Winchester Real Estate

Winchester Real Estate

Welcome to Winchester, a charming subdivision nestled in the heart of the United States, where community spirit and scenic beauty come together to create an idyllic living environment. This picturesque neighborhood is known for its welcoming atmosphere and family-friendly vibe, making it an ideal choice for those seeking a peaceful yet vibrant place to call home.

Winchester boasts a variety of beautifully designed homes that cater to diverse lifestyles and preferences. From cozy single-family residences to spacious townhomes, there’s something for everyone in this inviting community. Lush green parks and well-maintained walking trails provide residents with ample opportunities for outdoor recreation, while the tree-lined streets create a serene setting for leisurely strolls or bike rides.

Conveniently located near essential amenities, Winchester offers easy access to shopping, dining, and entertainment options. Local schools are highly regarded, ensuring that families have access to quality education. The community hosts regular events and activities, fostering connections among neighbors and creating a strong sense of belonging.

For those who appreciate nature, Winchester is just a stone's throw away from beautiful parks and recreational areas, perfect for weekend getaways or family outings. With its blend of tranquility and convenience, Winchester is not just a place to live; it's a place to thrive.

Whether you’re a first-time homebuyer, looking to downsize, or seeking a vibrant community to raise your family, Winchester welcomes you with open arms. Discover the charm and warmth of this delightful subdivision, where your dream home awaits!

Newest Listings in Winchester

$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: 4436609229
$30,000
3 Beds ⋅ 1 Baths

1202 Ashburton St, Baltimore

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124
$20,000
3 Beds ⋅ 2 Baths
List price is Opening Bid at the Online auction to be conducted on Auctioneers website. - Auction ends Thursday, September 24, 2026 at 11:00 AM. Welcome to 1208 N Longwood St., a classic Baltimore City townhouse offering a functional layout, multiple living spaces, and a covered front porch in the Winchester area. Whether you're looking for a primary residence or an investment opportunity, this property provides a solid foundation with room to make it your own. The main level features an inviting entryway, spacious living room, and separate dining room, all showcasing wood flooring. The kitchen offers laminated wood flooring and provides a functional space for everyday living and entertaining. Upstairs, you'll find three bedrooms, each with wood flooring, along with a versatile bonus room/office that can serve as a home office, study, dressing room, or additional flex space. There is also a full bathroom. The partially finished lower level adds valuable additional space with a family/recreation room, half bathroom, carpeted storage room, and utility area. Mechanical features include gas water heater, forced-air heating, electric panel, and interior gas meter. Outside, enjoy a covered front porch and a fully fenced backyard, offering private outdoor space for relaxing, gardening, entertaining, or recreation. The exterior electric meter is also located outside. With its traditional Baltimore rowhouse layout, generous room count, hardwood flooring throughout much of the home, and flexible lower-level space, 1208 N Longwood St. offers an opportunity to create a home that fits your needs or add another property to your portfolio.

1208 N Longwood St, Baltimore

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

$99,950
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
$145,000
3 Beds ⋅ 2 Baths
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, September 23, 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: 4103120000
$50,000
3 Beds ⋅ 2 Baths
ONLINE AUCTION: Bidding begins 9/14/2026, 10:00 AM. Bidding ends 9/16/2026, 12:30 PM. List Price is Suggested Opening Bid. Deposit: $10,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. 2 Story Townhouse located in the Winchester area of Baltimore City. Residents can enjoy the nearby attractions such as Coppin State University, Leon Day Park, West Baltimore MARC Station, Mondawmin Mall, Walbrook Junction Shopping Center. Property is Vacant. Easy Access to Major Traffic Artery North Ave.

1231 Ashburton St, Baltimore

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124
$64,900
3 Beds ⋅ 2 Baths
2810 Ellicott Drive is a 1,200 sq ft brick-front townhouse featuring three bedrooms, a full bath and an unfinished basement ripe 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.

2810 Ellicott Dr, Baltimore

Listing courtesy of LPT Realty, LLC. Contact: 8773662213
$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. 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: 3027337000
$350,000
3 Beds ⋅ 3 Baths
** Price improvement!** 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 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
$189,000
4 Beds ⋅ 3 Baths
Welcome to 2903 Winchester Street, a fully renovated 4-bedroom, 3-bathroom home on Baltimore’s west side that delivers modern finishes without losing its city character. Great Investment property. Currently occupied but can be delivered vacant. More equity in property This property is eligible for up to $10,000 through Baltimore City’s Vacants to Value Booster program (buyer must meet DHCD guidelines). The open-concept layout connects the living, dining, and kitchen areas for practical everyday living and easy entertaining. Luxury vinyl plank flooring runs throughout, giving the home a clean, durable, cohesive look. The kitchen is finished with stainless steel appliances, generous cabinetry, and contemporary touches that make it both functional and inviting. Off the rear, a 200-square-foot deck extends your living space outdoors, overlooking a private fenced yard ideal for gatherings, pets, or quiet evenings. Washer and dryer are included. Upstairs, the spacious primary suite features a private en-suite bath. With three full bathrooms total, the layout offers flexibility for families, guests, or work-from-home needs. Renovated top to bottom and move-in ready.

2903 Winchester St, Baltimore

Listing courtesy of CORE Principles Real Estate Group. Contact: 4102583792
$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:

Start Your Search