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Winchester, KY Homes for Sale under $200,000

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  • /22

    $147,000

    • 2 Beds
    • 1 Bath
    • 807 Sq Ft

    3208 Ford Hampton Rd, Winchester, KY 40391

    Escape to a lifestyle defined by the peace and natural beauty of this delightful two bedroom property just steps away from the majestic Kentucky River, this home isn't just a place to iive, it is a dedicated sanctuary whether you are seeking a cozy year round residence or a recreational retreat. One of the standout features is the exceptioal connection to the outdoors with generous porches on

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    (859) 765-6889

    3208 Ford Hampton Rd, Winchester, KY 40391
  • /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
  • /2

    $150,000

    • Land
    • 2.77 Acres
    • $54,152 per Acre

    3385 Colby Rd, Winchester, KY 40391

    Small acreage lot on Colby Road! Accessed by easement from neighbors driveway.

    Steve Adams Steven D Adams Real Estate Services, LLC

    3385 Colby Rd, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.47 Acre
    • $234,043 per Acre

    139 Jacob Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    139 Jacob Ct, Winchester, KY 40391
  • /2

    $150,000

    • Land
    • 2.11 Acres
    • $71,090 per Acre

    125 Knox Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    125 Knox Ct, Winchester, KY 40391
  • /17

    $129,900

    • 2 Beds
    • 1 Bath
    • 876 Sq Ft

    122 Calloway St, Winchester, KY 40391

    Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless

    Darrell Tackett Dream Maker Realty, LLC

    122 Calloway St, Winchester, KY 40391
  • /4

    $137,500

    • Land
    • 3.94 Acres
    • $34,898 per Acre

    12569 Ironworks Rd, Winchester, KY 40391

    Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it gows in value. Offering unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by

    Kathryn Cheuvront Coldwell Banker McMahan

    12569 Ironworks Rd, Winchester, KY 40391
  • /19

    $125,000

    • Land
    • 4.01 Acres
    • $31,172 per Acre

    1940 Athens Boonesboro Rd, Winchester, KY 40391

    Escape to tranquility with this beautiful 4-acre lot in Clark County, offering the perfect setting to build your dream home. Tucked away on a quiet road, this property is surrounded by expansive farmland, ensuring ultimate privacy and peaceful living. A serene pond adds to the charm, providing a perfect spot to relax and enjoy the natural beauty of the land. This lot sits directly across from the

    Laura Sizemore Kentucky Land and Home

    1940 Athens Boonesboro Rd, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.32 Acre
    • $343,750 per Acre

    250 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    250 Duclair Dr, Winchester, KY 40391
  • /21

    $139,000

    • 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
  • /26

    $184,000

    • 2 Beds
    • 1.5 Baths
    • 1,102 Sq Ft

    356 Colby Ridge Blvd, Winchester, KY 40391

    This cozy 2-bedroom, 1.5-bath home is the perfect fit for first-time buyers or anyone looking to expand their investment portfolio. The inviting living room features a propane-operated fireplace that provides a reliable backup heat source. The spacious primary bedroom includes his-and-her closets, and both bedrooms are equipped with additional split units for personalized comfort. A full

    Nena Honaker Tom Goebel & Company

    356 Colby Ridge Blvd, Winchester, KY 40391
  • /2

    $195,000

    6699 Boonesboro Rd, Winchester, KY 40391

    READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

    Jennifer Ray RE/MAX Elite Lexington

    6699 Boonesboro Rd, Winchester, KY 40391
  • /6

    $110,000

    • Land
    • 2.06 Acres
    • $53,398 per Acre

    1185 Craig Crossing Rd, Winchester, KY 40391

    Lot # 30 contains 2.058 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

    Keith Wilson Coldwell Banker McMahan

    1185 Craig Crossing Rd, Winchester, KY 40391
  • /2

    $150,000

    • Land
    • 2.16 Acres
    • $69,444 per Acre

    120 Knox Ct, Winchester, KY 40391

    Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    120 Knox Ct, Winchester, KY 40391
  • /27

    $198,000

    • 2 Beds
    • 1 Bath
    • 1,223 Sq Ft

    616 Boone Ave, Winchester, KY 40391

    Begin the New Year in your own home! It's a new beginning...Make an appoint to look at this two bedroom, one bath ranch. It has new paint and updated flooring. Range refrigerator and dishwasher are included, There is a nice size laundry room. The kitchen has lots of cabinets and there is an additional pantry in the hall. The dining room is off the kitchen and overlooks the living room. The rear

