Winchester Homes

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  /48

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft

  401 Cedar Ct, Winchester, KY 40391

  Step into this beautifully updated 3-bedroom, 2-bath gem and fall in love with the perfect blend of charm and modern finishes! From the moment you walk through the door, you'll be greeted by an open concept living area with vaulted ceilings that fill the home with light and warmth.Enjoy new luxury vinyl plank flooring throughout the home, complemented by stylish, updated tile in the kitchen and

  Geneva Wilder Selling the South Realty

  401 Cedar Ct, Winchester, KY 40391
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• 

  

  

  /35

  $800 - $1,300 per month

  Summit Apartments

  1-3 Beds

  260 Oxford Dr, Winchester, KY 40391

  The Summit located in Winchester; KY is just minutes away from major employers. We are just a short drive from Lexington, KY. Come see our pet friendly community with lots of green space. We have spacious one-, two-, and three-bedroom apartment homes with caring on-site management. Our homes feature walk-in closets, new Laminate Vinyl Plank Flooring, fully equipped kitchens, washer/dryer

  260 Oxford Dr, Winchester, KY 40391
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  /48

  $330,000 Sold May 23, 2025

  • 2,090 Sq Ft
  • $158/SF
  • 35 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1970

  113 Holiday Rd, Winchester, KY 40391

  You must see this lovely brick home on a basement in Holiday Hills! If you like pickleball, disc golf, or anything else Wiseman Park has to offer, you will love this convenient location! 3 bedrooms, 2 and a half baths. Very practical kitchen featuring granite countertops and a brand new refrigerator. Plenty of room for entertaining with a beautiful deck just off the open concept kitchen / dining

  Jason Townsend Kentucky Residential Real Estate, LLC

  113 Holiday Rd, Winchester, KY 40391
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  /21

  Est $216,029 Not Listed For Sale

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

  227 Leslie Dr, Winchester, KY 40391

  227 Leslie Dr, Winchester, KY 40391
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  /3

  $380,000

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  270 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a

  Rex Hall United Real Estate Bluegrass

  270 Evergreen Dr, Winchester, KY 40391
• 

  

  /25

  $1,450 - $1,800 per month

  7 North Main

  1-2 Beds

  7 N Main St, Winchester, KY 40391

  Brand New Apartments in the Heart of Downtown WinchesterMultiple Layouts AvailableHighlights:-Quartz Countertops, New Cabinets, and New Appliances (Dishwasher, Fridge, Range)-New LVP Floors-Off-Street Parking Lot for Tenants and Guests-Prime Downtown Location on Main St-Close to Interstate to Lexington-In the Heart of Downtown Winchester

  7 N Main St, Winchester, KY 40391
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  /37

  $149,900 Sold May 23, 2025

  • 920 Sq Ft
  • $163/SF
  • 68 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  502 N Maple St, Winchester, KY 40391

  First Time Homebuyers, here is your opportunity to take advantage of Welcome Home Funds and make the move from renting to owning and investing in your future financial freedom! Check out this adorable 2 bedroom 1 bath home all on one level with an open kitchen and dining area. This home comes with plenty of storage in the 340 plus square foot metal building that has recently had electric added in

  Christa Joynt Keller Williams Commonwealth

  502 N Maple St, Winchester, KY 40391
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  /45

  Est $230,844 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  334 Vanover Way, Winchester, KY 40391

  334 Vanover Way, Winchester, KY 40391
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  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  265 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, walkout unfinished basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  265 Evergreen Dr, Winchester, KY 40391
• 

  /2

  Call for Price

  Cambridge Square Apartments - Income Based

  1-3 Beds

  300 C G Stephenson Dr, Winchester, KY 40391

  This community is open by appt only. Office hours are 9am to 12pm and 1pm to 4pm. Please call to schedule your appt!Cambridge Square is a community with beautifully maintained grounds, offering one, two and three bedroom apartment homes with some one bedroom homes reserved for the elderly/dis-abled, all rent based on income. We are located in quiet Winchester, Kentucky, with easy

  300 C G Stephenson Dr, Winchester, KY 40391
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  /82

  $275,000 Sold May 23, 2025

  • 2,994 Sq Ft
  • $92/SF
  • 202 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1920

