221 Winchester, KY Real Estate Listings

Sort by:
$182,500Est. Payment
3 Beds | 2 Baths | 1,340 Sqft
32 Hillcrest Drive, Winchester, KY 40391
House For Sale

This lovely brick home sits on a large level lot in a quiet mature subdivision, conveniently located close to everything Winchester has to offer. MOVE IN condition this desirable one story offers 3 bedrooms, 2 full baths and some very nice updates along with original hardwood floors. Newer replacement windows, new shingles in 2016, newer double back doors, tile in kitchen and both baths along with new HAVC in 08. Enjoy your views - either from your welcoming front porch or the privacy of back covered deck. A picture perfect extra large back yard offers room for anything you might desire plus a good storage building (also with new shingles) Back yard and is fully fenced (less one gate.) All these features and more make this home a must see. Take advantage of the low interest rates with a new place to call home!

Stuart Raney

$250,000Est. Payment
3 Beds | 2 Baths | 1,806 Sqft
1616 Gay Evans Road, Winchester, KY 40391
House For Sale

If you're looking for a home with a little space in a country sitting and not too far out from town, this is it. Sitting on 2 acres, the main level has a large kitchen with oak cabinets, a dining area, a living area, 3 bedrooms and 2 full baths. The basement has a rec room, a bonus room and a finished, heated/cooled 2 car garage. Just outside the kitchen/dining area is a large private partially-covered deck where you can enjoy grilling and relaxing. A 2nd drive leads to the 23.5' x 30' detached garage/workshop with a little attic storage, a 14'W x 30'L x 10.5'H RV shed and extra parking. Just 9 minutes from I-64 Exit 96, 7 minutes from the bypass and 15 minutes from both Paris and Mt Sterling. New roof on house in 2017. Kwikset Smartkey system for easy rekeying. Basement unfinished area is partially finished. Buyer to verify all measurements.

$319,900Est. Payment
3 Beds | 3 Baths | 2,949 Sqft
71 Mockingbird Valley Road, Winchester, KY 40391
House For Sale

Location, Location, Location! Highly sought after Hampton Manor - convienetly located to the best Winchester has to offer. This property features beautiful hardwood floors, granite countertops, updated bathrooms, and a large backyard with patio space. Bonus room on the first floor offers great flexibility for an office or guest room. This property has so much to offer! Don't miss out!

$325,000Est. Payment
8 Beds | 8 Baths | 4,000 Sqft
17 W Lexington Avenue, Winchester, KY 40391
Multi Family For Sale

The Historic Beam building is for sale! This 100+ year old building has 8 studio apartments in it. also has a 2,000 sqft basement that can be rented out separate for more income. electric, water, and sewer has been updated. New water heater installed in basement. has sprinkler system and security system that goes with property. beams on back deck were replaced this past year. roof was recoated last year.

$469,000Est. Payment
4 Beds | 3 Baths | 5,516 Sqft
14 Redbud, Winchester, KY 40391
House For Sale

Relax and enjoy on the serene back screened-in porch. Walk to Winchester's charming downtown to shop, dine or antique. Spacious and elegantly appointed home featuring formal and informal rooms for all to enjoy. Situated on large treed lot located minutes from golf, swimming and tennis at the Winchester Country Club. Custom plantation shutters in all main level bedrooms and family room. Quaint, elegant, and spacious a combination you will have to see. Call today for your private viewing.

$130,000Est. Payment
3 Beds | 1 Bath | 1,213 Sqft
608 1/2 College Street, Winchester, KY 40391
House For Sale

Charming home in College Park area 3 bedroom 1 bath single story brick home with screened porch deck and covered front entry. Alley access and parking in back. Nice storage barn and fire pit to enjoy comes with this sweet cottage. Great condition. Appliances are included. Very reasonable utility costs. Screened porch, deck and front stoop. Lots of updates Roof shingles replaced 2 years ago Windows and HVAC are around 4 years old Water Heater 5 years so this home is move in condition.

$229,900Est. Payment
4 Beds | 3 Baths | 2,042 Sqft
199 Prescott Lane, Winchester, KY 40391
House For Sale

Need more room ?? Don't let this one slip away!! This home offers 4 Bedrooms 2 1/2 Bathrooms and 2 car garage. Close to schools shopping and restaurants. Home Warranty offered with accepted offer.

$355,000Est. Payment
4 Beds | 2 Baths | 2,520 Sqft
413 South Maple, Winchester, KY 40391
House For Sale

This spacious all brick home has all of the charm & character you could dream of with tons of space for everyone. This 4 bedroom 1 and a half bath home with hardwood flooring has 3 stories plus the plus a dining room is big enough to comfortable accommodate your family & friends for those get togethers or summer celebrations!

