Winchester Homes with Basement Parking Features

Winchester Homes with Basement Parking Features

Welcome to Winchester, Kentucky—a charming city nestled in Clark County that beautifully blends small-town warmth with modern conveniences. Known for its rich history and vibrant community spirit, Winchester is a place where you can truly feel at home. With its picturesque landscapes, friendly neighborhoods, and a variety of local amenities, this city offers an inviting atmosphere for families, retirees, and young professionals alike.

One of the standout features of homes in Winchester is the availability of properties with basement parking. This practical and sought-after amenity not only provides protection for your vehicle from the elements but also offers additional storage space, which is a significant advantage for many homeowners. Imagine the convenience of having direct access to your home from the comfort of your basement, especially during those rainy Kentucky days!

Winchester's real estate market is diverse, with homes ranging from charming historic properties to modern constructions, all designed to cater to various lifestyles. The presence of basement parking features in many of these homes adds a layer of functionality and appeal, making them ideal for those who value both comfort and practicality.

In addition to its beautiful homes, Winchester boasts an array of parks, shops, and dining options, ensuring that residents have everything they need right at their fingertips. Whether you’re exploring the local farmer’s market, enjoying a leisurely stroll through one of the city's many parks, or indulging in a meal at a quaint café, Winchester has something for everyone.

Discover the charm and convenience of Winchester, KY, where your dream home with basement parking awaits!

Newest Winchester Homes with Basement Parking Features

4 Beds ⋅ 4 Baths ⋅ 26023265 MLS

Magnificent Home sitting on 2.446 Acres, Fantastic Location --Great Views on this 4 Bedroom, 4 Bath Brick Home with over 5,600 Sq. Ft. of Living space. This has a Huge Primary Bedroom with walk in Shower, 2 closets, Large Formal Dining Rm,--Stone Fireplace, Large Sun room with lots of Windows, Another Primary Bedroom upstairs w/Full Bath, Large Finished Basement, with Mother's in Law Quarters. Don't Miss this Great opportunity--Come se this huge Magnificent Home-- Buyer to measure for exact sq.ft of Home Home is vacant and nearing Completion.

1400 Craig Xing, Winchester

2 Beds ⋅ 2 Baths ⋅ 26022926 MLS

Unique Kentucky Riverfront retreat with fascinating history! This elevated 2-bedroom, 1.5 bath home was originally constructed from two wood rail cars, giving it a one-of-a kind character you won't find anywhere else. Thoughtfully updated with new windows, roof, HVAC and an updated shower, plus a spacious new deck perfect for relaxing and enjoying the beautiful river setting. Whether you are looking for a full-time residence, weekend retreat, or investment property, this charming riverfront property offers a wonderful opportunity to enjoy the beauty of Kentucky River living!

148 Hidden Grove Ln, Winchester

3 Beds ⋅ 3 Baths ⋅ 26022409 MLS

Welcome home to this spacious, low-maintenance townhome offering 3 levels of living space in a well established neighborhood. Thoughtfully maintained, a 3 year old roof, with recently replaced windows. This home offers plenty of room to spread out while keeping everyday living comfortable and convenient. The main level features a generously sized kitchen and family room with plenty of space for entertaining or gathering with family and friends. The lower level adds even more flexibility with a bonus room that could serve as a home office, recreation room, workout space, or additional living area. Upstairs you'll find 3 bedrooms, 2 full bathrooms, and ample closet space throughout. Outside, enjoy a large backyard backing to green space, along with the convenience of a rear-facing garage and a neighborhood walking trail. Ideally located with quick access to I-64 and approximately 20 minutes from Lexington's Hamburg area, this home combines space, updates, low-maintenance living, and a convenient location in one inviting package. Schedule your private showing today!

127 Bay Hill Dr, Winchester

4 Beds ⋅ 5 Baths ⋅ 26022150 MLS

This gorgeous home is a rare find. Perfect for anyone looking for a spacious home with room to grow. The beautiful sunroom overlooks the luxurious in-ground salt water pool. Inside the home you'll find over 4,000 square feet of easy living. A beautiful kitchen with a breakfast nook and bar top, a formal dining area, large living room, a family room with a fireplace, spacious bedrooms, and a partially finished basement with a bathroom.

132 Lana Ln, Winchester

4 Beds ⋅ 3 Baths ⋅ 26020651 MLS

Wow! Pack your belongings and get ready to move! Your dream house just hit the market and It is going to go quick. Imagine sitting on the back deck , sipping your favorite beverage while your children and pets play safely in this large fenced in back yard. Or set up your home theatre in the spacious finished basement. This home has so much to offer, very spacious with the primary bed room and bathroom on the main floor, cathedral ceiling , covered front porch, large basement garage facing the rear of the home. Home is very convenient to downtown area and I-64. Dont drag your feet this one wont be on the market long.

