Trolley Square Real Estate

Welcome to Trolley Square, a vibrant and charming neighborhood nestled in the heart of Wilmington, Delaware. Known for its rich history and eclectic atmosphere, Trolley Square is a delightful blend of urban convenience and suburban tranquility, making it one of the most sought-after areas for residents and visitors alike.

Originally developed in the early 20th century, Trolley Square earned its name from the trolley lines that once traversed the area, connecting Wilmington to surrounding communities. Today, this picturesque subdivision boasts tree-lined streets, beautifully preserved architecture, and an inviting sense of community. The neighborhood features a mix of historic homes and modern townhouses, providing a diverse array of housing options that appeal to families, young professionals, and retirees.

One of the highlights of Trolley Square is its vibrant commercial district, where you'll find a variety of local shops, cafes, and restaurants. From charming boutiques to gourmet eateries, there's something for everyone to enjoy. Residents often take advantage of the nearby parks and recreational areas, perfect for leisurely strolls, picnics, or outdoor activities.

Trolley Square is also conveniently located near major transportation routes, making it easy to access downtown Wilmington and the surrounding areas. With its strong sense of community, rich cultural offerings, and proximity to urban amenities, Trolley Square is not just a place to live—it's a lifestyle. Whether you're looking to explore the local art scene, enjoy a night out, or simply relax in a beautiful neighborhood, Trolley Square has it all. Discover your new home in this enchanting Wilmington enclave today!

Newest Listings in Trolley Square

1208 Shallcross Ave, Wilmington $415,000

Welcome to 1208 Shallcross Avenue, a beautifully maintained home in the heart of Wilmington's sought-after Trolley Square neighborhood. Featuring 3 bedrooms, 1.5 bathroom...

3 Beds
2 Baths

Courtesy of Long & Foster Real Estate, Inc.

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

1401 Pennsylvania Ave Unit 104, Wilmington image

1401 Pennsylvania Ave Unit 104, Wilmington — None Available $194,900

# Spacious Ground-Floor Office Condo on Pennsylvania Avenue Discover the versatility and convenience of this spacious ground-floor office condominium, ideally situated...

Courtesy of Patterson-Schwartz-Middletown

Listing courtesy of Patterson-Schwartz-Middletown. Contact:

1401 Pennsylvania Ave Unit 614, Wilmington image

1401 Pennsylvania Ave Unit 614, Wilmington — 1401 Pennsylvania Ave. $129,900

Natural light, comfortable living, and a walkable location come together in Unit 614 at 1401 Pennsylvania Avenue. Expansive windows fill the living and dining area with l...

1 Beds
1 Baths

Courtesy of Compass

Listing courtesy of Compass. Contact:

1400 & 1408 Delaware Ave, Wilmington image

1400 & 1408 Delaware Ave, Wilmington $2,200,000

Investment Opportunity – Monument Square Apartments | Trolley Square, Wilmington, DE Monument Square Apartments presents a rare opportunity to acquire a stabilized 8-uni...

Courtesy of Long & Foster Real Estate, Inc.

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

1506 N Rodney St, Wilmington $575,000

Nestled in the vibrant heart of Trolley Square, this contemporary multilevel townhome is part of Georgian Row on Rodney Street, a distinctive collection of just six uniqu...

3 Beds
3 Baths

Courtesy of Compass

Listing courtesy of Compass. Contact:

1401 Pennsylvania Ave Unit 103, Wilmington image

1401 Pennsylvania Ave Unit 103, Wilmington — 1401 Pennsylvania Ave $139,000

Position your business in one of Wilmington’s recognizable Pennsylvania Avenue locations. Welcome to 1401 Pennsylvania Ave, Suite 103, a beautifully updated main-level co...

Courtesy of EXP Realty, LLC

Listing courtesy of EXP Realty, LLC. Contact:

1403 Shallcross Ave Unit 107, Wilmington image

1403 Shallcross Ave Unit 107, Wilmington — None Available $169,900

Come see this lovely 1 bedroom home in Hamilton House in the heart of Trolley Square. This marvelous condo features a spacious open floor plan, a terrific private balcony...

1 Beds
1 Baths

Courtesy of Patterson-Schwartz-Hockessin

Listing courtesy of Patterson-Schwartz-Hockessin. Contact:

1711 N Broom St, Wilmington $510,000 ▼

Nestled in the charming Trolley Square neighborhood, this beautifully renovated twin home offers a perfect blend of traditional elegance and modern convenience. Built in ...

3 Beds
4 Baths

Courtesy of Concord Realty Group

Listing courtesy of Concord Realty Group. Contact:

1722 Hancock St, Wilmington $299,999 ▼

Coming soon 2 / 3 Bedroom in the Heart of Trolley Square! Massive Deck, spiral staircase, upstairs laundry, and much more!

3 Beds
2 Baths

Courtesy of Real Broker LLC

Listing courtesy of Real Broker LLC. Contact:

1401 Pennsylvania Ave Unit 1511, Wilmington image

1401 Pennsylvania Ave Unit 1511, Wilmington $239,900

Perched high above the surrounding treetops, this beautifully updated 15th-floor corner residence combines an exceptionally spacious interior with a remarkable private ba...

2 Beds
2 Baths

Courtesy of Realty Mark Associates-Newark

Listing courtesy of Realty Mark Associates-Newark. Contact:

1401 Pennsylvania Ave Unit 202, Wilmington image

1401 Pennsylvania Ave Unit 202, Wilmington $127,500 ▼

Enjoy effortless city living with 24-hour valet parking, 24-hour security, and low-maintenance convenience. Wall-to-wall windows give you views overlooking the courtyard,...

1 Beds
1 Baths

Courtesy of Harrison Properties, Ltd.

Listing courtesy of Harrison Properties, Ltd.. Contact:

1401 Pennsylvania Ave Unit 1010, Wilmington image

1401 Pennsylvania Ave Unit 1010, Wilmington $269,900 ▼

Welcome to Unit 1010, ideally positioned in the quintessential location in the heart of Trolley Square, where vibrant city living meets exceptional comfort and convenienc...

3 Beds
3 Baths

Courtesy of Monument Sotheby's International Realty

Listing courtesy of Monument Sotheby's International Realty. Contact: