Recently Sold Winchester, KY Homes

/30
$237,750 Sold Sep 26, 2024
- 1,916 Sq Ft
- $124/SF
- 26 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1989
408 Skylark Dr, Winchester, KY 40391

Welcome to your new retreat! This 3-bedroom, 2.5-bathroom home offers a perfect blend of comfort & potential. Step outside to a spacious 14' x 12' porch that overlooks the serene backyard, ideal for morning coffee or evening relaxation. The backyard features an above-ground swimming pool, complete with a deck. While the home does require TLC, it presents an incredible opportunity to customize and

Debra Ward Coldwell Banker McMahan

408 Skylark Dr, Winchester, KY 40391
/22
$1,815,000 Sold Sep 25, 2024
- 2,212 Sq Ft
- $821/SF
- 12 Days On Market
2070 Boonesboro Rd, Winchester, KY 40391

Live On-Site w/Internet Bidding Auction, Bid now at: Bid.Noelauctioneers.comLive Auction Date: Saturday, August 10, 2024 at 10:00 AM (EST)Closing date on or before: Wednesday, September 25, 2024 before 5:00 PM (EST)10% down the day of the auction with the balance due in full within 45 days. Balance: Due in full within 45 days. Buyer's Premium: 10% added to the final

Jonathan Noel Noel Auctioneers and Real Estate Advisors

2070 Boonesboro Rd, Winchester, KY 40391
/58
$180,000 Sold Sep 24, 2024
- 1,191 Sq Ft
- $151/SF
- 27 Days On Market
- 2 Beds
- 1 Bath
- Built 1955
219 Locust Grove Rd, Winchester, KY 40391

Don't miss your chance to own this ranch home located on a dead end street AND in the county with no city tax bill. Located just minutes from I-64 and the Mountain Parkway via Veteran Bypass. There is a bonus room on the homes first level that could easily be converted to a 3rd bedroom complete with a cedar lined closet. The home is move-in ready and backs up to green space with room for a

Josh Wood Freedom Realty & Property Management

219 Locust Grove Rd, Winchester, KY 40391
/75
$276,000 Sold Sep 23, 2024
- 1,844 Sq Ft
- $150/SF
- 23 Days On Market
- 3 Beds
- 2 Baths
- Built 1999
314 Fern Ct, Winchester, KY 40391

This is the one you have been waiting for. This Gorgeous home is MOVE in READY. This Beautiful home has 3 bedrooms upstairs with a jetted tub in the Primary Bathroom, as well as an extra, very large room in the basement that could be a 4th bedroom, game room, music room, or office. The Possibilities are endless here. A beautiful living room upstairs as well as one downstairs. Just wait until

Sherry Stephens Murphy Realty Group

314 Fern Ct, Winchester, KY 40391
/86
$271,900 Sold Sep 20, 2024
- 1,904 Sq Ft
- $143/SF
- 3 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1970
222 Vaught Rd, Winchester, KY 40391

This lovely brick, split-foyer home is conveniently located with easy access to the Winchester Bypass and everything Winchester has to offer. Enjoy many delicious family dinners in the spacious eat-in kitchen, or take a step out the back door onto a private deck overlooking a generous back yard with plenty of room for your family to enjoy cool summer evenings. Downstairs includes a cozy den or

Josh Wood Freedom Realty & Property Management

222 Vaught Rd, Winchester, KY 40391
/49
$103,500 Sold Sep 20, 2024
- 1,280 Sq Ft
- $81/SF
- 7 Days On Market
- 3 Beds
- 2 Baths
- Built 1998
251 Kerry Dr, Winchester, KY 40391

Where else can you find a 3 bedroom 2 full baths home for under 100,000? You are in luck!!! Move in ready!!! 16' x 80' single wide mobile home. Walk-in tile shower. Several laminate floors. Curb appeal. Corner lot--by the way, you own your own lot. Mostly new deck in front; porch in back. Garden in back. 2 buildings. Trees. Selling property AS IS!!! Inspections welcome. No repairs or

Joyce Ratliff Tom Goebel & Company

251 Kerry Dr, Winchester, KY 40391
/30
$68,000 Sold Sep 19, 2024
- Land
- 4.20 Acres
- $16,190 per Acre
- 1 Day On Market
690 Lisletown Ln, Winchester, KY 40391

