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Explore Similar Condos Within 25 Miles of Winchester, KY

  • /35

    $270,000

    • 1 Bed
    • 1.5 Baths
    • 862 Sq Ft

    121 N Martin Luther King Blvd Unit 401, Lexington, KY 40507

    If you are looking for a great corner unit with a view than you have found it. This 4th floor unit has a great view of downtown Lexington along with garage parking and an elevator and secured entry. Unit 401 is located in the historic Nunn building and just moments from the Kentucky Theater, Rupp, The Opera House, Gratz Park, UK and Transy along with Bars, Dining and so so much more.

    Brandon Hedinger Keller Williams Bluegrass Realty

    121 N Martin Luther King Blvd Unit 401, Lexington, KY 40507
  • /62

    $329,000

    • 2 Beds
    • 2 Baths
    • 1,737 Sq Ft

    906 Paddock Ct, Richmond, KY 40475

    Beautifully maintained and incredibly spacious, this 2-bedroom, 2-bath home seamlessly blends style and function. The open-concept layout features a large kitchen with granite countertops, abundant cabinet space, an island, and a sunny eat-in area, plus a formal dining room—ideal for entertaining. The inviting living room boasts a gas log fireplace, while gleaming hardwood floors flow throughout

    Angela Murray RE/MAX Elite Lexington

    906 Paddock Ct, Richmond, KY 40475
  • /29

    $459,900

    • 2 Beds
    • 2 Baths
    • 1,727 Sq Ft

    200 W Second St Unit 300, Lexington, KY 40507

    Rare opportunity to own a two-story penthouse in a prime downtown location—just steps from Rupp Arena, Transylvania University, Gratz Park, the Opera House, and a variety of local dining and entertainment options. This open-concept loft features exposed brick, hardwood floors, and a striking spiral staircase. Large windows flood the space with natural light. The first-floor bedroom includes a

    Emily Miller Bluegrass Sotheby's International Realty

    200 W Second St Unit 300, Lexington, KY 40507
  • /39

    $379,900

    • 3 Beds
    • 2.5 Baths
    • 2,764 Sq Ft

    2408 Aristocracy Cir, Lexington, KY 40509

    Located in the sought-after Hamburg Farms community, this well maintained condo boasts interior upgrades and modern finishes. The main level includes the primary bedroom with vaulted ceiling and updated ensuite, a spacious two-story family room with large windows, gorgeous kitchen with granite countertops, stainless appliances & pantry, and a separate dining area. Two large bedrooms and a guest

    Amanda Thomas The Agency

    2408 Aristocracy Cir, Lexington, KY 40509
  • /59

    $499,900

    • 3 Beds
    • 3 Baths
    • 2,650 Sq Ft

    248 Clairmont Dr, Richmond, KY 40475

    Stunning 3 Bedroom, 3 Full Bath Condo in gated community, Clairmont at Grey Oaks! This meticulously maintained home offers hardwood floors throughout the main level, a spacious open layout, and a serene, private setting. The main floor features a large primary suite with a walk-in closet, soaking tub, and separate shower, as well as an additional ensuite bedroom. The kitchen opens to the dining

    Kim Caywood The Real Estate Co.

    248 Clairmont Dr, Richmond, KY 40475
  • /59

    $319,900

    • 2 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    2626 Old Rosebud Rd, Lexington, KY 40509

    Looking for maintenance free living? Come see this beautiful, totally remodeled condo in the heart of Hamburg! Some features include two spacious primary bedrooms with ensuite bathrooms, open airy concept from great room to the kitchen including custom cabinets with soft close doors, added kitchen island with drawers and granite countertops, new flooring throughout, gas fireplace, finished

    Jennifer Jordan United Real Estate Bluegrass

    2626 Old Rosebud Rd, Lexington, KY 40509
  • /27

    $451,000

    • 2 Beds
    • 2 Baths
    • 1,691 Sq Ft

    257 S Limestone Unit 101, Lexington, KY 40508

    This is a great opportunity to own a first floor condo in the historic Kimball House Square. Designed and built in the mid-1800s by Architect Cincinnatus Shryouck and famed builder John McMurtry, this condo is ideal for those seeking a blend of historic charm and character with modern amenities. In 2007, the building was renovated and converted into two condos. This unit features a spacious

    Lee King Kinglander Company

    257 S Limestone Unit 101, Lexington, KY 40508
  • /13

    $312,000

    • 1 Bed
    • 1 Bath
    • 790 Sq Ft

    535 S Upper St Unit 317, Lexington, KY 40508

    Say Hello To A Good ''Buy''!Enjoy Downtown living close to Uk Campus.Walk to restaurants, outside venues, and a variety of entertainment that Lexington has to offer.

