Olde Towne Homes under $500,000

Olde Towne Homes under $500,000

Welcome to Olde Towne, a charming neighborhood nestled in the heart of Central Portsmouth, Virginia. Known for its rich history and picturesque streets, Olde Towne offers a unique blend of timeless architecture and modern amenities, making it a perfect place for families, young professionals, and retirees alike.

As you stroll through the tree-lined streets, you’ll be captivated by the beautifully preserved 18th and 19th-century homes, many of which boast stunning colonial and Victorian styles. The sense of community is palpable here, with friendly neighbors and local events that bring everyone together. Olde Towne is also conveniently located near the Elizabeth River, providing residents with scenic waterfront views and opportunities for outdoor activities like kayaking and fishing.

For those looking to settle in this enchanting neighborhood, you’ll be delighted to find a variety of homes available under $500,000. Whether you’re searching for a cozy bungalow, a spacious family home, or a charming townhouse, Olde Towne has something to suit every taste and budget. The affordable housing options, combined with the neighborhood’s vibrant culture and proximity to downtown Portsmouth, make it an attractive choice for homebuyers.

In addition to its beautiful homes, Olde Towne offers a wealth of local amenities, including boutique shops, delightful cafes, and historic landmarks. With easy access to public transportation and major highways, commuting to nearby cities like Norfolk and Chesapeake is a breeze.

Discover the charm of Olde Towne, where history meets modern living, and find your dream home today!

Newest Olde Towne Homes under $500,000

361 Court Street, Central Portsmouth
$379,900
4 Beds ⋅ 2 Baths ⋅ 10658880 MLS
Some homes offer history. This one invites you to become part of it. Built in 1860, the same year Abraham Lincoln was elected President, this beautifully maintained Federal-style home blends timeless character with thoughtful updates in the heart of Olde Towne Portsmouth. Original pine floors, refreshed bathrooms, and an updated kitchen with solid surface countertops and quality cabinetry preserve the home’s character while providing the comforts of modern living. Recent improvements include a new HVAC system (2023) and updated sewer and water lines for added peace of mind. A rare double lot creates a private, fenced backyard with an oversized shed featuring electric and water. Located on one of Olde Towne’s most historic streets with convenient off-street parking and just blocks from local restaurants, shops, and entertainment, this is an opportunity to become the next steward of a remarkable piece of Portsmouth’s history.

361 Court Street, Central Portsmouth
449 Dinwiddie Street, Central Portsmouth
$388,000
4 Beds ⋅ 3.1 Baths ⋅ 10657598 MLS
Welcome to 449 Dinwiddie St - a beautiful, 2714 sqft home in the historic Olde Towne district of Portsmouth. With 4 bedrooms and 3.5 bathrooms, this home provides a spacious layout set over 3 levels, plus basement - a rare find! Modernly updated whilst maintaining its historic charm, it is close to shopping, dining, major interstates and schools - this home is in a prime location! Schedule your showing today!

449 Dinwiddie Street, Central Portsmouth
1 Crawford Circle Unit 906, Central Portsmouth
$220,000
2 Beds ⋅ 1.1 Baths ⋅ 10654823 MLS
Experience elevated city living in the heart of Downtown Portsmouth! Located within  walking  distance to the Naval Medical Center Portsmouth and directly across from the Elizabeth River, This oversized 9th-floor condo offers expansive views of the harbor and city skyline. Enjoy a evening concert at the Portsmouth Pavilion, or watch a film at the historic Commodore Theatre, spend an afternoon at the Children’s Museum, or explore the dozens of established restaurants just outside your door. Best of all, the condo fee covers electricity, water, sewer, gas, trash, cable, security, and pool access—no separate utility bills!

1 Crawford Circle Unit 906, Central Portsmouth
408 Court Street, Central Portsmouth
$390,000
4 Beds ⋅ 3 Baths ⋅ 10653765 MLS
Live in the heart of historic Olde Towne Portsmouth at 408 Court Street. Enjoy stunning historic details including original Victorian wavy cylinder glass windows, soaring ceilings, and authentic period millwork. The interior boasts gorgeous pocket doors, gas radiant heat, dual-zone high-velocity central air, and a unique library with a ladder and backlit panels. A bright kitchen features a Dacor professional gas range and anchors a layout ready for your personal updates. Outside, a primary suite deck with a spiral staircase leads to a fully fenced backyard with a large workshop and shed. Experience the peak of Olde Towne living moments strolling along the waterfront. Spend weekends at the Saturday farmers market, catching Pavilion concerts, visiting the local brewery and new winery. This premier location offers an effortless commute to the Naval Hospital, USCG installations, and regional bases. Plus, the Elizabeth River Ferry is nearby for seamless access to Norfolk.

