Winchester, KY Homes for Sale with Garage

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  $262,500

  • 3 Beds
  • 2 Baths
  • 1,234 Sq Ft

  433 Wellington Way, Winchester, KY 40391

  Completely renovated and move-in ready! This 3-bedroom, 2-bath home offers 1,234 sq. ft. of stylish living with beautiful hardwood floors, fresh finishes, and a bright open layout. The vaulted ceiling in the main living area adds space and light, while the updated kitchen features modern cabinetry and new appliances. Both bathrooms have been tastefully redone, and every detail reflects quality

  Stephen Brashear Real Broker LLC

  433 Wellington Way, Winchester, KY 40391
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  /30

  $349,000

  • 3 Beds
  • 2.5 Baths
  • 2,475 Sq Ft

  212 Woodbine Ct, Winchester, KY 40391

  Step right up - come on in! Its appeal is undeniable, both inside and out! Move-in ready. This well-maintained all-brick ranch on a full basement is full of charm and functionality! — Inside, you'll love having two separate living areas, 1 upstairs and 1 in the basement with a wood burning fireplace in both rooms. Enjoy the cold winter evenings in front of either of the fireplaces with family and

  Kathy Burton Coldwell Banker McMahan

  212 Woodbine Ct, Winchester, KY 40391
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  /53

  $279,500

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  724 Terry Dr, Winchester, KY 40391

  Charming Split-Level Home in a Peaceful Winchester Neighborhood Discover this beautiful 3-bedroom, 2 full bath split-level home featuring a cozy finished basement perfect for relaxing or entertaining. Enjoy both front and rear porches, ideal for morning coffee or evening gatherings. The spacious, fenced-in backyard offers privacy and room to play, garden, or unwind. Nestled in a quiet

  Darrell Tackett Dream Maker Realty, LLC

  724 Terry Dr, Winchester, KY 40391
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  /41

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft

  118 Windridge Dr, Winchester, KY 40391

  Imagine spending summers in your own private backyard retreat, complete with an in-ground pool featuring a newer liner, pump, and filter, secure iron fencing, and a roomy concrete patio that's ideal for relaxing or entertaining. This well-cared-for brick ranch in Windridge offers 3 bedrooms, 2 full baths, and hardwood and tile floors throughout with no carpet. Inside, the kitchen offers generous

  Michelle Blackburn RE/MAX Creative, Winchester

  118 Windridge Dr, Winchester, KY 40391
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  /18

  $209,900

  • 3 Beds
  • 1 Bath
  • 1,074 Sq Ft

  245 Ecton Rd, Winchester, KY 40391

  Welcome to this fully updated home that is cozy and full of character. Featuring brand new central heating and air, electric, drywall, spray foam insulation, kitchen cabinets, water heater, and stunning hardwood floors throughout. This beautiful kitchen boasts all brand new appliances, butcher block countertops, sage green cabinets, a 30 inch farmhouse sink, and also features a 6 foot island

  Anthony Gigilo ListWithFreedom.com

  245 Ecton Rd, Winchester, KY 40391
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  $319,000

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  410 Corinne Ct, Winchester, KY 40391

  Charming Ranch-Style Home with Lots of Room- Step inside this 8 year old beautiful 1,604 sq. ft. ranch-style home featuring 9-foot ceilings and an open, inviting layout. With 3 comfortable bedrooms and a large, laundry room and back hallway, this home offers both style and functionality. The spacious living areas are enhanced by wood and tile flooring, adding a modern touch and easy maintenance.

  Shelly Sutton Kentucky Realty Group, LLC

  410 Corinne Ct, Winchester, KY 40391
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  $349,000 Open Sun 1:30PM - 3:30PM

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  121 Fitch Ave, Winchester, KY 40391

  This beautifully updated 4-bedroom, 3-bath ranch home includes a private mother-in-law suite, offering flexible living options for guests or extended family. With 2,100 square feet of inviting living space and an attached two-car garage, this home perfectly combines timeless charm with thoughtful modern updates. Conveniently located just minutes from the interstate close to Lexington, it offers

  Ashley Spencer Keller Williams Commonwealth

  121 Fitch Ave, Winchester, KY 40391
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  /53

  $275,000 Open Sun 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft

  174 Hidden Grove Ln, Winchester, KY 40391

  Welcome home to your Kentucky River retreat! This freshly remodeled 2-bedroom, 2-bath charmer offers two inviting covered decks with beautiful river views, a fenced yard for pets or play and even a personal lift for easy access. Inside, enjoy warm, modern updates, with a bright open floor plan. All new flooring, kitchen, baths and much more! Perfect for full-time living or a peaceful getaway just