    Garnett Davis Tom Goebel & Company

    616 Boone Ave, Winchester, KY 40391
  • /23

    $180,000

    • 2 Beds
    • 1 Bath

    220 Jackson St, Winchester, KY 40391

    Welcome to 3769 Winthrop Drive in Lexington, KY 40514 - a fantastic opportunity to own a home in one of South Lexington's most convenient and sought-after areas. Tucked into an established neighborhood, this property offers the perfect combination of comfort, accessibility, and everyday functionality. Step inside to discover a welcoming layout designed for both relaxing and entertaining. The

    Hunter Miller GSP Homes

    220 Jackson St, Winchester, KY 40391
  • /14

    $129,800

    • Land
    • 2.3 Acres
    • $56,435 per Acre

    110 Knox Ct, Winchester, KY 40391

    The largest and most desirable lot in The Reserve is now available! Nestled in a cul-de-sac, this 2.3 acre tract offers exceptional views of Bluegrass farmland. Build your custom dream home and watch the sun set over the pond, right from your porch. Located in one of Winchester's newest luxury subdivisions, featuring carefully crafted guidelines to preserve the community's character. All of this

    Amanda Thomas The Agency

    110 Knox Ct, Winchester, KY 40391
  • /16

    $169,900

    • 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
  • /2

    $110,000

    • Land
    • 0.27 Acre
    • $407,407 per Acre

    125 Jacob Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    125 Jacob Ct, Winchester, KY 40391
  • /8

    $195,000

    • Land
    • 6.15 Acres
    • $31,707 per Acre

    990 Craig Crossing Rd, Winchester, KY 40391

    Lot # 13 contains 6.153 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

    Keith Wilson Coldwell Banker McMahan

    990 Craig Crossing Rd, Winchester, KY 40391
  • /3

    $146,000

    • 3 Beds
    • 1 Bath
    • 1,020 Sq Ft

    228 Jackson St, Winchester, KY 40391

    Here's your chance to own a nice investment property. This single family home has a 3 bed 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

    David Espinosa Bluegrass Realty Pros, Inc

    228 Jackson St, Winchester, KY 40391
  • /4

    $115,000

    • 4 Beds
    • 2.5 Baths
    • 2,131 Sq Ft

    205 E Washington St, Winchester, KY 40391

    PRICE DROP!!! FLIP This House! Seller Has Added A Large Primary Addition And Front Porch. This 4 Bedroom 2 1/2 Bath Home Is Ready For Your Finishes And Has A Fantastic Floor Plan With Large Loft (Whole Home At Stud Level). Finish This Home It Will Be A Showstopper Better Than New Construction With Large Sq Ft What Many Buyers Are Looking For. Great Opportunity To Make Money Or Live In This

    Patrick Arvin Keller Williams Commonwealth

    205 E Washington St, Winchester, KY 40391
  • /4

    $199,900

    • Land
    • 11.36 Acres
    • $17,597 per Acre

    2996 Irvine Rd, Winchester, KY 40391

    Are you looking to build your dream home in a quiet country setting with easy access to the Interstate? Look no further! This property offers it all! Gorgeous setting with the best views and creek access. This lovely farm is 11.36 acres of gently rolling country land, in a highly desirable area with easy access to interstate 64, the Mountain Parkway and Hamburg. No city sewage. Deed restrictions

    Lura Justice Rector Hayden Realtors

    2996 Irvine Rd, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.32 Acre
    • $343,750 per Acre

    115 Jacob Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    115 Jacob Ct, Winchester, KY 40391
  • /27

    $165,000

    • 2 Beds
    • 1 Bath
    • 1,088 Sq Ft

    233 E Washington St, Winchester, KY 40391

    Welcome to 233 E. Washington Street, a charming ranch-style home offering comfort, space, and convenience in the heart of Winchester. The Roof, Windows and HVAC are updated. This 2-bedroom, 1-bath residence features an open-concept layout designed for easy living and everyday functionality. LVP flooring runs throughout the home, providing a clean, modern look that's both durable and low

    Lukas Owens The Brokerage

    233 E Washington St, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.5 Acre
    • $220,000 per Acre

    260 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    260 Duclair Dr, Winchester, KY 40391
  • /27

    $175,000

    • 3 Beds
    • 2 Baths
    • 1,305 Sq Ft

    6 Monroe Ave, Winchester, KY 40391

    Charming and Updated Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a beautifully maintained 3-bedroom, 2-bath home full of character and modern touches. Step inside to find an inviting family room with an updated shiplap fireplace surround, perfect for cozy evenings. The kitchen is filled with natural light and features granite countertops, making it both stylish and functional.