    Andy Conners Conners Real Estate & Auction

    535 S Upper St Unit 317, Lexington, KY 40508
  • /17

    $275,000

    • 1 Bed
    • 1 Bath
    • 582 Sq Ft

    650 S Mill St Unit 219, Lexington, KY 40508

    Discover the perfect blend of comfort and convenience in this condo located in the heart of Lexington. Featuring sleek stainless steel appliances and an open-concept layout, this second-floor unit provides ample natural lighting. Enjoy your morning coffee or unwind after a long day on your private balcony. Just steps away from the University of Kentucky's campus, this prime location offers easy

    Cherise Wilson Diamond Key Realtors

    650 S Mill St Unit 219, Lexington, KY 40508
  • /18

    $263,850

    • 3 Beds
    • 2 Baths
    • 1,025 Sq Ft

    205 Simpson Ave Unit 310, Lexington, KY 40504

    Rare opportunity to own a unit in Campus Downs Condominiums. Walking distance to UK, close to downtown, Rupp Arena, Transylvania University, St.Joseph Hospital, UK Hospitals and Red Mile. 3 bedroom, 2 full bath condo are great for investors, first-time homebuyers, or someone who wants to downsize. Walking distance to nearby restaurants-great location! 3 BR 2 BA Condo

    Diana C Brooker Lifstyl Real Estate

    205 Simpson Ave Unit 310, Lexington, KY 40504
  • /8

    $285,000

    • 2 Beds
    • 1 Bath
    • 870 Sq Ft

    1802 Carolyn Dr Unit 3, Lexington, KY 40502

    Updated condo in highly sought after 40502 area. The condo features hardwood floors, updated bathroom and kitchen, wonderful new light fixtures and tile work, storage area in the basement, and lots of parking in the private lot and on a quiet street. The patio area is in the process of being expanded.

    Hill Parker Turf Town Properties

    1802 Carolyn Dr Unit 3, Lexington, KY 40502
  • /23

    $299,000

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft

    1802 Carolyn Dr Unit 4, Lexington, KY 40502

    Updated condo in highly sought after 40502 area. The condo features hardwood floors, updated bathroom and kitchen, wonderful new light fixtures and tile work, storage area in the basement, and lots of parking in the private lot and on a quiet street. The patio area is in the process of being expanded. A similar unit is coming in March if you want to pick your own colors and cabinets.

    Hill Parker Turf Town Properties

    1802 Carolyn Dr Unit 4, Lexington, KY 40502
  • /22

    $269,500

    • 2 Beds
    • 2.5 Baths
    • 1,130 Sq Ft

    2621 Calgary, Lexington, KY 40509

    Diana C Brooker Lifstyl Real Estate

    2621 Calgary, Lexington, KY 40509
  • /23

    $189,500

    • 2 Beds
    • 1.5 Baths
    • 1,104 Sq Ft

    2905 Affirmed Ct Unit D, Lexington, KY 40509

    Updated condo for sale in desired Hamburg Neiborhood. New roof, gutters, and freshly painted throughout. Back corner unit, very private and quiet. Great for an investment property or easy condo living. Two dedicated parking spaces. Tenant lease expires 8/31 or can be renewed.

