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 suburban tranquility meets modern convenience. This delightful community offers a perfect blend of picturesque landscapes, friendly neighbors, and a warm sense of belonging. With homes priced under $500,000, Winchester is an ideal destination for first-time homebuyers, families, and anyone seeking an affordable slice of paradise.

As you explore Winchester, you'll find a variety of architectural styles that cater to diverse tastes, from cozy single-family homes to spacious townhouses. Each residence is thoughtfully designed, showcasing modern amenities and inviting outdoor spaces where you can unwind or entertain. The homes in this subdivision not only offer comfort and style but are also surrounded by lush greenery and scenic parks, perfect for weekend picnics or leisurely strolls.

Winchester is conveniently located near essential amenities, including shopping centers, schools, and recreational facilities, making it an ideal place for families and professionals alike. The community is also well-connected to major highways, ensuring easy access to nearby cities and attractions.

In addition to its affordability and accessibility, Winchester boasts a vibrant community spirit with regular events and activities that foster connections among residents. Whether you’re enjoying a summer barbecue or participating in local festivals, you’ll quickly feel at home in this welcoming enclave.

Discover the charm of Winchester today, where your dream home awaits at an unbeatable price. Embrace a lifestyle of comfort, community, and convenience in this enchanting subdivision!

Newest Winchester Homes under $500,000

2711 Ellicott Dr, Baltimore
$64,900
3 Beds ⋅ 2 Baths

2711 Ellicott Dr, Baltimore

Listing courtesy of Long & Foster Real Estate, Inc.. 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.

2834 Riggs Ave, Baltimore

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

125 Fox Dr, Winchester
$419,000
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:

1221 Ashburton St, Baltimore
$180,000
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
$149,900
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:

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
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:

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 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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