Winchester, KY Homes for Sale under $300,000

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  /27

  $149,900

  $3K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft

  65 Fitch Ave, Winchester, KY 40391

  Lovely older home, located witin waking distance to collage park whice offers Pickle Ball, Pool, Tennis, play gound and Walking Trail, also walking distance to Historic Downtown Winchester, with a little love house brings large rooms and a nostlogic atmosphire, take a look, view today, this a a great price for 3 bedrooms, 1 1/2 baths, nice back yard, with parking, call today! Selling "AS IS",

  Mila Ensor Ensor Real Estate, LLC

  65 Fitch Ave, Winchester, KY 40391
• 

  

  

  /40

  $244,000

  • 3 Beds
  • 2 Baths
  • 1,692 Sq Ft

  54 Locust Dr, Winchester, KY 40391

  SHORT SALE OPPORTUNITY! 54 Locust Dr. is an all-brick ranch in Westland Park offering 3 bedrooms, 2 baths and 1,692 sq. ft. of finished living space, plus a full unfinished basement. The home features hardwood flooring, a 2-car attached garage, fenced backyard and covered patio. Previous owners completed structural work in the basement that includes a transferable lifetime warranty. The home

  Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  54 Locust Dr, Winchester, KY 40391
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  /5

  $29,000

  $4K PRICE DROP

  • Land
  • 20,037 Sq Ft
  • $63,043 per Acre

  102 Augusta Dr, Winchester, KY 40391

  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.

  Dale Hatton Dream Maker Realty, LLC

  102 Augusta Dr, Winchester, KY 40391
• 

  

  /2

  $110,000

  • Land
  • 13,939 Sq Ft
  • $343,750 per Acre

  135 Jacob Ct, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  135 Jacob Ct, Winchester, KY 40391
• 

  

  /2

  $110,000

  • Land
  • 13,939 Sq Ft
  • $343,750 per Acre

  115 Jacob Ct, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  115 Jacob Ct, Winchester, KY 40391
• 

  

  /23

  $194,900

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  143 Spruce Ct, Winchester, KY 40391

  Welcome to 143 Spruce Court in Winchester! This charming brick ranch offers comfortable one-level living with 3 bedrooms and 1 full bath. Inside, you'll find beautiful hardwood flooring and a warm, inviting layout. Outside, enjoy a well-manicured yard with plenty of space to relax or entertain. Conveniently located near a local park featuring a splash park and recreational amenities, this home

  John Wilson Bluegrass Properties Group

  143 Spruce Ct, Winchester, KY 40391
• 

  

  /23

  $204,900

  • 3 Beds
  • 1 Bath
  • 1,128 Sq Ft

  38 Mackay Ave, Winchester, KY 40391

  Beautiful 3-bedroom, 1-bath home located at the end of a quiet, well established neighborhood within walking distance to downtown Winchester. This home features hardwood floors, a versatile in home office or bonus room, and several recent upgrades including a new stove, microwave, refrigerator, cabinets, and HVAC (1 year old). The property offers a backyard with a storage shed, providing

  Nena Honaker Tom Goebel & Company

  38 Mackay Ave, Winchester, KY 40391
• 

  

  /22

  $234,500

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,130 Sq Ft

  527 Hidden Hills Way, Winchester, KY 40391

  NEW roof, NEW kitchen appliances, NEW deck, and more! Welcome to 527 Hidden Hills Way! Located on a quiet cul-de-sac, this renovated one level home is ready for you to move right in. Vaulted ceilings give an open and airy feel, while fresh paint throughout offers a neutral palette for any design style. The spacious kitchen includes plenty of oak cabinetry, a separate pantry, stainless steel

  Jarran Thomas The Agency

  527 Hidden Hills Way, Winchester, KY 40391
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  /2

  $110,000

  • Land
  • 21,780 Sq Ft
  • $220,000 per Acre

  260 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  260 Duclair Dr, Winchester, KY 40391
• 

  

  /7

  $150,000

  $30K PRICE DROP

  • Land
  • 4.21 Acres
  • $35,629 per Acre

  1030 Craig Crossing Rd, Winchester, KY 40391

  Lot # 14 contains 4.21 acres of gently rolling land with small stream perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  1030 Craig Crossing Rd, Winchester, KY 40391
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  /27

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,108 Sq Ft

  227 Leslie Dr, Winchester, KY 40391

  This 3 Bedroom, 2 bath home is quietly nestled within the Saddle Brook subdivision. Conveniently located just outside of Winchester New Bypass, this property also qualifies for zero down rural housing financing. Updates can be seen throughout along with spacious master bedroom with on-suite, large back yard and open concept living. Schedule your showing today!