  Kathryn Cheuvront Coldwell Banker McMahan

  174 Hidden Grove Ln, Winchester, KY 40391
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  /19

  $294,900

  • 3 Beds
  • 2 Baths
  • 1,966 Sq Ft

  729 Wayland Dr, Winchester, KY 40391

  This charming 3-bedroom, 2-bath split level home offers the perfect blend of comfort and convenience-located just minutes from Lexington's popular Hamburg area with endless shopping, dining and entertainment options right at your fingertips! Step inside to find a beautifully updated kitchen featuring brand-new granite countertops and a stylish new island, perfect for family meals or entertaining

  Brittany Beer EXP Realty, LLC

  729 Wayland Dr, Winchester, KY 40391
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  /21

  $195,500

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft

  109 Quail Ridge Rd, Winchester, KY 40391

  Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townhome offering comfort, style, and convenience in every detail. The spacious living room features a cozy fireplace, soft neutral tones, and natural light that make it easy to feel at home. The open layout flows to the kitchen and dining area, creating the perfect setting for everyday living or entertaining

  Kim Dice EXP Realty, LLC

  109 Quail Ridge Rd, Winchester, KY 40391
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  /19

  $197,500

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft

  111 Quail Ridge Rd, Winchester, KY 40391

  Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townhome offering comfort, style, and convenience in every detail. The spacious living room features a cozy fireplace, soft neutral tones, and natural light that make it easy to feel at home. The open layout flows to the kitchen and dining area, creating the perfect setting for everyday living or entertaining

  Kim Dice EXP Realty, LLC

  111 Quail Ridge Rd, Winchester, KY 40391
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  /31

  $234,000

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

  209 Allan Place, Winchester, KY 40391

  Charming 3 Bedroom Home with Vaulted Ceilings and Wooded Views Welcome to this inviting 3-bedroom, 2-bath home offering an open-concept layout filled with natural light and soaring vaulted ceilings. The spacious living area flows seamlessly into the kitchen and dining spaces—perfect for both everyday living and entertaining. Enjoy peace of mind with a brand-new HVAC system, Gutter guards

  Julie Wiggington RE/MAX Creative, Winchester

  209 Allan Place, Winchester, KY 40391
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  /31

  $274,900

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  407 Corinne Ct, Winchester, KY 40391

  Welcome to 407 Corinne Court a beautifully maintained 3-bedroom, 2-bath all-electric home offering a perfect blend of comfort, style, and functionality. This one-level open-concept ranch sits on a crawl space foundation with a brick and vinyl exterior and features an attached two-car garage. Step inside to find fresh paint throughout, new carpet in the living room and bedrooms, and hardwood

  Shane Underwood Keller Williams Commonwealth

  407 Corinne Ct, Winchester, KY 40391
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  /34

  $325,000

  • 2 Beds
  • 1 Bath
  • 1,531 Sq Ft

  1508 Ford Hampton Rd, Winchester, KY 40391

  Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character

  Michelle Blackburn RE/MAX Creative, Winchester

  1508 Ford Hampton Rd, Winchester, KY 40391
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  $235,000

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft

  23 Kittison Dr, Winchester, KY 40391

  ONE-OWNER BRICK RANCH HOME!! Now that I have your attention, schedule a showing quickly, this one won't last long!! This cozy home has 3 spacious bedrooms, 2 bath, and a family room and kitchen area that are wonderful for family gatherings. You will love the beautiful hardwood floors throughout the home. Don't forget the garage /workshop area out back with room to grow if needed.

  Teresa Richmond Freedom Realty & Property Management

  23 Kittison Dr, Winchester, KY 40391
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  /23

  $218,500

  • 3 Beds
  • 2.5 Baths
  • 1,348 Sq Ft

  363 Silverton Way, Winchester, KY 40391

  Unique Setting... Unlike Any Other! Wake up to the beauty of the surrounding countryside every single day. This 3-bedroom, 2.5-bath townhome is nestled in the desirable Royal Oaks Village, just one mile from I-64, making it a perfect location for both homeowners and renters alike. This low-maintenance property features tile flooring in the foyer, kitchen, and baths. The kitchen comes fully

  Kim Dice EXP Realty, LLC

  363 Silverton Way, Winchester, KY 40391
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  /50

  $824,900

  • 4 Beds
  • 3 Baths
  • 3,311 Sq Ft

  7300 Old Boonesboro Rd, Winchester, KY 40391

  This beautiful home sits on over 7 acres of peaceful countryside. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275 square feet equipment building there is plenty of space for all of

