Winchester KY Homes for Rent

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Type:
Single Family
Sq.Ft.:
2,105
Status:
Active
Beds:
4
Lot size:
0.55 Acres
Year built:
1970
Baths:
3.00
MLS#:
24023888
Subdivision:
Greenfield

ADDITIONAL INFORMATION

Nestled in a quiet cul-de-sac, minutes from shopping, dining, interstate, this unique & spacious ranch-style home offers a rare blend of location & space. Originally used as a duplex, this property provides an ideal layout for multigenerational living or other flexible living arrangements. Each side of the home features its own entrance, primary suite, full kitchen, & utility room, making it perfect for privacy & versatility. The main living area welcomes you with a light-filled, open plan that flows into a renovated kitchen w/island, leathered granite countertops & stainless-steel appliances, including a gas range. The remodeled primary suite boasts a private BA & an expansive walk-in closet, providing a luxurious retreat. Across the home, the secondary living area includes an additional kitchen, 3BR's/2BA's, offering plenty of space for extended family or guests. With 2 driveways, this home allows ample parking, while a large, usable yard offers plenty of space for outdoor activity. A detached garage is perfect for parking, storage, or workshop. Sold as-is but open to inspections, this rare property is a fantastic find for those seeking space, flexibility & convenience.

Type:
General Commercial
Sq.Ft.:
2,310
Status:
Active
Beds:
n/a
Lot size:
0.23 Acres
Baths:
MLS#:
24023619
Subdivision:
Downtown

ADDITIONAL INFORMATION

Discover this exceptional, versatile space in the heart of downtown Winchester. With beautiful wood floors, a vaulted ceiling, and original raw wood details, this property exudes charm and modern functionality. The space is currently set up as a gym but offers endless potential - ideal for retail, a yoga studio, a creative workspace, or a trendy boutique. This unique property is the perfect blend of historic charm and modern upgrades. Embrace the opportunity to make this space your own - whether as a thriving business location or an inspired community hub. Don't miss out on owning a piece of Wincity! Schedule an appointment today!

Type:
Land
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
0.55 Acres
Baths:
MLS#:
24023551
Subdivision:
Mallard Place

ADDITIONAL INFORMATION

Prime Reserve building lot in the new luxury subdivision located on the West side of Winchester. This is your opportunity to own one of the prime lots in Mallard Place. Enjoy the peaceful quiet of this subdivision while enjoying the beautiful views.

Type:
Single Family
Sq.Ft.:
1,997
Status:
Active
Beds:
4
Lot size:
0.11 Acres
Year built:
2024
Baths:
3.00
MLS#:
24023332
Subdivision:
Oakmont

ADDITIONAL INFORMATION

Contract writing period through 12:00 noon on Thursday, November 7th.The Laurel Square, part of the Trend Collection by Ball Homes, is two story plan with a very open first floor layout. The island kitchen offers both a breakfast area and countertop dining, and a large pantry. Granite kitchen counter tops with stainless steel 50/50 under-mount sink and full back splash. Stainless steel appliances including smooth top range, microwave and dishwasher. The kitchen opens to the family room at the rear of the home. Upstairs are the primary bedroom suite, two bedrooms and a hall bath, plus a spacious loft. The primary bedroom suite includes a bedroom with vaulted ceiling, large closet, and spacious bath with tub/shower, window, and linen storage. Raised vanities in baths and 12x10 concrete patio.

Type:
Single Family
Sq.Ft.:
2,269
Status:
Active
Beds:
4
Lot size:
0.13 Acres
Year built:
2024
Baths:
3.00
MLS#:
24023337
Subdivision:
Oakmont

ADDITIONAL INFORMATION

The Haywood Park, part of the Trend Collection by Ball Homes, is a two story plan on a walk-out basement with plenty of room to grow! When you walk through the front door, you're greeted with a versatile flex space then down the hall opens up to the large living room and spacious kitchen. Cozy up next to the fireplace or sip your morning coffee outside on the covered deck. The kitchen offers both a breakfast area and countertop dining at the island plus a large walk-in pantry. Granite counter tops with stainless steel microwave, dishwasher, stove, and refrigerator complete the kitchen. Upstairs are the primary suite, three bedrooms and a hall bath. The primary bedroom suite includes a bedroom with vaulted ceiling, large closet, and spacious shower and linen storage.

