Español  |  Fine Homes  |  Commercial Real Estate  |  Global  |  C21 Blog
CENTURY21 Real EstateKentuckyWinchesterHomes for Sale
My C21: Sign In  |  Register  |  My Favorites
Your Current Search

Homes for Sale

Winchester, KY

Property Type

Single Family Home (remove)
Refine Your Search
to
Search by Schools

More Search Options
Sort By:
Per Page:
Page:
1 | 2 | 3 | 416 Next

$1,100,000

6326 Colby Road Winchester, KY 40391
4 Beds
3 Full Baths
Courtesy Of Homes & Horse Farms Real Estate
MLS# 1506960
PROPERTY DESCRIPTION: 
Sellers Will Divide! This treasure is brimming with history as it is the last remaining parcel of an original land grant of 2,000 plus acres given to this family in the late 1700's. Currently owned by the 10th generation, this lovingly maintained Circa 1845 home is now available with 50 +/- acres of gently rolling pasture land. The handsome brick 2 story is graced with Italianate trim work and the multiple floor to ceiling windows and doors flood the interior with natural light. A gracious and welcoming entry gives way to large rooms, high ceilings, HW floors, pocket doors, built in cabinetry, fireplaces, matching parlors, sweeping staircase & original light fixtures. Additional improvements include a perfectly charming 2BR/2FB cottage with fireplaces & 2 zone HVAC, guest house, garage, an extensive 15 bent barn & tenant house. Fully fenced, this property has over a mile of road frontage. Desirably located w/easy access to Lex, Hamburg Pl & the interstate!
FEATURES:
Age: Over 50 Years Old
Amenities: Patio, Basement, Ceiling Fan, Attic
Appliances: Range
Architecture Style: Other
Cooling System: Heat Pumps
Exterior Type: Brick Veneer
Fireplace: Fireplace
Floor Covering: Hardwood
Heating System: Forced Air, Fireplace
Lot Size: 50 Acres
Roof Type: Unknown
Rooms: Basement, Bedroom, Den, Dining Room, Family Room, Foyer, Full Bath, Kitchen, Living Room, Utility

$849,900

6870 Old Boonesboro Road Winchester, KY 40391
3 Beds 3,396 Sq. Ft
2 Full Baths
Courtesy Of Tom Goebel & Company
MLS# 1523182
PROPERTY DESCRIPTION: 
Peace and beauty combined with tremendous QUALITY in this wonderful home located on 125+ private acres of working farm land. Gorgeous views in every direction and lovingly tended by same family for over 6 decades. Offering spacious rooms, high ceilings, geo-thermal, hardwoods throughout, newer windows and metal roof. It will make a perfect pallet for your choice of decor and todays lifestyle. Perfect for horses or cattle etc. with barn, ponds, infield water and fully fenced. Truly only minutes from I64 and I75 offering quick access to Lexington, Winchester, Richmond and all points beyond. This is a very special opportunity - be certain to put it on your MUST SEE list soon.
FEATURES:
Age: Over 50 Years Old
Amenities: Patio, Basement, Ceiling Fan, Attic
Appliances: Dishwasher, Dryer, Microwave, Oven - Double, Refrigerator, Washer
Architecture Style: Other
Exterior Type: Stone
Fireplace: Fireplace
Floor Covering: Hardwood, Vinyl
Heating System: Geothermal, Fireplace
Lot Size: 125.53 Acres
Roof Type: Metal
Rooms: Basement, Bedroom, Den, Dining Room, Family Room, Foyer, Full Bath, Kitchen, Living Room, Utility

$745,000

6400 Colby Road Winchester, KY 40391
4 Beds 5,088 Sq. Ft
3 Full Baths
Courtesy Of Homes & Horse Farms Real Estate
MLS# 1521163
PROPERTY DESCRIPTION: 
This gracious Circa 1845 home has certainly stood the test of time well. Lovingly maintained and in the same family for 10 generations this house overlooks a spring fed small lake and is framed by majestic trees. The welcoming entry gives way to matching parlors, high ceilings, HW flooring, pocket doors and built-ins, multiple fireplaces and a lovely staircase of yesteryear. On this private compound there is a charming two bedroom guest house with two fireplaces, 2 zone HVAC & hardwood & tile floors thru out...several other outbuildings complete Stanley Place....additional acreage with barns is available. Nicely located between Lexington & Winchester.
FEATURES:
Age: Over 50 Years Old
Amenities: Patio, Basement, Ceiling Fan, Attic
Appliances: Dishwasher, Range, Refrigerator
Architecture Style: Other
Cooling System: Zoned A/C
Exterior Type: Brick Veneer, Masonry
Fireplace: Fireplace
Floor Covering: Carpet, Hardwood, Tile
Heating System: Forced Air, Fireplace
Lot Size: 16 Acres
Roof Type: Composition Shingle
Rooms: Basement, Bedroom, Den, Dining Room, Family Room, Foyer, Full Bath, Kitchen, Living Room, Utility