    Perry Tussey ERA Select Real Estate

    2905 Affirmed Ct Unit D, Lexington, KY 40509
  • /32

    $235,000

    • 2 Beds
    • 2 Baths
    • 1,457 Sq Ft

    2312 Remington Way Unit 3311, Lexington, KY 40511

    Welcome to this bright and airy 2-bedroom, 2-bath condo with a versatile den/office—perfect for working from home or creating a cozy den. Located on the 3rd floor, this unit boasts soaring vaulted ceilings and an open-concept layout that feels very spacious and inviting!Enjoy the convenience of an automatic garage plus a close, assigned parking spot. The community offers fantastic

    Abby Jones Bluegrass Sotheby's International Realty

    2312 Remington Way Unit 3311, Lexington, KY 40511
  • /39

    $165,000

    • 2 Beds
    • 2 Baths
    • 784 Sq Ft

    404 Bainbridge Ct Unit E3, Lexington, KY 40509

    Now Available! - Updated 2-bedroom, 2-bath condo located in the Hamburg neighborhood. Situated on the second floor, this unit features a spacious living room with vaulted ceilings that create an open, airy feel. The home is enhanced with modern LVT flooring throughout and a contemporary kitchen complete with stainless steel appliances. Step outside to enjoy your private deck — perfect for

    Kristi Osborne Bluegrass Property Exchange

    404 Bainbridge Ct Unit E3, Lexington, KY 40509
  • /24

    $225,000

    • 2 Beds
    • 1.5 Baths
    • 1,095 Sq Ft

    131 Regency Point Path, Lexington, KY 40503

    This adorable quaint gated community, Regency Point is tucked away with a beautiful pool and common area near UK, hospitals, shopping and dining. Adorable condo main floor features an inviting living room, spacious eat in kitchen with great cabinetry, appliances and a area for dining table, laundry closet, washer dryer stays and a half bath. Upstairs with a well appointed primary bedroom, one

    Debbie Pennington CENTURY 21 Advantage Realty

    131 Regency Point Path, Lexington, KY 40503
  • /40

    $659,000

    • 2 Beds
    • 2 Baths
    • 1,437 Sq Ft

    355 S Broadway Unit 102, Lexington, KY 40508

    Coming Soon!! In the heart of downtown Lexington. No expense spared in this head turning remodeled '23, 2 full BDRM 2 full BA condo. Experience true indoor/outdoor living in the city with the folding glass doors open to the wrap around terrace with its' own living/bar area. Terrace area also features gas fire-pit and turf. Seldom offered 1st floor unit. Only 4 in the building have this extended

    Lynne Sneed Lynne Sneed Real Estate

    355 S Broadway Unit 102, Lexington, KY 40508
  • /32

    $244,900

    • 2 Beds
    • 2.5 Baths
    • 1,248 Sq Ft

    2629 Calgary, Lexington, KY 40509

    Welcome to effortless living in the heart of desirable Hamburg Farms! This move-in ready condominium offers comfort and style with a low-maintenance lifestyle. Featuring two spacious primary suites—each with private en-suite bathrooms showcasing granite countertops and ceramic tile floors—this home is perfect for roommates, guests, or flexible living. The open-concept main floor is ideal for

    Lura Justice Rector Hayden Realtors

    2629 Calgary, Lexington, KY 40509
  • /19

    $142,900

    • 2 Beds
    • 1.5 Baths
    • 850 Sq Ft

    305 Lake St Unit 13, Nicholasville, KY 40356

    Cute 2 bed 1 1/2 bath condo with patio. Updated with new kitchen with tiled backsplash, new carpet, new linoleum, new toilets, tiled shower, new windows, new doors and freshly painted. Washer/Dryer hookup in unit. HOA includes common area maintenance, insurance, management, trash collection as well as water & sewer. Located near shopping, restaurants and walking distance to park.

    Kenneth Watts WATTS REALTORS & AUCTIONEERS

    305 Lake St Unit 13, Nicholasville, KY 40356
  • /73

    $539,900 Open Sun 2PM - 4PM

    • 4 Beds
    • 2.5 Baths
    • 3,188 Sq Ft

    236 Clairmont Dr, Richmond, KY 40475

    Spacious and stylish, this 2-story condo offers over 3,000 sq ft of living space plus a walkout basement that's pre-framed and plumbed for a full bath—ready for your finishing touch! The main level features a luxurious primary suite, a gas fireplace in the living room, crown molding in select rooms, and soaring ceilings that open to an upstairs catwalk. The kitchen includes a large island, tile