  Vickie Skeens RE/MAX Elite Lexington

  7300 Old Boonesboro Rd, Winchester, KY 40391
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  $314,000

  • 2 Beds
  • 1 Bath
  • 1,170 Sq Ft

  398 Pine Ridge Rd, Winchester, KY 40391

  Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment you walk in. Enjoy the outdoors from the

  Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
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  /34

  $235,000

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

  37 7th St, Winchester, KY 40391

  Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

  Andrew Fugitt Coldwell Banker McMahan

  37 7th St, Winchester, KY 40391
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  /24

  $189,900

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft

  27 Ashland Ave, Winchester, KY 40391

  Motivated Seller! Move right in and enjoy this well-maintained 3-bed, 2-bath ranch in the heart of Massie Addition! Thoughtfully updated with a recent roof on both the home and garage, a brand-new hot water heater (2025), and a modern, fresh interior paint palette, this home is ready for you. A home warranty covering all major systems and appliances is included for added peace of mind. This

  Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

  27 Ashland Ave, Winchester, KY 40391
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  /94

  $849,900

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

  4040 Muddy Creek Rd, Winchester, KY 40391

  A Farmhouse Retreat with Timeless Craftsmanship on 13.6 AcresNestled on 13.6 rolling acres in Clark County, this custom built farmhouse captivates with soaring tongue-and-groove ceilings, rich woodwork, and thoughtful craftsmanship that sets this home apart. Oversized doors, custom cabinetry, and detailed finishes showcase the quality throughout, while two wood-burning fireplaces with

  Julie Wiggington RE/MAX Creative, Winchester

  4040 Muddy Creek Rd, Winchester, KY 40391
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  $1,149,000

  • 3 Beds
  • 3.5 Baths
  • 3,672 Sq Ft

  2100 Irvine Rd Unit 40391, Winchester, KY 40391

  Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths,

  Mila Ensor Ensor Real Estate, LLC

  2100 Irvine Rd Unit 40391, Winchester, KY 40391
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  $612,900

  • 4 Beds
  • 5 Baths
  • 4,374 Sq Ft

  600 Boone Ave, Winchester, KY 40391

  Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the

  Holly Goeing The Agency

  600 Boone Ave, Winchester, KY 40391
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  /84

  $849,900

  • 4 Beds
  • 3.5 Baths
  • 4,922 Sq Ft

  2509 Mount Sterling Rd, Winchester, KY 40391

  Embrace Bluegrass living with this beautiful fieldstone ranch on 10+ acres in the heart of horse country. Just minutes from interstate access, yet surrounded by rolling hills and scenic views, this mini farm offers a larger barn with 6 stalls, including water and electric connection, 90 foot roof hangover on the barn, 5 paddocks, each with their own gate and water ran along each paddock. The home

  Josh Wood Freedom Realty & Property Management

  2509 Mount Sterling Rd, Winchester, KY 40391
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  /6

  $171,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  102 W Hickman St, Winchester, KY 40391

  102 W Hickman St, Winchester, KY 40391Cozy and full of potential! This 11⁄2-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown

  David Espinosa Bluegrass Realty Pros, Inc

  102 W Hickman St, Winchester, KY 40391
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  /103

  $3,330,000

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 78-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
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  /36

  $345,000

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  208 Citation Ct, Winchester, KY 40391

  One owner, all electric, 2 BR/2Ba ranch with a bonus room that could be an office or a third bedroom. Great for downsizing or first time homeowner! The open floor great room with ample windows to brighten it supports the handicapped features of the primary bedroom, primary bathroom, garage and more. Enjoy the large pantry off the kitchen area and the island that has room to slide a chair under.

  Garnett Davis Tom Goebel & Company

  208 Citation Ct, Winchester, KY 40391
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  /62

  $259,500

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

  3614 Stamper Dr, Winchester, KY 40391

  Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

  Darrell Tackett Dream Maker Realty, LLC

  3614 Stamper Dr, Winchester, KY 40391
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  /14

  $250,000

  • 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
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  /103

  $2,650,000

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 10-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
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  /61

  $524,900

  • 4 Beds
  • 2 Baths
  • 2,940 Sq Ft

  5515 Van Meter Rd, Winchester, KY 40391

  Welcome to your dream home, perfectly nestled in a highly desired location. This stunning property spans a generous 5 acres, offering an idyllic setting for homesteading. Experience the best of country living with the convenience of nearby amenities. The home boasts beautiful views that will take your breath away every morning. Imagine waking up to the serene beauty of nature, right at your

