Winchester, KY Homes

/81
$599,500 Sold Aug 18, 2025
- 2,222 Sq Ft
- $270/SF
- 1 Day On Market
- 3 Beds
- 2 Baths
- Built 2018
2615 Crowe Ridge Rd, Winchester, KY 40391

This one-owner, custom-built home sits on approximately 8 acres of beautiful Bluegrass land and offers space, comfort, and thoughtful design throughout. The open-concept great room and kitchen feature exposed beam ceilings and custom-stained concrete floors. The kitchen is a dream for cooks,with abundant counter space, storage, a large island, and window overlooking the backyard and pool. Just

ROBIN TRIMBLE HomeFirst Real Estate

2615 Crowe Ridge Rd, Winchester, KY 40391

/17
Est $204,424 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,221 Sq Ft
2504 Irvine Rd, Winchester, KY 40391

2504 Irvine Rd, Winchester, KY 40391

/20
$289,000
- 2 Beds
- 2 Baths
- 1,674 Sq Ft
800 Country Club Ct, Winchester, KY 40391

Great Investment Property. This cozy Winchester duplex is in a prime location. Just minutes from the Bypass and downtown. Two bedrooms with 2 full baths. The location is close to several retail stores, restaurants, and golf courses. Property is being sold together and will not separate.

Dale Hatton Dream Maker Realty, LLC

800 Country Club Ct, Winchester, KY 40391
/73
$799,000 Sold Aug 18, 2025
- 3,664 Sq Ft
- $218/SF
- 64 Days On Market
- 5 Beds
- 3 Baths
- Built 1989
1183 the Ridings Rd, Winchester, KY 40391

This beautiful 5 bedroom 3 full bath home sits on 5 acres in The Ridings at Colby. This neighborhood has horseback riding trails throughout & is a 15 minute drive to the Hamburg/Lexington area. Large eat in kitchen with island & stainless steel appliances. Entertain in your custom dining room featuring a tray ceiling & wainscoting, or on your covered outdoor Trex deck. Relax in either your living

Libby VanMeter Marshall Lane Real Estate - Lexington

1183 the Ridings Rd, Winchester, KY 40391

/49
Est $296,683 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 2,333 Sq Ft
373 Old Ironworks Rd, Winchester, KY 40391

373 Old Ironworks Rd, Winchester, KY 40391

/31
$174,900
- 3 Beds
- 1 Bath
- 1,332 Sq Ft
120 E Lexington Ave, Winchester, KY 40391

Looking for an affordable home? Look no further than this recently updated 3 bedroom 1 bath with possible 4th bedroom or bonus room. New flooring, appliances, fixtures and new hvac. Replacement windows before current owner. Great starter home located convenient to downtown area and shopping.

Chris Johnson Plum Tree Realty

120 E Lexington Ave, Winchester, KY 40391
/21
$173,000 Sold Aug 15, 2025
- 964 Sq Ft
- $179/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 1998
222 Buffalo Trace, Winchester, KY 40391

Welcome home to this darling home located in the Buffalo Trace Subdivision. This home is one floor living and features 3 bedrooms and 2 baths and is freshened up and ready for a new owner! All electric, off-street parking.

Elizabeth Herrington Bluegrass Sotheby's International Realty

222 Buffalo Trace, Winchester, KY 40391

/45
Est $477,937 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,244 Sq Ft
1159 Cabin Creek Rd, Winchester, KY 40391

1159 Cabin Creek Rd, Winchester, KY 40391

/21
$149,000
- 2 Beds
- 1 Bath
- 886 Sq Ft
9 Linden Ave, Winchester, KY 40391

Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court

Emily Hacker-Todd CENTURY 21 Advantage Realty

9 Linden Ave, Winchester, KY 40391
/22
$217,000 Sold Aug 15, 2025
- 1,400 Sq Ft
- $155/SF
- 14 Days On Market
- 4 Beds
- 2 Baths
- Built 2001
517 Acadia Way, Winchester, KY 40391

This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

Tyler I Back The Brokerage

517 Acadia Way, Winchester, KY 40391

/15
Est $292,917 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,580 Sq Ft
158 Cabin Creek Heights, Winchester, KY 40391

158 Cabin Creek Heights, Winchester, KY 40391

/26
$215,000
- 3 Beds
- 2.5 Baths
- 1,224 Sq Ft
388 Colby Ridge Blvd, Winchester, KY 40391

Need to see inside of this one! Seller bought in May 2021. Remodeled kitchen. Removed one wall between kitchen and living room. Installed a granite bar/island and countertops. Installed all new kitchen cabinets. Installed all new stainless steel appliances (including a top-of-the-line Kitchen Aid dishwasher). Put in deep sink and garbage disposal. Pantry cabinet beside refrigerator.