$339,500Est. Payment
3 Beds | 2 Baths | 1,848 Sqft
4675 Paris Rd, Winchester, KY 40391
House For Sale

Newly renovated ranch home located on 1.762 acres with to-die-for metal/concrete block building located on Paris Road. Home features 3 bedrooms, 2 full bathrooms, Kitchen with new granite, Stove, Microwave, and Dishwasher, Living Room, Family Room and Utility Room. Home has new hardwood and carpeting plus all new windows. Beautiful countryside views all around is a bonus. For the man of the house there is a 3640 sq. ft. shop that will be the envy of any man. Call today before it's too late.

$1,400,000Est. Payment
61 Acres
1305 Irvine Road, Winchester, KY 40391
Lots Land For Sale

61 acres ready for development. Zoned R1 and R4. Utilities available. Backs to Buffalo Trace subdivision. .5 mile from downtown Winchester,

$299,900Est. Payment
3 Beds | 2 Baths | 3,524 Sqft
233 Boone Avenue, Winchester, KY 40391
House For Sale

Beautiful 1920's home with hardwood floors, woodwork and fireplaces, recently renovated kitchen and bathrooms, three bedrooms or 4th which is currently used as a office, 2nd floor laundry room, mudroom and separate butler pantry off kitchen, large front porch, fenced lot and pergola-covered back deck ready for entertaining or leisurely evenings outside. 2 car detached garage and detached shop with a 2 car carport at the rear with alley access

$259,000Est. Payment
4 Beds | 3 Baths | 2,100 Sqft
616 Reims Court, Winchester, KY 40391
House For Sale

This adorable ranch home has 4 bedrooms, 2.5 baths, formal living room, family room, dining area, remodeled kitchen, and home office. You can move right in and relax because the sellers updated the home in 2017 with new laminate/carpet/vinyl tile, bathroom vanities/toilets, custom shaker style kitchen cabinets, granite countertops, stainless steel appliances, lighting, and a fresh coat of paint. A new roof and 6-inch gutters with leaf guard were installed 6/2019. Located in a quiet cul-de-sac on a large lot in Calmes Subdivision, this home is a rare find in this condition. Call today!

$203,500Est. Payment
3 Beds | 2 Baths | 1,562 Sqft
220 Prescott, Winchester, KY 40391
House For Sale

Welcome Home! This well maintained 3 bedroom 2 bath, 2 car garage cozy cottage await a new owner. Upgrades include hardwood and tile flooring throughout, quartz and granite countertops in the kitchen and bathrooms, soft touch light switches, the primary bath features a fully tiled shower with seamless door, heated tile flooring, a double bowl vanity and a large tub for soaking. The great room opens to the maintenance free raised deck with railing and the newer metal roof has spray foam for added insulation. The garage front and back doors have been replaced, the motion light in the garage adds a dimension of safety. Cabinets in the garage do convey. The primary bedroom closet has been professionally designed. The tankless water heater provides hot water immediately. As you see, this home has many upgrades for you to enjoy. Come see for yourself, you will be delighted to see all the upgrades in this one level home.

$549,000Est. Payment
5 Beds | 3 Baths | 3,785 Sqft
1183 The Ridings Rd, Winchester, KY 40391
House For Sale

This beautiful home in a quiet equestrian-friendly development is just minutes outside Winchester and only 15 minutes from Lexington. The stately 5 bedroom, 3 full bath home has a first floor primary suite and laundry, formal living and dining rooms, large eat-in kitchen, and den with unique vaulted ceiling and wet bar. The second level includes 4 generous sized bedrooms, two full guest baths and access to unfinished bonus room over the garage for extra storage. The custom millwork throughout the home is beyond compare with oversized dentil crown molding, wainscoting and trim. All hardwood flooring and carpeting was replaced in 2018. The large custom kitchen has quartz countertops, pantry, stainless appliances, and wonderful view of the countryside. New Marvin windows along the back of the home in 2016. Don't wait to see this unique property in a very desirable location.

$290,000Est. Payment
3 Beds | 3 Baths | 2,947 Sqft
308 Runnymeade Dr, Winchester, KY 40391
House For Sale

This roomy brick ranch is situated on a large lot with features that include hardwood floors, ceramic tile, spacious eat-in kitchen, formal dining room, a living room that shares the fireplace with the kitchen, a large master bedroom suite with a fireplace and walk in closet. The extra room off the kitchen could easily be an extra den or used for a craft room. Sellers had a very nice 16x24 sunroom constructed off the back of the house where you will enjoy your morning cup of coffee or just relaxing in the evenings out of the elements. They also had a workshop added off the rear of the garage. The workshop offers a woodburning stove complete with a sawdust collection system, a woodworker's dream! Roof and HVAC are both approximately 2.5 years old.

$419,000Est. Payment
5 Beds | 4 Baths | 4,400 Sqft
118 Teal Lane, Winchester, KY 40391
House For Sale

Beautiful brick ranch with a full basement that leads out to the back yard in Mallard Place Subdivision! Hardwood floors, granite countertops, large living room, a great deck that has wonderful views. This house has 5 bedrooms and 3.5 bathrooms. Seller is also a licensed real estate agent. More pictures to come!

version="1.1" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" width="30px" height="24px" >