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Explore Similar Homes Within 25 Miles of Winchester, KY

  • /31

    $275,000

    • 1 Bed
    • 1 Bath
    • 1,641 Sq Ft

    201 Price Rd Unit 217, Lexington, KY 40511

    Trendy Loft-Style Condo Just 1 Mile from Downtown & Manchester - Under $300K! Looking for modern, urban living in one of Lexington's most exciting locations? Welcome to this ultra-stylish 1.5-story condo, ideally located just one mile from both prime downtown Lexington and the buzzing Manchester/Distillery District. With industrial-chic design elements like polished concrete floors, exposed brick

    Carrie Lepore Coldwell Banker McMahan

    201 Price Rd Unit 217, Lexington, KY 40511
  • /57

    $525,000

    • 1 Bed
    • 1 Bath
    • 1,413 Sq Ft

    514 W Short St Unit 103, Lexington, KY 40507

    Unique, elegant condo in the heart of downtown Lexington offering a refined blend of modern luxury and artistic design. The Great Room showcases a distinctive fireplace that seamlessly connects to the Kitchen. At the same time, a sparkling silver handmade crystal chandelier serves as a stunning focal point, casting sophisticated, ambient light throughout the space. The Kitchen is thoughtfully

    Lana Rovinelli RE/MAX Creative Realty

    514 W Short St Unit 103, Lexington, KY 40507
  • /32

    $429,900

    • 1 Bed
    • 1 Bath
    • 297 Sq Ft

    9501 Campton Rd, Stanton, KY 40380

    Rare Red River Gorge opportunity on over 5 acres just off the main Gorge exit in Stanton, KY. This unique property features a private river with a natural swimming hole, a steel covered bridge over the water, a climbing rock, and expansive usable land with room to build additional structures. Improvements include a studio cabin, a barn currently used with a camper setup, a renovated outdoor

    Jenny Perron EXP Realty, LLC

    9501 Campton Rd, Stanton, KY 40380
  • /13

    $109,000

    • 1 Bed
    • 1 Bath
    • 854 Sq Ft

    318 E Sixth St, Lexington, KY 40508

    As-Is listing. Cozy 1-bedroom, 1-bath home just minutes from downtown Lexington — priced to move. This vacant property is move-in ready and offers a fantastic opportunity for buyers at every level. Whether you're looking for an affordable starter home in a prime location, or a cash-flowing addition to your investment portfolio, this one delivers. Sold as-is at an attractive price point — schedule

    Dylan Palmer Bluegrass Rental Management LLC

    318 E Sixth St, Lexington, KY 40508
  • /14

    $145,000

    • 1 Bed
    • 1 Bath
    • 825 Sq Ft

    186 Eddie St, Lexington, KY 40508

    Quaint starter home or investment property. Home has 1 bedroom, 2 small bonus rooms are long and narrow suitable for office space, storage or bunk beds. Completely fenced front and back with a sliding gate in the back. Large concrete slab in the back that can be used for parking or for a patio area. Home is heated and cooled with split hvac systems.

    Cynthia Hubbard RE/MAX Creative Realty

    186 Eddie St, Lexington, KY 40508
  • /24

    $129,900

    • 1 Bed
    • 1 Bath
    • 742 Sq Ft

    421 Redding Rd Unit 72, Lexington, KY 40517

    Freshly updated and move-in ready, this third-floor, one-bedroom condo in Aintree offers comfort, convenience, and a prime location. New flooring enhances the main living areas, complementing the open floor plan and abundant closet space. Step outside to a spacious private deck overlooking peaceful green space--perfect for relaxing or entertaining. The unit comes fully equipped with all

    S Ann Wesley Assurance Realty & Property Management

    421 Redding Rd Unit 72, Lexington, KY 40517
  • /31

    $200,000

    • 1 Bed
    • 1 Bath
    • 815 Sq Ft

    101 S Hanover Ave Unit 5H, Lexington, KY 40502

    One bedroom condo at the beautiful classy Hanover Towers with views of the park area in the median of Hanover Avenue. Amenities include two parlors in the entry. Weekly Happy Hours on site. Rooftop Deck with great views of the city and neighborhoods. Basement laundry, fitness room, individual locked storage area, restrooms. Walk to so many restaurants , retail, Chevy Chase, downtown, Henry Clay's

    Kathy Winger Prestige Investments

    101 S Hanover Ave Unit 5H, Lexington, KY 40502
  • /21

    $225,000

    • 1 Bed
    • 384 Sq Ft

    1649 High Rock Rd, Stanton, KY 40380

    2-Acre Off-Grid Tiny House Paradise Cozy tiny house with loft ideal for minimalist living or a serene getaway. Wired for electricity, offering convenience with off-grid potential. Several areas for garden sites for growing your own produce. Access to a fresh spring water for natural water supply. Nestled in a nature lovers paradise surrounded by serene landscapes. Just 25 minutes from The Natural

