Ranch Style Homes for Sale in Winchester, KY

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  /12

  $185,900

  $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,116 Sq Ft

  41 7th St, Winchester, KY 40391

  Welcome to 41 7th Street. This brick ranch offers 3 bedrooms, 2 full baths, and hardwood floors throughout the living room, hallway, and bedrooms, ready to be refreshed with a re-sand and polish. The layout provides a foundation for a buyer looking to add personal updates and make it their own. Located at the end of the street, the home offers added privacy along with peaceful farm views behind

  

  Austina Bruton

  Re/Max Elite Realty - Hamburg

  (859) 695-6124

  41 7th St, Winchester, KY 40391
• Explore Winchester

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  /18

  $550,000

  $6K PRICE DROP

  • 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) 695-3879

  110 White Conkwright Rd, Winchester, KY 40391
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  /72

  $775,000

  • 5 Beds
  • 3 Baths
  • 4,437 Sq Ft

  465 Morris Rd, Winchester, KY 40391

  Dreaming of wide-open spaces and country charm? This beautiful 16-acre property in Clark County offers the perfect blend of comfort and functionality. The stately brick home provides generous living space with classic appeal, offering endless potential. With five bedrooms and three full baths, the home accommodates a variety of living arrangements, whether you need space for guests, a home

  

  Brenda Leigh Walters

  United Real Estate Bluegrass

  (859) 459-0504

  465 Morris Rd, Winchester, KY 40391
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  /31

  $310,000

  $20K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,624 Sq Ft

  28 Churchill Dr, Winchester, KY 40391

  ***Motivated Sellers*** Beautifully updated ranch on a new, fully finished walk out basement. 5 bedrooms, 2 being primary suites, one on the main level and one in the basement. This house is perfect for multigenerational living. New paint, floors, back splash, kitchen cabinets and granite counter tops. The fully finished basement has a newly added primary bedroom and bath. The updated bathroom

  Libby VanMeter Marshall Lane Real Estate - Lexington

  28 Churchill Dr, Winchester, KY 40391
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  /47

  $427,000

  • 3 Beds
  • 2.5 Baths
  • 2,289 Sq Ft

  20 Edgewood Dr, Winchester, KY 40391

  Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a

  Libby VanMeter Marshall Lane Real Estate - Lexington

  20 Edgewood Dr, Winchester, KY 40391
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  /60

  $257,000

  $42K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,273 Sq Ft

  119 Tower Ln, Winchester, KY 40391

  A rare and refined retreat set on five unrestricted acres in Winchester. Privately positioned and surrounded by natural beauty, this renovated berm-style residence offers the perfect balance of seclusion and sophistication. Inside, you'll find thoughtfully curated updates including fresh designer paint, updated flooring, and a bright, inviting interior that feels both modern and timeless. The

  Shawna Wever Wever Realty LLC

  119 Tower Ln, Winchester, KY 40391
• 

  

  /18

  $260,000

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  280 Pine Ridge Rd, Winchester, KY 40391

  Bring your vision to life on 12+ beautiful acres in Winchester! This 3-bedroom, 1-bath home offers the charm of a 1964 build and the opportunity to create your own private retreat. With plenty of room for gardens, animals, workshops, or expansion, this property is perfect for those dreaming of country living. Renovate the existing home or reimagine the space to fit your needs — the possibilities

  Derek Blankenship Keller Williams Commonwealth

  280 Pine Ridge Rd, Winchester, KY 40391
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  /59

  $499,900

  • 4 Beds
  • 3 Baths
  • 5,646 Sq Ft

  16 Manor Dr, Winchester, KY 40391

  One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

  Zella Rosenthal Tom Goebel & Company

  16 Manor Dr, Winchester, KY 40391
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  /38

  $484,900

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,418 Sq Ft

  414 Fairholme Way, Winchester, KY 40391

  Step into a lifestyle where modern luxury and brand-new construction come together seamlessly in Fairholme Estates of Winchester. Perfectly positioned with golf course views and unforgettable sunset skies, this newly built home offers the kind of setting that turns ordinary evenings into your favorite part of the day—without sacrificing style, comfort, or convenience. Inside, soaring vaulted

  Morgan Withrow The Brokerage

  414 Fairholme Way, Winchester, KY 40391
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  /24

  $365,900

  New Construction $4K PRICE DROP

  • 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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  /10

  $550,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  107 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

  Shane Underwood Keller Williams Commonwealth

  107 Bella Shae Way, Winchester, KY 40391
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  /55

  $569,900

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  108 Bella Shae Way, Winchester, KY 40391

  Nearly new French country ranch that has been gently lived in. This classy home has magnificent curb appeal. When you walk through the front door you are welcomed by a tasteful foyer area. Stroll into the wide-open space of the great room with a towering, coffered ceiling and tons of natural light. The gas fireplace adds a nice focal point to the living space. The kitchen space is equipped with

  Vickie Skeens RE/MAX Elite Lexington

  108 Bella Shae Way, Winchester, KY 40391
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  /29

  $344,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,858 Sq Ft

  23 Windridge Dr, Winchester, KY 40391

  Welcome home!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family room. The

  Holly Goeing The Agency

  23 Windridge Dr, Winchester, KY 40391
• 

  

  /22

  $665,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,643 Sq Ft

  414 Alexis Way, Winchester, KY 40391

  Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added

  Shane Underwood Keller Williams Commonwealth

  414 Alexis Way, Winchester, KY 40391
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  /5

  $365,900

  New Construction $4K PRICE DROP

  • 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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  /55

  $359,900

  • 3 Beds
  • 2 Baths
  • 2,835 Sq Ft

  27 Hampton Ave, Winchester, KY 40391

  Located on desirable Hampton Avenue, this all-brick ranch is full of timeless character and thoughtful updates. Beautiful original hardwood floors run throughout the main level, highlighted by detailed craftsmanship and charm you don't find every day. The spacious living room features built-ins, a fireplace, and flows into the dining area, creating a warm and inviting space for everyday living or

  Terra Long Keller Williams Commonwealth

  27 Hampton Ave, Winchester, KY 40391
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  /55

  $329,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  1291 Muddy Creek Rd, Winchester, KY 40391

  Rare opportunity with TWO lots!! This cozy ranch home, originally built in 1952, but was completely remodeled down to the studs in 2023 (per Seller), offering the charm of an established home with the feel of modern construction. The open concept floor plan features a spacious family room flowing seamlessly into the kitchen, perfect for every day, living and entertaining. The layout provides

  Terri McGraw FC Tucker Bluegrass

  1291 Muddy Creek Rd, Winchester, KY 40391
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  /43

  $319,900

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft

  3622 Stamper Dr, Winchester, KY 40391

  This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. With recently installed vinyl siding, gutters and gutter guard properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming

  Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
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  /32

  $249,900

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

  528 Estes Dr, Winchester, KY 40391

  Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
• 

  

  /20

  $210,000

  • 3 Beds
  • 1 Bath
  • 1,386 Sq Ft

  301 Snowden Dr, Winchester, KY 40391

  Charming all-brick ranch offering timeless character and everyday functionality! Step inside to a light-filled living room featuring beautiful hardwood floors and a warm, welcoming feel throughout. This home offers three bedrooms and one full bathroom, along with an eat-in kitchen perfect for casual dining and gathering. A dedicated laundry/mud room just off the kitchen provides convenient access

  Julia Lark The Brokerage

  301 Snowden Dr, Winchester, KY 40391
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  /87

  $2,999,000

  $101K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 3,693 Sq Ft

  3049 Ironworks Rd, Winchester, KY 40391

  Some properties are special simply because of the story behind them. This 150-acre farm in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function

  Zova Rothchild Keller Williams Legacy Group

  3049 Ironworks Rd, Winchester, KY 40391
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  /9

  $785,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  425 Alexis Way, Winchester, KY 40391

  Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for

  Shane Underwood Keller Williams Commonwealth

  425 Alexis Way, Winchester, KY 40391
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  /21

  $139,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  9 Linden Ave, Winchester, KY 40391

  Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval,

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
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  /3

  $670,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,261 Sq Ft

  113 Bella Shae Way, Winchester, KY 40391

  Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

  Shane Underwood Keller Williams Commonwealth

  113 Bella Shae Way, Winchester, KY 40391
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  /84

  $775,000

  $25K PRICE DROP

  • 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
• 

  

  /20

  $312,000

  $95K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,858 Sq Ft

  200 Dubuy Dr, Winchester, KY 40391

  Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full

  Wayne Elkins RE/MAX Creative Realty

  200 Dubuy Dr, Winchester, KY 40391
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  /34

  $444,000

  • 3 Beds
  • 2 Baths
  • 2,442 Sq Ft

  1478 Donaldson Rd, Winchester, KY 40391

  Tucked away at the end of a long, private driveway, this unique brick ranch sits on just over 5 manicured acres and offers the perfect blend of space, comfort, and functionality. Designed for easy one-level living, the home features extra-wide hallways and doorways, a desirable split-bedroom floor plan and an open-concept layout ideal for everyday living and entertaining. The spacious kitchen

  Jim Woodrum RE/MAX Creative, Winchester

  1478 Donaldson Rd, Winchester, KY 40391
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  /12

  $179,000

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  175 Magnolia St, Winchester, KY 40391

  Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to

  A. Rebecca Woods Woods Realty Group

  175 Magnolia St, Winchester, KY 40391
• 

  

  /31

  $255,900

  • 3 Beds
  • 2 Baths
  • 1,446 Sq Ft

  123 Sunset Heights, Winchester, KY 40391

  You will love the atmosphere of this remodeled 3 bedroom, 2 bath home located in a secluded location. The large privacy fenced back yard is perfect for the children or pets. Renovated kitchen includes granite countertops, new range, dishwasher , and refrigerator. Home has a full partially finished walk out basement. You will love the large outbuilding as well as storage closet off of carport.

  Keith Wilson Coldwell Banker McMahan

  123 Sunset Heights, Winchester, KY 40391
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  /11

  $148,000

  $7K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  19 3rd St, Winchester, KY 40391

  3BR/1BA | Winchester, KY Affordable single-family homes are hard to come by at this price — here's your chance. This cozy 3-bedroom, 1-bath home in Winchester sits on a generous lot with a large backyard, long driveway with plenty of parking, a welcoming covered front porch, and accessible front entry with both steps and a ramp. it's efficient and easy to maintain — and don't let the square

  Anthony Gigilo ListWithFreedom.com

  19 3rd St, Winchester, KY 40391
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  /50

  $250,000

  • 3 Beds
  • 1 Bath
  • 1,042 Sq Ft

  217 Short St, Winchester, KY 40391

  This charming ranch home in a desirable neighborhood offers the perfect opportunity for first-time buyers, downsizers, or anyone looking for a move-in ready home with simple, comfortable living. Featuring 3 bedrooms and 1 full bath, this home includes plank flooring, fresh paint updates, updated kitchen appliances, and a functional layout designed for everyday convenience. The extended carport

  Josh Wood Freedom Realty & Property Management

  217 Short St, Winchester, KY 40391
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  /16

  $160,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,097 Sq Ft

  220 E Washington St, Winchester, KY 40391

  Investors take note, tenant occupied home, 3 bedrooms, 1 bathroom, one level living! Flippers, downsizing, or First-time buyers get ready! Wood style floors, covered front porch, back yard with patio...Do not miss an opportunity to add to your rental portfolio investment, start your real estate adventure, or make this home your own! Home is occupied 24-hour notice is required to show.

  Whitney Ensor Ensor Real Estate, LLC

  220 E Washington St, Winchester, KY 40391
• 

  

  /4

  $625,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,405 Sq Ft

  424 Alexis Way, Winchester, KY 40391

  Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile

  Shane Underwood Keller Williams Commonwealth

  424 Alexis Way, Winchester, KY 40391
• 

  

  /55

  $525,000

  • 3 Beds
  • 2 Baths
  • 2,563 Sq Ft

  935 Stoner-Ephesus Rd, Winchester, KY 40391

  Picture this: over five acres of Kentucky countryside, a handsome ranch-style home, and enough elbow room to finally breathe. This stunning 2,563 square foot retreat delivers the rare combination of refined interior finishes and genuine rural charm, all without sacrificing modern convenience. Inside, discover a generous family room anchored by a striking stone fireplace — the kind of space that

  Timothy Saylor Threshold Real Estate Services

  935 Stoner-Ephesus Rd, Winchester, KY 40391
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  /15

  $139,900

  • 2 Beds
  • 1 Bath
  • 986 Sq Ft

  174 Cook Ave, Winchester, KY 40391

  Charming Fixer-Upper with Endless Potential - Priced to Sell!! This older gem is full of character and opportunity! Featuring solid bones and classic charm, this property is perfect for buyers with a vision who are not afraid to add a little TLC! Whether you're an investor, DIY entusiast, or someone dreaming of restoring a home to its former glory, this is your chance to build equity and create

  A. Rebecca Woods Woods Realty Group

  174 Cook Ave, Winchester, KY 40391
• 

  

  /21

  $249,900

  $20K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,610 Sq Ft

  120 Windsor Dr, Winchester, KY 40391

  Welcome home to this cozy brick charmer in the desirable Belair Subdivision of Winchester, KY! This inviting 4 bedroom, 1 bath home offers comfortable living with a warm electric fireplace perfect for relaxing evenings. The spacious layout provides flexibility for family, guests, or a home office. Step outside to a fully fenced backyard ideal for pets, play, or enjoying quiet mornings with your

  Team Farthing - Mitch Farthing Southern Legacy Realty

  120 Windsor Dr, Winchester, KY 40391
• 

  

  /31

  $189,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  5434 Pine Ridge Rd, Winchester, KY 40391

  Jim Woodrum RE/MAX Creative, Winchester

  5434 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /38

  $299,900

  • 3 Beds
  • 2 Baths
  • 2,128 Sq Ft

  147 Sunset Heights, Winchester, KY 40391

  This charming 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and potential! On a large corner lot in a cute, established neighborhood, this property features a spacious detached garage ideal for storage, hobbies, or workshop space. Inside, you'll find a functional layout with plenty of natural light and room to make it your own. The large partially unfinished basement provides

  Lyndsey Martin Kentucky Land and Home

  147 Sunset Heights, Winchester, KY 40391
• 

  

  /3

  $825,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,995 Sq Ft

  111 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. Thespacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a

  Shane Underwood Keller Williams Commonwealth

  111 Bella Shae Way, Winchester, KY 40391
• 

  

  /27

  $235,000

  • 4 Beds
  • 2 Baths
  • 1,431 Sq Ft

  13 Arlington Rd, Winchester, KY 40391

  One Level Living!!!! This home boasts all the curb appeal with new vinyl siding, new roof and new leaf filter gutter system on home all in 2025!! A vinyl style privacy fenced in back yard, mature trees and beautiful landscaping! 4 bedrooms, 2 full bathrooms, Kitchen with all appliances (range, dishwasher, refrigerator, microwave) with updated flooring! Hardwood floors are showcased in the main

  Whitney Ensor Ensor Real Estate, LLC

  13 Arlington Rd, Winchester, KY 40391

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