Winchester, KY Homes

/30
$289,000
- 3 Beds
- 2.5 Baths
- 1,606 Sq Ft
223 Bartram Ct, Winchester, KY 40391

Incredible value in the highly desirable Oakmont subdivision! This completely remodeled 3 bedroom, 2.5 bath home is truly move-in ready with all new paint, flooring, and granite countertops in every bathroom and kitchen. The stylish kitchen shines with an abundance of cabinetry, updated appliances and tile backsplash, flowing into the dining area that overlooks the deck and oversized

Jennifer Parsons RE/MAX Elite Lexington

223 Bartram Ct, Winchester, KY 40391
/46
$195,000 Sold Jul 29, 2025
- 1,167 Sq Ft
- $167/SF
- 66 Days On Market
- 3 Beds
- 2 Baths
- Built 1940
115 Georgia St, Winchester, KY 40391

✨ ''Warm, inviting, and full of character—your dream home awaits!'' 🔥 ''Cozy up by the fireplace in a home that feels like home!'' 🏡 ''Classic charm meets modern convenience in this Winchester gem!'' 🌳 ''Tranquility meets accessibility—peaceful neighborhood, minutes from downtown!'' 🚗 ''Detached garage = extra storage, workspace, and convenience!'' 💎

Darrell Tackett Dream Maker Realty, LLC

115 Georgia St, Winchester, KY 40391

/18
Est $185,218 Not Listed For Sale
- 3 Beds
- 1 Bath
- 960 Sq Ft
11 Apache Trail, Winchester, KY 40391

11 Apache Trail, Winchester, KY 40391

/61
$239,900
- 3 Beds
- 1 Bath
- 1,232 Sq Ft
313 Snowden Dr, Winchester, KY 40391

This charming mid-century home was completely renovated in 2022 and has been beautifully maintained. Step inside and enjoy the warmth of a cozy living room complete with a wood burning fireplace to keep warm on cool fall evenings. Around the corner, the kitchen gleams with stainless appliances, white cabinets and granite countertops. New tile flooring and new carpet completed the renovation

Josh Wood Freedom Realty & Property Management

313 Snowden Dr, Winchester, KY 40391
/34
$333,900 Sold Jul 28, 2025
- 2,162 Sq Ft
- $154/SF
- 2 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2001
366 Hanover Dr, Winchester, KY 40391

Gorgeous 2 Story Home, Offering 4 Bedrooms, 3 Baths, Oversized Bonus Room, First Floor Primary, With Large Walk-In Closet, And En-Suite, Separate Dining, Attached Garage, First Floor Laundry & Mud Room.... You Need To Schedule! Centrally Located To All Main Shopping, Hospitals And Schools, This Home Has Everything! Choose From Two Covered Porches For Morning Coffee Or An Evening Tea. Or Spend

Melissa Brown Keller Williams Legacy Group

366 Hanover Dr, Winchester, KY 40391

/30
Est $181,650 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,584 Sq Ft
1 Apache Trail, Winchester, KY 40391

1 Apache Trail, Winchester, KY 40391

/78
$674,500
- 4 Beds
- 2.5 Baths
- 2,770 Sq Ft
420 Alexis Way, Winchester, KY 40391

Check out 420 Alexis Way in Winchester! This stunning home features a beautiful great room, fully equipped kitchen, extra garage and an inground pool. The primary suite is a luxurious retreat with a spa-like bathroom. With three additional bedrooms and a bonus room, there is plenty of space. The outdoor area is perfect for relaxing by the heated pool. Extra touches include crown molding and

Edwin Burden McCormick Realty Inc.

420 Alexis Way, Winchester, KY 40391
/48
$222,500 Sold Jul 28, 2025
- 2,055 Sq Ft
- $108/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 1955
217 Locust Grove Rd, Winchester, KY 40391

This lovely ranch on a Walk-out basement offers 3BR, 2BA, Utility Rm, Family/dining Rm, Kitchen with a covered outside deck. Basement area with family room, bonus room, small workshop & 1 car garage. Completely fenced backyard with fenced area perfect for small garden or pet enclosure. Many updates & fresh paint upstairs. B-Dry Warranty. Enjoy morning coffee on your back deck & watch wildlife in

Robin Murray The Agency

217 Locust Grove Rd, Winchester, KY 40391

/22
Est $160,358 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 918 Sq Ft
10 Pocahontas Trail, Winchester, KY 40391

10 Pocahontas Trail, Winchester, KY 40391

/11
$50,000
- Land
- 0.41 Acre
- $121,951 per Acre
308 Duclair Dr, Winchester, KY 40391

Tucked away on a quiet cul-de-sac in Mallard Place, this .41-acre lot is ready for your vision. Imagine your dream home in a neighborhood known for its charm and convenience. Bring your house plans—your future starts here!