    Lindsey Bivens Berkshire Hathaway de Movellan Properties

    6 Monroe Ave, Winchester, KY 40391
  • /7

    $180,000

    • Land
    • 4.45 Acres
    • $40,449 per Acre

    1030 Craig Crossing Rd, Winchester, KY 40391

    Lot # 14 contains 4.450 acres of gently rolling land with small stream perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

    Keith Wilson Coldwell Banker McMahan

    1030 Craig Crossing Rd, Winchester, KY 40391
  • /14

    $159,900

    • Land
    • 2.66 Acres
    • $60,113 per Acre

    590 Craig Crossing, Winchester, KY 40391

    Don't let this opportunity pass you by again. This prime lot in Thoroughbred Estates is back on the market due to Current owners change of plans. This lot is ready for your new home with a beautiful setting and located close to Winchester and Lexington in a new Luxury Subdivision. Watch the sun set each night from your rear deck or pool. Call today!!!

    Keith Wilson Coldwell Banker McMahan

    590 Craig Crossing, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.68 Acre
    • $147,059 per Acre

    100 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    100 Duclair Dr, Winchester, KY 40391
  • /21

    $189,500

    • 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
  • /12

    $189,900

    • 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

    41 7th St, Winchester, KY 40391
  • /12

    $110,000

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

    400 Wexford Dr, Winchester, KY 40391

    Welcome! This home offers a practical layout with 3 bedrooms and 1.5 baths on a manageable 0.2-acre lot. The interior has been well maintained, and fenced backyard creates a private outdoor space ideal for gatherings, pets, or future improvements. A detached 2-car garage provides secure parking and storage. Approximately 5 minutes to downtown Winchester and 15 minutes to Lexington, positioning

    Katie Allen Keller Williams Legacy Group

    400 Wexford Dr, Winchester, KY 40391
  • /39

    $175,000

    • 2 Beds
    • 1.5 Baths
    • 1,202 Sq Ft

    1494 Amster Grove Rd, Winchester, KY 40391

    Welcome to this charming river front house. Step out your back door and you are immediately at the river. Open floor plan with a wood burning fireplace. Metal cabinets and epoxy floors on the first level are designed to survive in case of a flood. First floor bedroom with enough room for a King sized bed. Upstairs you will find another bedroom and a half bath. Sip your morning coffee on your back

    Libby VanMeter Marshall Lane Real Estate - Lexington

    1494 Amster Grove Rd, Winchester, KY 40391
  • /9

    $102,000

    • 2 Beds
    • 1 Bath
    • 552 Sq Ft

    39 S Highland St, Winchester, KY 40391

    Here's your chance to own a nice investment property. This Single Family home has 2 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

    David Espinosa Bluegrass Realty Pros, Inc

    39 S Highland St, Winchester, KY 40391
  • /12

    $144,000

    • 3 Beds
    • 1 Bath
    • 805 Sq Ft

    150 Cook Ave, Winchester, KY 40391

    Here's your chance to own a nice investment property. This has a single family has 3 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

    David Espinosa Bluegrass Realty Pros, Inc

    150 Cook Ave, Winchester, KY 40391
  • /12

    $194,900

    • 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
  • /20

    $134,900

    • 3 Beds
    • 1 Bath
    • 1,150 Sq Ft

    103 Yorktowne Ct, Winchester, KY 40391

    Affordable and move in ready! This home will qualify for FHA, VA &/or Rural Housing Loan. This charming 3 bedroom, 1 bath home offers the perfect opportunity for first-time buyers, down-sizers, or investors. With a welcoming layout, comfortable living spaces, and a great location in Winchester, this property is an excellent value in today's market. Enjoy the convenience of nearby shopping,

    Susy Esquivel Allied Realty

    103 Yorktowne Ct, Winchester, KY 40391
  • /13

    $140,000

    • 2 Beds
    • 1 Bath
    • 1,254 Sq Ft

    208 4th St, Winchester, KY 40391

    Discover the potential of this spacious 0.27-acre residential home nestled in a neighborhood community on clear and level land located in a Cul-de-sac of Lincoln Park Subdivision. This Property features 2-bedrooms, 1-Bathroom, a large family room with a fireplace. There is also a large versatile barn on the property as well. This could be an investment opportunity as well, for ideal savvy

    Anita McDermott Keller Williams Bluegrass Realty

    208 4th St, Winchester, KY 40391

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$255,000
Median Single Family Sale Price
$260,500
Median Townhouse Sale Price
$191,750
Average Price Per Sq Ft
$162
Number of Homes for Sale
78
Last 12 months Home Sales
328
Months of Supply
2.90
Median List Price
$265,500
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
9%
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