  Michael Hilario The Agency

  227 Leslie Dr, Winchester, KY 40391
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  /2

  $150,000

  • Land
  • 2.77 Acres
  • $54,074 per Acre

  3385 Colby Rd, Winchester, KY 40391

  Parcel 4 in the photos. This 2.774 acre lot is available on Colby Road just 1.5 miles from the Winchester Bypass. No building restrictions other than no manufactured housing and a paved driveway must be completed within a year of finishing a residence.

  Steve Adams Steven D Adams Real Estate Services, LLC

  3385 Colby Rd, Winchester, KY 40391
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  /2

  $100,000

  • Land
  • 29,620 Sq Ft
  • $147,059 per Acre

  100 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  100 Duclair Dr, Winchester, KY 40391
• 

  

  /23

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,319 Sq Ft

  3 Nunnelly Ct, Winchester, KY 40391

  Welcome to 3 Nunnelly Ct, Winchester, KY This charming 3-bedroom, 2-bathroom home offers comfortable living with several important updates already in place. Featuring a newer HVAC system and newer roof, this home provides peace of mind for its next owner while offering plenty of opportunity to make the space your own. Inside, you'll find a bright, inviting layout with fresh, neutral finishes,

  Yasir Ahmed Black Mountain Realty

  3 Nunnelly Ct, Winchester, KY 40391
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  /37

  $259,000

  $37K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft

  33 Bon-Haven Ave, Winchester, KY 40391

  Welcome home to this beautifully renovated home in the desirable Bon Haven subdivision! From the moment you step inside, you'll appreciate the bright and inviting living room that flows seamlessly into the updated kitchen, creating a warm and functional space for everyday living. The main level features two spacious bedrooms and two full bathrooms, while the second floor offers a private third

  Erika Beatty Plum Tree Realty

  33 Bon-Haven Ave, Winchester, KY 40391
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  /36

  $125,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  16 Denny Ave, Winchester, KY 40391

  Well priced and well located, 16 Denny Avenue is conveniently located near Eugene Gay Splash Park, downtown Winchester, shopping and schools. Home features 1152 sq ft with 3 bedrooms, 1 full bath, eat in kitchen and living room. Enclosed porch is located on front of house. Upgrades include laminate flooring, ductless heating and cooling and roof. Property has been tenant occupied and is sold as

  ROBIN TRIMBLE HomeFirst Real Estate

  16 Denny Ave, Winchester, KY 40391
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  /2

  $110,000

  $10K PRICE INCREASE

  • Land
  • 12,632 Sq Ft
  • $379,310 per Acre

  160 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  160 Duclair Dr, Winchester, KY 40391
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  /27

  $289,900

  • 4 Beds
  • 2 Baths
  • 1,752 Sq Ft

  198 Hilltop Dr, Winchester, KY 40391

  Excellent location! 4 bedroom, 2 bath. This home offers one level living on the edge of town and close to the interstate! AMAZING VIEWS of country side! Two living room spaces! Split bedroom design. Covered back patio. NEW LVP flooring. NEW electric service panel and meter base. Freshly painted throughout. NEW appliances. Fully fenced backyard. This home is move in ready. Come see today!

  Stephanie Hacker Kentucky Residential Real Estate, LLC

  198 Hilltop Dr, Winchester, KY 40391
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  /24

  $225,000

  • Land
  • 24 Acres
  • $9,375 per Acre

  3934 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Wonderful 24 acre retreat with gentle sloping land, and a creek bed running thru part of the front portion of the lots (6.1 acre parcel & 18.4 acre parcel at the rear). Build your dream home or just use as recreational or farm land until you do. 1 1/2 miles to the first exit on the Mountain Parkway exit #10. 12 miles to I-64 at Winchester. See attached pictures & plat/overhead pictures.