Joseph Miller Keller Williams Commonwealth

308 Duclair Dr, Winchester, KY 40391
/30
$262,500 Sold Jul 25, 2025
- 2,808 Sq Ft
- $93/SF
- 68 Days On Market
- 4 Beds
- 2 Baths
- Built 1947
16 Taylor Ave, Winchester, KY 40391

STOP scrolling and LOOK! This charming and pristine home is clean as a whistle and just a short walk to active and historic downtown Winchester. Sit on the covered front porch in the summertime shade or on the deck/patio overlooking the spacious/private backyard. Move-in ready with lots of space inside and out (over 2800 sq.ft. finished!), 4 large bedrooms, 2 full baths (one upstairs and one

Jim Woodrum RE/MAX Creative, Winchester

16 Taylor Ave, Winchester, KY 40391

/15
Est $203,982 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,006 Sq Ft
13 Hiawatha Trail, Winchester, KY 40391

13 Hiawatha Trail, Winchester, KY 40391

/3
$59,000
- Land
- 1.69 Acres
- $34,911 per Acre
200 Tartan Ct, Winchester, KY 40391

Over 1.6 acres of conveniently located multi-family property ready for your new builds. Property is accessible from 2 streets. Tartan Ct and Porter Ct

Louis Baldwin Rector Hayden Realtors

200 Tartan Ct, Winchester, KY 40391
/58
$290,000 Sold Jul 25, 2025
- 2,240 Sq Ft
- $129/SF
- 16 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1968
19 Valley Ct, Winchester, KY 40391

This beautiful home has been completely redone. New flooring, HVAC, and much more. It also has new Whirlpool appliances. Three bedrooms upstairs and plenty of room in the basement to make 3 more. This home is in a well established neighborhood and close to several amenities. Just minutes from the Winchester Bypass, golf courses, and Boonseborough State Park. Come take look at your new home today.

Dale Hatton Dream Maker Realty, LLC

19 Valley Ct, Winchester, KY 40391

/33
Est $273,469 Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,831 Sq Ft
16 Apache Trail, Winchester, KY 40391

16 Apache Trail, Winchester, KY 40391

/84
$879,900
- 4 Beds
- 3.5 Baths
- 4,922 Sq Ft
2509 Mount Sterling Rd, Winchester, KY 40391

Embrace Bluegrass living with this beautiful fieldstone ranch on 10+ acres in the heart of horse country. Just minutes from interstate access, yet surrounded by rolling hills and scenic views, this mini farm offers a larger barn with 6 stalls, including water and electric connection, 90 foot roof hangover on the barn, 5 paddocks, each with their own gate and water ran along each paddock. The home

Josh Wood Freedom Realty & Property Management

2509 Mount Sterling Rd, Winchester, KY 40391
/36
$179,000 Sold Jul 23, 2025
- 1,020 Sq Ft
- $175/SF
- 11 Days On Market
- 3 Beds
- 2 Baths
- Built 1999
218 Buffalo Trace, Winchester, KY 40391

Must see this nice home located in Buffalo Trace! Ranch with fenced in back yard, covered porch/patio, storage area, concrete drive, and nice yard with landscaping. Vinyl siding and metal roof. Features: Open floor plan, Living room, dining area, kitchen is fully applianced, and laundry area with washer and dryer included. Vaulted ceilings. Primary bedroom has large full bath. Two

Sandy Statom ERA Team Realtors

218 Buffalo Trace, Winchester, KY 40391

/29
Est $243,945 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
46 Hiawatha Trail, Winchester, KY 40391

46 Hiawatha Trail, Winchester, KY 40391

/37
$1,595,000
- 37 Beds
- 19.5 Baths
- 26,124 Sq Ft
2 N Main St, Winchester, KY 40391

