Winchester, KY Homes

• 

  

  

  /18

  $574,000

  • 5 Beds
  • 3 Baths
  • 3,102 Sq Ft

  110 White Conkwright Rd, Winchester, KY 40391

  Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

  

  Philip 'PJ' Elder

  Omega Real Estate Brokerage LLC

  (859) 209-6934

  110 White Conkwright Rd, Winchester, KY 40391
• 

  

  

  /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
• 

  

  

  /24

  $198,000 Sold Jul 18, 2025

  • 1,075 Sq Ft
  • $184/SF
  • 0 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1983

  113 Colonial Park Dr, Winchester, KY 40391

  Conveniently located just off Veterans Memorial Bypass, this adorable brick ranch offers easy access to everything Winchester has to offer. Inside, you'll find a freshly painted interior, new flooring, new windows, a new roof and a new HVAC system. The nice-sized kitchen features plenty of cabinet space, perfect for home-cooked meals and gatherings. Nestled in a quiet, well-established

  Janet Baldwin Kentucky Land and Home

  113 Colonial Park Dr, Winchester, KY 40391
• 

  

  

  /31

  Est $251,464 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,356 Sq Ft

  421 Jameson Way, Winchester, KY 40391

  421 Jameson Way, Winchester, KY 40391
• 

  

  

  /67

  $699,000

  • 3 Beds
  • 4 Baths
  • 4,123 Sq Ft

  1775 Irvine Rd, Winchester, KY 40391

  Just 12 minutes from Lexington, own the most charming home atop a scenic hill at Blue Ridge Manor, a breathtaking 5.13 acre retreat where modern comfort meets classic elegance. As you drive up the long, private driveway, you'll feel like you're entering your own exclusive retreat, a sanctuary of peace and tranquility. Lovingly maintained by its original owner for the past 30 years, this

  

  Oxana Lopetegui-Pineda

  Lifstyl Real Estate

  (859) 659-6462

  1775 Irvine Rd, 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
• 

  

  /49

  $392,000 Sold Jul 18, 2025

  • 3,200 Sq Ft
  • $122/SF
  • 261 Days On Market

  • 3 Beds
  • 3.5 Baths

  228 Moundale Ave, Winchester, KY 40391

  Freshly painted and full of charm! This colonial-style home in Winchester's historic Thomson Addition offers a spacious, inviting layout. The foyer opens to a formal dining room, great room, and a kitchen with custom maple cabinets, breakfast nook, and cozy living space. French doors lead to a screened-in porch and large deck which is perfect for relaxing or entertaining. The main floor features

  Michelle Blackburn RE/MAX Creative, Winchester

  228 Moundale Ave, Winchester, KY 40391
• 

  

  /20

  Est $217,336 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,060 Sq Ft

  415 Walnut St, Winchester, KY 40391

  415 Walnut St, Winchester, KY 40391
• 

  

  /50

  $465,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,784 Sq Ft

  701 Lisletown Ln, Winchester, KY 40391

  Perfectly nestled at the end of shared private lane, this mid-century modern home w/full finished walkout basement offers luxury, privacy & natural beauty. Designed by architect R.L. Isenhour, this distinctive property is situated on just over 3 wooded acres, surrounded by forest & overlooking the Kentucky River. Step inside to soaring ceilings, expansive windows & a striking floor-to-ceiling

  

  Robin Jones

  Keller Williams Legacy Group

  (859) 470-2988

  701 Lisletown Ln, Winchester, KY 40391
• 

  

  /20

  $1,280 - $1,499 per month

  SPECIALS: The Reserve & Enclave at Fairholme

  2-3 Beds

  100-145 Sam Winston Way, Winchester, KY 40391

  Beautiful Townhomes with 2 Bedrooms and 2.5 Baths, located within both The Enclave at Fairholme & The Reserve at Fairholme Townhome Communities. Built between 2019-2022. Fully equipped kitchens feature Stainless Steel Appliances, and includes Stove, Refrigerator, Dishwasher, and Microwave. Washer and Dryer Included! Hardwood LVT Flooring throughout.Off-Street Parking. Select Units Have a

  100-145 Sam Winston Way, Winchester, KY 40391
• 

  

  /27

  $199,900 Sold Jul 15, 2025

  • 1,348 Sq Ft
  • $148/SF
  • 18 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1940

