Winchester is a changing neighborhood 4 miles from downtown Baltimore
With ongoing efforts to breathe new life into the area, Winchester is awaiting its moment to blossom. Hidden amongst a sea of gridded streets, the neighborhood offers more than meets the eye—especially to those outside the city. As Alison Debraux, an agent with Taylor Properties, says, “You have to know Baltimore to understand Baltimore.”
Winchester’s classic brick rowhouses display a mix of vibrant painted facades.
Carver Vocational alumni celebrate homecoming with a lively park gathering near Winchester.
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Brick row houses date back to the early 20th century
Located less than 4 miles from downtown, the neighborhood comprises brick row houses between 1,000 and 1,800 square feet. Home construction dates range from 1900 to 1940, so architectural design varies based on the decade of construction. Some homes feature bay windows and white accents, while others feature stone porches. Because homes line each block from end to end, you won’t find new builds nearby. You will, however, see some updated houses. “The neighborhood in the south there is being totally remodeled or renovated,” explains Debraux. Renovated homes range from $95,000 to $263,000, while homes needing repair cost between $19,800 and $83,500.
Security bars on doors and windows are a frequent sight in Winchester.
Brick rowhouses in Winchester show mixed renovation levels and modest front porches.
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Rosemont Elementary/Middle School is nearby
During the school year, students attend Rosemont Elementary/Middle, rated C-minus by Niche. Rosemont offers after-school athletic options like basketball and flag football and welcomes students each year with a back-to-school cookout. For high school, students choose where to attend. The closest option is Carver Vocational, which offers career training and certification for paths like cosmetology, electrical and business administrative services. Carver scores a C minus on Niche.
Rosemont Elementary/Middle near Winchester hosts a back-to-school cookout each year.
Carver Vocational High School near Winchester offers career-focused programs.
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Residents spend time at local parks like Leon Day Park
After school, dribble a basketball or climb on the playground at Leon Day Park, located along the edge of Gwynns Falls/Leakin Park. Jump on the Gwynns Falls Trail to extend your outdoor adventure and find over 20 miles of walkable paths through 1,200 acres of woodlands. For rainy days, play indoors at one of the two recreation centers nearby. At the Easterwood Recreation Center, operated by Omega Baltimore, a mile away, take advantage of fitness classes, adult learning opportunities, and college readiness courses. Bentalou Recreation Center, also about a mile away, hosts the Project Survival youth basketball league every summer and winter.
Leon Day Park offers a playground and green space close to Winchester homes.
Easterwood Park offers open space for skating and recreation near Winchester.
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Restaurants include Lucky’s Pizza, Subs & Wings and TGI Fridays
Once you work up an appetite, order a cheesesteak from Lucky’s Pizza, Subs & Wings, a takeout restaurant only blocks from home. For a place to dine in, make your way to TGI Fridays at Mondawmin. After you eat, shop at national and local retailers in the mall or buy groceries at Shoppers.
Shoppers grocery store sits just a short drive from Winchester for everyday needs.
Grab pizza and wings at Lucky’s Pizza, a local favorite in Winchester.
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Locals volunteer with organizations like Jonah House
To volunteer and contribute to community support and outreach efforts, walk to Jonah House in St. Peter’s Cemetery, an organization dedicated to bringing people together and promoting sustainability. Assist with the garden and groundskeeping or help with distribution at the food pantry each week. For more opportunities to connect with neighbors for the greater good, keep an eye on the Alliance of Rosemont Community Organization’s calendar. The group brings together 10 neighborhoods to build a bond between nearby locales and renew shared spaces.