  111 S Burns Ave, Winchester, KY 40391

  Reduced for quick sale!! Don't miss out on your opportunity to own a 100+ year old home located near historic downtown Winchester, KY. The detail and charm located within the walls of this 2 story craftsman are what many dream of. Tall ceilings, fireplaces, in almost evey room, beautiful original wood work is abundant as you enter from the quintessential front porch that's perfect for casual

  Melodie Lincavage RE/MAX Elite Realty

  111 S Burns Ave, Winchester, KY 40391
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  /27

  Est $214,661 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  300 Vanover Way, Winchester, KY 40391

  300 Vanover Way, Winchester, KY 40391
• 

  

  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,885 Sq Ft

  250 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
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  /11

  $1,000 per month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  127 W Hickman St Unit 5, Winchester, KY 40391

  Please read all details before contacting:1. Unit has 4 rooms: 1 Bedroom with 1 walk-in closet, Living Room, Kitchen & Dining Room in one with pantry, 1 Bathroom.2. Apartment is on the second floor, but it is not wheelchair accessible3. Parking space available in rear parking lot and/or front street parking.4. Tenant pays for electric, gas (optional for extra heat),

  127 W Hickman St Unit 5, Winchester, KY 40391
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  /35

  $248,000 Sold May 22, 2025

  • 1,773 Sq Ft
  • $140/SF
  • 20 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1997

  206 Moss Cir, Winchester, KY 40391

  This 3 bedroom 2 bathroom home is located in the established Spring Hill Subdivision. Separate Utility/Mud room and one car garage. Two very spacious full bathrooms. Covered front porch creates nice space for relaxing. The rear patio overlooks a nice fenced in back yard with storage building. Roof shingles replaced in 2022.

  David Baesler Kentucky Dreams Realty

  206 Moss Cir, Winchester, KY 40391
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  /20

  Est $219,961 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,246 Sq Ft

  209 Allan Place, Winchester, KY 40391

  209 Allan Place, Winchester, KY 40391
• 

  

  /3

  $380,000

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  230 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

  Rex Hall United Real Estate Bluegrass

  230 Evergreen Dr, Winchester, KY 40391
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  /44

  $206,500 Sold May 21, 2025

  • 1,107 Sq Ft
  • $187/SF
  • 23 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1962

  206 W Clark Dr, Winchester, KY 40391

  Don't miss out on this move-in ready home in Winchester, 15 minutes from Lexington. The beautifully updated home features a NEW furnace & water heater. It has stylish laminate flooring throughout and modern stainless steel appliances. The kitchen shines with updated cabinets, countertops, backsplash, and light fixtures, while the bathroom boasts new tiles and a sleek vanity. A detached single-car

  Peggy Baldridge HomeFirst Real Estate

  206 W Clark Dr, Winchester, KY 40391
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  /20

  Est $189,147 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  100 Colonial Park Dr, Winchester, KY 40391

  100 Colonial Park Dr, Winchester, KY 40391
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  /50

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,928 Sq Ft

  113 Olde Potomac Ave, Winchester, KY 40391

  This phenomenal property has had so many updates including the addition of a full bath on the second floor, an updated electric panel, including new wiring throughout the entire home and added electrical outlets, all new plumbing throughout the home, a heat pump for the second floor (there is gas heat on the first floor) and a walk-in closet for the master bedroom on the first floor. The owners

  Susan Colwell Colwell Realty Professionals

  113 Olde Potomac Ave, Winchester, KY 40391
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  /28

  $205,000 Sold May 19, 2025

  • 1,080 Sq Ft
  • $190/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2023

  303 W Washington St, Winchester, KY 40391

  Built in 2023 this home features 3 bedrooms, 2 bathrooms with a great amount of closet space, beautiful LVP flooring, stainless steel appliances and granite countertops in the kitchen. Located near downtown Winchester and I-64.

