Simonsdale Real Estate

Welcome to Simonsdale, a charming neighborhood nestled in the heart of Central Portsmouth, Virginia. This delightful community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, young professionals, and retirees alike.

Simonsdale is characterized by its tree-lined streets, friendly neighbors, and a strong sense of community. The neighborhood boasts a variety of well-maintained homes, ranging from cozy bungalows to spacious two-story residences, ensuring there’s something for everyone. The lush greenery and beautifully landscaped yards create a picturesque backdrop that invites outdoor living and leisure.

One of the standout features of Simonsdale is its accessibility to essential amenities. Residents enjoy proximity to local parks, schools, and shopping centers, making daily errands a breeze. The nearby Simonsdale Park offers recreational opportunities, including playgrounds, walking trails, and picnic areas, perfect for family outings or a peaceful afternoon stroll.

The neighborhood is also well-connected to major roadways, providing easy access to downtown Portsmouth and the bustling Norfolk area. This makes commuting to work or exploring the vibrant cultural scene of Hampton Roads effortless.

In addition to its convenient location, Simonsdale is known for its strong community spirit. Residents often gather for neighborhood events, fostering friendships and creating lasting memories. Whether you’re looking for a place to settle down or simply want to explore a welcoming community, Simonsdale is sure to capture your heart. Discover the charm and warmth of this hidden gem in Portsmouth, VA!

Newest Listings in Simonsdale

$275,000

3 Beds ⋅ 1 Baths ⋅ 10652871 MLS

Great ranch home! New roof and kitchen appliances installed in 2021. In 2023, owner upgraded the electrical panel from 120 to 220 amps, had central HVAC installed and finished the interior of the garage. New LVP flooring installed in 2026. Conveniently located near City Park with easy access to shopping, dining and area amenities. Many valuable updates already completed! Portsmouth City Park offers quite a bit more than golf and tennis. It sits along the Western Branch of the Elizabeth River and includes a 9-hole executive golf course and lighted driving range, tennis courts, playgrounds, picnic areas and shelters, fishing piers, boat ramps, waterfront trail areas, and the Pokey Smokey miniature train.

114 Sykes Avenue, Central Portsmouth

$189,900

3 Beds ⋅ 1 Baths ⋅ 10631843 MLS

Come view this charming ranch home in the desirable Simonsdale neighborhood of Portsmouth! This 3-bedroom, 1-bath home features an eat-in kitchen, sunroom overlooking a large fenced backyard, and laminate/LVP flooring throughout. The real gem is the detached 2-car garage already equipped with plumbing and electrical — offering exciting potential as an accessory dwelling unit (ADU) for rental income, multigenerational living, or a private home office, buyer to verify ADU feasibility with City of Portsmouth zoning and local authorities. Plus a generous storage shed for even more versatility. Sitting on a quarter-acre lot, you’re just minutes from Portsmouth City Park & Golf Course, Chesapeake Square Shopping, interstates, military bases, and shipyards. Don’t miss this incredible opportunity — whether you’re a first-time buyer or savvy investor! SHORT SALE subject to third-party approval. Property sold as-is. Seller will make no repairs. All offers must include proof of funds or pre-approval letter. Allow time for lender review and approval . Great opportunity for investors or buyers willing to wait for lender approval.

515 Jewell Avenue, Central Portsmouth

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Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.