$725,000

221 Windy Lane Winchester, KY 40391
4 Beds 1,700 Sq. Ft
3 Full Baths
Courtesy Of Keller Williams Greater Lexington
MLS# 1510404
PROPERTY DESCRIPTION: 
Farm Paradise! * Gently rolling 164 acres of beautiful Central Kentucky farmland * 2 combined tracts * Frontage on 89 Irvine Road runs completely from Pilot View Rd. to Wils Rupard Rd. * 4 total barns * 1 cattle shed * 23 bents * 5 paddocks * 6 fields * Wildlife with turkey & deer * Large metal workshop building * Double wide trailer & single wide trailer for additional investment properties * Storage trailers * Present farm use for cattle, crops, pasture - possible horse farm operation * Property lines all fenced * Brick ranch home on full basement * Attached 2-car garage * 18 x 14 Sunroom * 4 bedrooms, 3 full baths * Kitchen features real oak cabinets, built-in dining table * 2 fireplaces * Champion vinyl windows * New roof 2012 * New furnace 2003 * New central vacuum system 2013 * Rain Soft water softener system * Additional building sites with fabulous views * Great development property potential - Brandenburg Acres? * Approx. 7 miles to downtown * Short drive to 1-64 * Must See!
FEATURES:
Age: 31-40 Years Old
Amenities: Basement, Ceiling Fan, Attic
Appliances: Range, Refrigerator, Vacuum System
Architecture Style: Other
Cooling System: Heat Pumps
Exterior Type: Brick Veneer
Fireplace: Fireplace
Floor Covering: Carpet, Hardwood, Vinyl
Heating System: Heat Pump, Fireplace
Lot Size: 164 Acres
Parking Type: Garage
Roof Type: Composition Shingle
Rooms: Basement, Bedroom, Bonus Room, Dining Room, Family Room, Full Bath, Kitchen, Living Room, Utility

$719,000

5838 Old Boonesboro Road Winchester, KY 40391
4 Beds 3,516 Sq. Ft
3 Full Baths 1 Half Bath
Courtesy Of Steven D Adams Real Estate Services, LLC
MLS# 1526331
PROPERTY DESCRIPTION: 
Kentucky country living with easy access to Richmond, Winchester and Lexington. Great neighbors, actively farming. Large rooms, bright and sunny. Golf tee & target green for family fun (previously riding ring). Lengthy asphalt drive with large parking apron. This farm is well fenced with a stock pen, barnyard, three paddocks, a three bent barn with three boxed stalls, workbench, lights, electrical service & water. Gravel drive from house to barn/pond/stock pen area. The pond has electrical service and an aerator. Spring fed spring pond (open water for stock year round). Old rock fencing at road front and in the spring pond. Concrete block tractor garage near the barn with lights and electrical service. Two nice run in sheds (one has concrete floor). Water service at the front gate.
FEATURES:
Age: 11-20 Years Old
Amenities: Patio, Ceiling Fan, Security System, Security System, Attic
Appliances: Dishwasher, Dryer, Garbage Disposer, Microwave, Range, Refrigerator, Vacuum System, Washer
Architecture Style: Other
Cooling System: Heat Pumps
Exterior Type: Brick Veneer, Vinyl Siding
Fireplace: Fireplace
Floor Covering: Carpet, Hardwood, Tile
Heating System: Heat Pump, Fireplace
Lot Size: 23.16 Acres
Parking Type: Garage
Roof Type: Unknown
Rooms: Bedroom, Dining Room, Family Room, Foyer, Full Bath, Half Bath, Kitchen, Living Room, Utility

