Winchester Real Estate

Winchester Real Estate

Welcome to Winchester, a charming subdivision nestled in the heart of the United States, where community spirit and natural beauty come together to create an idyllic living environment. Known for its picturesque landscapes and friendly atmosphere, Winchester is the perfect place for families, young professionals, and retirees alike.

As you stroll through the tree-lined streets of Winchester, you'll be greeted by a warm sense of community. The neighborhood boasts a diverse mix of architectural styles, from cozy single-family homes to modern townhouses, catering to various tastes and lifestyles. Residents take pride in their well-maintained properties, creating a vibrant and inviting ambiance.

Winchester is not just about beautiful homes; it's also about the lifestyle it offers. The subdivision is conveniently located near a variety of amenities, including top-rated schools, shopping centers, and recreational facilities. Families can enjoy weekends at nearby parks, where children can play and adults can relax amidst nature. For those who appreciate an active lifestyle, Winchester features walking trails and sports fields, encouraging residents to stay fit and engaged.

Additionally, Winchester fosters a strong sense of community with regular events and gatherings, from seasonal festivals to farmers' markets, ensuring that neighbors become friends. The local community center offers classes and activities for all ages, making it easy to connect and make lasting memories.

In Winchester, you’ll find not just a place to live, but a place to thrive. Discover the charm and warmth of this delightful subdivision, where your dream home awaits!

Newest Listings in Winchester

117 E Pall Mall St, Winchester
$350,000
3 Beds ⋅ 3 Baths
**SPECIAL FINANCING INCENTIVE! Sellers to offer up to $8133 in seller subsidy for temporary rate buy down (with Preferred lender) to subsidize and lower monthly payment for the first 2 years of ownership!** Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump pump & new hot water heater, 2025 - new sewer line under driveway & from driveway to street, new LVP in kitchen, 2026 - replaced / leveled living room floor & subfloor, new LVP. Perfect for the first time homebuyers or investors looking for a home with great rental potential! Schedule your tour today!

117 E Pall Mall St, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

1214 N Dukeland St, Baltimore
$144,700
3 Beds ⋅ 2 Baths
MOVE-IN READY • 3 BEDROOMS • 2 FULL BATHS • FINISHED BASEMENT • $144,700! Discover affordable homeownership at 1214 N Dukeland Street! This updated brick home offers 3 bedrooms, 2 full bathrooms, and three levels of living space. Enjoy updated flooring, recessed lighting, a bright living area, and a kitchen featuring granite countertops, stainless-steel appliances, gas cooking, and a breakfast bar opening to the dining area. The fully finished basement with a second full bathroom provides flexible space for entertaining, a home office, recreation room, or guest area. Basement laundry and all appliances included add even more value! MOVE-IN READY • IMMEDIATE POSSESSION • GREAT VALUE!

1214 N Dukeland St, Baltimore

Listing courtesy of Homecoin.com. 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
$409,000
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:

2726 Ellicott Driveway, Baltimore
$188,900
3 Beds ⋅ 2 Baths
Start the New Year with a home of your own. Let’s take a look at this renovated brick end-unit townhome on Ellicott Drive, now offered at $189,000. It also comes with a full-size garage and the furniture currently in the home conveys at no additional cost. As you step inside, you’ll find a living room that opens to the dining area and kitchen. The home offers approximately 1,650 finished square feet, three bedrooms, and two full bathrooms. Upstairs, there’s a bright primary bedroom, two additional bedrooms, and a full bathroom. One of the bedrooms has its own private balcony. The finished lower level gives you flexible space for a recreation room, home office, gym, or hobby area. You’ll also find laundry, storage, and a full bathroom on this level. Outside, enjoy the front porch, extra outdoor space that comes with the end-unit location, off-street parking, and that full-size garage. The home also features new central air conditioning, updated flooring, and nice appliances. The seller is offering $1,500 in closing assistance. With the improved price, included furniture, and room to make the home your own, this could be a chance to move from renting to ownership and start building equity. Take a look—or come back for a second look—and see if Ellicott Drive can be 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:

