Winchester Homes under $250,000

Winchester Homes under $250,000

Welcome to Winchester, a charming subdivision nestled in the heart of Baltimore City, Maryland. This vibrant community is a hidden gem, offering a unique blend of urban convenience and suburban tranquility. Winchester is characterized by its tree-lined streets, friendly neighbors, and a strong sense of community, making it an ideal place for families, young professionals, and anyone looking for a welcoming atmosphere.

One of the standout features of Winchester is its affordability, with homes available under $250,000. This makes it a fantastic option for first-time homebuyers or those looking to invest in real estate without breaking the bank. The homes in Winchester range from cozy bungalows to quaint two-story houses, each with its own unique charm and character. Many properties boast spacious yards, perfect for outdoor gatherings, gardening, or simply enjoying the fresh air.

Living in Winchester means you'll have easy access to all that Baltimore has to offer. The neighborhood is conveniently located near major highways, public transportation, and a variety of local amenities, including parks, shops, and dining options. Whether you’re looking to explore the rich history of Baltimore or enjoy a leisurely day at one of the nearby parks, Winchester is perfectly situated to meet your lifestyle needs.

If you’re searching for an affordable home in a friendly community with a vibrant spirit, look no further than Winchester. Discover the potential of this delightful subdivision and make it your new home sweet home!

Newest Winchester Homes under $250,000

1215 Oakhurst Pl, Baltimore
$155,000
3 Beds ⋅ 1 Baths ⋅ MDBA2233132 MLS
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
2726 Ellicott Driveway, Baltimore
$200,000
3 Beds ⋅ 2 Baths ⋅ MDBA2232368 MLS
Why keep renting when you could own for comparable monthly cost? Priced to sell, this renovated brick townhome offers an excellent opportunity to move from paying rent to building equity in a home of your own. With three bedrooms, two full bathrooms, new central air conditioning, flooring and other items and approximately 1,600 finished square feet, it provides comfortable and easy living space and room to grow to call home. The main level offers an open space living room, dining area, and a nice kitchen, while the upper level features nice size spacious bright master bedroom and two additional bedrooms and a full bath. The third bedroom has a private balcony for relaxation. The finished lower level adds flexible space for a recreation room, home office, gym, or hobby area, along with laundry, storage, and a convenient full bath. The end-unit location provides significantly more outdoor space than an interior townhome, along nice size front porch, with a full size garage and off street parking. Situated on a quiet street near St. Agnes Hospital, Coppin State University. This all brick townhome offers practical living space, a convenient location, with an affordable price point.

2726 Ellicott Driveway, Baltimore
2817 Winchester St, Baltimore
$140,000
3 Beds ⋅ 2 Baths ⋅ MDBA2231382 MLS
Motivated seller, fully renovated federal-style Baltimore rowhome with modern updates throughout. Recent improvements include new flooring, and refreshed interior finishes. The updated kitchen features granite countertops,new cabinetry, stainless steel appliances, and modern finishes. Enjoy an open, light-filled main level with a newly added half bath for added convenience. Fresh drywall and updated paint create a clean, move-in-ready interior. Home includes central air conditioning and an unfinished basement offering additional storage or future finishing potential. This home also include a front porch and backyard perfect for entertaining. Located in the Winchester neighborhood near Gwynn Falls Park, Leon Day Park, and Coppin State University. Just minutes from Mondawmin Mall, shopping, dining, and neighborhood amenities. Convenient access to Edmondson Ave (Route 40), public transit, Downtown Baltimore, the Inner Harbor, Johns Hopkins, and the University of Maryland Medical Center.

2817 Winchester St, Baltimore
1202 Ashburton St, Baltimore
$30,000
3 Beds ⋅ 1 Baths ⋅ MDBA2230916 MLS

1202 Ashburton St, Baltimore
1208 N Longwood St, Baltimore
$20,000
3 Beds ⋅ 2 Baths ⋅ MDBA2230710 MLS
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
2737 Riggs Ave, Baltimore
$145,000
3 Beds ⋅ 2 Baths ⋅ MDBA2229096 MLS
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, October 7, 2026 at 4:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME.

2737 Riggs Ave, Baltimore
2810 Ellicott Dr, Baltimore
$64,900
3 Beds ⋅ 2 Baths ⋅ MDBA2228380 MLS
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
2919 Belmont Ave, Baltimore
$59,900
4 Beds ⋅ 1 Baths ⋅ MDBA2222842 MLS
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
1221 Ashburton St, Baltimore
$174,900
3 Beds ⋅ 2 Baths ⋅ MDBA2219782 MLS
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
2826 Winchester St, Baltimore
$65,000
3 Beds ⋅ 1 Baths ⋅ MDBA2214562 MLS
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
1130 N Longwood St, Baltimore
$189,000
4 Beds ⋅ 2 Baths ⋅ MDBA2213450 MLS
** AVAILABLE SOON ** 4 BEDROOM 2 BATHROOM

1130 N Longwood St, Baltimore
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