Winchester Real Estate

Winchester Real Estate

Welcome to Winchester, a charming subdivision nestled in the heart of the United States, where small-town charm meets modern convenience. This picturesque community is known for its welcoming atmosphere, beautiful landscapes, and a strong sense of community spirit.

Winchester boasts an array of amenities that cater to residents of all ages. From well-maintained parks and playgrounds to scenic walking trails, outdoor enthusiasts will find plenty of opportunities to enjoy nature right at their doorstep. Families can take advantage of the highly-rated local schools, ensuring that children receive a quality education within a nurturing environment.

The real estate options in Winchester are as diverse as its residents. Whether you’re looking for a cozy single-family home, a spacious townhome, or a charming cottage, this subdivision has something to fit every lifestyle and budget. Many properties feature modern finishes and spacious layouts, making them perfect for entertaining or simply enjoying quiet evenings at home.

Community events are a highlight in Winchester, with seasonal festivals, farmers' markets, and neighborhood gatherings that foster connections among residents. The friendly atmosphere encourages neighbors to come together, creating lasting friendships and a true sense of belonging.

Conveniently located near major highways, Winchester offers easy access to nearby cities, shopping centers, and dining options, making it an ideal location for commuters and those seeking a vibrant lifestyle.

Discover the allure of Winchester, where you can find your dream home and become part of a thriving community. Embrace the charm and warmth of this delightful subdivision, where every day feels like a step into a welcoming embrace.

Newest Listings in Winchester

2711 Ellicott Dr, Baltimore
$64,900
3 Beds ⋅ 2 Baths

2711 Ellicott Dr, Baltimore

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

1215 Poplar Grove St, Baltimore
$34,900
4 Beds ⋅ 2 Baths
The perfect opportunity for an investor looking for a project. 3 levels with rear bedroom balcony and level basement walkout.Tall ceilings. Skylites.Sold strictly AS IS. Call your favorite agent or call me.for details.

1215 Poplar Grove St, Baltimore

Listing courtesy of RE/MAX Excellence Realty. Contact:

2834 Riggs Ave, Baltimore
$135,000
3 Beds ⋅ 4 Baths
Nestled in the charming Winchester neighborhood, this exquisite end-of-row townhouse exudes timeless elegance and modern comfort. Built in 1920, the property showcases traditional architectural style with its classic brick façade, inviting you into a world where history meets contemporary living. Step inside to discover a thoughtfully designed interior that seamlessly blends functionality with warmth. Natural light pours in, enhancing the inviting atmosphere throughout the home. The heart of this residence is the well-appointed kitchen, featuring high-end appliances including a sleek dishwasher, a modern refrigerator, and a stylish stove. Whether you're a culinary enthusiast or simply enjoy the convenience of a well-equipped kitchen, this space is designed to inspire your culinary creations. With three generously sized bedrooms, this home provides ample space for relaxation and rejuvenation. Each room is a sanctuary, offering a peaceful retreat at the end of the day. The two full bathrooms and two half bathrooms are elegantly designed, ensuring comfort and privacy for all. The full basement presents endless possibilities, whether you envision a cozy entertainment area, a home gym, or additional storage space. The potential for customization allows you to tailor this area to suit your lifestyle needs. Outside, the property boasts a modest lot size of 0.03 acres, providing just the right amount of outdoor space for gardening or enjoying a morning coffee. On-street parking ensures convenience for you and your guests. This home is not just a place to live; it's a lifestyle choice. Experience the charm of the Winchester community, where local shops, parks, and dining options are just a stone's throw away. Embrace the opportunity to create lasting memories in a residence that combines classic charm with modern amenities. Don't miss your chance to own this beautiful townhouse, where every detail has been carefully considered to provide a warm and inviting atmosphere. This is more than just a home; it's a place where you can truly thrive. AS IS SALE

