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 the perfect living environment. This picturesque neighborhood offers a unique blend of suburban tranquility and urban convenience, making it an ideal choice for families, young professionals, and retirees alike.

As you stroll through the tree-lined streets of Winchester, you'll be greeted by a warm and inviting atmosphere. The subdivision boasts a variety of beautifully designed homes, ranging from cozy single-family residences to spacious modern estates, ensuring there’s something for everyone. With well-maintained parks, playgrounds, and walking trails, outdoor enthusiasts will find plenty of opportunities to enjoy nature right at their doorstep.

Winchester is not just about beautiful homes; it’s also about community. Residents take pride in their neighborhood, hosting regular events that foster connections and create lasting friendships. From summer barbecues to seasonal festivals, there’s always something happening that brings the community together.

For those who value convenience, Winchester is ideally located near major highways and public transportation options, making commuting a breeze. A short drive will take you to vibrant shopping districts, gourmet dining options, and top-rated schools, ensuring that all your needs are met without sacrificing the peaceful suburban lifestyle.

Embrace the charm of Winchester, where a strong sense of community meets the comforts of modern living. Come discover your new home in this delightful subdivision, and experience the perfect blend of serenity and accessibility that makes Winchester truly special!

Newest Listings in Winchester

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 approximately 1.35 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:

1215 Oakhurst Pl, Baltimore
$155,000
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:

1208 N Longwood St, Baltimore
$20,000
3 Beds ⋅ 2 Baths
List price is Opening Bid at the Online auction to be conducted on Auctioneers website. Bidding begins Saturday, October 10th and ends Thursday, October 15, 2026 at 12:30 PM.. 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:

2737 Riggs Ave, Baltimore
$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, November 4, 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:

117 E Pall Mall St, Winchester
$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:

2919 Belmont Ave, Baltimore
$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:

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