Winchester Homes under $250,000

Winchester Homes under $250,000

Welcome to Winchester, a vibrant and inviting subdivision nestled in the heart of Baltimore City, Maryland. This charming community offers a unique blend of urban convenience and suburban tranquility, making it an ideal choice for first-time homebuyers, families, and anyone looking to embrace the charm of city living without breaking the bank.

One of the standout features of Winchester is its affordability, with homes available for under $250,000. This makes it a fantastic opportunity for those seeking to invest in their future or find their perfect starter home. The architecture in Winchester reflects a rich history, showcasing a variety of styles that add character and warmth to the neighborhood. Imagine stepping into a cozy abode with charming details and modern amenities, all while enjoying the benefits of a community that values connection and growth.

Residents of Winchester enjoy easy access to a plethora of local attractions, including parks, shops, and dining options that cater to a diverse array of tastes. The community is well-connected to public transportation, making commutes to downtown Baltimore a breeze. Outdoor enthusiasts will appreciate the nearby green spaces, perfect for leisurely strolls, picnics, or weekend gatherings.

In Winchester, you’ll not only find a house to call home but also a welcoming community that fosters friendships and a sense of belonging. With homes priced affordably under $250,000, your dream of homeownership is within reach in this delightful Baltimore enclave. Discover all that Winchester has to offer, and make it your next home sweet home!

Newest Winchester Homes under $250,000

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:

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:

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:

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:

2826 Winchester St, Baltimore
$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:

1130 N Longwood St, Baltimore
$189,000
4 Beds ⋅ 2 Baths
** AVAILABLE SOON ** 4 BEDROOM 2 BATHROOM

1130 N Longwood St, Baltimore

Listing courtesy of EXP Realty, LLC. Contact:

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