    Heather Isaacs Lifstyl Real Estate

    1649 High Rock Rd, Stanton, KY 40380
  • /7

    $108,000

    • 1 Bed
    • 1 Bath
    • 552 Sq Ft

    369 Massie Ave, Paris, KY 40361

    Attention investors!!! Here's an opportunity to add to your portfolio, 1 Bed / 1 Bath home with updates that has a nice partially fenced back yard. Walking distance from downtown. Appliances stay with the home. New lease just signed for $1000.00

    Chad S. Nichols Nichols Real Estate

    369 Massie Ave, Paris, KY 40361
  • /13

    $112,000

    • 1 Bed
    • 1 Bath
    • 604 Sq Ft

    175 Malabu Dr Unit 96, Lexington, KY 40503

    BACK ON MARKET .Buyers financing fell thru. Malabu Terrace Condo Available for sale AS-IS . Enjoy your private balcony, In ground pool, in a park like setting. Electric, water, sewer, trash, ground maintenance are all included in your HOA fee. All you need is a phone. Close to shopping, hospitals and UK. Laundry room available in same building.

    Glen Lesnau Keller Williams Legacy Group

    175 Malabu Dr Unit 96, Lexington, KY 40503
  • /21

    $92,450

    • 1 Bed
    • 1 Bath
    • 560 Sq Ft

    105 Patricia Rd, Clay City, KY 40312

    Affordable 560 square foot home conveniently located between Stanton and Clay City. This 1-bedroom, 1-bath property offers a functional layout with an open kitchen and living area. The home is equipped with a stove and an installed heat source and features a walk-in shower. The efficient footprint allows for low-maintenance living and easy upkeep. Ideal for buyers seeking a primary residence,

    Jacqueline Townsend RE/MAX Creative, Winchester

    105 Patricia Rd, Clay City, KY 40312
  • /45

    $194,500

    • 1 Bed
    • 1 Bath
    • 805 Sq Ft

    101 S Hanover Ave Unit 8K, Lexington, KY 40502

    Experience the height of luxury at downtown's most prestigious address 101 South Hanover Avenue. This upscale residence offers a lifestyle of security and sophistication, beginning with an extravagant secure entry monitored week days by a doorman and featuring two elegant recreation areas perfect for enjoying social gatherings plus a rooftop patio. Would be ideal for a young professional or a

    Cathy Cornett-Wilson Rector Hayden Realtors

    101 S Hanover Ave Unit 8K, Lexington, KY 40502
  • /61

    $899,900

    • 1 Bed
    • 1 Bath
    • 1,920 Sq Ft

    1751 West Ln, Nicholasville, KY 40356

    Equestrian Paradise in the Heart of Jessamine County! This exceptional 32+ acre farm offers the ideal canvas to bring your equine dreams to life. At the heart of the property is a charming barndominium featuring 1 bedroom, 2 full baths, a spacious eat-in kitchen, dining room, office, and a large family room, perfect for comfortable living or a weekend retreat. Attached is a 5-stall barn complete

    Maggie Taylor RE/MAX Creative Realty

    1751 West Ln, Nicholasville, KY 40356
  • /28

    $269,000

    • 1 Bed
    • 1 Bath
    • 1,152 Sq Ft

    645 Right Fork Fixer Rd, Irvine, KY 40336

    Cabin + Campground at Peaceful Valley Resort Near Red River Gorge. Rare investment opportunity. This rustic cabin with an established campground sits inside Peaceful Valley Resort, offering a creekside retreat near Hollerwood Off-Road Park, PMRP climbing area, and Red River Gorge. Ideal for outdoor enthusiasts, short-term rentals, or expanding into a glamping destination. The property features a

    Heather Isaacs Lifstyl Real Estate

    645 Right Fork Fixer Rd, Irvine, KY 40336
  • /28

    $102,500

    • 1 Bed
    • 1 Bath
    • 869 Sq Ft

    409 Ash St, Lexington, KY 40508

    Affordability in a very convenient location, 409 Ash Street offers an entry foyer, living room, full bath, kitchen, laundry and primary bedroom on main level, upstairs is finished with foyer area and two bonus rooms that could be used as bedrooms. This area is noncompliant and not included in room count or square footage. Home was built before 1978 and Lead Based paint potentially exists. No

    Kimberly Brunson Hunter Real Estate

    409 Ash St, Lexington, KY 40508
  • /17

    $110,000

    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    334 Oak St, Lexington, KY 40508

    Affordable, updated, and close to it all! 334 Oak St offers spacious rooms, updated flooring, fresh paint, and a new water heater. Enjoy a fully fenced yard plus a cozy covered front porch. Minutes from downtown, Newtown Rd, Georgetown Rd, and New Circle — this move-in-ready home is a fantastic find at this price point.

    Chaney Hughes Red 1 Realty

    334 Oak St, Lexington, KY 40508
  • /33

    $149,900

    • 1 Bed
    • 1 Bath
    • 660 Sq Ft

    840 Malabu Dr Unit 110, Lexington, KY 40502

    Opportunity for homeowners and investors alike. Well established, quiet and welcoming, this condo offers privacy as well as convenience, shopping, dining, main roads and entertainment are all within walking distance or just a short drive away. You won't want to miss out on this opportunity, Call today for your private showing.