Major CAPEX in 2022 & 2024 — Facade transformation, fully restored and renovated.Current grossing $168,000 annual rent, with $4,000/month upside — beats the 1% rule!The Kerr Building, the largest downtown historical landmark, features structural repairs, new roofing, brick tuck-pointing, secure key-fob entrances, central HVAC, modern kitchens, updated baths, and new flooring. 18 LIHTC

Blanca Cheung Tsubaki Group, LLC

2 N Main St, Winchester, KY 40391
/37
$305,000 Sold Jul 22, 2025
- 1,936 Sq Ft
- $158/SF
- 0 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1984
848 Stratton Ln, Winchester, KY 40391

Welcome to your next happy place—located in the heart of Winchester, just a short cruise to the energy of Lexington! This well-loved and beautifully updated 4-bedroom, 3-bath home has all the space and style you've been looking for.Step inside to a bright open floor plan where the kitchen flows into the living room—perfect for entertaining or just keeping an eye on the game while you

Joey Hamilton EXP Realty LLC

848 Stratton Ln, Winchester, KY 40391

/33
Est $263,572 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 950 Sq Ft
14 Hiawatha Trail, Winchester, KY 40391

14 Hiawatha Trail, Winchester, KY 40391

/6
$171,000
- 2 Beds
- 1 Bath
- 870 Sq Ft
102 W Hickman St, Winchester, KY 40391

102 W Hickman St, Winchester, KY 40391Cozy and full of potential! This 11⁄2-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown

David Espinosa Bluegrass Realty Pros, Inc

102 W Hickman St, Winchester, KY 40391
/91
$395,000 Sold Jul 22, 2025
- 1,536 Sq Ft
- $257/SF
- 29 Days On Market
- 3 Beds
- 2 Baths
- Built 2015
101 Dorset Ln, Winchester, KY 40391

***Click on the Virtual Tour section to see the video walk through!*** Welcome to your perfect home retreat! This beautifully updated ranch home features a 2-car garage, spacious open layout, and large bedrooms. The backyard is a showstopper — relax under the covered patio or take a dip in the heated in-ground pool, newly installed in 2022 and surrounded by a sleek concrete patio. Inside, enjoy

Josh Wood Freedom Realty & Property Management

101 Dorset Ln, Winchester, KY 40391

/20
Est $199,502 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,593 Sq Ft
4 Hiawatha Trail, Winchester, KY 40391

4 Hiawatha Trail, Winchester, KY 40391

/103
$3,330,000
- 6 Beds
- 5.5 Baths
- 7,274 Sq Ft
5045 Van Meter Rd, Winchester, KY 40391

Welcome to a truly exceptional 78-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

The Prather Team - Michael Prather Keller Williams Bluegrass Realty

5045 Van Meter Rd, Winchester, KY 40391
/24
$249,900 Sold Jul 21, 2025
- 1,644 Sq Ft
- $152/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 1991
114 Bayberry Ln, Winchester, KY 40391

Back on the market! No fault of the seller. Move right in! 3-bedroom 2 bath 1/2 story home. Upstairs bedrooms have been freshly painted. Both bathrooms have been updated. Garage was converted to a family room and laundry area in 2016. The home as 2 freestanding fireplaces (no blowers) Fenced in backyard with firepit area and 8x8 pergola. 10x16 storage shed with separate meter. 2 sump pumps.

Debra Ward Coldwell Banker McMahan

114 Bayberry Ln, Winchester, KY 40391

/38
Est $264,195 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,216 Sq Ft
116 Dixon Way, Winchester, KY 40391

116 Dixon Way, Winchester, KY 40391

/17
$299,000
- Land
- 14.51 Acres
- $20,606 per Acre
3056 Irvine Rd, Winchester, KY 40391

Own a genuine piece of Kentucky splendor! Beautiful 14.5 acres of gently rolling land is ideal for building your custom home! The property offers creek access and a barn with electric and water. Don't miss this opportunity to own a farm only 20 miles to Hamburg and 5 miles to Winchester Bypass. No city sewage. Deed restrictions apply. Additional parcel with 11.36 acres is also available. Perfect

Lura Justice Rector Hayden Realtors

3056 Irvine Rd, Winchester, KY 40391
/24
$198,000 Sold Jul 18, 2025
- 1,075 Sq Ft
- $184/SF
- 0 Days On Market
- 3 Beds
- 1 Bath
- Built 1983
113 Colonial Park Dr, Winchester, KY 40391

