Newest Homes for Sale in Winchester, KY

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  /50

  $639,000

  • 5 Beds
  • 3.5 Baths
  • 5,011 Sq Ft

  104 Teal Ln, Winchester, KY 40391

  Space, craftsmanship, and versatility come together in this stunning all-brick 1.5-story home with a finished basement, located in the desirable Mallard Place subdivision! Designed to maximize every square foot, this home offers three levels of comfortable and flexible living space. The main level welcomes you with beautiful hardwood floors, vaulted ceilings, and a cozy gas fireplace. The

  Jennifer Ray RE/MAX Elite Lexington

  104 Teal Ln, Winchester, KY 40391
• Explore Winchester

• 

  

  

  /63

  $785,000

  • 5 Beds
  • 2.5 Baths
  • 4,676 Sq Ft

  217 Wades Mill Rd, Winchester, KY 40391

  Escape to the peace and privacy of country living with this spacious brick one-and-a-half story home situated on just over 5 acres. With plenty of room to spread out, the main level offers a welcoming foyer, formal dining room, living room with a wood-burning fireplace, kitchen featuring granite countertops, tile backsplash, breakfast nook, and laundry room, along with the primary suite, three

  Michelle Blackburn RE/MAX Creative, Winchester

  217 Wades Mill Rd, Winchester, KY 40391
• 

  

  

  /21

  $135,000

  • 2 Beds
  • 1 Bath
  • 807 Sq Ft

  3208 Ford Hampton Rd, Winchester, KY 40391

  Set on a half-acre in a rural Winchester setting, this 2-bedroom, 1-bath home offers an efficient one-level layout with approximately 807 square feet of living space. The eat-in kitchen provides a comfortable spot for everyday meals, while main-level laundry hookups add convenience. Front and rear porches extend the living space outdoors and offer places to enjoy the surrounding trees,

  Bob Sophiea eXp Realty, LLC

  3208 Ford Hampton Rd, Winchester, KY 40391
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  /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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  /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
• 

  

  /26

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  528 Estes Dr, Winchester, KY 40391

  *NEW ROOF!* Welcome home to this well-maintained 3-bedroom, 2-bath brick ranch offering easy one-level living in a convenient location close to shopping, dining, parks, and the community pool. The spacious open family room flows into the kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range—perfect for everyday living and entertaining.

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
• 

  

  /46

  $1,400,000

  New Construction

  • 4 Beds
  • 4 Baths
  • 5,613 Sq Ft

  1400 Craig Crossing, Winchester, KY 40391

  Magnificent Home sitting on 2.446 Acres, Fantastic Location --Great Views on this 4 Bedroom, 4 Bath Brick Home with over 5,600 Sq. Ft. of Living space. This has a Huge Primary Bedroom with walk in Shower, 2 closets, Large Formal Dining Rm,--Stone Fireplace, Large Sun room with lots of Windows, Another Primary Bedroom upstairs w/Full Bath, Large Finished Basement, with Mother's in Law Quarters.

  Ken Ritter Coldwell Banker McMahan

  1400 Craig Crossing, 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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  /12

  $258,000

  $2K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,996 Sq Ft

  59 Hillcrest Dr, Winchester, KY 40391

  PRICED TO SELL | BRING AN OFFER! Highly Motivated Seller! 59 Hillcrest Dr, Winchester, KY 40391 3 Beds | 2 Baths | ~2,066 Total Sq Ft | Full Basement | Large Lot Attention buyers, DIYers, and investors: Don't miss this incredible value! The seller is highly motivated and ready to entertain offers, making this attractive ranch home priced to sell immediately with the oppurtunity to unlock instant

  Dylan Langdon The Agency

  59 Hillcrest Dr, Winchester, KY 40391
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  /3

  $42,500

  • Land
  • 8,712 Sq Ft
  • $212,500 per Acre

  108 Dorset Ln, Winchester, KY 40391

  The restictions state that if it is a ranch plan, there is a minimun of 1300 sq ft. It it is a 1 1/2 story or two story then 1800 sq ft will be required. A two car garage must be attached. Developer will need to approve plans before starting construction This lot is ideal for a walkout basement. Perfect setting for watching the sunsets

  Jo Gawthrop Keller Williams Bluegrass Realty

  108 Dorset Ln, Winchester, KY 40391
• 

  

  /25

  $235,500

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  125 Kittison Dr, Winchester, KY 40391

  Charming ranch home featuring 3 bedrooms, 1 full bath with a spacious layout and inviting curb appeal. Enjoy relaxing or entertaining on the covered back patio overlooking the large backyard with plenty of room for pets, play, or gardening. The kitchen offers beautiful granite countertops, ample cabinet space, and all appliances stay for added convenience. A wonderful opportunity for comfortable