  Katherine G Pate Bluegrass Properties Group

  303 W Washington St, Winchester, KY 40391
• 

  

  /26

  Est $185,351 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,028 Sq Ft

  129 Buffalo Trace, Winchester, KY 40391

  129 Buffalo Trace, Winchester, KY 40391
• 

  

  /62

  $275,950 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,247 Sq Ft

  3614 Stamper Dr, Winchester, KY 40391

  'Fully renovated to perfection, this property features brand-new upgrades throughout. Highlights include newly installed windows, doors, and flooring, complemented by modern appliances and updated cabinetry. A new deck provides an ideal space for outdoor enjoyment, while contemporary fixtures add a touch of elegance. This home is truly a remarkable opportunity and an absolute must-see.'

  Darrell Tackett Dream Maker Realty, LLC

  3614 Stamper Dr, Winchester, KY 40391
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  /36

  $390,513 Sold May 19, 2025

  • 2,698 Sq Ft
  • $145/SF
  • 32 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1980

  21 Edgewood Dr, Winchester, KY 40391

  This spacious 4-bedroom, 2.5-bathroom, 2,698 sq. ft. ranch in Hampton Manor sits on nearly an acre double lot just 20 minutes from Lexington/Hamburg. The primary suite boasts a walk-in closet, Jacuzzi tub, and ample storage, while three additional large bedrooms offer flexibility for guests or a home office. A well-equipped kitchen, a laundry/pantry room, and formal living with fireplace and

  Kelly Nisbet Coldwell Banker McMahan

  21 Edgewood Dr, Winchester, KY 40391
• 

  

  /18

  Est $183,558 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  107 Buffalo Trace, Winchester, KY 40391

  107 Buffalo Trace, Winchester, KY 40391
• 

  

  /32

  $275,000

  • 4 Beds
  • 2 Baths
  • 2,808 Sq Ft

  16 Taylor Ave, Winchester, KY 40391

  STOP scrolling and LOOK! This charming and pristine home is clean as a whistle and just a short walk to active and historic downtown Winchester. Sit on the covered front porch in the summertime shade or on the deck/patio overlooking the spacious/private backyard. Move-in ready with lots of space inside and out (over 2800 sq.ft. finished!), 4 large bedrooms, 2 full baths (one upstairs and one

  Jim Woodrum RE/MAX Creative, Winchester

  16 Taylor Ave, Winchester, KY 40391
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  /36

  $214,000 Sold May 19, 2025

  • 1,402 Sq Ft
  • $153/SF
  • 38 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2000

  509 Hidden Hills Way, Winchester, KY 40391

  This home is a must-see and would be perfect for a Welcome Home Grant, a program that gets the buyer a chance for a $20,000 purchase grant. Offering 3 or 4 bedrooms and 2 full baths, this home also features a large covered back patio and secluded back yard area so you can enjoy the Spring days ahead. If you have a lot of 'stuff', no worries. The storage building stays also. Need more info on

  Teresa Richmond Freedom Realty & Property Mgt

  509 Hidden Hills Way, Winchester, KY 40391
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  /33

  Est $270,550 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,885 Sq Ft

  560 E Broadway St, Winchester, KY 40391

  560 E Broadway St, Winchester, KY 40391
• 

  

  /48

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft

  40 N Burns Ave, Winchester, KY 40391

  This stunning fully remodeled 3-bedroom, 2-bathroom home is move-in ready with top-to-bottom updates. Every detail has been thoughtfully upgraded, from the modern lighting in every room to the brand-new flooring and fresh paint throughout. The kitchen is a standout with granite countertops, new cabinetry, and brand-new appliances, while the bathrooms boast quartz countertops and elegant tiled

  Ernesto Martinez Berkshire Hathaway HomeServices Foster Realtors

  40 N Burns Ave, Winchester, KY 40391
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  /44

  $515,000 Sold May 19, 2025

  • 4,091 Sq Ft
  • $126/SF
  • 294 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1958

  31 Bonnie Brook Ln, Winchester, KY 40391

  This Warfield Gratz designed rare beauty and history is located in the heart of Winchester. Embrace the essence of elegance in this beautifully appointed brick home, offering 5 bedrooms, 3 full baths and formal rooms. Main level of home boasts the primary suite as well as an additional bedroom. The large fully equipped kitchen is a delight for any chef. Home features a full walk-up basement