    Tina Witt Keller Williams Legacy Group

    236 Clairmont Dr, Richmond, KY 40475
  • /19

    $245,000

    • 1 Bed
    • 1 Bath
    • 1,358 Sq Ft

    201 Price Rd Unit 103, Lexington, KY 40511

    Enjoy living in a true loft building in downtown Lexington. FULLY FURNISHED from sheets to silverware. High ceilings, large windows and lots of flexible space, indoor garage and storage building. Gym also included. This is an estate sale, call for your private showing today

    Melisa McDonald Wrenn Realty

    201 Price Rd Unit 103, Lexington, KY 40511
  • /17

    $160,000

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft

    421 Redding Rd Unit 99, Lexington, KY 40517

    Welcome to Aintree Condominium Community | Unit 99 features One-Level living with NO STEPS | TWO Bedrooms and TWO Bathrooms |Kitchen FULLY RENOVATED in 2025 features all NEW Stainless-steel Range, Built-In Microwave, Dishwasher, & Refrigerator | HARDWOOD FLOORING through Living Room and Bedrooms | TILE FLOORING in both Bathrooms | In-Unit Laundry with Washer & Dryer to REMAIN | MOVE-IN READY

    Melissa Gabehart Homepage Realty

    421 Redding Rd Unit 99, Lexington, KY 40517
  • /28

    $235,000

    • 2 Beds
    • 2 Baths
    • 1,124 Sq Ft

    600 Vincent Way Unit 4305, Lexington, KY 40503

    Welcome to effortless living at Wellington Chase! This top-floor 2-bed, 2-bath condo features vaulted ceilings and a spacious open layout that instantly feels like home. The living and dining areas are perfect for cozy nights in or hosting your people, while the kitchen opens right into the action.Enjoy a private deck for morning coffee or sunset views, a generous primary suite with a walk-in

    Dalis Alvarez The Agency

    600 Vincent Way Unit 4305, Lexington, KY 40503
  • /20

    $155,000

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft

    421 Redding Rd Unit 56, Lexington, KY 40517

    Tired of lawn work and mending fences? Come check out carefree living where you don't have to mow, paint or shovel snow again. And it comes with a pool - that you don't have to maintain. This beautiful 2 bedroom, 2 bath condo has new LVP flooring throughout (NO carpet) and has been freshly painted so it is move in ready. And location? You can't beat it. Close to downtown Lex, UK, shopping and

    Diana Nash Bluegrass Home Group

    421 Redding Rd Unit 56, Lexington, KY 40517
  • /61

    $3,795,000

    • 3 Beds
    • 3.5 Baths
    • 5,989 Sq Ft

    103 S Limestone Unit 1150, Lexington, KY 40507

    Welcome to this stunning high-end fully furnished luxury condo located in The Penthouses of City Center in the heart of downtown Lexington. This state of the art condo boasts of marble flooring throughout and breathtaking floor-to-ceiling glass windows that offer panoramic views of three different city skylines. Step outside onto one of the two balconies and experience the bustling energy of

    Whitney Durham Bluegrass Sotheby's International Realty

    103 S Limestone Unit 1150, Lexington, KY 40507
  • /24

    $240,000

    • 2 Beds
    • 2 Baths
    • 1,454 Sq Ft

    2312 Remington Way Unit 1203, Lexington, KY 40511

    Gorgeous thoughtfully updated and spacious 2 bed 2 full bath condo with convenient access to the interstate, New Circle and within a 5 minute walk to Publix. Updates include new flooring throughout, kitchen countertops, kitchen sink, light and plumbing fixtures, and more. The primary bedroom is off the hallway that also leads to the flex area and both bedrooms have walk in closets. The kitchen

    Joseph Smallwood Christies International Real Estate Bluegrass

    2312 Remington Way Unit 1203, Lexington, KY 40511
  • /22

    $135,000

    • 1 Bed
    • 1 Bath
    • 599 Sq Ft

    175 Malabu Dr Unit 60, Lexington, KY 40503

    This newly remodeled 1 bedroom condo is located in the sought after Malabu Terrace area with close access to downtown Lexington and the University of KY, New Circle Rd, with lots of shopping and restaurant options. With all new appliances and luxury vinyl plank flooring this move-in ready condo is a must-see. The Malabu Terrace Condominium Association offers two laundry room facilities, a pool,