Type:
Single Family
Sq.Ft.:
1,100
Status:
Active
Beds:
3
Lot size:
0.33 Acres
Year built:
1985
Baths:
1.00
MLS#:
24023173
Subdivision:
Rural

ADDITIONAL INFORMATION

Great location close t o down town Winchester, shopping, school, recreation areas, I 64 ,in beautiful Winchester,nice 3 bedroom ,1 bath , all brick home, with all appliances, including washer and dryer roof 1 year old, fenced yard, storage building private drive. nice back yard and more.

Type:
Single Family
Sq.Ft.:
5,220
Status:
Active
Beds:
4
Lot size:
71 Acres
Year built:
1994
Baths:
6.00
MLS#:
24023048
Subdivision:
Rural

ADDITIONAL INFORMATION

Discover your own slice of paradise at this stunning colonial-style home nestled on 71 picturesque acres RIGHT on the Fayette County/Clark County line. 10 minutes to Hamburg. As you approach via a private, gated lane, you'll be captivated by the breathtaking views and tranquil surroundings.The residence offers a perfect blend of charm and modern comforts. With ample living space, the home features elegant interiors, inviting gathering areas, and large windows that bathe each room in natural light, all while showcasing the spectacular sunsets that grace the horizon.Equestrian enthusiasts will be thrilled by the meticulously renovated barn, complete with 12 stalls, a temperature controlled office, tack room, laundry area and bathroom. Both a 50' x 150' indoor arena and a 120' x 220' outdoor ring, making it ideal for training and leisure. Each pasture is equipped with insulated electric waterers (9 total). 3.71 acre tract is deeded separately and could be built on - a rare opportunity!Whether you're looking to enjoy serene country living, cultivate your passion for horses, or simply escape the hustle and bustle of city life, this property offers endless possibilities.

Type:
Land
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
0.46 Acres
Baths:
MLS#:
24022901
Subdivision:
Fairway Woods

ADDITIONAL INFORMATION

This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

Type:
Single Family
Sq.Ft.:
2,681
Status:
Active
Beds:
5
Lot size:
0.12 Acres
Baths:
3.00
MLS#:
24022885
Subdivision:
College Park

ADDITIONAL INFORMATION

Welcome to this beautifully remodeled gem where classic charm meets modern luxury! This spacious 5-bedroom, 3 FULL bathroom home has been completely and meticulously updated from top to bottom, with no detail overlooked. Step inside to discover all-new features, from the roof and windows to the electrical to HVAC systems and spray foam insulation in the entire home and stunning wood floors!! Each bathroom has been tastefully updated with luxurious marble showers, creating a spa-like experience right at home. The gourmet kitchen is a showstopper, bathed in natural light through abundant windows and outfitted with sleek granite countertops, perfect for family gatherings and entertaining. Downstairs, find two generously sized bedrooms, while upstairs hosts three more--including the primary suit. Upstairs you will love a light-filled bonus area offers versatility as a home office, playroom, or creative space. This home is move-in ready and priced under appraisal value, making it an incredible find!Enjoy easy access to five nearby parks, a short 5-minute drive to downtown, and only 25 minutes to Lexington. Don't miss the opportunity to own this stunning, fully upgraded home!!