    Robin Morgan Keller Williams Commonwealth

    840 Malabu Dr Unit 110, Lexington, KY 40502
  • /25

    $124,900

    • 1 Bed
    • 1 Bath
    • 512 Sq Ft

    633 Ohio St, Lexington, KY 40508

    This compact home is conveniently located near downtown Lexington. Warm bamboo hardwood floors throughout the living room, bedroom, and kitchen. The kitchen has white shaker style cabinets, butcher block countertops, and includes a range, refrigerator, and over the range microwave. The bathroom is finished with ceramic tile including a walk in ceramic tile shower. There is even a washer/dryer

    Brian Raisler Mayca Property Solutions

    633 Ohio St, Lexington, KY 40508
  • /31

    $124,900

    • 1 Bed
    • 1 Bath
    • 622 Sq Ft

    342 Waller Ave Unit 6D, Lexington, KY 40504

    Enjoy easy, budget-friendly living just minutes from the University of Kentucky and downtown Lexington. This bright and cheerful one-bedroom condo at 342 Waller Place offers a smart, open layout designed for comfort and convenience. The sunny living area features laminate hardwood floors and opens to a cute kitchen with stainless steel appliances. The spacious bedroom includes a walk-in closet

    Gwen Mathews Bluegrass Sotheby's International Realty

    342 Waller Ave Unit 6D, Lexington, KY 40504
  • /14

    $100,000

    • 1 Bed
    • 1 Bath
    • 1,300 Sq Ft

    7650 Chase Ln, Jeffersonville, KY 40337

    Located in the heart of downtown Jeffersonville, 7650 Chase Lane offers a rare opportunity to own a distinctive 1-bedroom, 1-bath property with a fascinating history. Formerly a restaurant, this versatile space has been thoughtfully converted for either residential living or business use, blending character with functionality. The open layout highlights its commercial roots while providing

    Bob Sophiea eXp Realty, LLC

    7650 Chase Ln, Jeffersonville, KY 40337
  • /22

    $230,000

    • 1 Bed
    • 1 Bath
    • 985 Sq Ft

    5100 Kendall Springs Rd, Owingsville, KY 40360

    Adorable 2023 Home on 1 Acre - Move-In Ready! Discover easy living in this charming 1-bedroom, 1.5-bath home featuring nearly 1,000 sq. ft. of thoughtfully designed space! Built in 2023, this modern home offers an open floor plan that feels bright, comfortable, and welcoming from the moment you step inside. The kitchen comes fully equipped with appliances, and the washer and dryer are

    Jill Ratliff Paragon Realty Partners

    5100 Kendall Springs Rd, Owingsville, KY 40360
  • /5

    $95,000

    • 1 Bed
    • 1 Bath
    • 200 Sq Ft

    7482 W Tunnel Hill Rd, Sharpsburg, KY 40374

    Discover simple country living at 7482 W Tunnel Hill Road — a peaceful rural retreat surrounded by rolling Kentucky countryside. This 2023-built tiny home offers efficient, modern living with 1 bedroom, 1 bath, and a full kitchen inside approximately 200 sq. ft. of well-designed space. Enjoy the comfort of city water and sewer, and low-maintenance living on a .32-acre lot. A 10x30 storage trailer

    Bart Daily EXP Realty, LLC

    7482 W Tunnel Hill Rd, Sharpsburg, KY 40374
  • /12

    $225,000

    • 1 Bed
    • 1 Bath
    • 640 Sq Ft

    1237 High Rock Rd, Stanton, KY 40380

    Charming New Construction Retreat on 1.68 Acres. Welcome to your brand new getaway nestled in a beautiful forest setting along scenic High Rock Road! This thoughtfully crafted 1 bedroom, 1 bathroom home blends rustic charm with modern comforts, offering an ideal escape or year-round residence. Built on a durable pier, beam & block foundation, this home features high-end finishes

    Heather Isaacs Lifstyl Real Estate

    1237 High Rock Rd, Stanton, KY 40380
  • /15

    $148,000

    • 1 Bed
    • 1 Bath
    • 1,248 Sq Ft

    69 Pecks Ridge Tilton Rd, Flemingsburg, KY 41041

    Welcome to this cute little home that is approx. 1248 sf. and sits on .8 acre. Has 1 bedroom & 1 bath. This property is located in the community of Tilton. Includes 2 Amish buildings & a gazebo & has area for garden. Has a covered front porch and a covered patio for your outdoor entertaining!

    Robyn Ramey 606 Real Estate & Auctions

    69 Pecks Ridge Tilton Rd, Flemingsburg, KY 41041

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$259,400
Median Single Family Sale Price
$262,500
Median Townhouse Sale Price
$194,000
Average Price Per Sq Ft
$161
Number of Homes for Sale
80
Last 12 months Home Sales
330
Months of Supply
2.90
Median List Price
$268,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
10%
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