Joyce Ratliff Tom Goebel & Company

388 Colby Ridge Blvd, Winchester, KY 40391
/77
$2,075,000 Sold Aug 15, 2025
- 5,984 Sq Ft
- $347/SF
- 14 Days On Market
- 3 Beds
- 6 Baths
- Built 1994
27 Sundown Ln, Winchester, KY 40391

Tucked just 10 minutes from Hamburg on the Fayette/Clark County line, this 71+acre estate on Sundown Lane truly lives up to its name—offering breathtaking sunset views, along with peaceful luxury in a scenic country setting. At the end of a gated driveway, a stately colonial-style home combines refined living with countryside charm. Highlights include hardwood floors, two stone fireplaces, dual

Abby Jones Bluegrass Sotheby's International Realty

27 Sundown Ln, Winchester, KY 40391

/43
Est $556,070 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,060 Sq Ft
2100 Ecton Rd, Winchester, KY 40391

2100 Ecton Rd, Winchester, KY 40391

/20
$159,900
- 3 Beds
- 1 Bath
- 1,150 Sq Ft
103 Yorktowne Ct, Winchester, KY 40391

Affordable and move-in ready! This charming 3 bedroom, 1 bath home offers the perfect opportunity for first-time buyers, down-sizers, or investors. With a welcoming layout, comfortable living spaces, and a great location in Winchester, this property is an excellent value in today's market. Enjoy the convenience of nearby shopping, dining, and easy access to I-64 while still tucked away on a quiet

Susy Esquivel Allied Realty

103 Yorktowne Ct, Winchester, KY 40391
/65
$275,000 Sold Aug 15, 2025
- 1,873 Sq Ft
- $147/SF
- 130 Days On Market
- 4 Beds
- 1.5 Baths
- Built 1960
151 Hilltop Dr, Winchester, KY 40391

Lovely ranch on a basement home in a small rural neighborhood. This location is the perfect blend of rural living but very convenient to everything! Less than 1 mile from the eastern bypass that provides fast access to I-64, downtown Winchester, parks, and shopping. Large half acre lot with fenced in backyard and a chicken coop! Large deck on the back for entertaining or just relaxing while

Jason Townsend Kentucky Residential Real Estate, LLC

151 Hilltop Dr, Winchester, KY 40391

/99
Est $628,802 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,695 Sq Ft
1700 Cabin Creek Rd, Winchester, KY 40391

1700 Cabin Creek Rd, Winchester, KY 40391

/47
$395,000
- 8 Beds
- 4 Baths
- 3,706 Sq Ft
23 1/2 Wheeler Ave, Winchester, KY 40391

Prime investment opportunity in Winchester! This 4-plex offers four unique 2-bedroom, 1-bath units, each approximately 900 sqft, with washer/dryer hookups and kitchen appliances included. Tenants enjoy a quiet neighborhood setting just steps from College Park, close to the Public Library and downtown. Alley access for parking makes it feel private and secluded. Units feature wide hallways,

Michelle Blackburn RE/MAX Creative, Winchester

23 1/2 Wheeler Ave, Winchester, KY 40391
/32
$360,000 Sold Aug 14, 2025
- 2,746 Sq Ft
- $131/SF
- 12 Days On Market
- 5 Beds
- 2.5 Baths
- Built 1990
418 Skylark Dr, Winchester, KY 40391

There's a certain kind of comfort you feel the moment you pull up, a classic brick home, shaded by mature trees, in a quiet neighborhood where kids still ride bikes and neighbors wave from their driveways. Inside, the layout just works. The kitchen has the kind of space that makes everyday life easier, granite counters, shaker cabinets, and an island that's seen everything from cereal mornings to

Kymberly McCreary EXP Realty, LLC

418 Skylark Dr, Winchester, KY 40391

/44
Est $501,362 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,070 Sq Ft
601 Wades Mill Rd, Winchester, KY 40391

601 Wades Mill Rd, Winchester, KY 40391

/33
$170,000
- 4 Beds
- 2 Baths
- 1,534 Sq Ft
646 Laura Dr, Winchester, KY 40391

Ranch style home located in Verna Hills just across the Scott County line off Winchester Road. Home features four bedrooms, two full baths, eat in kitchen with laundry closet, primary bedroom with adjoining bath, Hall guest bathroom and large guest bedroom on the right side of the home. Backyard is fenced and has a large deck. Case # 201-735718 Insured with Escrow.