This very unique piece of property on 4.2 acres with a view of the Kentucky River. It is a dream for the buyer looking to build residential or cabin, add tiny homes to airbnb, or just to enjoy the property for hiking and the peacefulness it has to offer. This property is close to Boonesboro State Park and backs up to Lower Howard's Creek Nature Preserve. The property is bordered by an old stone

Alyssa M Boley Coldwell Banker McMahan

690 Lisletown Ln, Winchester, KY 40391
/49
$350,000 Sold Sep 19, 2024
- 3,095 Sq Ft
- $113/SF
- 34 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1967
21 Colby Hills Dr, Winchester, KY 40391

Craving a home that offers room to breathe and a place to call your own? Look no further than 21 Colby Hills! This charming Winchester residence boasts 4 bedrooms and 2.5 baths, providing ample space for families or those who love to host. Imagine cozy movie nights by the fireplace or festive gatherings in the formal dining room. The eat-in kitchen allows for casual meals and connection, while

Robert Coburn Kentucky Realty Group, LLC

21 Colby Hills Dr, Winchester, KY 40391
/25
$50,000 Sold Sep 18, 2024
- 1,465 Sq Ft
- $34/SF
- 27 Days On Market
- 3 Beds
- 1 Bath
- Built 1940
248 Cook Ave, Winchester, KY 40391

Nice investment opportunity/fixer upper for this spacious 3 bed 1 bath in downtown Winchester. Being sold as-is.

Chris Johnson Plum Tree Realty

248 Cook Ave, Winchester, KY 40391
/54
$260,000 Sold Sep 18, 2024
- 1,776 Sq Ft
- $146/SF
- 121 Days On Market
- 3 Beds
- 2 Baths
- Built 2002
427 Jameson Way, Winchester, KY 40391

This lovely 3 bedroom 2 bath home has been freshly painted throughout the inside and features two spacious living areas with cathedral ceilings. This one-owner home features beautiful well kept hardwood floors and tile flooring. Enjoy evenings on the deck over the large back yard. Some additional features this home's next owner will enjoy include , and a new roof in November, an updated primary

Christa Joynt Keller Williams Commonwealth

427 Jameson Way, Winchester, KY 40391
/86
$294,000 Sold Sep 17, 2024
- 3,220 Sq Ft
- $91/SF
- 2 Days On Market
- 4 Beds
- 3 Baths
- Built 1935
112 Olde Potomac Ave, Winchester, KY 40391

This gorgeously maintained, craftsman style, home sits comfortably in the heart of Winchester: Easy walking distance to college park and in a lovely, walkable neighborhood. Enjoy the perfect front porch for morning coffee or dinners outside in the evening shade. Take a step inside to view the wonderful craftsmanship of years gone by in a home that has been well maintained, but also updated as

Josh Wood Freedom Realty & Property Management

112 Olde Potomac Ave, Winchester, KY 40391
/14
$61,000 Sold Sep 16, 2024
- 800 Sq Ft
- $76/SF
- 1 Day On Market
- 2 Beds
- 1 Bath
- Built 1987
318 W Washington St, Winchester, KY 40391

Welcome to this quaint 2-bedroom, 1-bathroom home nestled in the heart of vibrant downtown Winchester. With its prime location, this property offers a unique opportunity to create a personalized retreat or investment gem. The home is in need of moderate rehab, making it the perfect canvas for your renovation vision. Whether you're looking to make it your own cozy haven or seeking a promising

Chelsea Morguson Haven Homes Group

318 W Washington St, Winchester, KY 40391
/42
$200,000 Sold Sep 16, 2024
- 1,440 Sq Ft
- $139/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 1978
111 Mccullough Ln, Winchester, KY 40391

This property has a lot to offer. 3 bedrooms, 2 full bathrooms, and sitting on over 5 acres. It also has a 2112 Square feet barn, 720 square feet detached garage, and a huge storage shed. The home is just minutes from the new Winchester Bypass coming through. You can also be in downtown Winchester or the Bypass with shopping and restaurants in just minutes. The home has been well maintained

Dale Hatton Dream Maker Realty, LLC

111 Mccullough Ln, Winchester, KY 40391
/31
$259,900 Sold Sep 16, 2024
- 1,490 Sq Ft
- $174/SF
- 1 Day On Market
- 3 Beds
- 2 Baths
- Built 1970
101 Skylark Dr, Winchester, KY 40391