$639,500

250 Calloway- White Road Winchester, KY 40391
5 Beds 6,957 Sq. Ft
4 Full Baths 1 Half Bath
Courtesy Of Kentucky Residential Real Estate, LLC
MLS# 1600326
PROPERTY DESCRIPTION: 
Close to Hamburg! Mostly brick home, sitting on 5.4 acres with two bedrooms on the main floor. Bring your toys! 40x80 Auxiliary Garage out back made with steel, has electric, is insulated, has water line, communication cables, and various garage door heights. This home is super clean and move in ready! Features include: home generator, media room, shelter area in crawlspace (access from inside home), 3 car garage, 10 ft ceiling height on main floor, 9 ft on second floor, upgraded 1 inch water supply line, dual fuel fireplace w/ remote, laundry chute, granite & tile back splash in kitchen, large tiled shower and over sized bathtub in master bedroom, TWO large septic tanks, a large covered patio out back with a gas line for the grill, dedicated home office w/ tall glass doors, large kitchen pantry, double oven, electric cook top w/ dual fuel, stainless steel appliances and more! THIS HOME is your little piece of land on the edge of town! Over 6900 sq ft.
FEATURES:
Age: 6-10 Years Old
Amenities: Patio, Ceiling Fan, Security System, Security System, Attic
Appliances: Dishwasher, Garbage Disposer, Microwave, Oven - Double, Refrigerator, Vacuum System
Architecture Style: Other
Cooling System: Heat Pumps, Zoned A/C
Exterior Type: Brick Veneer, Vinyl Siding
Fireplace: Fireplace
Floor Covering: Hardwood, Tile
Heating System: Heat Pump, Humidifier, Fireplace
Lot Size: 5.41 Acres
Parking Type: Garage
Roof Type: Unknown
Rooms: Bedroom, Foyer, Full Bath, Great Room, Half Bath, Kitchen, Office, Utility

$575,000

511 Boone Avenue Winchester, KY 40391
5 Beds 4,740 Sq. Ft
3 Full Baths 1 Half Bath
Courtesy Of Signature Real Estate
MLS# 1502757
PROPERTY DESCRIPTION: 
This beautiful early 19th century home has been completely remodeled with a gorgeous gourmet kitchen with granite countertops, custom cabinets, stainless appliances, and tile backsplash. Features gorgeous formal dining and living rooms with fireplaces. Five bedrooms and three and a half baths, including a completely remodeled luxurious master bath with a custom tile shower, separate whirlpool tub, and large granite vanity. Beautiful hardwood floors throughout. Personal elevator, making trips upstairs an ease. Freshly scraped and painted outside of home! Family room, den, library and so much more on a beautiful 2.7 acre, must see lot!
FEATURES:
Amenities: Patio, Ceiling Fan, Security System, Security System, Attic
Appliances: Dishwasher, Garbage Disposer, Range, Refrigerator
Architecture Style: Other
Cooling System: Heat Pumps, Zoned A/C
Exterior Type: Stone, Wood
Fireplace: Fireplace
Floor Covering: Hardwood, Tile
Heating System: Heat Pump, Fireplace
Lot Size: 2.7 Acres
Parking Type: Garage
Roof Type: Composition Shingle
Rooms: Bedroom, Dining Room, Family Room, Foyer, Full Bath, Half Bath, Kitchen, Living Room, Utility

$574,000

3815 Old Boonesboro Road Winchester, KY 40391
4 Beds
3 Full Baths
Courtesy Of Justice Real Estate
MLS# 1513450
PROPERTY DESCRIPTION: 
Wonderfully redone home featuring beautiful vistas and winding creek across the front. Spacious rooms and hallways, original hardwoods throughout the home and gorgeous hand-carved mantles above fireplaces are a small sampling of unique features. Kitchen and baths are updated. A study, utility room, and mud room with slate floors were added. Farm house has multiple patios, covered porches, heated in-ground pool, deluxe playhouse, over-sized 3-car garage with storage above. A 3 stall barn and tack room, stone entrance, paved driveway, and mature landscaping. Must see to appreciate!! Motivated Sellers!!
FEATURES:
Amenities: Patio, Sky light, Wet Bar, Basement, Ceiling Fan, Attic
Appliances: Dishwasher, Garbage Disposer, Microwave, Oven - Double, Range, Refrigerator
Architecture Style: Other
Cooling System: Heat Pumps, Zoned A/C
Exterior Type: Brick Veneer, Vinyl Siding
Fireplace: Fireplace
Floor Covering: Carpet, Hardwood, Slate, Tile
Heating System: Forced Air, Heat Pump, Fireplace
Lot Size: 11.69 Acres
Roof Type: Composition Shingle
Rooms: Basement, Bedroom, Bonus Room, Dining Room, Family Room, Foyer, Full Bath, Kitchen, Living Room, Office, Utility