  Travis Emnett Top Ten Realty

  3934 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /46

  $174,900

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  148 Hidden Grove Ln, Winchester, KY 40391

  Unique Kentucky Riverfront retreat with fascinating history! This elevated 2-bedroom, 1.5 bath home was originally constructed from two wood rail cars, giving it a one-of-a kind character you won't find anywhere else. Thoughtfully updated with new windows, roof, HVAC and an updated shower, plus a spacious new deck perfect for relaxing and enjoying the beautiful river setting. Whether you are

  Kathryn Cheuvront Coldwell Banker McMahan

  148 Hidden Grove Ln, Winchester, KY 40391
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  /38

  $275,000

  • 2 Beds
  • 1 Bath
  • 1,231 Sq Ft

  682 Athens Boonesboro Rd, Winchester, KY 40391

  Discover the timeless charm of this storybook river house, perfectly nestled on a private 2 acres with river views and access.Completely renovated, new stove, full of character and warmth, this unique 2 bedroom, one bath retreat offers a peaceful escape with an incredible connection to the water and quiet nature. Inside the charming shiplap walls and two fireplaces create a cozy, inviting

  Robin Owens Kirkpatrick & Company

  682 Athens Boonesboro Rd, Winchester, KY 40391
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  /4

  $42,500

  • Land
  • 8,276 Sq Ft
  • $223,684 per Acre

  113 Mayfair Ct, Winchester, KY 40391

  Wowser! Looking for a lot that backs up to greenspace and will NOT have another home on one side? Here it IS! This may be just what you're looking for. Originally, the street was supposed to connect, but due to the changes in grade, this won't be happening! Plus, with the way the lot sits, you can enjoy many beautiful sunsets. It's a hidden gem just waiting for you to find it! The home to be

  Jo Gawthrop Keller Williams Bluegrass Realty

  113 Mayfair Ct, Winchester, KY 40391
• 

  

  /31

  $300,000

  • 4 Beds
  • 2 Baths
  • 2,479 Sq Ft

  224 W Hickman St, Winchester, KY 40391

  Classic character and generous living space come together at 224 W Hickman Street in Winchester. This single-family residence offers 4 bedrooms, 2 full bathrooms, and approximately 2,479 square feet, providing a flexible layout with room for a variety of everyday living needs. The home's substantial interior footprint creates opportunities for comfortable gathering spaces, private bedrooms, a

  Bob Sophiea eXp Realty, LLC

  224 W Hickman St, Winchester, KY 40391
• 

  /2

  $110,000

  $10K PRICE INCREASE

  • Land
  • 16,552 Sq Ft
  • $289,474 per Acre

  120 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  120 Duclair Dr, Winchester, KY 40391
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  /49

  $165,000

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,202 Sq Ft

  1494 Amster Grove Rd, Winchester, KY 40391

  Welcome to this charming river front house. Step out your back door and you are immediately at the river. Open floor plan with a wood burning fireplace. Metal cabinets and epoxy floors on the first level are designed to survive in case of a flood. First floor bedroom with enough room for a King sized bed. Upstairs you will find another bedroom and a half bath. Sip your morning coffee on your back

  Libby VanMeter Marshall Lane Real Estate - Lexington

  1494 Amster Grove Rd, Winchester, KY 40391
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  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $312,500 per Acre

  141 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  141 Duclair Dr, Winchester, KY 40391
• 

  

  /6

  $299,000

  $151K PRICE DROP

  550 E Broadway St, Winchester, KY 40391

  Prime land located on the outskirts of Winchester ready for possible development. Parcel has frontage on both East Broadway and Washington Street. Land is currently zoned A-1. Utilities available. The future awaits!!!