2834 Riggs Ave, Baltimore

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

125 Fox Dr, Winchester
$419,000
3 Beds ⋅ 2 Baths
Welcome to 125 Fox Drive! This charming brick rancher is ideally situated in the heart of Winchester City, offering a wonderful combination of classic character, modern updates, flexible living space, and an unbeatable location. The main level features three bedrooms, a full bathroom with tile flooring, tile shower walls, and a tub/shower combination, along with beautiful hardwood floors throughout. The updated kitchen boasts bright white cabinetry, granite countertops, and stainless steel appliances. The inviting living room is highlighted by a wood-burning fireplace and distinctive accent wall, creating a warm and welcoming space to relax or entertain. Need additional space? The fully finished basement offers endless possibilities, with multiple rooms ideal for additional bedrooms, a playroom, home gym, hobby space, or home office. A second full bathroom features granite countertops, tile flooring, tile walls, and a tub/shower combination. A separate utility and storage room provides additional functionality and convenience. Step outside and enjoy the fantastic backyard! The level, fully fenced yard features a privacy fence, mature trees, and a brick paver patio, making it the perfect setting for summer barbecues, outdoor gatherings, or simply unwinding in your own private outdoor retreat. The welcoming front porch features Trex decking, vinyl railings, and columns, while the paved driveway offers parking for up to three vehicles. Solar panels provide an added opportunity to help reduce electricity costs. LOCATION, LOCATION, LOCATION! Enjoy the convenience of city living with NO HOA! Located approximately one mile from historic downtown Winchester, this home offers convenient access to local restaurants, shops, entertainment, and community events. You're also close to Valley Health Winchester Medical Center and numerous medical specialty practices, as well as the Museum of the Shenandoah Valley and Whittier Park. Enjoy the excitement of Winchester's famous Shenandoah Apple Blossom Festival and all the charm this vibrant community has to offer. Don't miss your chance to make this home your own!

125 Fox Dr, Winchester

Listing courtesy of Samson Properties. Contact:

1564 Perry Rd, Winchester
$579,900
4 Beds ⋅ 3 Baths
Peaceful country living with everyday conveniences just minutes away! Tucked away from the hustle and bustle of main roads, yet less than 10 minutes from shopping, grocery stores, gas stations, and other amenities, this spacious home offers a wonderful combination of privacy, tranquility, and convenience. Offering nearly 3,000 square feet of above-grade living space, this spacious single-level home features four bedrooms, three full bathrooms, and an impressive collection of thoughtful features—all situated on 1.35 UNRESTRICTED acres in Winchester. Originally constructed in 1954, the home underwent extensive reconstruction and expansion in 2009, with portions of the original foundation retained and additional foundation constructed. Step inside and discover a huge, open-concept kitchen, living, and dining area, offering wonderful flexibility for everyday living, gatherings, and entertaining. Hardwood floors, generously sized bedrooms, and a welcoming kitchen featuring stainless steel appliances and attractive wood cabinetry add to the home's appeal. All four bedrooms and three full bathrooms are conveniently located on the main level. Thoughtful features throughout the home include a whole-house humidifier, enhanced HVAC air filtration with ultraviolet treatment, a water softener, and accessibility features including 32-inch doorways and wide hallways. Rigid foam board insulation along the basement foundation walls adds another practical benefit. A Vector security and life-safety system is also installed. Looking for room to grow? The full walk-up basement offers abundant additional space, including plumbing rough-ins for two future bathrooms and a second kitchen. Above the main level, an expansive unfinished attic accessed by pull-down stairs features standing headroom and a large window that fills the space with natural light. Both areas offer excellent storage and possibilities for future improvements, subject to applicable permits and approvals. Outside, choose between relaxing on the covered wraparound porch or enjoying the screened-in back deck, both offering inviting spaces to take in the peaceful surroundings and beautiful, mature trees. Situated on approximately 1.35 acres, this corner lot provides a tranquil setting away from busy roads, with little through traffic. It's an inviting place to unwind, enjoy your morning coffee, or simply appreciate the outdoors. A portable one-car garage and separate storage shed offer convenient space for vehicles, outdoor equipment, and hobbies. With its extensive reconstruction, expansive open living areas, convenient single-level layout, peaceful setting, and possibilities for future improvements, this property offers a wonderful combination of space, comfort, and convenience. Schedule your showing and discover the possibilities at 1564 Perry Road!

1564 Perry Rd, Winchester

Listing courtesy of Samson Properties. Contact:

1303 Poplar Grove St, Baltimore
$99,900
3 Beds ⋅ 2 Baths
Welcome to 1303 Poplar Grove Street! This brick interior rowhome offers a welcoming front porch, hardwood floors, and three bedrooms with two bathrooms. The spacious kitchen provides plenty of room for meal preparation, while the fully finished basement adds flexible living space for a recreation room, home office, or hobbies. Enjoy nearby shopping at Walbrook Junction and Mondawmin Mall, along with outdoor recreation at Gwynns Falls Trail and Gwynns Falls–Leakin Park. Convenient access to the West Baltimore MARC station connects you to destinations throughout the region.

1303 Poplar Grove St, Baltimore

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

1119 Ellicott Drwy, Baltimore
$10,000
3 Beds ⋅ 1 Baths
ABSOLUTE ONLINE REAL ESTATE AUCTION TO THE HIGHEST BIDDER OVER $10,000! Online Bidding Opens - Monday, November 2, 2026. Online Bidding Closes - Tuesday, November 3, 2026. List price is opening bid only. 1119 Ellicott Driveway is situated in the Winchester neighborhood of western Baltimore City, north of Franklintown Road, east of Gwynns Falls/Leakin Park, west of Poplar Grove Street and south of Presstman Street. The surrounding area is a mixture of townhomes and garden apartments. Public bus transportation and MARC Train service are nearby.

