Winchester Homes under $500,000

Winchester Homes under $500,000

Welcome to Winchester, a charming subdivision nestled in the heart of the United States, where community spirit and suburban tranquility come together. Known for its picturesque landscapes and friendly atmosphere, Winchester offers a perfect blend of modern living and small-town charm. This vibrant community is an ideal place for families, young professionals, and retirees alike, making it a sought-after destination for homebuyers.

One of the most appealing aspects of Winchester is its diverse selection of homes available for under $500,000. Whether you're searching for a cozy single-family home, a spacious townhome, or a delightful condo, Winchester has something to fit every lifestyle and budget. These affordable properties often feature modern amenities, open floor plans, and beautiful outdoor spaces, ensuring that you can enjoy comfort without compromising on quality.

Residents of Winchester benefit from a wealth of local amenities, including parks, schools, and shopping centers, all within easy reach. The community hosts various events throughout the year, fostering a strong sense of belonging and camaraderie among neighbors. With its convenient location, Winchester also offers easy access to major highways, making commuting to nearby cities a breeze.

If you're looking for a place to call home where affordability meets charm, Winchester is the perfect choice. Explore the delightful homes under $500,000 and discover the community that could be your next great adventure. Embrace the lifestyle you've always dreamed of in Winchester, where your future awaits!

Newest Winchester Homes under $500,000

117 E Pall Mall St, Winchester
$350,000
3 Beds ⋅ 3 Baths
**SPECIAL FINANCING INCENTIVE! Sellers to offer up to $8133 in seller subsidy for temporary rate buy down (with Preferred lender) to subsidize and lower monthly payment for the first 2 years of ownership!** 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 Century 21 Redwood Realty. Contact:

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:

125 Fox Dr, Winchester
$409,000
3 Beds ⋅ 2 Baths
Welcome to 125 Fox Drive! This charming brick rancher is ideally situated in the heart of Winchester City, offering a wonderful combination of classic character, modern updates, flexible living space, and an unbeatable location. The main level features three bedrooms, a full bathroom with tile flooring, tile shower walls, and a tub/shower combination, along with beautiful hardwood floors throughout. The updated kitchen boasts bright white cabinetry, granite countertops, and stainless steel appliances. The inviting living room is highlighted by a wood-burning fireplace and distinctive accent wall, creating a warm and welcoming space to relax or entertain. Need additional space? The fully finished basement offers endless possibilities, with multiple rooms ideal for additional bedrooms, a playroom, home gym, hobby space, or home office. A second full bathroom features granite countertops, tile flooring, tile walls, and a tub/shower combination. A separate utility and storage room provides additional functionality and convenience. Step outside and enjoy the fantastic backyard! The level, fully fenced yard features a privacy fence, mature trees, and a brick paver patio, making it the perfect setting for summer barbecues, outdoor gatherings, or simply unwinding in your own private outdoor retreat. The welcoming front porch features Trex decking, vinyl railings, and columns, while the paved driveway offers parking for up to three vehicles. Solar panels provide an added opportunity to help reduce electricity costs. LOCATION, LOCATION, LOCATION! Enjoy the convenience of city living with NO HOA! Located approximately one mile from historic downtown Winchester, this home offers convenient access to local restaurants, shops, entertainment, and community events. You're also close to Valley Health Winchester Medical Center and numerous medical specialty practices, as well as the Museum of the Shenandoah Valley and Whittier Park. Enjoy the excitement of Winchester's famous Shenandoah Apple Blossom Festival and all the charm this vibrant community has to offer. Don't miss your chance to make this home your own!

125 Fox Dr, 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:

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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