  139 W Hickman St, Winchester, KY 40391

  Welcome Home! Featuring 3 bedrooms and 2 bathrooms, this home is everything you have been looking for. Recent updates include new flooring, appliances, roof, HVAC, and even the water heater. Sit out on your front porch and drink your morning coffee, or enjoy your large back deck for a weekend cookout. This home also has plenty of attic storage. The driveway makes a perfect place to plug in your

  Clay David Sutherland ERA Select Real Estate

  139 W Hickman St, Winchester, KY 40391
• 

  

  /32

  Est $294,654 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft

  228 Holiday Rd, Winchester, KY 40391

  228 Holiday Rd, Winchester, KY 40391
• 

  

  /40

  $239,900

  • 2 Beds
  • 2 Baths
  • 1,628 Sq Ft

  635 Lisletown Ln, Winchester, KY 40391

  Tucked away on a private lane behind a charming stone wall, this storybook 2BR/2BA dome-style cottage is a one-of-a-kind retreat. Greeted by a peaceful koi pond, the home's unique wood siding and architectural flair set the tone for something truly special. Inside, natural light pours in through skylights and stained-glass accents, creating a warm, ethereal atmosphere. The inviting living room

  

  Robin Jones

  Keller Williams Legacy Group

  (859) 328-1145

  635 Lisletown Ln, 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
• 

  

  /26

  $239,500 Sold Jul 15, 2025

  • 2,017 Sq Ft
  • $119/SF
  • 26 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  129 Bay Hill Dr, Winchester, KY 40391

  Located in an established neighborhood this low maintenance spacious townhome with over 2000 square foot has curb appeal and backs to a greenspace with a large backyard and rear facing garage. The home has been well maintained and updated with a new roof and new flooring. The kitchen and family room are nice sized for all your gatherings. For an added convenience the lower level offers a bonus

  Tonya Skeens RE/MAX Elite Lexington

  129 Bay Hill Dr, Winchester, KY 40391
• 

  

  /24

  Est $712,520 Not Listed For Sale

  • 3 Beds
  • 3 Baths

  703 Kiddville Rd, Winchester, KY 40391

  703 Kiddville Rd, Winchester, KY 40391
• 

  

  /117

  $3,175,000

  • 8 Beds
  • 7.5 Baths
  • 12,702 Sq Ft

  4664 Lexington Rd, Winchester, KY 40391

  Visitors to the farm are greeted by a substantial stone entry before traveling a gently winding path to the circular drive. There rests the grand residence, offering an ideal setting for entertaining family & friends. Ten minutes from Hamburg, the farm is located on the convenient Lexington/Winchester Road. Lovely views abound and the property retains remarkable privacy. The 13,500 square foot

  Zach Davis Kirkpatrick & Company

  4664 Lexington Rd, Winchester, KY 40391
• 

  

  /3

  Call for Price

  Westwood Apartments - Income Based

  1-3 Beds

  900 Westwood Dr, Winchester, KY 40391

  Pick up your application for our WAIT LIST at the office door! Westwood is a charming property in a great location in Winchester, Kentucky with rents based on income. Spacious one, two and three bedroom apartments for rent, each featuring a fully equipped kitchen, your choice of a patio or balcony, and they are wired for cable. Fun in the sun is just a outside your door at our playground, or

  900 Westwood Dr, Winchester, KY 40391
• 

  

  /14

  $222,500 Sold Jul 15, 2025

  • 1,064 Sq Ft
  • $209/SF
  • 112 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1995

  313 Vanover Way, Winchester, KY 40391

  Charming 3-bedroom, 2-bath brick home with both an attached and detached 1-car garage for added storage and convenience! This 1,064 sq ft home features a welcoming front entry with a ramp for easy access. Inside, enjoy a functional layout with comfortable living spaces. Outside, the detached garage offers extra workspace or storage. Conveniently located with easy access to I-64 and just minutes

  Bob Sophiea eXp Realty, LLC

  313 Vanover Way, Winchester, KY 40391
• 

  

  /52

  Est $351,975 Not Listed For Sale

  • 2 Beds
  • 1 Bath

  670 Lillies Ferry Rd, Winchester, KY 40391

  670 Lillies Ferry Rd, Winchester, KY 40391
• 

  