Welcome to Your Perfect Home! Step into this warm, cozy, and inviting 3-bedroom, 2-bathroom haven, where comfort meets convenience. From the moment you enter through the beautiful entryway, to the moment you get to snuggle up in the sunlit living room front of the beautiful gas fireplace on a chilly evening, creating the perfect ambiance for family gatherings or a quiet night in. Situated on a

Serena Cassidy Coldwell Banker McMahan

101 Skylark Dr, Winchester, KY 40391
/105
$719,000 Sold Sep 16, 2024
- 2,557 Sq Ft
- $281/SF
- 11 Days On Market
- 4 Beds
- 3 Baths
- Built 1977
1039 Cole Rd, Winchester, KY 40391

*See attached drone video* This stunning home looks like it came right off the pages of a magazine, plus 30+ acres of beautiful Kentucky farmland in your backyard make this house the perfect place to settle in and call home! From the floors to the ceilings, inside and out, including the new farmhouse kitchen sink, this home has been remodeled and updated to perfection. From first look at the

Josh Wood Freedom Realty & Property Management

1039 Cole Rd, Winchester, KY 40391
/9
$70,000 Sold Sep 16, 2024
- Land
- 3.39 Acres
- $20,649 per Acre
- 23 Days On Market
160 Rector Ln, Winchester, KY 40391

Tucked away on a private lane, this 3.390-acre property is a hidden gem. With a small pond, flat land, and the exclusivity of being surrounded by trees, this setting is truly unique. Convenience is key with this property. Water is readily available at the main road, Internet has been thoughtfully extended down the lane, and electricity is accessible for connection.Deed

Lucy Martin Jenkins United Real Estate Bluegrass

160 Rector Ln, Winchester, KY 40391
/27
$350,000 Sold Sep 16, 2024
- 3,428 Sq Ft
- $102/SF
- 84 Days On Market
- 4 Beds
- 3 Baths
- Built 1960
200 Moundale Ave, Winchester, KY 40391

Beautiful home located in the heart of Winchester's Thompson Addition. Amazing hardwood floors and spacious bedrooms located on the main level. Enjoy the backyard while sitting on the brick patio with pergola. Hurry this home will not last long. Basement has been freshly painted and is ready for you to pick out the flooring with a $4000 allowance. New roof to be put on this lovely home.

Kelly Nisbet Coldwell Banker McMahan

200 Moundale Ave, Winchester, KY 40391
/2
$110,000 Sold Sep 16, 2024
- Land
- 0.58 Acre
- $189,655 per Acre
- 663 Days On Market
120 Jacob Ct, Winchester, KY 40391

Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

John Wilson Bluegrass Properties Group

120 Jacob Ct, Winchester, KY 40391
/70
$265,000 Sold Sep 13, 2024
- 2,321 Sq Ft
- $114/SF
- 45 Days On Market
- 3 Beds
- 2 Baths
- Built 1960
1131 Ironworks Rd, Winchester, KY 40391

Own a little slice of heaven in the country, within a stones throw of being right in town. This three bedroom two bath home has plenty of space to grow in to with a Florida room on the back and large, open living/dining room/kitchen areas. There is also a large suite in the basement. The basement could easily be converted into a separate living space as there is a walk out exit. The attached

Christa Joynt Keller Williams Commonwealth

1131 Ironworks Rd, Winchester, KY 40391
/14
$36,000 Sold Sep 11, 2024
- Land
- 0.17 Acre
- $211,765 per Acre
- 15 Days On Market
538 S Maple St, Winchester, KY 40391

Location! Ever wanted to live on Maple Street with all its stately victorian homes, large mature trees and conveniences? This lot is ready to build on with all utilities in place. Save time and money and start your new build. Lot has alley street access, expansive mature tree canopy for those shady days enjoying the outdoors. Zoned R-1C Lot has no deed restrictions. See Planning and Zoning for

Maggie Napier Napier Realtors

538 S Maple St, Winchester, KY 40391
/44
$490,000 Sold Sep 11, 2024
- 2,070 Sq Ft
- $237/SF
- 7 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2000
601 Wades Mill Rd, Winchester, KY 40391

Your country oasis awaits. This lovely Cape Cod style home has been freshly painted and has updated kitchen and primary bath. This property features 3 bd rms and 2.5 baths with a finished room over the garage all situated on 5 beautiful acres. The acreage is fenced and has a 2 stall run in barn and a chicken coop. There is also an additional storage building. This property also has an

