Stuarts Addition Real Estate

Stuarts Addition Real Estate

Welcome to Stuarts Addition, a charming subdivision nestled in the heart of Winchester, KY. This quaint neighborhood is located in Clark County, offering a peaceful and close-knit community for residents to call home.

Stuarts Addition is known for its tree-lined streets, well-maintained sidewalks, and a variety of home styles to suit every taste. Whether you're looking for a cozy bungalow or a spacious family home, you'll find it here in Stuarts Addition.

Residents of this lovely subdivision enjoy easy access to local amenities, including nearby parks, schools, and shopping centers. Winchester's vibrant downtown area is just a short drive away, where you can explore local boutiques, restaurants, and community events.

With its convenient location and friendly atmosphere, Stuarts Addition is the perfect place to settle down and enjoy all that Winchester has to offer. Come and discover the charm and beauty of Stuarts Addition – where community, comfort, and convenience come together to create the perfect place to call home.

Newest Listings in Stuarts Addition

$270,000
6 Beds ⋅ 4 Baths ⋅ 26019498 MLS
Outstanding opportunity for investors or owner-occupants! This beautifully updated duplex is located in Winchester's desirable Stuarts Addition and offers two spacious units, each featuring approximately 1,545 square feet with 3 bedrooms and 2 full bathrooms. Both units have been thoughtfully renovated and feature hardwood flooring throughout the main living areas with tile in the wet areas for style and durability. Major improvements include newer HVAC systems, roof, stainless steel appliances, windows, doors, vinyl siding, and fresh interior paint, providing true move-in-ready convenience and low-maintenance ownership. Ideally located within walking distance of College Park and historic downtown Winchester, this property also offers quick access to I-64, shopping, restaurants, schools, and everyday amenities. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this well-maintained duplex offers the perfect combination of modern updates, strong income potential, and an exceptional location.

21 Beckner St, Winchester
$515,000
26002170 MLS
This versatile mixed-use property offers a rare opportunity to combine business potential with built-in residential income. Formerly operated as a neighborhood market, the commercial building spans over 3,000 square feet and is thoughtfully equipped with a full kitchen and laundry area, making it ideal for a wide range of business concepts. Whether you envision a café, restaurant, retail shop, office space, event venue, service-based business, or creative studio, the layout and infrastructure provide a flexible foundation ready to be reimagined. With strong visibility and a neighborhood presence, this property is well-positioned for an owner-operator or investor seeking adaptability and long-term value. Adding to its appeal is the separate 3-bedroom residential home located at 35 Hays, which is currently income-producing and leased through 2027. This creates an immediate revenue stream while you develop, occupy, or lease the commercial space a powerful advantage for offsetting costs or maximizing returns. Opportunities like this offering commercial flexibility, residential income, and long-term potential are increasingly rare. Whether you're expanding a business, launching something new, or investing with vision, this property delivers the space, structure, and upside to make it happen.

35-37 Hays St, Winchester
$149,900
3 Beds ⋅ 2 Baths ⋅ 26013935 MLS
Lovely older home, located witin waking distance to collage park whice offers Pickle Ball, Pool, Tennis, play gound and Walking Trail, also walking distance to Historic Downtown Winchester, with a little love house brings large rooms and a nostlogic atmosphire, take a look, view today, this a a great price for 3 bedrooms, 1 1/2 baths, nice back yard, with parking, call today! Selling "AS IS", inspections welcome, the are no utilties on at the present, Estate Please make sure all doors are locked when you leave, buyer to verifye size of home & Lot

65 Fitch Ave, Winchester
$299,999
3 Beds ⋅ 3 Baths ⋅ 26004053 MLS
This beautiful 1.5-story home offers all the charm of downtown in a small town, with a library, park, and restaurants nearby. Plus, just minutes to Lexington when the city is calling your name. This home has been remodeled for modern living, featuring an open floor plan. There is plenty of room for entertaining with a beautiful, well-equipped kitchen and a large island open to both the dining space and the living room. The first floor features all the luxuries, including a primary suite with an ensuite bathroom and a large walk-in closet, a dedicated laundry/mud room, and a powder room. Upstairs, you'll find two spacious bedrooms and an additional bathroom. The entertaining doesn't have to stop inside, as there is also a covered patio and a large fenced-in backyard ready for play. There's so much to this charmer, including a covered parking spot and an unfinished basement for additional storage.

322 S Burns Ave, Winchester
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