  Kelly Nisbet Coldwell Banker McMahan

  31 Bonnie Brook Ln, Winchester, KY 40391
• 

  

  /15

  Est $195,377 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,006 Sq Ft

  13 Hiawatha Trail, Winchester, KY 40391

  13 Hiawatha Trail, Winchester, KY 40391
• 

  

  /79

  $249,900

  • 4 Beds
  • 2 Baths
  • 3,295 Sq Ft

  133 S Burns Ave, Winchester, KY 40391

  Beautiful, Old-World style in the heart of Winchester! From the red, domed porch roof to the arched doorways and multiple fireplaces, this home is full of character and class. Being sold as-is, but with many renovations and updates already done to maintain and restore the charm of this old beauty including a new shingle roof (2024), replaced porch boards, and a fresh coat of interior paint. The

  Josh Wood Freedom Realty & Property Mgt

  133 S Burns Ave, Winchester, KY 40391
• 

  

  /41

  $240,000 Sold May 16, 2025

  • 1,874 Sq Ft
  • $128/SF
  • 16 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1974

  860 Harkins Dr, Winchester, KY 40391

  Welcome to 860 Harkins Drive! This spacious split-foyer home features 4 bedrooms, 2 full bathrooms, a garage, and a large back deck perfect for outdoor entertaining. Conveniently located near public parks, the public library, and easy access to the Winchester Bypass. A fantastic opportunity for comfortable living in Winchester!

  Joseph Miller Keller Williams Commonwealth

  860 Harkins Dr, Winchester, KY 40391
• 

  

  /29

  Est $227,387 Not Listed For Sale

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

  46 Hiawatha Trail, Winchester, KY 40391

  46 Hiawatha Trail, Winchester, KY 40391
• 

  

  /14

  $285,000

  • 3 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  10 Upper St, Winchester, KY 40391

  Modern Ranch residence full un-finished basement, large lot.

  E. Clark Toleman Real Estate Appraisal Services

  10 Upper St, Winchester, KY 40391
• 

  

  /24

  $186,000 Sold May 14, 2025

  • 1,188 Sq Ft
  • $157/SF
  • 77 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1994

  205 Arbor Ct, Winchester, KY 40391

  Charming 3 bedroom, 2 bath cottage with a fenced side yard, perfect for the furbabies or just for outdoor relaxation. Property includes a shed for extra storage. Your cozy new home awaits!

  Kathryn Cheuvront Coldwell Banker McMahan

  205 Arbor Ct, Winchester, KY 40391
• 

  

  /33

  Est $247,868 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,875 Sq Ft

  14 Hiawatha Trail, Winchester, KY 40391

  14 Hiawatha Trail, Winchester, KY 40391
• 

  

  /41

  $260,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  205 Beaumont Place, Winchester, KY 40391

  Immaculate 3-Bedroom Gem in Winchester! Step into this beautifully maintained 3-bedroom, 2-bath home where charm meets functionality. Gleaming hardwood floors and stylish LVP tile create a seamless flow throughout the living spaces. The fully fenced backyard offers a private oasis ideal for entertaining, relaxing, or play. Need extra space? The detached garage is perfect for a workshop, storage,

  Terry Billiter Premier Property Consultants

  205 Beaumont Place, Winchester, KY 40391
• 

  

  /20

  $135,000 Sold May 13, 2025

  • 1,194 Sq Ft
  • $113/SF
  • 13 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1920

  100 Dallas Alley, Winchester, KY 40391

  Check out this beautifully refreshed home featuring a brand-new metal roof and a unique floorplan designed for flexibility. Enjoy easy access to downtown and ample parking space for 4 to 6 vehicles. The versatile layout allows for additional bedrooms, making it perfect for growing families or guests. Don't miss this opportunity for modern comfort with convenient urban access!

  Emidio Figueroa Rector Hayden Realtors

  100 Dallas Alley, Winchester, KY 40391
• 

  

  /20

  Est $203,488 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,593 Sq Ft

  4 Hiawatha Trail, Winchester, KY 40391

  4 Hiawatha Trail, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 18