Winchester Homes under $250,000

Winchester Homes under $250,000

Welcome to Winchester, a charming subdivision nestled in the vibrant heart of Baltimore, Maryland. This delightful community offers a unique blend of urban convenience and suburban tranquility, making it an ideal choice for families, young professionals, and first-time homebuyers alike.

Winchester is known for its friendly atmosphere, where neighbors greet each other with smiles and community events foster connections. The subdivision boasts an array of amenities, including nearby parks, local shops, and dining options that reflect the rich culture of Baltimore. With its proximity to major transportation routes, residents enjoy easy access to downtown Baltimore and beyond, making it a perfect spot for commuters.

For those seeking affordable housing options, Winchester presents an exciting opportunity with homes priced under $250,000. These properties offer a variety of styles and layouts, ensuring there’s something to suit every taste and budget. Whether you're looking for a cozy bungalow or a charming townhouse, Winchester has homes that provide both comfort and value.

Investing in a home in Winchester means becoming part of a close-knit community that values connection and support. With the potential for appreciation in property values, this subdivision is not just a place to live; it's a place to grow and thrive. Don’t miss your chance to discover the warmth and charm of Winchester—your dream home awaits in this wonderful Baltimore neighborhood!

Newest Winchester Homes under $250,000

1221 Ashburton St, Baltimore
$169,900
3 Beds ⋅ 2 Baths
Welcome to 1221 Ashburton St — a beautifully renovated 3-bedroom, 1.5-bath home blending modern style with everyday comfort. The main level features new LVP flooring and an open-plan living area, highlighted by a custom accent wall that adds a designer touch. The brand-new kitchen impresses with quartz countertops, a stylish backsplash, and stainless steel appliances. Upstairs, you’ll find three comfortable bedrooms and a stylish full bath with large, dramatic wall tile and sleek black fixtures. The finished basement offers additional living space and a convenient half bath. A fenced-in yard provides private outdoor enjoyment. Located on a quiet street in a growing area with easy access to downtown, Druid Hill Park, shopping, and public transit, this home offers both comfort and convenience.

1221 Ashburton St, Baltimore

Listing courtesy of Realty Mark Associates. 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
$200,000
3 Beds ⋅ 2 Baths
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

Listing courtesy of The KW Collective. Contact:

2817 Winchester St, Baltimore
$140,000
3 Beds ⋅ 2 Baths
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

Listing courtesy of Samson Properties. 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, October 21, 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:

2810 Ellicott Dr, Baltimore
$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:

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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