Public transit and Interstate 83 go through Baltimore
If you’re traveling downtown, catch the bus on Poplar Grove St. With stops every 20 minutes, commuting to the heart of the city proves simple. For trips outside city limits, take Interstate 83 north to Towson or jump on Interstate 695 south to Glen Burnie.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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Baltimore/Washington International Thurgood Marshall
22 min drive
Bus
Poplar Grove St & Riggs Ave Sb
Bus
Bloomingdale Rd & Winchester St Sb
Reviews
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Crime and Safety
1 - Low Crime, 10 - High Crime
Winchester
US
Homicide
3
4
Sexual Assault
9
4
Assault with Weapon
7
4
Robbery
7
4
Burglary
4
4
Motor Vehicle Theft
4
4
Larceny
5
4
Crime Score
9
4
Source: WhatIsMyCrimeRisk.com
Winchester Demographics and Home Trends
On average, homes in Winchester, Baltimore sell after 62 days on the market compared to the national average of 53 days. The median sale price for homes in Winchester, Baltimore over the last 12 months is $62,000, down 17% from the median home sale price over the previous 12 months.
Renovated 3-Bedroom Rowhome in Baltimore’s Winchester Community Welcome to this beautifully updated three-bedroom, two-bathroom, three-level rowhome in the Winchester neighborhood of Baltimore, Maryland. This home features a comfortable layout with modern upgrades, including a bright open living area, updated kitchen, new flooring, and two full baths. A private backyard provides space for outdoor
Investors OR handy homeowners don’t miss out on this porch-front home! This property presents a golden opportunity to build equity and create your dream home. Put your makeover skills to work and unlock the hidden potential of this property. With its prime location and solid bones, the possibilities are limitless. Whether you’re an experienced investor or a first-time homeowner seeking an
Andrea MeansBerkshire Hathaway HomeServices PenFed Realty
This three-story town home with 3 bedrooms and one full bath is situated in the Winchester Neighborhood. As you arrive, you will find the all-brick front and big covered front porch create a welcoming first impression. As you walk in you see a large living room and separate dining room. Upstairs boasts 3 spacious bedrooms and 1 bathroom. The unfinished basement is large and awaits your design and
Solid 3-bedroom, 1.5-bath rental property featuring a covered porch and a backyard, offering outdoor space and long-term usability. The home is currently rented, providing immediate income for an investor. Located near major employers including UMMC, VA Medical Center, SSA (Woodlawn), and Baltimore City government offices. Convenient access to W North Ave, Reisterstown Rd, and nearby bus routes,
Well-maintained and full of potential, this 3-bedroom, 1-bath home at 1209 Dukeland St offers bright living spaces, a functional layout, and great value for both homeowners and investors. Featuring a comfortable main level, spacious bedrooms, and a convenient Baltimore location close to parks, schools, shopping, and major commuter routes, this property is ready for its next chapter. Don't miss
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
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 floor 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
Marta LopushanskaBerkshire Hathaway HomeServices Homesale Realty
Welcome to 2903 Winchester Street, a beautifully renovated 4-bedroom, 3-bathroom home nestled on the west side of Baltimore that perfectly blends modern comfort with classic city charm. This warm and inviting residence features an open floor concept that creates a seamless flow between the living, dining, and kitchen areas—ideal for both everyday living and entertaining. Luxury vinyl plank (LVP)
Welcome to 2706 Winchester Street, a well-kept three-bedroom, one-bath brick townhome offering classic Baltimore style and functional living space. The main level features a bright living room, a separate dining area, and a spacious kitchen with plenty of cabinet storage. Upstairs, you’ll find three comfortable bedrooms and a full bath with updated fixtures. The lower level provides clean, open
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
Property Id: 2070822**Private ROOM Available**Monthly Rent:1BR with PRIVATE BATH - $850/900Security Deposit same as rentLease:Units are SINGLE occupancy (1 Person)**$150/month for Double OccupancyMonth to Month LeaseNO smoking and NO petsUtilities Included in Rent:Water, Electric, A/C, Trash Removal, Laundry, Wifi (speeds may
Property Id: 2070821**Private ROOM Available**Monthly Rent:1BR with SHARED BATH - $800Security Deposit same as rentLease:Units are SINGLE occupancy (1 Person)**$150/month for Double OccupancyMonth to Month LeaseNO smoking and NO petsUtilities Included in Rent:Water, Electric, A/C, Trash Removal, Laundry, Wifi (speeds may
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Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.