Winchester Real Estate

Winchester Real Estate

Welcome to Winchester, a charming subdivision nestled in the heart of the United States, where suburban tranquility meets modern convenience. Known for its picturesque landscapes and friendly community atmosphere, Winchester is the perfect place to call home for families, young professionals, and retirees alike.

One of the standout features of Winchester is its beautifully designed homes, which showcase a variety of architectural styles to suit diverse tastes. From cozy single-family residences to spacious townhomes, each property is thoughtfully crafted to provide comfort and style. Tree-lined streets and well-maintained parks create a serene environment, ideal for leisurely strolls or afternoon picnics.

Winchester is not just about beautiful homes; it’s also about community. Residents enjoy a vibrant neighborhood spirit, with regular events and gatherings that foster connections among neighbors. The local community center offers a range of activities, from fitness classes to art workshops, ensuring there’s something for everyone to enjoy.

Convenience is another hallmark of Winchester. With easy access to major highways and public transportation, commuting to nearby cities for work or leisure is a breeze. Shopping, dining, and entertainment options are just around the corner, providing residents with everything they need within a short drive or a pleasant walk.

Families will appreciate the highly-rated schools in the area, which are dedicated to providing quality education and nurturing environments for students.

Whether you’re looking to settle down or invest in a new property, Winchester offers a welcoming community, beautiful homes, and an ideal location that truly captures the essence of suburban living. Come and discover the charm of Winchester—your next chapter awaits!

Newest Listings in Winchester

$649,999
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. 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: 3027337000
$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:

$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
$174,999
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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