  Robyn Bradley Woods Realty Group

  5515 Van Meter Rd, Winchester, KY 40391
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  /92

  $1,200,000

  • 5 Beds
  • 7 Baths
  • 8,236 Sq Ft

  6237 Bybee Rd, Winchester, KY 40391

  Step into timeless elegance with this breathtaking modern Victorian-style masterpiece, perfectly positioned on 4.39 acres with panoramic views of sunrises, sunsets, and distant mountains. Designed and built by Tom Padgett, this home is rich in character and detail—from hand-hewn wood beam ceilings to Waterford crystal chandeliers. The grand 2-story foyer welcomes you into a flowing layout that

  Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  6237 Bybee Rd, Winchester, KY 40391
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  /26

  $210,500

  • 3 Beds
  • 1 Bath
  • 1,354 Sq Ft

  40 Garner St, Winchester, KY 40391

  Check out this lovely all brick, beautifully renovated 3-bedroom,1bath home located in Winchester perfectly blending timeless charm with modern updates. This move-in ready home features a new roof, updated electrical and plumbing, an upgraded kitchen, new flooring, a fully renovated bathroom, fresh paint throughout, and all new appliances. Situated on a spacious corner lot, the property offers

  Nicole Seals Guide Realty, Inc.

  40 Garner St, Winchester, KY 40391
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  /24

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,306 Sq Ft

  110 Albany Ln, Winchester, KY 40391

  Lovely one level brick ranch on a corner lot conveniently located in the Meadows just off of McClure Rd. 3 bedroom, 2 full bath with a beautiful yard and a storage building out back.

  Jason Townsend Kentucky Residential Real Estate, LLC

  110 Albany Ln, Winchester, KY 40391
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  $899,000

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

  2447 Clintonville Rd, Winchester, KY 40391

  What a great opportunity to own 3 acres just 15 minutes from Man O War and 20 minutes to the Hamburg Shopping Area. The move in ready property features a beautiful brick home built by builder, Michael Childers, to use as his main residence. The property also has a 3 car detached Garage which is deep enough to hold 6 cars and one door is tall for storage of a Recreational Vehicle. It has been

  Suzanne Elliott Berkshire Hathaway de Movellan Properties

  2447 Clintonville Rd, Winchester, KY 40391
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  /34

  $330,000

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

  213 Orchid Ct, Winchester, KY 40391

  Kasey McCarty 5.23 Real Estate

  213 Orchid Ct, Winchester, KY 40391
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  /18

  $499,900 New Construction

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft

  414 Fairholme Way, Winchester, KY 40391

  Welcome to Fairholme Estates—where luxury meets comfort! This brand-new ranch-style home offers 4 bedrooms, 3 full baths, and 9' ceilings throughout for a spacious, airy feel. The designer kitchen features a huge island, beautiful finishes, and flows seamlessly into the vaulted great room filled with natural light from large windows. A Jack and Jill bath with separate sinks provides convenience,

  Kristin Ray Lifstyl Real Estate

  414 Fairholme Way, Winchester, KY 40391
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  /2

  $345,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  215 Evergreen Dr, Winchester, KY 40391

  Welcome to Triple Crown - a stunning proposed construction home nestled in the beautiful Locust Hill Acres community. Thoughtfully designed with an open-concept layout, this home offers 3 comfortable bedrooms, 2 full bathrooms, and versatile living spaces perfect for today's lifestyle.The expansive primary suite serves as a private sanctuary, complete with a spacious walk-in closet and a

  Rex Hall United Real Estate Bluegrass

  215 Evergreen Dr, Winchester, KY 40391
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  /3

  $345,000 New Construction

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

  225 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

  225 Evergreen Dr, Winchester, KY 40391
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  /69

  $925,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 2,842 Sq Ft

  1150 Craig Crossing, Winchester, KY 40391

  Stunning new construction featuring 5 bedroom. 3.5 bath nestled on roughly 2.5 serene acres, surrounded by picturesque farmland and panoramic views. Offering the perfect blend of space, style, and serenity. Features include open concept layout, spacious kitchen with kitchen island, granite counter tops, hidden walk in pantry with custom cabinets and well appointed appliances. Hardwood floors and

  Stephanie Hacker Kentucky Residential Real Estate, LLC

  1150 Craig Crossing, Winchester, KY 40391

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