  Keith Wilson Coldwell Banker McMahan

  550 E Broadway St, Winchester, KY 40391
• 

  

  /30

  $249,900

  • 3 Beds
  • 2.5 Baths
  • 1,416 Sq Ft

  330 Vanover Way, Winchester, KY 40391

  Bring your vision and make this home your own! Situated on a huge corner lot on the outskirts of Winchester, this three-bedroom, two-and-a-half-bath home offers plenty of space and potential. Features include a two-car garage and a convenient location just minutes from the Bypass and I-64. The interior needs some TLC, including new flooring and/or carpet, making this a great opportunity to update

  Darrell Tackett Dream Maker Realty, LLC

  330 Vanover Way, Winchester, KY 40391
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  /58

  $74,950

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  1860 Ford Rd, Winchester, KY 40391

  Freshly cleaned and ready for its next owner, this property offers exceptional potential. The spacious 1,800 sq. ft. block garage provides a solid foundation for countless uses — from a workshop or storage facility to a future business or hobby space. An older trailer is also located on the property. It will require a full renovation or removal, giving you the freedom to redesign the space

  Darrell Tackett Dream Maker Realty, LLC

  1860 Ford Rd, Winchester, KY 40391
• 

  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $312,500 per Acre

  129 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  129 Duclair Dr, Winchester, KY 40391
• 

  

  /19

  $205,400

  • 2 Beds
  • 1 Bath
  • 1,154 Sq Ft

  606 College St, Winchester, KY 40391

  606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom

  Jennifer Woods Marshall Lane Real Estate

  606 College St, Winchester, KY 40391
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  /5

  $70,000

  • Land
  • 1.72 Acres
  • $40,698 per Acre

  12541 Ironworks Rd, Winchester, KY 40391

  Discover the perfect place to build your dream home in Eskippakithiki Overlooks. This beautiful 1.72 acre parcel offers ample space, peaceful surroundings, and stunning natural views. Enjoy the serenity of country living, this land provides an ideal canvas for a custom home or family getaway. Don't miss this opportunity to secure your own piece of paradise.

  Daniela Virguez National Real Estate

  12541 Ironworks Rd, Winchester, KY 40391
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  /29

  $279,999

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  103 Southern Ct, Winchester, KY 40391

  Simply the Best! 3 Bedroom, 1 1/2 bath All Brick ranch home located within walking distance to historic downtown Winchester, Country Club, Middle School, great place to live, you will spend most of your time on the Sunporch off the Kitchen, large lot, many updates, floor, bathrooms, new furnace, fresh paint, don't miss looking at this jewel, call today

  Mila Ensor Ensor Real Estate, LLC

  103 Southern Ct, Winchester, KY 40391
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  /28

  $239,900

  • 3 Beds
  • 2 Baths
  • 1,665 Sq Ft

  106 Quail Ridge Rd, Winchester, KY 40391

  This is great space for the price, walk into a great room with firepalce, hardwood floors, dining area leads to enclosed sunporch, master suite with full bath on first floor, nice kitchen , large back yard, 2 bedrooms up with fill bath, semi finished basement, 1 car garage, don't miss out on this townhome in a great location

  Mila Ensor Ensor Real Estate, LLC

  106 Quail Ridge Rd, Winchester, KY 40391
• 

  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $312,500 per Acre

  165 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  165 Duclair Dr, Winchester, KY 40391
• 

  

  /24

  $280,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,260 Sq Ft

  209 Boone Ave, Winchester, KY 40391

  Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story home located in the heart of Winchester! Recently updated and full of character, this property offers a flexible layout with room for everyone. The main level offers a welcoming living room, large family room, dining area, kitchen, laundry room, full guest bath, and a spacious primary suite complete with a

  Todd Hyatt Lois Ann Disponett Real Est

  209 Boone Ave, Winchester, KY 40391
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  /42

  $134,900

  $14K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft

  404 Mount Vernon Dr, Winchester, KY 40391

  Ready to Stop Renting? Your Opportunity Is Here Step into the comfort and freedom of homeownership with this spacious, well maintained 2-bedroom, 2-bath modular home — and yes, the lot is included. An attached room addition provides even more flexibility, easily adaptable into a third bedroom, home office, hobby room, or bonus space to suit your lifestyle. --- Interior Highlights • 2 full

  Darrell Tackett Dream Maker Realty, LLC

  404 Mount Vernon Dr, Winchester, KY 40391
• 

  /2

  $110,000

  • Land
  • 25,700 Sq Ft
  • $186,441 per Acre

  255 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  255 Duclair Dr, Winchester, KY 40391

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