Kelly Nisbet Coldwell Banker McMahan

601 Wades Mill Rd, Winchester, KY 40391
/29
$350,000 Sold Sep 11, 2024
- 34 Days On Market
4330 Schollsville Rd, Winchester, KY 40391

Unspoiled splendor, this 37acres won't last long,located in the center of hunting paradise, everything you need is right here, escape from the city, your own Hidden Valley must have an appointment, cattle on the farm, make sure you close the gate when you arrive and close the gate when you leave, some of the fences are electric, seller will need 60 days to vacate the cattle. Seller has

Mila Ensor Ensor Real Estate, LLC

4330 Schollsville Rd, Winchester, KY 40391
/6
$127,500 Sold Sep 11, 2024
- Land
- 4.00 Acres
- $31,875 per Acre
- 27 Days On Market
2492 Athens Boonesboro Rd, Winchester, KY 40391

Prime building lot - 4.0 acres ready for your new dream home! Dual entrance approved. Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on your lot.

Megan McCoy Keller Williams Legacy Group

2492 Athens Boonesboro Rd, Winchester, KY 40391
/21
$281,000 Sold Sep 10, 2024
- 1,704 Sq Ft
- $165/SF
- 2 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2004
305 Newcastle Ln, Winchester, KY 40391

Convenient location close to Winchester shopping and dining and only 20 minutes to Hamburg. This well cared for home offers a 1st floor primary bedroom suite for your convenience. There are 2 additional bedrooms upstairs with a full bath and a large bonus room which would make the perfect office, workout room, or playroom. The bonus room also has the potential to become a 4th bedroom. The open

Tonya Skeens RE/MAX Elite Lexington

305 Newcastle Ln, Winchester, KY 40391
/2
$610,000 Sold Aug 29, 2025
- 1,848 Sq Ft
- $330/SF
- 1 Day On Market
- 3 Beds
- 2 Baths
- Built 1905
4560 Pine Ridge Rd, Winchester, KY 40391

Step back in time and embrace the tranquility of country living with this 2 story farmhouse built in 1905 and situated on over 88 acres of farmland in eastern Clark Co. This house blends historic character with modern potential, offering the perfect canvas for your dream rural retreat or working farm. The property includes a spacious 900 sq ft, three-car garage-ideal for vehicles, equipment, or a

Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

4560 Pine Ridge Rd, Winchester, KY 40391
/2
$257,000 Sold Aug 19, 2025
- 2,242 Sq Ft
- $115/SF
- 4 Beds
- 2 Baths
- Built 1991
641 Westmeade Dr, Winchester, KY 40391

For Comp only

Null Non-Member Non-Member Office

641 Westmeade Dr, Winchester, KY 40391
/2
$350,000 Sold Aug 14, 2025
- 3,672 Sq Ft
- $95/SF
- 4 Beds
- 2.5 Baths
- Built 1960
141 Milwood Dr, Winchester, KY 40391

FSBO

Null Non-Member Non-Member Office

141 Milwood Dr, Winchester, KY 40391
/2
$299,900 Sold Aug 08, 2025
- 2,054 Sq Ft
- $146/SF
- 3 Beds
- 3 Baths
- Built 1970
22 Cardinal Ln, Winchester, KY 40391

Very nice ranch home on a full basement in an excellent neighborhood.

Josh Wood Freedom Realty & Property Management

22 Cardinal Ln, Winchester, KY 40391
/2
$247,000 Sold Jul 31, 2025
- 2,250 Sq Ft
- $110/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 1980
724 Terry Dr, Winchester, KY 40391

Nestled in the Westmeade neighborhood, this home offers the perfect blend of comfort and convenience, just minutes from the Winchester Bypass and a short drive to Lexington. With approximately 2,250 square feet of living space, this home features an inviting foyer that leads into a bright eat-in kitchen and a welcoming main living area.Down the hall, you'll find three bedrooms, along with

Samantha Gray National Real Estate

724 Terry Dr, Winchester, KY 40391
/2
$180,000 Sold Jul 01, 2025
- 2,250 Sq Ft
- $80/SF
- 4 Beds
- 4 Baths
- Built 1953
23 Meadowbrook Dr, Winchester, KY 40391

Location, Location, Location! Property sold as is.