Type:
Single Family
Sq.Ft.:
1,732
Status:
Active
Beds:
3
Lot size:
2.02 Acres
Year built:
1960
Baths:
1.00
MLS#:
24022859
Subdivision:
Calmes Estates

ADDITIONAL INFORMATION

Location! Location! This is a prime spot in Winchester. There are so many possibilities with this property. It's minutes from all the local retail stores, golf courses, and beautiful downtown. It is just down the road from Boonesboro State Park. Take a short drive and you will be in Lexington. This land is very sought after. Due to the property being an estate, it is being sold as is.

Type:
Single Family
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
0.34 Acres
Year built:
1950
Baths:
MLS#:
24022580
Subdivision:
North Park

ADDITIONAL INFORMATION

Investors special! Flippers this one if for you! Home has already been gutted to the studs! Ready for you to put your own vision and make this the home the one you have always dreamed of! Double lot with a detached garage, home has a covered front porch and covered back patio. Home features off street parking! Easy access to downtown and conveniently located near shopping and food!

Type:
Single Family
Sq.Ft.:
1,072
Status:
Active
Beds:
3
Lot size:
0.18 Acres
Year built:
1998
Baths:
2.00
MLS#:
24022484
Subdivision:
Buffalo Trace

ADDITIONAL INFORMATION

NEW Price Reduction!!! Perfect 3 Bedroom 2 Bathroom Home For A First Time HomeBuyer Or Someone Downsizing. Location Is Convenient To The Interstate, Shopping And Downtown! Nice Size Backyard And Plenty Of Parking In The Front. Shed In The Backyard Is Included. Make This Beautiful And Affordable Home Yours Before The Holidays!

Type:
Single Family
Sq.Ft.:
3,882
Status:
Active
Beds:
6
Lot size:
0.17 Acres
Year built:
2005
Baths:
4.00
MLS#:
24022275
Subdivision:
Oakmont

ADDITIONAL INFORMATION

Owner is in construction and is very talented with remodeling. Apart from home being in a great location, right across the street from the Elementary School, home is minutes from shopping, food and entertainment (Applebees,Woody's Bar and Grill, Tjmaxx, Kroger, Movie Theatre, Ft. Boonesborough) & only a 20 minute drive to Hamburg in Lexington or 15 miutes to Mt. Sterling. This beautiful home is complete with a newly finished walk-out basement featuring a pool table & bar area along with two bedrooms, a full bath & lots of storage. On the main floor you have a living room/ potential office with french doors, dining room with new LVP flooring, kitchen with brand new granite countertops, new light fixtures, farm sink & stainless steel appliances, access to a large deck perfect for entertaining, large family room with beautiful stone fireplace. Top floor features Primary Bed/Bath with vaulted ceilings, Laundry, Full bath, 3 more bedrooms and a flex room. Outside you have fenced in backyard featuring a basketball court, under deck storage, patio and 50 amp connection for a hot tub. Seller will pay 1yr home warranty of buyers choice. This home move in ready!

Type:
Single Family
Sq.Ft.:
1,268
Status:
Active
Beds:
4
Lot size:
11.66 Acres
Year built:
1978
Baths:
3.00
MLS#:
24022254
Subdivision:
Rural

ADDITIONAL INFORMATION

This beautiful property has so much to offer. It has a beautiful 4 bedroom 3 bath home, a well established landscaping company, an office building, greenhouses, and much more. All equipment comes with the property. Just minutes from Interstate 64, Winchester Bypass, and Mount Sterling.

Type:
Single Family
Sq.Ft.:
2,520
Status:
Active
Beds:
4
Lot size:
0.44 Acres
Year built:
1962
Baths:
2.00
MLS#:
24022017
Subdivision:
Hampton Manor

ADDITIONAL INFORMATION

This stately, split-level brick home is situated in the beautiful and desirable Hampton Manor subdivision, right in the heart of Winchester. On the main level, gleaming hardwood floors extend throughout, including the newly renovated kitchen with new granite countertops, new cabinets, all new appliances, new faucet and a large island providing plenty of space to prepare family meals. Three bedrooms are located on the upper floor and a 4th bedroom is located in the basement along with another bonus room that would make a lovely office space or sitting room. The spacious family room includes a gas fireplace to keep the home cozy and warm on cold winter evenings. Take a step out the back door into a lovely, quiet outdoor living space. Take advantage of the covered back patio, a new HOT TUB that stays, plus nearly a half acre yard with mature trees and partial fencing. Take a visit soon!

