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 41 days on the market compared to the national average of 56 days. The median sale price for homes in Winchester, Baltimore over the last 12 months is $66,000, down 6% from the median home sale price over the previous 12 months.
Opportunity awaits! This 3-level interior townhome is ideal for a buyer, investor, or renovation enthusiast looking to complete an unfinished project and add significant value. The property was being renovated to feature 3 bedrooms and 3 full bathrooms The full basement spans the footprint of the home and includes a walkout to the rear. The renovation is incomplete, and the property is being sold
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
Price Improvement----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
Andrea MeansBerkshire Hathaway HomeServices PenFed Realty
NOT AN AUCTION, NOT A SHORT SALE, NOT A BANK OWNED, NOT A FORECLOSURE, NOT WHOLESALING---QUICK AND EASY. Buyer to pay all transfer and recording fees Minimum $2,000 EMD. Excellent Opportunity ...use your imagination! Property can be rehabbed for a nice rental investment or homeowner. Property sold "as is". Home Inspections for informational purposes only. Seller will make no repairs. . In
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
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
NOT AN AUCTION, NOT A SHORT SALE, NOT A BANK OWNED, NOT A FORECLOSURE, NOT WHOLESALING---QUICK AND EASY. Minimum $2,000 EMD. Excellent Opportunity ...use your imagination! Property can be rehabbed for a nice rental investment or homeowner. Property sold "as is". Home Inspections for informational purposes only. Seller will make no repairs. Ask LA about 5.75% financing program.
Newly Renovated Rowhome with 3 Finished Levels & Off-Street Parking! Exceptional value meets modern style in this beautifully renovated home offering spacious living across three finished levels. The open-concept main level features wood flooring throughout, a bright and inviting living room, dedicated dining area, and a stylish galley kitchen complete with Quartz countertops and stainless steel
Chris CookeBerkshire Hathaway HomeServices Homesale Realty
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
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
Property Id: 2598383 $550/mo Fees may apply 1026 Poplar Grove St, Baltimore, MD 21216 4 beds1 baths1,824 sqft 1 room 0 housemates Room details Rent by the room or take the entire home this bright 4-bedroom, 2-bath residence offers flexibility, space, and city convenience all in one. Perfect for professionals, students, or roommates looking for an
Welcome to 2728 Winchester Street, a beautifully renovated 3-bedroom, 1.5-bath home offering modern updates and comfortable living. Renovated in 2026, the home features new hardwood flooring throughout, an updated kitchen with modern appliances, and refreshed bathrooms. The spacious layout provides plenty of room for everyday living, while the recent improvements create a fresh, move-in-ready
Property Id: 2070821 **Private ROOM Available** Monthly Rent: 1BR with SHARED BATH - $600 Security Deposit same as rent Lease: Units are SINGLE occupancy (1 Person) **$150/month for Double Occupancy Month to Month Lease NO smoking and NO pets Utilities Included in Rent: Water, Electric, A/C, Trash Removal, Laundry, Wifi (speeds may vary)
Property Id: 2070822 **Private ROOM Available** Monthly Rent: 1BR with PRIVATE BATH - $700 Security Deposit same as rent Lease: Units are SINGLE occupancy (1 Person) **$150/month for Double Occupancy Month to Month Lease NO smoking and NO pets Utilities Included in Rent: Water, Electric, A/C, Trash Removal, Laundry, Wifi (speeds may vary)
** 3BDS / 1.5BTH** Newly Renovated Home!** Hardwood Flooring Throughout!** Spacious Rooms!** Finished Basement!** Front Porch and Rear Yard!** Ceiling Fans!** W/D!** Available Now!1203 Ashburton StreetBaltimore, MD21216$1,495/MonthProof of employment (Copies of your pay stubs for the last 30 days) and a copy of your driver's license or
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