$499,500

2750 Clintonville Road Winchester, KY 40391
5 Beds 4,391 Sq. Ft
3 Full Baths 1 Half Bath
Courtesy Of Bluegrass Sotheby's International Realty
MLS# 1515925
PROPERTY DESCRIPTION: 
Sellers have built a home closer to their children and made an incredible price reduction on this warm and welcoming farmhouse. Pastoral views from each window, this 5 BR, Cape Cod charmer with finished walk-out basement, surprises you with over 4000 sq feet of living space. 14.93 acres, with 467 sq ft of road frontage. Flowering trees and lush landscaping frame the house with a covered back porch to enjoy lazy afternoons on. Inside, a large open kitchen and huge pantry overlooks the back pasture. So much storage, closets were designed with space in mind! Separate guest quarters over the 2 car attached garage, with a BR, full BA, and Sitting/Office area allows for easy entertaining. A 2000 sq ft detached garage; roughed in for 1/2 ba and floored upstairs allow for more mind boggling storage or easy conversion to living or barn space. Two craftsmen lawn tractors with car, dethatcher and spreader convey with the property! The perfect family home with farm acres to roam and play!
FEATURES:
Age: 31-40 Years Old
Amenities: Basement, Ceiling Fan, Security System, Security System, Attic
Appliances: Dishwasher, Microwave, Oven - Double, Range, Refrigerator, Vacuum System
Architecture Style: Other
Exterior Type: Vinyl Siding, Wood
Fireplace: Fireplace
Floor Covering: Carpet, Hardwood, Tile, Vinyl
Heating System: Forced Air, Fireplace
Lot Size: 14.93 Acres
Parking Type: Garage
Roof Type: Composition Shingle
Rooms: Basement, Bedroom, Dining Room, Family Room, Foyer, Full Bath, Great Room, Half Bath, Kitchen, Living Room, Office, Utility

$499,500

1775 Irvine Road Winchester, KY 40391
4 Beds 3,800 Sq. Ft
4 Full Baths
Courtesy Of Hoffman International Properties
MLS# 1507279
PROPERTY DESCRIPTION: 
Blue Ridge Manor first time on the market. This gorgeous two story home has 3,800 sq. ft. living space with finished walk out basement. The fourth bedroom adjoins the master bedroom with second door to hallway that could be used as baby room. Two additional bedrooms with hard wood floors on the second level. Main level has formal dining room, living room, family room, kitchen bar, full bath and attached two car garage. Additional acreage available for purchase or can be purchased with adjacent 81 acre farm listing number 1507276
FEATURES:
Age: 6-10 Years Old
Amenities: Deck, Patio, Basement, Attic
Appliances: Dishwasher, Garbage Disposer, Microwave, Range, Refrigerator
Architecture Style: Other
Cooling System: Heat Pumps
Exterior Type: Brick Veneer
Fireplace: Fireplace
Floor Covering: Carpet, Hardwood, Tile
Heating System: Forced Air, Heat Pump, Fireplace
Lot Size: 5.13 Acres
Roof Type: Composition Shingle
Rooms: Basement, Bedroom, Dining Room, Family Room, Foyer, Full Bath, Kitchen, Living Room, Office, Utility
1 | 2 | 3 | 416 Next

Winchester, KY Real Estate & Homes for Sale - 157 Listings Found

MY PLACES
Locate important places on the map like school, work, and home of a relative or friend to help find the best properties for you.
Add, Edit, or View My Places
DRAWING TOOL
Draw the area on the map that you would like to search. Click the pencil icon again to turn the drawing tool off.
DRAWING TOOL
Points Of Interest
Area Overlay
$50K $1M+
Heat maps are viewable one at a time.
Click the buttons to toggle them on or off.