32

Winchester, KY Homes under $300,000

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  • /62

    $275,950

    • 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
  • /24

    $249,900

    • 3 Beds
    • 2 Baths
    • 1,644 Sq Ft

    114 Bayberry Ln, Winchester, KY 40391

    Move right in! 3-bedroom 2 bath 1/2 story home. Upstairs bedrooms have been freshly painted. Both bathrooms have been updated. Garage was converted to a family room and laundry area in 2016. The home as 2 freestanding fireplaces (no blowers) Fenced in backyard with firepit area and 8x8 pergola. 10x16 storage shed with separate meter. 2 sump pumps.

    Debra Ward Coldwell Banker McMahan

    114 Bayberry Ln, Winchester, KY 40391
  • /15

    $249,900

    • 3 Beds
    • 2 Baths
    • 1,463 Sq Ft

    234 Prescott Ln, Winchester, KY 40391

    Welcome Home! This stunning 1.5-story home is ready for its next owner! The primary suite is conveniently located on the ground floor, featuring a large walk-in closet for all your storage needs. The cozy living room boasts vaulted ceilings, creating an open, airy feel, while the brand-new tile shower in the full downstairs bathroom adds a touch of modern elegance. Upstairs, you'll find two

    Darrell Tackett Dream Maker Realty, LLC

    234 Prescott Ln, Winchester, KY 40391
  • /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, 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 have given attention to every

    Susan Colwell Colwell Realty Professionals

    113 Olde Potomac Ave, 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
  • /48

    $274,000

    • 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
  • /27

    $279,900

    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft

    707 Terry Dr, Winchester, KY 40391

    Welcome to 707 Terry Dr, Winchester, KY, a beautifully updated 3-bedroom, 2.5-bathroom home that blends modern comfort with a warm, inviting feel.Step inside to a spacious kitchen featuring custom cabinetry, updated appliances, and plenty of counter space perfect for everything from busy mornings to dinner with friends. The adjoining dining area with a cozy stone fireplace makes every

    Kymberly Clem EXP Realty, LLC

    707 Terry Dr, 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
  • /2

    $240,000

    • Land
    • 12 Acres
    • $19,835 per Acre

    155 Spring Ridge Way, Winchester, KY 40391

    Great opportunity to develop/ build on 12+ acres. The property has three street stubs adjoining it. Three different concepts are included under documents. They are-R-1E, 4000 sq. Ft lots for 80 lotsR-4- 14 Duplexes and 6 4plexes for 52 units R-1D - 6000 sq. Ft. Lots for 41 lots. Utilities are to the property and sewer availability should not be an issue. Please feel free to call the listing

    Jo Gawthrop Keller Williams Bluegrass Realty

    155 Spring Ridge Way, Winchester, KY 40391
  • /21

    $215,000

    • 4 Beds
    • 2 Baths
    • 1,480 Sq Ft

    523 Acadia Way, Winchester, KY 40391

    This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of AMI for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

    Tyler I Back The Brokerage

    523 Acadia Way, Winchester, KY 40391
  • /22

    $229,000

    • 3 Beds
    • 2 Baths
    • 1,210 Sq Ft

    122 Spruce Ct, Winchester, KY 40391

    RENOVATED Brick Ranch Home * 3 Bedrooms, 2 Full Baths, plus separate Laundry Room, Deck and Covered Front Porch! Updates in 2022 include: Tall White Kitchen Cabinets, Tile Backsplash, New Countertops, Sink, Faucet & Stainless Appliances * Primary Suite with Spacious Closet, New Vanity and Tiled Walk-in Shower with Body Sprayer Shower System * Guest Bath with New Vanity and Tiled Bathtub Area *

    Christal Browning Four Seasons Realty

    122 Spruce Ct, Winchester, KY 40391
  • /27

    $290,000

    • 3 Beds
    • 2.5 Baths
    • 1,690 Sq Ft

    602 Laura Dr, Winchester, KY 40391

    Is it summer yet? This updated ranch is perfect entertaining, featuring an in-ground pool and walk-out basement. Just 10 minutes from Hamburg, enjoy all the perks of Lexington in a quiet neighborhood just over the county line. This all-brick ranch home features 3 bedrooms, 3 bathrooms and a backyard perfect for a summer BBQ. Seller has made numerous upgrades, including all-new vinyl flooring on

    Ryan O'Gara Real Broker, LLC

    602 Laura Dr, Winchester, KY 40391
  • /16

    $210,000

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft

    128 Alabama St, Winchester, KY 40391

    Charm meets convenience in this delightful newly renovated home! Experience city living at its finest with the tranquility of your own spacious backyard, yet be within walking distance to shops and restaurants! Step inside the living room and let the natural light peeking through the large windows welcome you home. With a bedroom on the main floor, two bedrooms upstairs, and a bonus room that

    Paul Eads Woods Realty Group

    128 Alabama St, Winchester, KY 40391
  • /23

    $249,900

    • 3 Beds
    • 3 Baths
    • 2,536 Sq Ft

    244 Bay Hill Ct, Winchester, KY 40391

    A super rare opportunity to own a townhome with all the luxuries and space of a single family home! From the open floor plan to the gleaming hardwood floors, this home has so much to offer! With three bedrooms on the main floor and a potential fourth on the lower level, this home has room for everyone. Whether you like to play inside or out there's room for both. The basement has a huge bonus

    Destiny Darby Keller Williams Commonwealth

    244 Bay Hill Ct, Winchester, KY 40391
  • /46

    $229,500

    • 3 Beds
    • 2 Baths
    • 1,167 Sq Ft

    115 Georgia St, Winchester, KY 40391

    ✨ ''Warm, inviting, and full of character—your dream home awaits!'' 🔥 ''Cozy up by the fireplace in a home that feels like home!'' 🏡 ''Classic charm meets modern convenience in this Winchester gem!'' 🌳 ''Tranquility meets accessibility—peaceful neighborhood, minutes from downtown!'' 🚗 ''Detached garage = extra storage, workspace, and convenience!'' 💎

    Darrell Tackett Dream Maker Realty, LLC

    115 Georgia St, Winchester, KY 40391
  • /24

    $224,000

    • 3 Beds
    • 1 Bath
    • 1,420 Sq Ft

    13365 Ironworks Rd, Winchester, KY 40391

    Charming and fully renovated, this 3-bedroom, 1-bathroom home offers the perfect blend of modern style and cozy comfort. With a fresh white exterior accented in black and a brand-new metal roof, it stands out with timeless curb appeal and lasting durability.Inside, every detail has been thoughtfully updated, from the sleek modern kitchen to the stylish lighting fixtures that brighten the

    Joshua Davis The Agency

    13365 Ironworks Rd, 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
  • /21

    $229,900

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    520 Barlow Dr, Winchester, KY 40391

    Newly renovated home just waiting for a new owner. This 3 bedroom, 2 full bath home features all new appliances, new flooring, new paint, new roof, and much, much more. The fenced back yard is perfect for your children whether they be 2 legged or 4 legged. Located in Holiday Hills close to shopping, schools, parks, and medical care. Call your lender today to see if you qualify for the Welcome

    Keith Wilson Coldwell Banker McMahan

    520 Barlow Dr, 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
  • /10

    $215,000

    211 Ashton Oak Way, Winchester, KY 40391

    Here is the Blank Canvas to build your Dream Home in the Plantation Subdivision. This two story brick building, formerly the Sales Office for the Subdivision, has been gutted to offer the unique opportunity to build a 3118 Sq Ft Home consisting of Four Bedrooms, Two and Half Baths, an open concept on the main level with the addition of a two car garage. Contact listing agent to discuss current

    Melia Hord Keller Williams Bluegrass Realty

    211 Ashton Oak Way, Winchester, KY 40391
  • /25

    $240,000

    • 3 Beds
    • 2 Baths
    • 1,518 Sq Ft

    313 S Burns Ave, Winchester, KY 40391

    Great opportunity to own this historic charmer with 3 bedrooms and 2 bathrooms in the heart of Winchester. As you enter you will notice beautiful hardwood floors, beautiful woodwork, high ceilings, and a functional floor plan. The primary suite features two closets, a fireplace, and there is a renovated bathroom with tile shower. The backyard has a deck and a large 2 car detached garage. Most of

    Ryan Hilliard The Brokerage

    313 S Burns Ave, Winchester, KY 40391
  • /65

    $279,000

    • 4 Beds
    • 1.5 Baths
    • 1,873 Sq Ft

    151 Hilltop Dr, Winchester, KY 40391

    Lovely ranch on a basement home in a small rural neighborhood. This location is the perfect blend of rural living but very convenient to everything! Less than 1 mile from the eastern bypass that provides fast access to I-64, downtown Winchester, parks, and shopping. Large half acre lot with fenced in backyard and a chicken coop! Large deck on the back for entertaining or just relaxing while

    Jason Townsend Kentucky Residential Real Estate, LLC

    151 Hilltop Dr, Winchester, KY 40391
  • /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
  • /33

    $261,000 Open Sun 2PM - 4PM

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

    14 Calloway St, Winchester, KY 40391

    Beautiful and completely remodeled! Welcome to this stunning home. As you pull up, you will notice a brand new driveway and the inviting front entry.Upon entering, you will love the open floor plan and the brand new luxury vinyl plank flooring. The bright inviting kitchen is just waiting for you to cook and entertain. With brand new cabinets, quartz countertops, stainless steel appliances and

    Libby VanMeter Marshall Lane Real Estate - Lexington

    14 Calloway St, Winchester, KY 40391
  • /14

    $232,500

    • 3 Beds
    • 2 Baths
    • 1,064 Sq Ft

    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
  • /26

    $239,900

    • 3 Beds
    • 2 Baths
    • 1,878 Sq Ft

    134 Boone Ave, Winchester, KY 40391

    Step into this inviting home at 134 Boone Avenue, where timeless charm and thoughtful details create a warm and welcoming atmosphere. The classic front porch sets the tone, while inside, vintage wood floors, beautiful foyer, and large windows flood each room with natural light. The spacious living room has a cozy, intimate feel, perfect for family gatherings or quiet nights in. A delightful

    steven lindsey CENTURY 21 Commonwealth R E

    134 Boone Ave, Winchester, KY 40391
  • /27

    $285,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,726 Sq Ft

    216 Prescott Ln, Winchester, KY 40391

    Conveniently located near shopping centers, schools and 6 minutes from the hospital. This home opens to a large den area which could easily be used for dining or flex space. The kitchen has plenty of room for entertaining with an island that opens to a spacious living room with fireplace. Plenty of room for parking in the attached garage. Upstairs features a separate laundry room, bedrooms and

    Brittany Lewis National Real Estate

    216 Prescott Ln, Winchester, KY 40391
  • /38

    $289,900

    • 4 Beds
    • 2 Baths
    • 1,924 Sq Ft

    217 Morris Rd, Winchester, KY 40391

    BIG Price Reduction!!! This is The one You Have Been Waiting For! Room For The Whole Family In The Country But Within 5 Minutes Of The Interstate. This 4 Bedroom 2 Bathroom Home With A Living Room And Family Room/Den With Open Kitchen Has It All. Property Includes An Above Ground Swimming Pool, TinyHome/Shed That Has Plumbing Already Ran And Electric At The Pole Right There. This Would Be

    Patrick Arvin Keller Williams Commonwealth

    217 Morris Rd, Winchester, KY 40391
  • /30

    $265,000

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    2721 Pretty Run Rd, Winchester, KY 40391

    Situated on 5 scenic acres along a highly sought-after country road, this 3-bedroom, 2-bath property presents an excellent opportunity to create your dream rural retreat. The home features a functional layout with a spacious living area, an eat-in kitchen, and a primary suite with its own bath. Two additional bedrooms offer flexibility for family, guests, or work-from-home needs. Outside, the

    Michelle Blackburn RE/MAX Creative, Winchester

    2721 Pretty Run Rd, Winchester, KY 40391
  • /12

    $209,900

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft

    222 Holiday Rd, Winchester, KY 40391

    Great location close t o down town Winchester, shopping, school, recreation areas, I 64 ,in beautiful Winchester,nice 3 bedroom ,1 bath , all brick home, with all appliances, including washer and dryer roof 1 year old, fenced yard, storage building private drive. nice back yard and more.

    Sophia Herald Herald Real Estate

    222 Holiday Rd, Winchester, KY 40391
  • /58

    $235,000

    • 3 Beds
    • 1.5 Baths
    • 1,161 Sq Ft

    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
  • /26

    $205,000

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    305 Geronimo Ct, Winchester, KY 40391

    If you are looking for one-level living, your search ends here. Nestled in Buffalo Trace subdivision, this ranch boasts three bedrooms and two full bathrooms. As you step inside, you are welcomed by a spacious living room that seamlessly connects to the kitchen breakfast area. The kitchen is adorned with a charming bay window, a unique feature that adds character to the space. Off the kitchen,

    Lucy Martin Jenkins United Real Estate Bluegrass

    305 Geronimo Ct, Winchester, KY 40391

Home Trends in Winchester, KY

Home Trends

Median Price (12 Mo)
$240,940
Median Single Family Price
$265,000
Median Townhouse Price
$190,000
Average Price Per Sq Ft
$158
Number of Homes for Sale
112
Last 12 months Home Sales
334
Months of Supply
4.00
Median List Price
$269,950
Median Discount From 1st List Price
3%
Median Home Sale Price YoY Change
1%
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