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 blend seamlessly. This picturesque neighborhood offers a tranquil retreat from the hustle and bustle of city life while still providing easy access to urban amenities.

Winchester is renowned for its diverse architecture, featuring a delightful mix of traditional and modern homes that cater to various lifestyles and preferences. Tree-lined streets and beautifully landscaped yards create an inviting atmosphere, making it a perfect place for families, retirees, and young professionals alike.

One of the standout features of Winchester is its strong sense of community. Residents often gather for neighborhood events, fostering friendships and connections that make this subdivision feel like home. The local parks are perfect for weekend picnics, morning jogs, or enjoying a peaceful afternoon with a good book. Children can often be seen playing in the safe, friendly environment, creating lasting memories with their neighbors.

In addition to its community charm, Winchester boasts proximity to excellent schools, shopping centers, and recreational facilities. With a variety of dining options, from cozy cafes to vibrant restaurants, there’s something to satisfy every palate. For those who enjoy the outdoors, nearby hiking trails and lakes provide ample opportunities for adventure and relaxation.

Whether you’re looking to buy your first home, relocate, or invest, Winchester offers a unique blend of comfort, convenience, and community spirit. Discover your dream home in this enchanting subdivision, where every day feels like a breath of fresh air. Welcome to Winchester, where your ideal lifestyle awaits!

Newest Listings in Winchester

$360,000
3 Beds ⋅ 3 Baths
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. Schedule your tour today!

117 E Pall Mall St, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$59,900
4 Beds ⋅ 1 Baths
SPACIOUS END OF GROUP ROWHOME THAT'S READY FOR YOUR RENOVATIONS. Main level with a living room, dining room, and kitchen, upper level with 4 bedrooms and 1 full bath, and an unfinished basement. Great opportunity to update and resell or add to your rental portfolio. Sold As-Is! Buyer responsible for clearing any vacant property notice after settlement if one exists.

2919 Belmont Ave, Baltimore

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: (800) 383-3535
$1,724,000
Beautifully restored and fully modernized mixed-use building in the heart of historic Winchester. This exceptional offering includes a fully leased commercial building with three strong-credit tenants, a valuable adjacent parking lot approved for future mixed-use development, and a third floor ready for residential conversion. Located just one block from the historic Old Town Winchester Walking Mall, this legacy investment property offers more than 9,300 square feet of space with the first and second floors completely renovated and occupied. The third floor presents an outstanding value-add opportunity for apartment development, with potential eligibility for Historic Tax Credits. The property is also located within an Enterprise Zone, providing access to additional grant and incentive programs. The sale includes the adjacent parking lot (Tax ID 173-01-E-1), which is approved for multifamily development or can continue to serve as a highly desirable dedicated parking facility for tenants and customers. Current net operating income exceeds $80,000 annually, providing immediate cash flow with significant upside potential. Recent capital improvements include a metal roof, new HVAC systems, and modern tenant build-outs throughout the building. This unique asset offers a diversified income stream with retail and office tenants in place, while creating future opportunities for residential development on both the third floor and the adjacent parking lot. Ideal for a 1031 exchange buyer or investor seeking stable income, long-term appreciation, and redevelopment potential in one of the Shenandoah Valley's most desirable downtown locations. Conveniently located one block from the Braddock Street Parking Garage. Rarely does an opportunity of this caliber become available in Downtown Winchester. Contact the listing agent to schedule a private showing.

48 W Boscawen, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$399,900
3 Beds ⋅ 2 Baths
Welcome to 225 Fox Dr.! A very well maintained all brick ranch rambler. Has a fully updated kitchen with stainless steel appliances, quartz countertops, updated cabinetry with an induction oven. Very spacious open concept living room, good size bedrooms and hard flooring all around. The basement has plenty of potential and has recently been updated. The home offers paid off solar panels an EV Charger and a RV Charger. Solar panels are Wi-fi controlled with glow fiber for $70.00 dollars a month. Theres a detached garage/ storage with a rewiring that was done in 2024. Home also has a new updated HVAC system instead of gas is an electric heat pump. The filter only needs to be switched out every 6 months.

225 Fox Dr, Winchester

Listing courtesy of First Decision Realty LLC. Contact:

$899,000
3 Beds ⋅ 4 Baths
Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. Offering an exceptional combination of privacy, convenience, and quality. This home features spacious living areas, three fireplaces, including one in the primary bedroom. The finished lower level provides outstanding flexibility with a large rec room, full kitchen, and full bath-ideas for guests, extended family, or entertaining. Outdoor living is a grand feature, with multiple brick patios and private spaces designed to take full advantage of the tranquil park setting. The property also has a unique barn for storage or a workshop. Recent improvements include a newer metal roof, while the expansive lot offers a rare sense of seclusion within the City limits. A truly unique property that combines timeless all-brick construction, modern renovations, and an unbeatable location near medical facilities, shopping, dining, downtown Winchester, and the Museum of the Shenandoah Valley.