2737 Riggs Ave, Baltimore
$145,000
3 Beds ⋅ 2 Baths
BACK TO ACTIVE: Buyer unable to perform (Roof and HVAC replaced 2025) AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Welcome to 2737 Riggs Avenue in Baltimore, Maryland a beautifully renovated home where classic charm meets modern comfort. As you approach the property, you’ll be greeted by a brand-new front porch with durable Trex flooring, the perfect spot to enjoy your morning coffee or greet neighbors passing by. Step through the new front door, and you’ll immediately notice the attention to detail and high-quality craftsmanship throughout. The main level welcomes you with fresh paint, elegant crown molding, recessed lighting, and beautiful luxury vinyl plank flooring that flows seamlessly from the living room through the dining area and into the kitchen. This open-concept space feels bright, spacious, and inviting perfect for entertaining or relaxing at the end of the day. The kitchen has been fully updated with new cabinetry, sleek countertops, and brand-new stainless steel appliances, giving it both style and functionality. A rear entrance from the kitchen leads out to a fenced backyard overlooking a nearby playground, an ideal setup for children, pets, or simply enjoying a private outdoor retreat. Upstairs, you’ll find three comfortable bedrooms, each offering new flooring, fresh paint, modern light fixtures, and plenty of natural light through the updated windows. One of the bedrooms features a charming barn door, adding a touch of character and style. The full bath on this level has been completely renovated, showcasing designer tile, a quality vanity, and modern brushed-nickel fixtures for a spa-like feel. The unfinished basement offers extra space for storage and a half bath. Beyond its beautiful interior, this home offers peace of mind with all the major systems recently upgraded: New roof (Sept 2025) New heat and AC system (Sept 2025) New front and back doors (Sept–Oct 2025) New exterior front steps and porch floor (Oct 2025) New kitchen cabinets and appliances (Fall 2025) Located in a convenient Baltimore neighborhood, you’ll enjoy close proximity to Gwynns Falls/ Leakin Park, Mondawmin Mall, Coppin State University, and just minutes to downtown Baltimore for shopping, dining, and entertainment. Nearby schools, playgrounds, and public transit make this home ideal for both families and commuters. This property qualifies for the Baltimore City grant program, which offers $10k-$20k for down payment & closing costs for eligible buyers! This home is truly move-in ready. Come see what 2737 Riggs Avenue has to offer. Offers may be entered ONLINE through Wednesday, November 25, 2026 at 4:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME.

2737 Riggs Ave, Baltimore

Listing courtesy of Keller Williams Realty Centre. Contact:

384 Blacksnake Rd, Elkton
$639,999
3 Beds ⋅ 3 Baths
Discover the perfect blend of privacy, tranquility, and sustainable living in this one-of-a-kind historic farmhouse set on 10 picturesque acres. Originally built as a log home and thoughtfully expanded over time, this remarkable home seamlessly combines timeless craftsmanship with modern comfort. From the moment you step inside, you're transported to another era. Authentic log walls, exposed beams, stunning wide-plank wood floors, and a beautiful stone fireplace create warmth, character, and an unforgettable first impression. The inviting front den is filled with natural light and features wood-clad walls that enhance the home's rustic charm. The main living spaces flow effortlessly from the living room to the dining room and into the well-appointed kitchen. Home chefs will appreciate the Viking range, professional-style hood, and the convenient utility/laundry room located just beyond the kitchen. The home's three enclosed staircases each tell part of its story. From the kitchen, head to the primary suite, where vaulted ceilings, a dressing area/walk-in closet with additional storage, and a charming Juliet balcony overlook the surrounding woods and Little Elk Creek. The en suite bath offers a classic claw foot soaking tub, separate shower, and linen closet. The original staircase leads to the insulated attic, providing excellent storage. Just below the attic is the home's historic section, where the second bedroom showcases original log walls and abundant character. The third staircase leads to a spacious front bedroom with its own en suite bath, vaulted ceilings, exposed beams, and breathtaking natural light. Outside, relax on the expansive front porch overlooking the peaceful meadow and enjoy the beauty of your private surroundings year-round. There's a spring house, tack house and railroad bridge on the property as well. Designed with both comfort and efficiency in mind, this home features owned solar panels, geothermal HVAC, a tankless water heater, a whole-house water filtration system, a durable metal roof, and a propane-powered Generac generator for added peace of mind. The geothermal HVAC and solar panels impact the utility costs significantly. An oversized detached garage offers parking for two vehicles, a generous workshop area, and a loft for additional storage or workspace. Rich in history, full of character, and thoughtfully updated with sustainable features, this exceptional property offers a rare opportunity to own a truly distinctive home in a breathtaking natural setting. Come experience its charm for yourself and discover why this extraordinary farmhouse is unlike anything else on the market.

384 Blacksnake Rd, Elkton

Listing courtesy of Patterson-Schwartz-Newark. Contact:

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