  /29

  $427,900 Pending

  • 4 Beds
  • 3 Baths
  • 2,361 Sq Ft

  4732 Old Boonesboro Rd, Winchester, KY 40391

  NEW PRICE REDUCTION!!! This Is The One You Have Been Waiting For!!! This Completely Remodeled 4 Bedroom 3 Bathroom Home On An Unfinished Basement Has It All. Features Include An Open Floor Plan; Dining Room With Fireplace; Big Kitchen With Lots Of Cabinets; Granite Tops; Stainless Steel Appliances; Range Hood; Farmhouse Sink; Huge Laundry Room Off Kitchen/Master Bedroom; First Floor Master

  Patrick Arvin Keller Williams Commonwealth

  4732 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /6

  $1,300 per month

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  112 Old Bottom Rd, Winchester, KY 40391

  Great location! 3 bed 1 bath updated home with a huge backyard. Tenants pays water/sewer, electric and gas. Small dog accepted with a $300 pet fee and $25/month, Dog breed restrictions, Cats are not permitted.

  112 Old Bottom Rd, Winchester, KY 40391
• 

  

  /61

  $545,000 Sold Jul 15, 2025

  • 3,958 Sq Ft
  • $138/SF
  • 180 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2000

  1063 Wades Mill Rd, Winchester, KY 40391

  NEW ROOF INSTALLED MAY 28th. A fully remodeled 5-acre property offers a beautifully updated 3,958 sq ft home with 4 bedrooms, 3 full baths, and 1 half bath. Every inch of this spacious home has been thoughtfully updated, including brand-new flooring throughout and a newly installed HVAC unit upstairs for optimal comfort. The custom-designed primary closet provides a luxurious storage solution,

  Joseph Smallwood Christies International Real Estate Bluegrass

  1063 Wades Mill Rd, Winchester, KY 40391
• 

  

  /42

  Est $390,265 Not Listed For Sale

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

  920 Log Lick Rd, Winchester, KY 40391

  920 Log Lick Rd, Winchester, KY 40391
• 

  

  /39

  $479,000

  • 3 Beds
  • 2 Baths
  • 2,727 Sq Ft

  865 Pretty Run Rd, Winchester, KY 40391

  Situated on 1.5 acres along a sought after country road, this one level home features a split bedroom layout with a primary suite that includes an en suite bath and walk in closet. The living room offers vaulted ceilings, hardwood floors, and a gas log fireplace, opening to a dining area and an eat in kitchen. A sunroom provides additional living space with skylights and views of the backyard.

  Shane Underwood Keller Williams Commonwealth

  865 Pretty Run Rd, Winchester, KY 40391
• 

  

  /8

  $600 per month

  • Studio
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  192 Wabash Ave, Winchester, KY 40391

  This property at 192 Wabash Ave features a studio layout with 0 bedrooms and 1 bathroom, encompassing a total of 600 square feet. The living area is designed for efficiency, providing ample space for both relaxation and functionality. The property includes smoke-free living and access to on-site laundry facilities for added convenience. This unit is ideal for individuals seeking a compact

  192 Wabash Ave, Winchester, KY 40391
• 

  

  /20

  $189,900 Sold Jul 14, 2025

  • 1,056 Sq Ft
  • $180/SF
  • 2 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1970

  2342 Ironworks Rd, Winchester, KY 40391

  Welcome to 2342 Ironworks Road, where country charm meets effortless city access! Nestled on a lush, gently rolling lot, this brick ranch offers:Inviting Living Spaces: Original hardwood floors flow through a bright living room anchored by a classic painted-brick fireplace. The bonus room on the back side of the house would be ideal for a home office, nursery, or even a guest

  Dylan Justice GSP Homes

  2342 Ironworks Rd, Winchester, KY 40391
• 

  

  /45

  Est $334,410 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  1600 Crowe Ridge Rd, Winchester, KY 40391

  1600 Crowe Ridge Rd, Winchester, KY 40391
• 

  

  /80

  $574,900

  • 3 Beds
  • 2.5 Baths
  • 4,933 Sq Ft

  160 Agawam Rd, Winchester, KY 40391

  Welcome to this beautifully maintained brick ranch home set on a spacious and private 5-acre fenced lot. This versatile property offers the perfect blend of comfort, functionality, and rural charm - ideal for families, hobby farmers, or equestrian enthusiasts. Inside, you'll find 3 bedrooms and 3 bathrooms with a fully finished basement that offers ample space for additional bedrooms, a home gym,

  Megan McCoy Keller Williams Legacy Group

  160 Agawam Rd, Winchester, KY 40391
• 

  

