Simonsdale Homes for Sale

Welcome to Simonsdale, a charming neighborhood nestled in the heart of Central Portsmouth, Virginia. This inviting community is known for its rich history, friendly atmosphere, and beautiful tree-lined streets, making it an ideal place for families and individuals alike. With its close-knit community feel and convenient access to local amenities, Simonsdale truly embodies the essence of suburban living while still being just a stone's throw away from the vibrant culture of Portsmouth.

One of the standout features of Simonsdale is its diverse array of homes for sale. From quaint bungalows to spacious family residences, there is a perfect home for everyone in this delightful neighborhood. Many of these homes showcase classic architectural styles, offering both character and charm. Residents enjoy the benefits of well-maintained yards and nearby parks, providing ample opportunities for outdoor activities and relaxation.

In addition to its picturesque homes, Simonsdale boasts a variety of local shops, restaurants, and recreational facilities. The community is conveniently located near major highways, making commuting a breeze and allowing residents easy access to the bustling cities of Norfolk and Virginia Beach. Families will appreciate the proximity to reputable schools, ensuring a quality education for children of all ages.

Whether you're seeking a peaceful retreat or a vibrant community, Simonsdale is a gem waiting to be discovered. Explore the homes for sale in this delightful neighborhood and find your dream home in the heart of Portsmouth, where comfort and convenience come together in perfect harmony.

Newest Simonsdale Homes for Sale

$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.