Conveniently located just off Veterans Memorial Bypass, this adorable brick ranch offers easy access to everything Winchester has to offer. Inside, you'll find a freshly painted interior, new flooring, new windows, a new roof and a new HVAC system. The nice-sized kitchen features plenty of cabinet space, perfect for home-cooked meals and gatherings. Nestled in a quiet, well-established

Janet Baldwin Kentucky Land and Home

113 Colonial Park Dr, Winchester, KY 40391

/24
Est $245,528 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,377 Sq Ft
108 Dixon Way, Winchester, KY 40391

108 Dixon Way, Winchester, KY 40391

/4
$199,900
- Land
- 11.36 Acres
- $17,597 per Acre
2996 Irvine Rd, Winchester, KY 40391

Are you looking to build your dream home in a quiet country setting with easy access to the Interstate? Look no further! This property offers it all! Gorgeous setting with the best views and creek access. This lovely farm is 11.36 acres of gently rolling country land, in a highly desirable area with easy access to interstate 64, the Mountain Parkway and Hamburg. No city sewage. Deed restrictions

Lura Justice Rector Hayden Realtors

2996 Irvine Rd, Winchester, KY 40391
/49
$392,000 Sold Jul 18, 2025
- 3,200 Sq Ft
- $122/SF
- 261 Days On Market
- 3 Beds
- 3.5 Baths
228 Moundale Ave, Winchester, KY 40391

Freshly painted and full of charm! This colonial-style home in Winchester's historic Thomson Addition offers a spacious, inviting layout. The foyer opens to a formal dining room, great room, and a kitchen with custom maple cabinets, breakfast nook, and cozy living space. French doors lead to a screened-in porch and large deck which is perfect for relaxing or entertaining. The main floor features

Michelle Blackburn RE/MAX Creative, Winchester

228 Moundale Ave, Winchester, KY 40391

/19
Est $196,930 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,517 Sq Ft
170 Center Dr, Winchester, KY 40391

170 Center Dr, Winchester, KY 40391

/62
$269,950
- 3 Beds
- 2 Baths
- 1,247 Sq Ft
3614 Stamper Dr, Winchester, KY 40391

Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

Darrell Tackett Dream Maker Realty, LLC

3614 Stamper Dr, Winchester, KY 40391
/9
$190,000 Sold Jul 15, 2025
- 1,120 Sq Ft
- $170/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 2001
507 Hidden Hills Way, Winchester, KY 40391

Ranch with a large covered porch, a new roof, new appliances, new bath flooring, new sump pump and a new professional paint job. Vaulted living room ceilings. Clean and ready for occupancy.

Sondra Clark Taylor Real Estate, LLC

507 Hidden Hills Way, Winchester, KY 40391

/29
Est $192,113 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,228 Sq Ft
505 Bob o Link Dr, Winchester, KY 40391

505 Bob o Link Dr, Winchester, KY 40391

/22
$225,000
- 4 Beds
- 2 Baths
- 1,370 Sq Ft
521 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

521 Acadia Way, Winchester, KY 40391
/27
$199,900 Sold Jul 15, 2025
- 1,348 Sq Ft
- $148/SF
- 18 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1940
139 W Hickman St, Winchester, KY 40391

Welcome Home! Featuring 3 bedrooms and 2 bathrooms, this home is everything you have been looking for. Recent updates include new flooring, appliances, roof, HVAC, and even the water heater. Sit out on your front porch and drink your morning coffee, or enjoy your large back deck for a weekend cookout. This home also has plenty of attic storage. The driveway makes a perfect place to plug in your

Clay David Sutherland ERA Select Real Estate

139 W Hickman St, Winchester, KY 40391

/12
Est $210,379 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,169 Sq Ft
303 Hummingbird Rd, Winchester, KY 40391

303 Hummingbird Rd, Winchester, KY 40391

/20
$189,000
- 3 Beds
- 1 Bath
- 1,443 Sq Ft
31 Vine St, Winchester, KY 40391

Welcome to this beautifully updated 3-bedroom, 1-bath home, perfectly situated in the vibrant heart of Winchester. Bursting with charm and character, this home offers the best of modern updates and classic appeal. Step inside to discover a bright, open living area with new flooring, fresh paint, and stylish finishes throughout. The updated kitchen features sleek cabinetry, granite countertops,

Jana Hooten Rock N' Realty LLC

31 Vine St, Winchester, KY 40391

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