428 Waycross Dr, Winchester

4 Beds ⋅ 3 Baths ⋅ 26019848 MLS

Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15 minutes from Mt. Sterling, this property delivers the best of both worlds: tranquility and accessibility. From the inviting living spaces to the expansive grounds ideal for relaxing, entertaining, or simply enjoying the view, this home is truly one of a kind. Opportunities like this don't come often — this one will move fast. Don't miss your chance. Call today to schedule your private showing.

1780 Stoner-Ephesus Rd, Winchester

4 Beds ⋅ 2 Baths ⋅ 26017258 MLS

Classic Williamsburg inspired home with charming dormers, timeless character, and an exceptional location that's a short walk to historic downtown Winchester. This spacious 4-bedroom , 2 bath home offers a flexible floor plan with 2 main-level bedrooms and a full bath, plus two additional bedrooms and a full bath upstairs. Enjoy elegant formal living and dining rooms, a large home office, and a bright Florida room overlooking established flower gardens. The spacious eat-in kitchen features abundant cabinetry, a butler's pantry, and plenty of room for family gatherings and entertaining. Beautiful original hardwood floors flow throughout much of the home. The main level bathroom showcases distinctive brick flooring, adding unique character. Custom window treatments and ceiling fans throughout the home are included. You will love the abundant storage throughout the home! Four walk-in closets, including one oversized space that could be used as a nursery or dressing area. The unfinished basement offers endless possibilities for additional living space, a workshop, or recreation and inclues a storm shelter for added peace of mind. This home is just minutes from I-64, country clubs, schools, shopping, dining and everyday conveniences. Combining classic Williamsburg architecture, generous living spaces and original details, this is a rare opportunity to own a truly special home.

351 Boone Ave, Winchester

3 Beds ⋅ 1 Baths ⋅ 26016881 MLS

SELLING "AS IS" Welcome to country living!! approximately 1 acre lot with 3-car garage. updates include; new basement doctor system, new range, refrigerator, dishwasher, and washer/dryer. New LVP flooring, new light fixtures inside and out. New septic system, new front storm door and new sliding glass door in dining room. New electric outlets and switch plates. New garage door on lower one car garage. New gutters. Motivated seller. Move-in condition. Schedule your viewing appointment today!!

2379 Big Stoner Rd, Winchester

4 Beds ⋅ 3 Baths ⋅ 26008701 MLS

Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

229 S Highland St, Winchester

3 Beds ⋅ 3 Baths ⋅ 26009944 MLS

This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons of options await you with the covered front porch, the partially covered back deck or escape to the seclusion of the covered, separate structure at the back. Both the front and back yards are landscaped with many mature trees and perennials that require little attention during Spring, Summer and Fall. Inside, this expansive floor plan packs a lot of punch with a number of interior spaces with an easy flow. The wide entry hall foretells of large room sizes and fresh, neutral paint throughout. The newly renovated kitchen with light wood cabinets is timeless in it's appeal and the adjacent breakfast area is full of natural light. Another handsome fireplace in the next space, with built in shelves could easily function as a D R or Den and the sunroom gives a panoramic view of the beautiful back yard. Three bedrooms and two baths round out the first floor. The lower level features a massive two car garage, half bath, laundry and a large Family Room/Man Cave space for quiet reading or lively entertaining with a third fireplace. So many beautiful options await you in this wonderful home, located in a quiet, attractive, safe and neighborly enclave.

42 Mockingbird Valley Rd, Winchester

4 Beds ⋅ 2 Baths ⋅ 26008225 MLS

Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make a house a home. Out back, the large, lush yard provides a peaceful setting with plenty of space to gather, garden, or unwind. Inside, the main level offers generous and flexible living space, including a first-floor bedroom, formal living room, den, dining room, kitchen, full bath, and utility area. The standout sunroom is a bright and airy retreat, heated and cooled, with vaulted ceilings, skylights, and beautiful views of the backyard year-round. Upstairs features three bedrooms and a full bath, continuing the home's classic layout (note: no central heat and air on the second floor). An oversized one-car attached garage and ample driveway parking add everyday practicality, something not often found in homes of this era. Being offered as an estate sale, this home has been lovingly cared for over the years and reflects a lifetime of memories. It now awaits its next chapter, someone who will appreciate its history, honor its character, and bring new vision to what it can become.

443 S Maple St, Winchester

4 Beds ⋅ 5 Baths ⋅ 26013378 MLS

Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the tone for the elegance that flows throughout the home. The formal living room exudes Southern charm, featuring intricate moldings, and large windows that bathe the space in natural light. The formal dining room is perfect for hosting memorable gatherings, with ample space for entertaining in style. Designed for both beauty and function, this home seamlessly blends historic inspiration with modern amenities, creating a warm and inviting atmosphere. Whether you're enjoying a quiet evening on the spacious screened in porch or hosting lavish celebrations, this extraordinary estate is a true embodiment of Southern grace and hospitality. Owner/Agent

600 Boone Ave, Winchester

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