Type:
Single Family
Sq.Ft.:
2,132
Status:
Active
Beds:
3
Lot size:
5 Acres
Year built:
1999
Baths:
3.00
MLS#:
24022030
Subdivision:
Rural

ADDITIONAL INFORMATION

Priced at appraisal value! Discover your retreat in this 3-bedroom, 2.5-bath home, perfectly situated for serene country living. The foyer opens into a spacious family room featuring a wood-burning fireplace. Just off the family room is a large, eat-in kitchen. Also on the main level is the primary en suite and a versatile flex room with endless possibilities. Upstairs, two generous sized bedrooms and a full bath await. The partially fenced property consists of 5 acres with 2 ponds! Selling AS-IS. Inspections welcome.

Type:
Single Family
Sq.Ft.:
1,161
Status:
Active
Beds:
3
Lot size:
0.18 Acres
Year built:
1980
Baths:
2.00
MLS#:
24021990
Subdivision:
Holiday Hills

ADDITIONAL INFORMATION

Charming Brick Ranch Home in Holiday HillsWelcome to this inviting 1161 sq ft brick ranch home, lovingly maintained by the same family since 1980. Nestled in the desirable Holiday Hills subdivision, this property offers comfort and convenience with easy access to Wiseman Park.Inside, you'll find a cozy spacious living area that features beautiful hardwood flooring. The updated kitchen boasts brand-new cabinets, stunning granite countertops, and modern appliances, making it perfect for family gatherings.This home offers three comfortable bedrooms with ample closet space, and the bathroom has been updated with contemporary fixtures. Durable LVT and tile flooring make maintenance easy, and the roof is approximately six years old.Step outside to a lovely backyard ideal for relaxation and play. Wiseman Park is just a short stroll away, offering tennis and pickleball courts, T-ball and cornhole areas, a playground with swings, a basketball court, and a 6-hole disc golf course. Enjoy the covered shelter with picnic tables and a grill for gatherings.This charming home combines modern updates with classic appeal.

Type:
Land
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
11.47 Acres
Baths:
MLS#:
24021879
Subdivision:
Rural

ADDITIONAL INFORMATION

Discover the perfect blend of natural beauty and modern convenience with this 11.47-acre parcel, tucked away at the end of a peaceful lane. Offering approximately 3 acres of cleared land, this property is ideal for building your dream home or creating a tranquil weekend getaway. The remaining wooded borders provide privacy, while a meandering creek adds a touch of serenity to the landscape. With electricity, water, and a septic tank already in place (per Seller), this land is ready for you to bring your vision to life. Whether you're dreaming of a mini-farm or a quiet retreat, this versatile property has endless potential. Don't miss this unique opportunity to own your slice of country paradise!

Type:
General Commercial
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
1.23 Acres
Year built:
1983
Baths:
MLS#:
24021753
Subdivision:
Rural

ADDITIONAL INFORMATION

This freestanding building with approximately 375 feet of frontage overlooking the Kentucky River offers plenty of parking and convenient access to both Clark and Madison Counties. This restaurant has been completely remodeled with a large event room with overhead doors that open up to a spacious deck, perfect for hosting private events or a live music venue. Can seat up to 160 people inside and 60 outside

Type:
Single Family
Sq.Ft.:
1,380
Status:
Active
Beds:
4
Lot size:
0.17 Acres
Baths:
2.00
MLS#:
24021746
Subdivision:
North Park