Kimberly Brunson Hunter Real Estate

646 Laura Dr, Winchester, KY 40391
/54
$269,900 Sold Aug 12, 2025
- 1,536 Sq Ft
- $176/SF
- 11 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2006
137 Sturbridge Ln, Winchester, KY 40391

This lovely story and a half home is conveniently located close to Bypass road with easy access to everything Winchester has to offer. The main floor offers a comfortable living area that connects to the spacious eat-in kitchen, a convenient half bathroom, and the laundry room. Take a step out the back patio door to experience the generous, shaded, privacy fenced back yard perfect for kids or

Josh Wood Freedom Realty & Property Management

137 Sturbridge Ln, Winchester, KY 40391

/127
Est $696,696 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,514 Sq Ft
1924 Wades Mill Rd, Winchester, KY 40391

1924 Wades Mill Rd, Winchester, KY 40391

/64
$269,000 Open Sun 2PM - 4PM
- 3 Beds
- 2 Baths
- 1,928 Sq Ft
113 Olde Potomac Ave, Winchester, KY 40391

This phenomenal property has had so many updates including the addition of a full bath on the second floor, an updated electric panel, new wiring throughout, added electrical outlets, all new plumbing, a heat pump for the second floor (there is gas heat on the first floor) and a walk-in closet in the primary bedroom on the first floor. The owners have given meticulous attention to every

Susan Colwell Colwell Realty Professionals, Inc.

113 Olde Potomac Ave, Winchester, KY 40391
/41
$279,900 Sold Aug 12, 2025
- 1,808 Sq Ft
- $155/SF
- 8 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2006
225 Prescott Ln, Winchester, KY 40391

What are your thoughts on a residence featuring a prime location, within walking distance to several schools? Now that I've got your interest, the primary bedroom is situated on the main level. How do three or possibly four bedrooms, accompanied by 2.5 bathrooms, sound? This residence is located in the Oakmont subdivision and has been under the same ownership for over 15 years. Don't miss your

Teresa Richmond Freedom Realty & Property Management

225 Prescott Ln, Winchester, KY 40391

/3
Est $356,681 Not Listed For Sale
- 3 Beds
- 1,260 Sq Ft
1591 Gay Evans Rd, Winchester, KY 40391

1591 Gay Evans Rd, Winchester, KY 40391

/13
$185,000
- 2 Beds
- 1 Bath
- 902 Sq Ft
220 Pendleton St, Winchester, KY 40391

Fully renovated home with new exterior vinyl walls and dimensional shingle rood. Interior has received new insulation, drywall, all new wiring, partial windows, new appliances and counters, new bathroom vanity/tub/toilet, new LVP floor coverings, new interior/exterior doors, new heat pump/water heater.

Steve Adams Steven D Adams Real Estate Services, LLC

220 Pendleton St, Winchester, KY 40391
/29
$180,000 Sold Aug 11, 2025
- 1,025 Sq Ft
- $176/SF
- 0 Days On Market
- 3 Beds
- 1 Bath
- Built 1970
217 Blair Ave, Winchester, KY 40391

Welcome to 217 Blair Avenue in the heart of Winchester—a charming and move-in-ready home offering comfort, character, and convenience. This property features 3 spacious bedrooms, 1 full bath, and an inviting layout featuring hardwood floors, a light-filled living room, and an updated kitchen with ample cabinet space. Outside, enjoy a large backyard ideal for gatherings, gardening, or relaxing

Ashley Barreto Indigo & Co

217 Blair Ave, Winchester, KY 40391

/50
Est $670,160 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,200 Sq Ft
1909 Gay Evans Rd, Winchester, KY 40391

1909 Gay Evans Rd, Winchester, KY 40391

/36
$285,000
- 3 Beds
- 2.5 Baths
- 1,715 Sq Ft
103 Hampton Ave, Winchester, KY 40391

A timeless brick ranch in one of Winchester's most established neighborhoods on a corner lot. This 3 bedroom, 2.5 bath home offers two living areas and a cozy fireplace. Spacious backyard, covered front porch, and a wrap-around driveway for a private entrance. All just minutes from downtown, schools, and I-64. The home combines classic comfort, location, and room to grow on a walk-out basement.