  Kathryn Cheuvront Coldwell Banker McMahan

  125 Kittison Dr, Winchester, KY 40391
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  /65

  $359,900

  • 3 Beds
  • 2 Baths
  • 2,269 Sq Ft

  15 Moundale Ave, Winchester, KY 40391

  Welcome to this beautifully maintained all-brick home nestled in one of Winchester's most established and desirable neighborhoods. Offering over 2,200 square feet of finished living space, this 3-bedroom, 2-bath home combines timeless character with an impressive list of thoughtful updates. The main level features a spacious family room with ventless gas logs, a beautifully updated kitchen with

  Josh Wood Freedom Realty & Property Management

  15 Moundale Ave, 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
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  /2

  $42,500

  • Land
  • 11,369 Sq Ft
  • $162,835 per Acre

  105 Bella Ct, Winchester, KY 40391

  Jo Gawthrop Keller Williams Bluegrass Realty

  105 Bella Ct, Winchester, KY 40391
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  /36

  $460,000

  • 3 Beds
  • 2 Baths
  • 2,062 Sq Ft

  2195 Pretty Run Rd, Winchester, KY 40391

  Welcome to country living at its finest! This beautifully renovated three-bedroom, two-full-bath ranch home is situated on just over two acres in one of Clark County's most picturesque settings. Offering an exceptional blend of space, comfort, and functionality, this property is sure to impress from the moment you arrive—with a front porch view you'll truly appreciate. The main level features a

  Brittany Lewis National Real Estate

  2195 Pretty Run 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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  /47

  $484,900

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,381 Sq Ft

  410 Fairholme Way, Winchester, KY 40391

  Modern luxury meets everyday living in this beautiful new construction ranch home in Winchester's Fairholme Estates- where thoughtful details, timeless finishes, and incredible golf course view sunsets come together effortlessly. Inside, an inviting open-concept layout features vaulted ceilings and a fireplace anchoring the spacious living room. The timeless kitchen is designed to be both

  Morgan Withrow The Brokerage

  410 Fairholme Way, Winchester, KY 40391
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  /15

  $450,000

  • Land
  • 9,583 Sq Ft
  • $2,045,455 per Acre

  1320 Fulton Rd, Winchester, KY 40391

  Prime commercial opportunity in an ideally located area of Winchester! This versatile commercial building offers an excellent location for an established business, growing company, or investor seeking a property with strong potential. Conveniently situated with easy access to major roadways and surrounding communities, the property provides excellent visibility and accessibility for customers and

  Holly Spradlin KY Realty Co

  1320 Fulton Rd, 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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  /7

  $365,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  204 Jett Dr, Winchester, KY 40391

  New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

  Mila Ensor Ensor Real Estate, LLC

  204 Jett Dr, Winchester, KY 40391
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  /24

  $365,900

  New Construction $100K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  206 Jett Dr, Winchester, KY 40391

  New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

  Mila Ensor Ensor Real Estate, LLC

  206 Jett Dr, Winchester, KY 40391
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  /74

  $489,000

  • 4 Beds
  • 3.5 Baths
  • 3,584 Sq Ft

  1137 Lafayette Blvd, Winchester, KY 40391

  Welcome home to this 4 bedroom, 3.5 bathroom home offering plenty of room to spread out. The open kitchen and living room create a comfortable gathering space, while a separate dining room provides additional space for meals and entertaining. The fully finished basement offers even more living space, including a room with a closet that could provide flexibility for a home office, hobby room or

  Brittany Nester RO&CO Real Estate

  1137 Lafayette Blvd, Winchester, KY 40391
• 

  

  /27

  $279,500

  • 3 Beds
  • 2.5 Baths
  • 1,963 Sq Ft

  304 Newcastle Ln, Winchester, KY 40391

  This house is located within walking distance of Clark County Preschool, Strode Station and Baker and is within minutes of Winchester Bypass and I-64. The house has 3 bedrooms and 2.5 baths and a bonus room on the 2nd floor that would make a great game room or office. The bonus room would also make a nice 4th bedroom. The owner of the house has replaced all of the kitchen appliances and replaced

  Craig Bridgewater Bridgewater Real Estate

  304 Newcastle Ln, Winchester, KY 40391
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  /32

  $175,000

  • 3 Beds
  • 1 Bath
  • 1,173 Sq Ft

  24 Spring St, Winchester, KY 40391

  Lovely one story home located minutes from downtown Winchester with large detached garage ans shed! This home as three bedrooms and one bath with covered porch and walled patio outside. The garage is equipped with large ares for parking and storage and also has its own kitchen. Don't let this one pass by. Come see TODAY!!! Note: This is an auction property. Please call agent for more info Buyer

  Jason Szaks EXIT Town & Country Realtors

  24 Spring St, Winchester, KY 40391
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  /54

  $254,900

  • 3 Beds
  • 2.5 Baths
  • 1,664 Sq Ft

  127 Bay Hill Dr, Winchester, KY 40391

  Welcome home to this spacious, low-maintenance townhome offering 3 levels of living space in a well established neighborhood. Thoughtfully maintained, a 3 year old roof, with recently replaced windows. This home offers plenty of room to spread out while keeping everyday living comfortable and convenient. The main level features a generously sized kitchen and family room with plenty of space for

  Josh Wood Freedom Realty & Property Management

  127 Bay Hill Dr, 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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  /34

  $219,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,297 Sq Ft

  13 Long Ave, Winchester, KY 40391

  Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviting covered front porch, perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living room and dining room featuring beautiful hardwood floors that add warmth and character. The generous yard offers plenty of space for outdoor entertaining, gardening, play or future possibilities.