ADDITIONAL INFORMATION

Don't miss out on these 2 great income producing properties that are situated on the same lot near downtown Winchester! Both of the houses are 2 bedroom 1 bath occupied rentals with great cashflow! 112 Sycamore is currently rented for 950.00 with tenants paying all utilities. 110 Grant Alley which is located directly behind 112 Sycamore, is rented for 925.00 per month. Property being sold as-isOwner/Agent

Type:
Townhouse
Sq.Ft.:
1,450
Status:
Active
Beds:
3
Year built:
1994
Baths:
2.00
MLS#:
24021528
Subdivision:
Holiday Villa

ADDITIONAL INFORMATION

Beautifully renovated townhome in a prime Winchester location! Enjoy first-floor living with an additional bedroom and full bath in the basement. Convenient location to the bypass and downtown. Beautiful backyard, perfect for entertaining or pets.Selling AS IS. Inspections welcome.

Type:
Single Family
Sq.Ft.:
1,920
Status:
Active
Beds:
3
Lot size:
0.11 Acres
Year built:
2024
Baths:
3.00
MLS#:
24021508
Subdivision:
Fairholme Estates

ADDITIONAL INFORMATION

This beautiful home located in desirable Fairholme Estates is a must see!! Amazing open floor plan with kitchen granite countertops, a large island and upgraded Frigidaire Elite Stainless Appliances. The waterproof Pergo laminate flooring is throughout the home. Don't miss the primary bedrooms with walk in closet, double sinks and tile shower in the bathroom. The two car garage is located on the same level with plenty of on and off street parking.

Type:
Land
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
11.3 Acres
Baths:
MLS#:
24021256
Subdivision:
Rural

ADDITIONAL INFORMATION

Type:
Single Family
Sq.Ft.:
1,309
Status:
Active
Beds:
3
Lot size:
0.07 Acres
Year built:
1935
Baths:
1.00
MLS#:
24020925
Subdivision:
Downtown

ADDITIONAL INFORMATION

**Motivated Seller** Charming fully renovated ranch home just outside of downtown Winchester. Spacious open floor plan with tall ceilings. All new stainless appliances & beautiful granite countertops in kitchen. Covered front & back porches. Fenced in backyard and large workshop with roll up door. Take the time to check this one out.

Type:
Single Family
Sq.Ft.:
4,644
Status:
Active
Beds:
4
Lot size:
0.59 Acres
Year built:
1998
Baths:
4.00
MLS#:
24020882
Subdivision:
Hampton Manor

ADDITIONAL INFORMATION

Don't miss this rare opportunity to abide in one of Winchester's finest locations, Camelot Drive. A hidden gem tucked away in the back of Hampton Manor, this home boasts space and privacy on an idyllic cul-de-sac just off Boone Avenue. Details such as crown molding, built-in cabinetry, high ceilings, 2 fireplaces, transom windows, and hardwood floors fill this home with character and charm. Entertain or relax while enjoying the spacious, tree-lined yard from the screened porch, deck, or patio. This home has been beautifully updated and is conveniently located just a short golf cart ride from the Winchester Country Club, and just 15 minutes from Lexington or Richmond. A screened porch has been added to the home for entertaining or just relaxation (almost 400 sq ft). Beautiful kitchen--cherry cabinets--almost 9' long island where your family can enjoy meals together--refrigerator--Bosch dishwasher--cook top & new smart double ovens. Living room, dining room, office, & laundry room round out the first floor. Also a 3-car garage w/epoxy floor. In the basement there is a huge family room w/fireplace (gas logs), a bedroom, full bath, a pantry, an exercise room, and lots of storage.

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51–75 of 191 properties displayed
Andrea Conner, License 221773, Xome Inc., License 239054, [email protected], 844-400-XOME (9663), 1795 Alysheba Way Suite 1202 Lexington, KY 40509


The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Lexington Bluegrass Multiple Listing Service. The Broker providing this data believes them to be correct but advises interested parties to confirm them before relying on them in a purchase decision. Copyright 2025 Lexington Bluegrass Multiple Listing Service. All rights reserved.