A. Rebecca Woods Woods Realty Group

23 Meadowbrook Dr, Winchester, KY 40391
/2
$286,000 Sold Jun 12, 2025
- 2,394 Sq Ft
- $119/SF
- 0 Days On Market
- 4 Beds
- 2 Baths
- Built 1998
209 Locust Grove Rd, Winchester, KY 40391

For comp purposes

Lindsay Barsotti ERA Select Real Estate

209 Locust Grove Rd, Winchester, KY 40391
/2
$165,000 Sold May 30, 2025
- 1,200 Sq Ft
- $138/SF
- 3 Beds
- 1.5 Baths
- Built 1988
44 Heather Ln, Winchester, KY 40391

COMP SALE

Null Non-Member Non-Member Office

44 Heather Ln, Winchester, KY 40391
/2
$401,500 Sold May 15, 2025
- 2,000 Sq Ft
- $201/SF
- 3 Beds
- 2 Baths
- Built 1998
108 Royal Oak Dr, Winchester, KY 40391

FSBO For Comp Purposes Only ! High ceilings freshly painted home. Both bathrooms and kitchen remodeled in 2015. Roof replaced 2015.

Null Non-Member Non-Member Office

108 Royal Oak Dr, Winchester, KY 40391
/2
$195,000 Sold May 15, 2025
- 1,822 Sq Ft
- $107/SF
- 4 Beds
- 2 Baths
- Built 1980
105 Churchill Dr, Winchester, KY 40391

comp purposes

Null Non-Member Non-Member Office

105 Churchill Dr, Winchester, KY 40391
/2
$216,450 Sold Apr 30, 2025
- 1,628 Sq Ft
- $133/SF
- 0 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2005
408 Paisley Ct, Winchester, KY 40391

New Paint and Carpet.

John Wilson Bluegrass Properties Group

408 Paisley Ct, Winchester, KY 40391
/2
$201,000 Sold Apr 18, 2025
- 960 Sq Ft
- $209/SF
- 2 Beds
- 2 Baths
- Built 1993
203 Arbor Ct, Winchester, KY 40391

Beautifully remodeled and updated cottage home! Gorgeous kitchen with white cabinets & new stainless steel appliances. Primary bedroom has attached bath with new fixtures & 5' shower. Main bath has all new fixtures including soaking tub. All new laminate flooring thru-out. Upgraded 200 amp electrical service, new heat pump, new shingles, new windows & more! Relax on your screened in porch

Angie Conley Dixon Dixon Properties

203 Arbor Ct, Winchester, KY 40391
/2
$65,000 Sold Mar 13, 2025
- 1,589 Sq Ft
- $41/SF
- 4 Days On Market
- 2 Beds
- 1 Bath
- Built 1940
17 Beckner St, Winchester, KY 40391

Huge potential Fixer Upper! In-house financers, investors or cash buyers only. No FHA, RHS, VA, conventional, etc. Great location and large lot. Walking distance to the Public Library and College Park! Great price to allow for renovation and profit.

Steve Charles Freedom Realty & Property Management

17 Beckner St, Winchester, KY 40391
/2
$39,500 Sold Mar 05, 2025
- Land
- 0.38 Acre
- $103,947 per Acre
- 1594 Days On Market
418 Fairholme Way, Winchester, KY 40391

Lovely lot in Fairholme Estates which is near the Winchester Country Club. Natural gas is now available in Fairholme. Easy access to Hamburg in Lexington, I-75, I-64 and Mountain Parkway. Golf cart access to downtown Winchester and other residential streets. Other lots available in Fairholme.

Garnett Davis Tom Goebel & Company

418 Fairholme Way, Winchester, KY 40391
/2
$39,500 Sold Mar 05, 2025
- Land
- 0.38 Acre
- $103,947 per Acre
- 1596 Days On Market
416 Fairholme Way, Winchester, KY 40391

Lot in Fairholme Estates near Winchester Country Club and golf cart access to downtown Winchester. Natural gas is now available in Fairholme Estates. Easy access to Hamburg, I-75 and I-64. Additional lots available.

Garnett Davis Tom Goebel & Company

416 Fairholme Way, Winchester, KY 40391
/2
$39,500 Sold Mar 05, 2025
- Land
- 0.37 Acre
- $106,757 per Acre
- 1596 Days On Market
414 Fairholme Way, Winchester, KY 40391

Lot in beautiful Fairholme Estates with easy access to Lexington, I-75 and I-64. Fairholme now has Natural Gas. Easy to get to Winchester Country Club and Downtown Winchester. Golf cart access to downtown and downtown streets. Other lots available.

Garnett Davis Tom Goebel & Company

414 Fairholme Way, Winchester, KY 40391

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