Windsor Hills – Baltimore, MD

Located just 5.5 miles from downtown Baltimore, Windsor Hills is simply beautiful. Its lush lawns, stone walls, mature trees, and historic architecture blend to create an attractive community. Add in its proximity to downtown, the trail-head to the Conservation Trail, and good schools, and it's easy to see why Windsor Hills is one of Baltimore's most popular neighborhoods. The entire neighborhood is a National Historic District, with homes dating back to the late 1800s through 1929. Windsor Hills borders Gwynns Falls Park on its west side and the neighborhood of Garwyn Oaks on the east side. It sits between Fairfax Road to the north and Gwynns Falls Parkway to the south.

Schools in Windsor Hills

School data provided by GreatSchools

Restaurants & Nightlife

Locals don't mind traveling a few miles to downtown Baltimore for the wide variety of ethnic cuisines. Puerto 511 serves authentic Peruvian food and rates as one of the best restaurants in Baltimore. Regulars highly recommend the sweet yet savory ceviche clasico and say the lomo saltado, a Peruvian staple, makes the perfect entree. The dish comes with traditional Peruvian-style beef tenderloin, sauteed onions, tomatoes, cilantro, soy sauce, garlic, hand-cut fries, and steamed white rice. Top off this experience with Peruvian toast for dessert. Locals also enjoy Joe Benny's in the Little Italy district. With five stars across the board for quality of food, service, and prices, this establishment is a culinary gem. Regulars adore the salami-and-cheese appetizer, which comes with an assortment of cured meats and Italian cheeses. On your first visit, order the eggplant panini or fiore pizza. Supreme Oasis Bakery and Deli serves the best fried fish in town. Complement your dinner with the famous macaroni and cheese and bean pie. If you crave a more-traditional deli-style meal, delight in the turkey breast sandwich, but call ahead if you have time constraints because this place gets packed.

History & Culture

The Windsor Hills neighborhood was part of a land grant in the 1690s. Due to its hilly terrain, the area was unsuitable for farming, so mills were built instead. The neighborhood continued to grow along with the transportation lines. By the 1890s, it had acquired an amusement park and monorail. This neighborhood is close to Baltimore's arts and entertainment sector. Locals often travel downtown to the Walters Art Museum to admire art from around the globe. The museum features art that ranges from the third millennium B.C. to the 20th century. One of the most popular museum attractions is Watch a Conservator at Work, which allows visitors to observe the act of restoring artwork.


The neighborhood provides easy access to Interstates 73 and 80. If you have to drive into downtown for work, ample parking awaits along James Street and Guilford Avenue. Parking rates vary, but drivers appreciate a monthly pass option. Baltimore City's parking meters have fees of $2 per hour. While it is easy to hail a cab in downtown Baltimore, calling and scheduling a pickup proves to be more efficient if you reside in a surrounding neighborhood, such as Windsor Hills. Lyft and Uber service the neighborhood as well, and the area accommodates walking and cycling with sidewalks and biking lanes. The Maryland Transit Administration (MTA) serves as the area's reliable public transit system. MTA provides residents with convenient services, including bus, light rail, train, and metro subway transportation.


The cost of living in the Windsor Hills neighborhood is 0.8 percent higher than the Baltimore average and 4.8 percent lower than the national average. It costs $1.60 for a one-way ticket to the city center, and housing rates stand at around $775 per month for a one-bedroom apartment in Windsor Hills. Expect to pay around $3 for a beer at a local pub. Many bars host happy hours, which makes entertaining guests easy and affordable. Gas prices run 0.5 percent higher than the national average.


Locals go to Mondawmin Mall for a traditional shopping experience. The mall houses well-known stores, such as Marshall's and Target, and specialty shops, including Deals and Gold Brothers. Take a break and indulge in a Cinnabon, or enjoy a nice sit-down meal at Mamma Lucia's while you're there. Join the mall's exclusive club and receive special promotions, discounts, and the scoop on upcoming events. Party Dress, a local boutique, sells dresses for all occasions. Whether you need to attend a cocktail party or business meeting, Party Dress has the clothes that suit your needs. For basic grocery shopping, locals usually go to Save-A-Lot, which sells high-quality food at a discounted price. For fresh produce and other locally-made goods, check out the Druid Hill Farmers Market on Wednesday afternoons from June through September and enjoy live music while you shop.


Home of the Maryland Zoo, Druid Hill Park also houses a disc golf course, picnic areas, tennis courts, gardens, a playground, and a tranquil reservoir. This park remains popular among photographers because of the lush greenery and picturesque scenery. The 745-acre park stays open to the public year-round and does not require an admission fee. Locals also frolic at Federal Hill Park, a Baltimore City landmark. Offering visitors one of the most stunning views of the city, Federal Hill Park hovers over the great red bank of clay and features benches and picnic areas, a playground, basketball court, and access to restaurants and pubs. Every Thursday, Gwynns Falls/Leakin Park hosts the Gentle Hike, inviting members of the community to explore the historic features and nature along the park trails. The hike starts on a different section of the trail each week, so be sure to find out the starting point in advance.
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