Brett Bussell Turf Town Properties

103 Hampton Ave, Winchester, KY 40391
/50
$465,000 Sold Aug 11, 2025
- 2,784 Sq Ft
- $167/SF
- 2 Days On Market
- 2 Beds
- 2.5 Baths
- Built 2008
701 Lisletown Ln, Winchester, KY 40391

Perfectly nestled at the end of shared private lane, this mid-century modern home w/full finished walkout basement offers luxury, privacy & natural beauty. Designed by architect R.L. Isenhour, this distinctive property is situated on just over 3 wooded acres, surrounded by forest & overlooking the Kentucky River. Step inside to soaring ceilings, expansive windows & a striking floor-to-ceiling

Robin Jones Keller Williams Legacy Group

701 Lisletown Ln, Winchester, KY 40391

/96
Est $795,547 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,272 Sq Ft
1995 Gay Evans Rd, Winchester, KY 40391

1995 Gay Evans Rd, Winchester, KY 40391

/98
$789,900
- 6 Beds
- 5 Baths
- 4,843 Sq Ft
3900 Mount Sterling Rd, Winchester, KY 40391

More pictures coming! This extraordinary home located on 8.4 acres and nestled back from the main road, offers spectacular views from both the front and rear and those views can be enjoyed from the expansive covered front porch or the extra-large covered back porch. As you arrive, the meticulous care taken to maintain the property is apparent. Inside, discover a beautifully updated kitchen, five

Teresa Richmond Freedom Realty & Property Management

3900 Mount Sterling Rd, Winchester, KY 40391
/75
$289,900 Sold Aug 11, 2025
- 1,429 Sq Ft
- $203/SF
- 0 Days On Market
- 3 Beds
- 2 Baths
- Built 1992
126 Ashley Dr, Winchester, KY 40391

Don't miss out on this Beautiful RANCH Style home w/Private, new and Fully Fenced Yard. This Move-in Ready 3 Bed / 2 Bath is immaculate with many updates. Completely remodeled Bathroom with walk-in shower, Fresh Paint, Spacious living room w/ Vaulted Ceiling. Carpet all replaced with gorgeous, matching hardwood thru out. Granite Countertops, new can lighting and kitchen floor replaced with

Jennifer Guyton White Realty, LLC

126 Ashley Dr, Winchester, KY 40391

/60
Est $145,795 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,492 Sq Ft
1333 Jackson Ferry Rd, Winchester, KY 40391

1333 Jackson Ferry Rd, Winchester, KY 40391

/34
$299,000
- 4 Beds
- 3 Baths
- 1,850 Sq Ft
20 Bon-Haven Ave, Winchester, KY 40391

Welcome to 20 Bon Haven Avenue, a beautifully renovated 4-bedroom, 3 full bathroom home ideally located directly across from the new Legacy Grove Park in Winchester, KY. This spacious residence blends modern upgrades with timeless charm, offering the perfect retreat for families and entertainers alike.Step inside to find a bright and airy open floor plan, highlighted by brand-new plumbing and

Jacqueline Marchildon Lifstyl Real Estate

20 Bon-Haven Ave, Winchester, KY 40391
/39
$450,000 Sold Aug 08, 2025
- 2,076 Sq Ft
- $217/SF
- 32 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2003
600 Ferry Rd, Winchester, KY 40391

Experience abundant wildlife with turkey and deer in your own hunting retreat, or simply enjoy the views from your backyard on this stunning 33-acre property. Conveniently located near the Kentucky River, with a boat ramp nearby, this home offers the perfect blend of nature and accessibility, making it ideal for nature lovers or those who enjoy fishing and hunting.Step inside to the foyer,

Cathleen Gedeon CENTURY 21 Advantage Realty

600 Ferry Rd, Winchester, KY 40391

/10
Est $1,338,325 Not Listed For Sale
- Studio
- 3,351 Sq Ft
4479 Muddy Creek Rd, Winchester, KY 40391

4479 Muddy Creek Rd, Winchester, KY 40391

/43
$239,700
- 3 Beds
- 1 Bath
- 1,300 Sq Ft
2413 Log Lick Rd, Winchester, KY 40391

Charming 3 bedroom, 1 bath home situated on 1.8 acres in a peaceful country setting. This property offers plenty of space for horses, chickens, gardening, or an orchard, with an attached lean-to that can easily be converted into a horse stall. Enjoy scenic views from both the front and back porches. Recent updates include a brand-new roof, newer heat pump, new HVAC vent, fresh paint, and bamboo

E Anthony Phillips RE/MAX Creative Realty

2413 Log Lick Rd, Winchester, KY 40391
/39
$240,000 Sold Aug 08, 2025
- 1,235 Sq Ft
- $194/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 2018
172 Ryans Mill Rd, Winchester, KY 40391

This nicely maintained 3-bedroom, 2-bath ranch offers the perfect blend of comfort and convenience. Enjoy abundant natural light throughout the open floor plan, creating a bright and inviting atmosphere. The spacious kitchen and living areas are perfect for both daily living and entertaining. Step outside to a generous, fully fenced backyard, ideal for pets, play, or outdoor gatherings. Located

Elizabeth Herrington Bluegrass Sotheby's International Realty

172 Ryans Mill Rd, Winchester, KY 40391

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