    Donna Mink Mink Realty

    175 Malabu Dr Unit 60, Lexington, KY 40503
  • /33

    $263,500

    • 2 Beds
    • 2.5 Baths
    • 1,595 Sq Ft

    2429 Aristocracy Cir, Lexington, KY 40509

    Welcome to this move-in ready, 2-bedroom, 2.5-bath condo, located in the highly desirable Hamburg Farms community! This well-maintained home features an updated kitchen with solid surface countertops, minimal carpet, and a flexible, first-floor bonus space, perfect for a home office, play room, or guest space. Each bedroom offers its own private en suite bathroom, providing comfort and privacy

    Corey Brown The Brokerage

    2429 Aristocracy Cir, Lexington, KY 40509
  • /16

    $115,000

    • 1 Bed
    • 1 Bath
    • 690 Sq Ft

    1092 Armstrong Mill Rd Unit A, Lexington, KY 40517

    Convenient and affordable ground floor living! This one bedroom one bath unit is freshly painted with an updated bath. A private patio offers a bit of the outdoors without the upkeep. Wonderful location close to shopping, restaurants and parks. Call to tour this cozy condo!

    Lindsay Barsotti ERA Select Real Estate

    1092 Armstrong Mill Rd Unit A, Lexington, KY 40517
  • /39

    $262,500

    • 2 Beds
    • 2.5 Baths
    • 1,700 Sq Ft

    2605 Calgary, Lexington, KY 40509

    Beautiful one-owner condo in prime location! This spacious 3 story townhouse-style condo has been lovingly maintained by its original owner. The first floor features a private office/bonus room, coat closet and an attached 2 car garage. The second level offers a bright and open great room with a modern kitchen, generous dining area, and convenient half bath-perfect for entertaining. Upstairs,

    Jana Thore Kentucky Real Estate Group

    2605 Calgary, Lexington, KY 40509
  • /5

    $105,000

    • 1 Bed
    • 1 Bath
    • 604 Sq Ft

    175 Malabu Dr Unit 77, Lexington, KY 40503

    Investor Opportunity! Discover comfortable, low-maintenance living in this charming one-bedroom, one-bath condo ideally located near the Nicholasville Road corridor and the University of Kentucky. Situated in a well-maintained condo complex, this unit offers convenient access to shopping and dining. Enjoy community amenities like a swimming pool and beautifully landscaped grounds—all with the

    Karen Angelucci RE/MAX Elite Lexington

    175 Malabu Dr Unit 77, Lexington, KY 40503
  • /9

    $140,000

    • 2 Beds
    • 2 Baths
    • 894 Sq Ft

    1281 Village Dr Unit C9, Lexington, KY 40504

    Why rent when you can own for less. Call today it won't last. All utilities included in HOA. Tenants work nights showings between 5pm to 9pm

    Kevin Mangold Goshen Real Estate, LLC

    1281 Village Dr Unit C9, Lexington, KY 40504
  • /27

    $345,000

    • 1 Bed
    • 1.5 Baths
    • 851 Sq Ft

    369 E Main St Unit 304, Lexington, KY 40507

    Welcome to a sleek, updated modern condo nestled in the vibrant heart of downtown Lexington. This home is ideal for anyone looking to experience urban living at its finest, with easy walking access to a variety of shops, exciting events, and nightlife spots. Inside, the condo boasts a sophisticated design, blending contemporary finishes with clean lines and an open-concept layout that maximizes

    Michelle Gunter Bluegrass Home Group

    369 E Main St Unit 304, Lexington, KY 40507
  • /20

    $163,500

    • 2 Beds
    • 2 Baths
    • 970 Sq Ft

    1036 Armstrong Mill Rd Unit D, Lexington, KY 40517

    Move-in ready second floor 2 bedroom 2 full bath condo in Fox and Hound. $235/month Condo fees include gas, water, sewer, trash removal, building insurance, common area maintenance and snow removal