  /31

  $2,200 per month

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • House for Rent

  117 Gibson Way, Winchester, KY 40391

  Are you looking for a large, like new house at an affordable price. Well look no further! This 4 Bedroom 3 Full Bathroom house is conveniently located off of the Bypass in Winchester, KY. This is a new construction home on a quiet street with tons of upgrades and custom hardware and fixtures throughout the home. The many features of this home include: An enormous master suite w/ a massive

  117 Gibson Way, Winchester, KY 40391
• 

  

  /4

  $101,000 Sold Jul 14, 2025

  • Land
  • 4.02 Acres
  • $25,124 per Acre

  • 86 Days On Market

  2058 Athens Boonesboro Rd, Winchester, KY 40391

  Prime building lot - 4.15 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2058 and 2010 lots approved shared entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first

  Megan McCoy Keller Williams Legacy Group

  2058 Athens Boonesboro Rd, Winchester, KY 40391
• 

  

  /54

  Est $492,017 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,841 Sq Ft

  5600 Ecton Rd, Winchester, KY 40391

  5600 Ecton Rd, Winchester, KY 40391
• 

  

  /47

  $374,900

  • 3 Beds
  • 2.5 Baths
  • 1,750 Sq Ft

  714 Concord Ave, Winchester, KY 40391

  This beautiful modern home is conveniently located in the Colby Ridge subdivision with easy access to all that Winchester has to offer. From the comfortable front porch, take a step inside to enjoy the open floor plan great room with living space, dining space and a stunning kitchen. Also on the first floor is a bonus family room area that could be used as a small bedroom (without a closet) as

  Josh Wood Freedom Realty & Property Mgt

  714 Concord Ave, Winchester, KY 40391
• 

  

  /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
• 

  

  /58

  $232,500 Sold Jul 12, 2025

  • 1,161 Sq Ft
  • $200/SF
  • 235 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1980

  114 Holiday Rd, Winchester, KY 40391

  Price Improvement!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

  Karen Smith Emmerich Muzic Realty

  114 Holiday Rd, Winchester, KY 40391
• 

  

  /49

  Est $350,017 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,560 Sq Ft

  2068 Goshen Rd, Winchester, KY 40391

  2068 Goshen Rd, Winchester, KY 40391
• 

  

  /35

  $318,000

  • 3 Beds
  • 2.5 Baths
  • 1,903 Sq Ft

  329 Hanover Dr, Winchester, KY 40391

  Welcome home to this well-maintained two-story home on an unfinished basement! This home features 3 bedrooms, 2 bathrooms, a bonus room overlooking the living room, kitchen with all the appliances to convey, basement is roughed in for a bathroom already as well. Outside you will find a covered front porch, spacious deck and a patio. Located right off the bypass in Winchester this property is

  Bradley Warford Century 21 Pinnacle

  329 Hanover Dr, Winchester, KY 40391
• 

  

  /58

  $460,000 Sold Jul 11, 2025

  • 4,448 Sq Ft
  • $103/SF
  • 18 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1978

  150 Stone Crest Rd, Winchester, KY 40391

  IMMEDIATE OCCUPANCY! WELCOME HOME with Room to spread out in this SPACIOUS Home of over 4000 sq. ft. sitting on 5.5 Acres! Offering 4 Bedrooms, 4 Bathrooms, Living Room, Beautiful Kitchen with appliances and tons of cherry cabinets, Den, utility room and 2 Large Bonus Rooms in the Basement. one could be a bedroom. There is a 3-car Detached Garage, 2-car attached Garage, Large Carport, Huge Patio

  Brenda Murphy Murphy Realty Group

  150 Stone Crest Rd, Winchester, KY 40391
• 

  

  /53

  Est $283,409 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,126 Sq Ft

  1489 White Conkwright Rd, Winchester, KY 40391

  1489 White Conkwright Rd, Winchester, KY 40391
• 

  

  /37

  $379,000

  • 4 Beds
  • 2.5 Baths
  • 2,587 Sq Ft

  122 Le Ann Ln, Winchester, KY 40391

  Welcome to this spacious two-story brick home set on a beautiful half-acre lot in a quiet Winchester subdivision, just 10 miles from Hamburg. With approximately 2,600 square feet of living space, this residence offers an exceptional blend of comfort, functionality, and location—perfect for families or anyone seeking a peaceful retreat close to city conveniences.Inside, you'll find four

  Tracey Goebel Tom Goebel & Company

  122 Le Ann Ln, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 18