1119 Ellicott Drwy, Baltimore

Listing courtesy of A.J. Billig & Company. Contact:

1221 Ashburton St, Baltimore
$180,000
3 Beds ⋅ 2 Baths
Welcome to 1221 Ashburton St — a beautifully renovated 3-bedroom, 1.5-bath home blending modern style with everyday comfort. The main level features new LVP flooring and an open-plan living area, highlighted by a custom accent wall that adds a designer touch. The brand-new kitchen impresses with quartz countertops, a stylish backsplash, and stainless steel appliances. Upstairs, you’ll find three comfortable bedrooms and a stylish full bath with large, dramatic wall tile and sleek black fixtures. The finished basement offers additional living space and a convenient half bath. A fenced-in yard provides private outdoor enjoyment. Located on a quiet street in a growing area with easy access to downtown, Druid Hill Park, shopping, and public transit, this home offers both comfort and convenience.

1221 Ashburton St, Baltimore

Listing courtesy of Realty Mark Associates. Contact:

1215 Oakhurst Pl, Baltimore
$149,900
3 Beds ⋅ 1 Baths
Step inside this charming Baltimore home featuring generous room sizes, beautiful wood flooring, and inviting front and rear porches that extend the living space outdoors. The spacious rear yard offers plenty of room for relaxing, entertaining, gardening, or creating your own outdoor retreat. An unfinished basement provides excellent storage along with additional potential for future use. Just blocks from the park and only a short drive to Downtown Baltimore, this home combines classic character, outdoor space, and convenient access to everything the city has to offer.

1215 Oakhurst Pl, Baltimore

Listing courtesy of Blue Casa. Contact:

2726 Ellicott Driveway, Baltimore
$189,000
3 Beds ⋅ 2 Baths
Start your New Year from renting to ownership. New Improved Price & Close by end of year $1,500 closing assistance! Making it affordable ownership vs. renting! Own your home at same cost or less money per month. Start building equity when you purchase. Get more house with options to grow and the only house at this price with a bedroom private balcony and full size garage! With an improved buying price, this renovated brick townhome on Ellicott Drive is an opportunity worth a look or a second look! Even better, the seller is willing to include the beautiful furniture currently in the home at no additional cost, helping make your move into homeownership easier and saving you the expense of start up furnishing your new place. Featuring 3 bedrooms, 2 full bathrooms, new central air conditioning, updated flooring, nice appliances and approximately 1,650 finished square feet, this home offers comfortable living space with room to make it your own. The main level features a welcoming living room, dining area, and kitchen. Upstairs, you'll find a spacious, bright primary bedroom, two additional bedrooms, and a full bathroom. The third bedroom even has its own private balcony! The finished lower level provides flexible space for a recreation room, home office, gym, or hobby area, along with laundry, storage, and a convenient full bathroom. Enjoy the extra outdoor space that comes with the end-unit location, a welcoming front porch, a full-size garage, and off-street parking. Situated on a quiet street near Coppin State University, this all-brick townhome offers practical living and a convenient location. An improved price, beautiful furniture included at no extra cost, and a place to call your own!. This could be the opportunity you've been waiting for. Don't miss your chance to make Ellicott Driveway your new address!

2726 Ellicott Driveway, Baltimore

Listing courtesy of The KW Collective. Contact:

920 Whitmore Ave, Baltimore
$374,900
Fantastic opportunity to own a versatile church property with endless possibilities! Offering approximately 4,800 sq. ft. of space, this building features a carpeted main sanctuary with seating for around 100, complete with pews, pulpit area, and ceiling fans. The lower level accommodates up to 75 people at tables, making it ideal for fellowship meals, classrooms, meetings, or community events. The kitchen is equipped with a refrigerator, stainless steel sinks, microwave, gas stove, and oak cabinetry, providing everything needed for gatherings and events. Additional highlights include gas heat, hot water, double-pane windows, and both ramp and stair access for convenience. This property offers great potential for a variety of uses—church, community center, daycare, event space, or conversion opportunity. *Seller financing considered* 24-hour notice required for all showings.

920 Whitmore Ave, Baltimore

Listing courtesy of Keller Williams Legacy. Contact:

1202 Ashburton St, Baltimore
$30,000
3 Beds ⋅ 1 Baths

1202 Ashburton St, Baltimore

Listing courtesy of Ashland Auction Group LLC. Contact:

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