  Kathryn Cheuvront Coldwell Banker McMahan

  13 Long Ave, 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
• 

  

  /20

  $345,900

  New Construction

  • 3 Beds
  • 4.5 Baths
  • 1,559 Sq Ft

  Julia Plan at Boone's Crossing, Winchester, KY 40391

  Discover the Julia floor plan, a thoughtfully designed new construction home that blends elegant open-concept living with private, comfortable bedroom spaces. Built by one of the most trusted home builders in Central Kentucky, the Julia is a standout choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want modern style, everyday functionality,

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 41774552, Winchester, KY 40391
• 

  

  /9

  $381,900

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,218 Sq Ft

  Mary Plan at Boone's Crossing, Winchester, KY 40391

  Discover the Mary floor plan, a thoughtfully designed new construction home that perfectly balances open-concept gathering spaces with private, restful retreats. Built by one of the most trusted home builders in Central Kentucky, the Mary is an ideal fit for buyers searching for new construction homes in Lexington KY and surrounding communities who desire flexibility, modern style, and

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 41774533, Winchester, KY 40391
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  /27

  $265,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  15 Kittison Dr, Winchester, KY 40391

  Welcome home to 15 Kittison Drive! Perfectly blending classic 1960s character with modern convenience, this Winchester residence offers comfort, space, and an unbeatable location just one mile from I-64. Inside, you'll find three spacious bedrooms and two full bathrooms designed for effortless daily living. The versatile, light-filled layout includes a large living room, a functional kitchen, and

  Cheri Shaffer Lifstyl Real Estate

  15 Kittison Dr, Winchester, KY 40391
• 

  

  /30

  $140,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 630 Sq Ft

  108 Franklin Ave, Winchester, KY 40391

  Property includes a detached secondary structure, a 600 sq. ft., 1-bedroom, 1-bath. This structure offers potential for investment use. Property and secondary structure are being sold as-is. Buyer and buyer's agent to independently verify square footage, zoning, permitted use, occupancy requirements, and suitability for buyer's intended purpose.

  Cheri Shaffer Lifstyl Real Estate

  108 Franklin Ave, Winchester, KY 40391
• 

  

  /12

  $137,500

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  48 Judy Ann Ct, Winchester, KY 40391

  Affordable and inviting townhome conveniently located in Winchester! This well-maintained home offers a functional layout with a spacious kitchen featuring plenty of room for everyday cooking and dining. The main level includes a comfortable living room, convenient half bath, and access to a private patio, perfect for relaxing or enjoying your morning coffee. A dedicated storage area provides

  Holly Spradlin KY Realty Co

  48 Judy Ann Ct, Winchester, KY 40391
• 

  

  /110

  $724,889

  • 4 Beds
  • 4.5 Baths
  • 4,255 Sq Ft

  132 Lana Ln, Winchester, KY 40391

  This gorgeous home is a rare find. Perfect for anyone looking for a spacious home with room to grow. The beautiful sunroom overlooks the luxurious in-ground salt water pool. Inside the home you'll find over 4,000 square feet of easy living. A beautiful kitchen with a breakfast nook and bar top, a formal dining area, large living room, a family room with a fireplace, spacious bedrooms, and a

  Rebecca Harvey Napier Realtors

  132 Lana Ln, Winchester, KY 40391
• 

  

  /19

  $295,000

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft

  405 Nick Ln, Winchester, KY 40391

  Come see this beautiful 13-acre property in the Historic Boonesborough area of Clark County, offering peaceful country living with the convenience of being just minutes from Winchester, Richmond, and Lexington. The property features a 2-bedroom, 1-bath home with 1,344 sq. ft., surrounded by beautiful acreage with plenty of room for animals, recreation, gardening, or simply enjoying the outdoors.

  Taylor Norton McCallie Real Estate

  405 Nick Ln, 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
• 

  

  /40

  $410,000

  • 4 Beds
  • 2 Baths
  • 2,435 Sq Ft

  406 Lynnway Dr, Winchester, KY 40391

  Welcome to this inviting brick ranch in the desirable Stoney Brook neighborhood! Step inside through the foyer, where you'll find a formal dining room and a beautifully updated formal living room featuring fresh paint and wainscoting. The kitchen opens to the cozy living room/den with a masonry fireplace, making it a great space to relax or gather with friends and family. Just off the living area

  Michelle Blackburn RE/MAX Creative, Winchester

  406 Lynnway Dr, 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
• 

  

  /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
• 

  

  /31

  $455,000

  $50K PRICE DROP

  • 8 Beds
  • 4 Baths
  • 5,058 Sq Ft

  265 S Highland St, Winchester, KY 40391

  Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8

  J Corey Griffo RE/MAX Elite Lexington

  265 S Highland St, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 6