466 Merrimans Ln, Winchester

Listing courtesy of Colony Realty. Contact:

$174,900
3 Beds ⋅ 2 Baths
This beautifully renovated 3-bedroom, 2-bathroom rowhome is the perfect opportunity for a first-time homebuyer looking for style, comfort, and value. Step inside and enjoy a bright, modern interior featuring updated finishes, spacious living areas, and a thoughtfully designed layout that's ready for you to move right in. The updated kitchen offers contemporary cabinetry, sleek countertops, and plenty of space for cooking and entertaining. Both full bathrooms have been tastefully renovated with modern fixtures and finishes. The generous bedrooms provide comfort and flexibility for growing families, guests, or a home office. Located in a convenient Baltimore neighborhood with easy access to major commuter routes, shopping, dining, parks, and public transportation, this home combines affordability with modern living. Why rent when you can own? Don't miss your chance to make this fully renovated gem your new home. Schedule your private tour today!

1221 Ashburton St, Baltimore

Listing courtesy of Keller Williams Legacy. Contact: 4436609229
$179,999
3 Beds ⋅ 2 Baths
Welcome to this beautifully updated 3-bedroom, 1.5-bath rowhome offering the perfect blend of classic charm and modern convenience. The open-concept main level is designed for comfortable everyday living and effortless entertaining, featuring gleaming hardwood floors, recessed lighting throughout, and a spacious layout that flows seamlessly from the living room to the dining area and kitchen. The well-appointed kitchen offers a center island with seating for bar stools, ample cabinet and counter space, and a separate dining area with plenty of room for a table and chairs. A convenient powder room and mudroom complete the main level, with the mudroom providing direct access to the newly cemented, fully fenced backyard—an ideal space for outdoor entertaining, gardening, or relaxing in privacy. Upstairs, you'll find three comfortable bedrooms with beautifully preserved original hardwood flooring and a newly renovated full bathroom that combines timeless style with modern finishes. The full-length unfinished basement offers exceptional storage space and endless potential to create additional living space, a home gym, workshop, or recreation area. Whether you're a first-time homebuyer or looking to add to your investment portfolio, this move-in-ready home offers a functional layout, thoughtful updates, and plenty of room to make it your own.

1077 Ellicott Dr, Baltimore

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$82,500
3 Beds ⋅ 1 Baths
NOT AN AUCTION, NOT A SHORT SALE, NOT A BANK OWNED, NOT A FORECLOSURE, NOT WHOLESALING---QUICK AND EASY. Buyer to pay all transfer and recording fees Minimum $2,000 EMD. Excellent Opportunity ...use your imagination! Property can be rehabbed for a nice rental investment or homeowner. Property sold "as is". Home Inspections for informational purposes only. Seller will make no repairs. . In addition, this property qualifies for a special 5.75% mortgage program—a rare financing opportunity that makes this high-quality home even more affordable. Ask Listing Agent for details. Photos are old and new

2730 Winchester St, Baltimore

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

$399,999
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: 4436609229
$115,000
2 Beds ⋅ 1 Baths
MOVE IN READY TOWNHOME IN BALTIMORE!! END ROW TOWNHOME FRESHLY PAINTED THROUGH OUT, UPDATED LVP FLOORING...PREVIOUS RENTAL PROPERTY - WAS RENTED FOR $1660 PER MONTH!! Welcome to 1044 Ellicott Driveway in Baltimore, MD, a charming and inviting home offering a wonderful combination of comfort, character, and convenience. This well-maintained residence features spacious living areas filled with natural light, creating a warm and welcoming atmosphere throughout. The thoughtfully designed layout provides comfortable everyday living along with flexible spaces perfect for entertaining, working from home, or relaxing with family and friends. The kitchen offers ample cabinetry, quartz counters, gas cooking and workspace, flowing seamlessly into the dining and living areas for easy functionality. Generous bedrooms provide peaceful retreats, while the bathrooms are designed with both comfort and practicality in mind. Outside, enjoy private outdoor space ideal for relaxing, gardening, or entertaining guests. Conveniently located near shopping, dining, parks, commuter routes, and all that Baltimore has to offer, this home presents an exceptional opportunity for buyers seeking style, convenience, and value in a desirable location.

1044 Ellicott Driveway, Baltimore

Listing courtesy of Winning Edge. Contact: 4434636009
$95,000
3 Beds ⋅ 2 Baths
NOT AN AUCTION, NOT A SHORT SALE, NOT A BANK OWNED, NOT A FORECLOSURE, NOT WHOLESALING---QUICK AND EASY. Ask me about 5.75% financing program.

2813 Riggs Ave, Baltimore

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

$65,000
3 Beds ⋅ 1 Baths
This is a 1,350 sq ft brick-front end-unit townhouse featuring three bedrooms, a full bath and an unfinished basement ready for customization. Situated in the heart of Baltimore’s Winchester neighborhood, this property offers easy access to Upton Park, Mondawmin Mall, and multiple bus routes, making it attractive to long-term tenants. The upside is endless with this prime investment opportunity making it an excellent opportunity for both homeowners and investors alike. Price adjusted for quick sale. Serious inquiries only.

2826 Winchester St, Baltimore

Listing courtesy of Honest Realty INC. Contact: (443) 405-2535
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