    Diana C Brooker Lifstyl Real Estate

    1036 Armstrong Mill Rd Unit D, Lexington, KY 40517
  • /40

    $395,000

    • 3 Beds
    • 3 Baths
    • 2,400 Sq Ft

    1646 Old Silo Hill Dr, Mount Sterling, KY 40353

    Nestled in the heart of Silver Creek Subdivision this remarkable property offers all the amenities of a retirement community and a residential neighborhood, making it an ideal choice for those 55+ seeking a unique and comfortable living experience. The condo boasts a large living room and dining area perfect for family gatherings and entertaining guests and a kitchen equipped with ample granite

    Pam Murphy Kentucky Realty Group, LLC

    1646 Old Silo Hill Dr, Mount Sterling, KY 40353
  • /46

    $399,900

    • 2 Beds
    • 1.5 Baths
    • 937 Sq Ft

    369 E Main St Unit 501, Lexington, KY 40507

    Upscale Downtown Living at its Finest, located Across the Street from Carson's and Within Walking Distance to Everything—Don't Miss Out on this 2 Bedroom, 1.5 Bath Condo—Large Master 12x14 and Home Office 10x12 that Can Easily be Used as a 2nd Bedroom (no closet)---Top Floor Unit Allows for Taller Ceilings than the Other Units Providing a Much More Spacious Feel---Checkout ALL the

    Bret Hansen Four Seasons Realty

    369 E Main St Unit 501, Lexington, KY 40507
  • /21

    $261,500

    • 3 Beds
    • 2 Baths
    • 959 Sq Ft

    1081 S Broadway Unit 104, Lexington, KY 40504

    Rare opportunity to own a unit in Campus View Condominiums. Walking distance to UK, close to downtown, Transylvania University, St.Joseph Hospital, UK Hospitals and Red Mile. 3 bedroom, 2 full bath condo are great for investors, first-time homebuyers, or someone who wants to downsize. Walking distance to nearby restaurants-great location!

    Diana C Brooker Lifstyl Real Estate

    1081 S Broadway Unit 104, Lexington, KY 40504
  • /19

    $251,500

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft

    251 Simpson Ave Unit 222, Lexington, KY 40504

    Great investment opportunity within walking distance of the University of Kentucky.

    Diana C Brooker Lifstyl Real Estate

    251 Simpson Ave Unit 222, Lexington, KY 40504
  • /21

    $257,500

    • 3 Beds
    • 2 Baths
    • 1,050 Sq Ft

    251 Simpson Ave Unit 220, Lexington, KY 40504

    Rare opportunity to own a unit in Campus Downs Condominiums. Walking distance to UK, close to downtown, Rupp Arena, Transylvania University, St.Joseph Hospital, UK Hospitals and Red Mile. 3 bedroom, 2 full bath condo are great for investors, first-time homebuyers, or someone who wants to downsize. Walking distance to nearby restaurants-great location! 3 BR 2 BA Condo

    Diana C Brooker Lifstyl Real Estate

    251 Simpson Ave Unit 220, Lexington, KY 40504

Why Live in Winchester

Winchester, nestled in Clark County, offers a blend of historical charm and modern amenities. Known for its beer cheese and Ale-8-One soda, Winchester boasts a thriving local economy with numerous unique recipes. The neighborhood features Victorian-era homes, Sears homes, and newer properties suitable for families, often with spacious lawns and gravel driveways. College Park, centrally located, offers basketball, tennis, hiking, and picnic spots, while Lykins Park provides a playground, skate park, and a nine-hole disc golf course. Legacy Grove Park, a 30-acre space, includes a playground, paved walking paths, and a dog park. Main Street is the hub for dining, with popular spots like La Trattoria and Loma’s, and the Beer Cheese Trail featuring around 15 restaurants with signature recipes. Local attractions include the annual Daniel Boone Pioneer Festival and the Beer Cheese Festival, which draw large crowds. The Bluegrass Heritage Museum showcases Central Kentucky's history. Winchester is 16 miles from Lexington and about 20 miles from Richmond, making it a convenient location for commuters. Clark Regional Medical Center has expanded its services in recent years, enhancing local healthcare options.

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$245,000
Median Single Family Sale Price
$270,000
Median Townhouse Sale Price
$194,000
Average Price Per Sq Ft
$162
Number of Homes for Sale
104
Last 12 months Home Sales
372
Months of Supply
3.40
Median List Price
$274,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
1%
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