property at 901 Lane Allen, Lexington, KY 40504, 4 beds, 2 baths

$372,000

4 beds2 baths1,945 sq ft

901 Lane Allen, Lexington, KY 40504

Property at 136 Garrett Ave, Lexington, KY 40504, 3 beds, 2 baths

$195,000

3 beds2 baths1,412 sq ft

136 Garrett Ave, Lexington, KY 40504

Property at 208 Savoy Rd, Lexington, KY 40504, 3 beds, 1.5 baths

$219,000

3 beds1.5 baths933 sq ft

208 Savoy Rd, Lexington, KY 40504

Property at 1867 Parkers Mill Rd, Lexington, KY 40504, 8 beds, 7.5 baths

$2,457,500

8 beds7.5 baths9,233 sq ft

1867 Parkers Mill Rd, Lexington, KY 40504

Property at 106 Woodford Dr, Lexington, KY 40504, 2 beds, 1 bath

$195,000

2 beds1 bath1,320 sq ft

106 Woodford Dr, Lexington, KY 40504

Property at 122 Westgate Dr, Lexington, KY 40504, 3 beds, 2.5 baths

$319,000

3 beds2.5 baths1,238 sq ft

122 Westgate Dr, Lexington, KY 40504

Property at 1943 Natchez Trl, Lexington, KY 40504, 3 beds, 1.5 baths

$339,900

3 beds1.5 baths1,960 sq ft

1943 Natchez Trl, Lexington, KY 40504

Property at 149 Chantilly St, Lexington, KY 40504, 3 beds, 1 bath

$190,000

3 beds1 bath1,090 sq ft

149 Chantilly St, Lexington, KY 40504

Property at 236 Mockingbird Ln, Lexington, KY 40503, 3 beds, 1 bath

$299,900

3 beds1 bath1,002 sq ft

236 Mockingbird Ln, Lexington, KY 40503

Property at 123 Henton Rd, Lexington, KY 40508

$79,999

— beds— baths— sq ft

123 Henton Rd, Lexington, KY 40508

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ABOUT THIS HOME
Vintage Home for sale in 40544, KY:
Welcome to 574 Sheridan Drive, a delightful residence tucked into the heart of Lexington's coveted Southland neighborhood. This beautifully maintained home offers a rare blend of mid-century character and modern livability — ideal for anyone seeking the perfect balance between neighborhood warmth and city accessibility. This 2 bedroom (dining room could be converted back to a 3rd bedroom), 2 full bath ranch has been updated with beautiful hardwood floors, a shaker white kitchen with stainless appliances, partially finished basement and amazing covered back patio. The inviting basement includes a large second living area, tons of storage and laundry room/bathroom. You will love the lar

$399,900

2 beds2 baths1,527 sq ft

574 Sheridan Dr, Lexington, KY 40503

Stainless appliances • Covered back patio • Shaker white kitchen

ABOUT THIS HOME
Vintage Home for sale in 40544, KY:
Don't overlook this sweet Southland charmer! This adorable home features a fully updated kitchen with a subway tile backsplash, granite countertops, and stainless steel appliances. The bathroom has been beautifully upgraded with a subway-tile shower, tile flooring, a modern vanity, and more. You'll also love the refinished original hardwood floors, the fenced backyard, and the spacious garage — all adding to this home's irresistible appeal!

$278,000

2 beds1 bath864 sq ft

656 Sheridan Dr, Lexington, KY 40503

Upgraded bathroom • Subway tile shower • Updated kitchen

ABOUT THIS HOME
Vintage Home for sale in 40544, KY:
ONLINE ONLY ABSOLUTE AUCTION!!! Online BIDDING ENDS Tuesday, December 9, 2025 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. Add to your investment portfolio with this Southland cape cod!

$319,000

3 beds2 baths1,836 sq ft

636 Stratford Dr, Lexington, KY 40503

7,200 sq ft lot • Parking • Built 1952

ABOUT THIS HOME
Vintage Home for sale in 40544, KY:
Historic Charm Meets Modern Living in the Heart of Downtown Lexington! Welcome to the Hall Pettit Headley Houseâ€”a rare opportunity to own a piece of Lexington history in one of the city's most sought-after locations. Situated directly across from the iconic Botherum property, this beautifully maintained home blends rich character with thoughtful updates throughout. From the intricate millwork in the formal dining room to the private wraparound porch and spacious deck, every detail invites relaxation and entertaining. The lush backyard offers a serene escape and hot tub, while inside, you'll find a chef-friendly kitchen with gas range and breakfast bar, two soaking tubs, t

$799,000

5 beds3 baths2,942 sq ft

344 Madison Pl, Lexington, KY 40508

Lush backyard • Hot tub • Spacious deck

ABOUT THIS HOME
Vintage Home for sale in 40544, KY:
Located in desirable Southland subdivision, close to Southland Park, shopping, and several restaurants. This 4 bedroom has a lot of potential. Investors or those looking for some sweat equity should take notice. Sitting on a fabulous flat lot this property offers an opportunity to personalize this home exactly the way that you would like. As-is inspections welcome.

$279,999

4 beds1 bath1,625 sq ft

634 Cardinal Ln, Lexington, KY 40503

Flat lot • Southland park • 0.25 acre lot

ABOUT THIS HOME
Vintage Home for sale in 40544, KY:
This 2 bed, 2 bath home is full of charm and just minutes from downtown Lexington. Inside, you'll find fresh paint, updated flooring and new kitchen appliances. Both bathrooms have been updated, and the home has a warm, welcoming feel throughout. The backyard is a great size too, perfect for relaxing, playing, or hosting a cookout. If you're looking for something with character and updates, this one's a must-see!

$190,000

2 beds2 baths2,016 sq ft

416 Douglas Ave, Lexington, KY 40508

Great size backyard • Fresh paint • Updated bathrooms

Property at 114 Pin Oak Dr, Lexington, KY 40503, 4 beds, 1 bath

$329,000

4 beds1 bath1,344 sq ft

114 Pin Oak Dr, Lexington, KY 40503

Property at 631 Cardinal Ln, Lexington, KY 40503, 3 beds, 2 baths

$339,900

3 beds2 baths1,380 sq ft

631 Cardinal Ln, Lexington, KY 40503

Property at 657 Cardinal Ln, Lexington, KY 40503, 3 beds, 1 bath

$339,900

3 beds1 bath1,550 sq ft

657 Cardinal Ln, Lexington, KY 40503

Property at 712 Florence Ave, Lexington, KY 40508, 3 beds, 1 bath

$124,900

3 beds1 bath1,146 sq ft

712 Florence Ave, Lexington, KY 40508

Property at 923 Whitney Ave, Lexington, KY 40508, 4 beds, 1 bath

$175,000

4 beds1 bath1,302 sq ft

923 Whitney Ave, Lexington, KY 40508

Vintage Homes for Sale in 40544

There are currently 20 vintage homes for sale in 40544. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. This map is refreshed with the newest listings in 40544 every 15 minutes.

Find your dream home in 40544 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 40544 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 40544. If you're looking to sell your home in the 40544 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 40544 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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