Winchester Real Estate

The median home value in Winchester, KY is $238,250. This is higher than the county median home value of $206,000. The national median home value is $338,100. The average price of homes sold in Winchester, KY is $238,250. Approximately 52.42% of Winchester homes are owned, compared to 38.21% rented, while 9.38% are vacant. Winchester real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Winchester real estate agent to arrange a tour today!

Winchester, Kentucky has a population of 18,993. Winchester is less family-centric than the surrounding county with 25.63% of the households containing married families with children. The county average for households married with children is 25.74%.

The median household income in Winchester, Kentucky is $47,034. The median household income for the surrounding county is $59,294 compared to the national median of $69,021. The median age of people living in Winchester is 36.9 years.

Winchester Weather

The average high temperature in July is 85.8 degrees, with an average low temperature in January of 22 degrees. The average rainfall is approximately 45.8 inches per year, with 9.4 inches of snow per year.

Winchester Real Estate Market Conditions

  • Median sales price

    $238,250
    19.3% change since last quarter
  • # Active listings

    191
    30-day change

Winchester Schools and Demographics

Education near Winchester, KY

Metric City County
High School Graduates 86.63 89.23
College Degree - 2 year 8.6 9.97
College Degree - 4 year 19.04 20.05
Graduate Degree 4.07 5.81
Expenditures per Student 14,536 14,536
Students per Teacher 13.6 13.6

Elementary Schools near Winchester, KY

School Grades Students P/T Ratio ZIP
Athens-Chilesburg Elementary School KG - 05 745 14.9 40509
Camargo Elementary School PK - 04 612 13.2 40353
Clark County Preschool PK - PK 296 24.7 40391
Clay City Elementary School PK - 05 535 16.7 40312
Mapleton Elementary School KG - 04 674 14.7 40353
Montgomery County Early Learning Center PK - PK 109 18.2 40353
Mount Sterling Elementary School KG - 04 635 15.1 40353
North Middletown Elementary School KG - 05 155 14.8 40357
Shearer Elementary School KG - 04 423 12 40391
Strode Station Elementary School KG - 04 613 12.4 40391
William G. Conkwright Elementary KG - 04 563 20 40391
Willis H. Justice Elementary School KG - 04 491 16.2 40391

Middle Schools near Winchester, KY

School Grades Students P/T Ratio ZIP
Edythe Jones Hayes Middle School 06 - 08 1,095 15.6 40509
McNabb Middle School 07 - 08 718 16.2 40353
Mercer County 9th Grade Academy 09 - 09 224 16.2 40391
Montgomery County Intermediate School 05 - 06 712 15.6 40353
Rev. Henry E. Baker SR. Interm. School 05 - 06 858 19.5 40391
Robert D. Campbell Jr. High 07 - 08 801 18.2 40391
Willis H. Justice Elementary School KG - 05 0 13.7 40391

High Schools near Winchester, KY

School Grades Students P/T Ratio ZIP
George Rogers Clark High School 09 - 12 1,672 18.2 40391
Montgomery County High School 09 - 12 1,338 18.4 40353

Ungraded Schools near Winchester, KY

School Grades Students P/T Ratio ZIP
* Gateway Children's Services 07 - 12 18 9 40353
* Hillcrest Hall Treatment Center 09 - 12 12 12 40353
* Phoenix Academy 07 - 12 22 4.4 40391
* The Sterling School 09 - 12 51 11.3 40353
Clark County Area Technology Center UG - UG 0 40392
Hayes Pre-School UG - UG 93 30.5 40509
Montgomery County Accelerated Academy UG - UG 0 40353
Montgomery County Area Technology Center UG - UG 0 40353

Demographics near Winchester, KY

Metric City County
Neighborhood Type Suburban
Population 18,993 36,716
Population Density 2,078 145
Median Age 36.9 41.5
People per Household 2.3 2.5
Median Household Income 47,034 59,294
Average Income per Capita 28,337 33,205