408 Court Street, Central Portsmouth
306 Worthington Square, Central Portsmouth
$279,000
3 Beds ⋅ 1.2 Baths ⋅ 10652878 MLS
Rare Find! Convenient Waterfront Living at an Affordable Price! Opportunities like this don’t come along often! Condos in this sought-after waterfront community rarely hit the market, especially one of this size. Fresh paint & new flooring create a bright, inviting, move-in-ready space you’ll be proud to call home. Add a prime waterfront location & surprisingly low condo fees, & it’s easy to see why owners love to stay! Enjoy the best of Portsmouth’s revitalized waterfront district, just 1 block from the Naval Medical Center, marina, & ferry service to Norfolk’s Waterside District. Head to High Street, just a few blocks away, for an exciting mix of restaurants, entertainment, museums, street vendors, concerts, fireworks, cruise ship docks, & more. Convenient access to the Norfolk Naval Shipyard & 3 major interstate connectors, getting around Hampton Roads is a breeze. Don’t miss your chance to enjoy the charm of waterfront living & the lifestyle you deserve in this terrific home!

306 Worthington Square, Central Portsmouth
111 High Street Unit 402, Central Portsmouth
$139,900
2 Beds ⋅ 2.1 Baths ⋅ 10651744 MLS
Quiant 2-bedroom, 2-bath condo in the heart of Downtown Portsmouth! This home features an open floor plan with kitchen, dining, and living areas. Building amenities include secured code access, covered parking garage, elevator, and storage. Condo fee covers water, sewer, trash, secured parking, and building/flood insurance. Conveniently located near the Elizabeth River Ferry, Downtown Tunnel, interstates, Portsmouth Naval Medical Center, shops, restaurants, and Olde Towne attractions. Easy access with the Olde Towne shuttle. Enjoy city living with comfort and convenience

111 High Street Unit 402, Central Portsmouth
320 London Street, Central Portsmouth
$385,000
10651284 MLS
Tremendous investment opportunity offered at a great price in Olde Towne Portsmouth! Ready for a buy and hold or update and dramatically increase equity. 3 Units: Building sq ft: 3,430, All units have central AC. All units have auto 1 yr renewal, 60 day renewal notice periodUnit 1A: 2 bedroom, 1 bath, sq ft. Rents for $1,500 a month*Lease end date 01/31/2025 Unit 2A: 1 bedroom, 1 bath, 700 sq ft. Rents for $800 a month (barely raised in 10 years)*Lease end date 10/31/2017 Unit 2B: 1 bedroom, 1 bath, 700 sq ft. Rents for $825 a month*Lease end date 03/31/2019Total Rental Income: $3,125

320 London Street, Central Portsmouth
400 Court Street, Central Portsmouth
$499,000
4 Beds ⋅ 4 Baths ⋅ 10651236 MLS
A teasure of a home in the heart of Olde Towne Portsmouth! Dating to 1805, this historically significant English-basement residence once belonged to the British Naval Attaché before the American Revolution. Offering approximately 3,877 square feet across three levels, the home combines remarkable period character—including two beautiful stained-glass windows—with an adaptable layout. The first floor provides flexible options for remote or professional work, guest accommodations, or potential additional rental income. Spacious living areas, a fireplace, four bedrooms and four baths provide plenty of room, while the third-floor studio offers another private and versatile retreat. A rare opportunity to own a distinctive piece of Portsmouth history near the waterfront, restaurants, shops, museums and entertainment. Back on the Market Due to No Fault of the Sellers.

400 Court Street, Central Portsmouth
1 Crawford Parkway Unit 1702, Central Portsmouth
$295,500
3 Beds ⋅ 3 Baths ⋅ 10647701 MLS
Located in the heart of Downtown Portsmouth within half a mile of the Naval Hospital, restaurants, and across the street from the Elizabeth River, enjoy expansive views of the harbor and the city skyline in this 17th floor, oversized condo with fresh paint and newer flooring. Catch a show at the Portsmouth Pavilion, a film at the historic Commodore Theatre, or an afternoon at the Children's Museum. Dozens of well-established restaurants are just outside your door. Condo fee covers 100% of everything: Electric, Water Sewer, Gas, Trash, Cable, Security, Pool, No Other Bills!!!

1 Crawford Parkway Unit 1702, Central Portsmouth
One Crawford Parkway Unit 1107, Central Portsmouth
$165,000
1 Beds ⋅ 1 Baths ⋅ 10646275 MLS
Incredible Value! Million dollar waterfront view from your own private balcony. Enjoy unobstructed views of Harbor and Norfolk Skyline. This light and bright condo offers open floor plan, pretty parquet flooring, new carpet in bedroom and fresh paint. Condo fee includes all utilities ( electric, gas, cable, water, HVAC maintenance /replacement) Other included amenities feature newly renovated swimming pool with cabana and grilling area. The building features gated parking lots, secured entry, a welcoming lobby with daytime receptionist and an on-site manager & maintenance staff. Plus Brand new elevators! Super convenient location to Historic Old Towne, restaurants, Naval Hospital, and ferry.

One Crawford Parkway Unit 1107, Central Portsmouth
710 Dinwiddie Street, Central Portsmouth
$349,000
3 Beds ⋅ 3 Baths ⋅ 10642820 MLS
A great opportunity for investors, this duplex features two units with terrific space, stable tenants and many recent upgrades. The first-floor unit is over 1200 square feet with a large living room, large open kitchen, three bedrooms and three full bathrooms. It includes hardwood floors, high ceilings and a washer and dryer in the unit. The second-floor unit is 1000 square feet of well-used space with 1 large bedroom, 1 bathroom and a comfortable living room. The high ceilings make it feel even larger. Upstairs also includes a washer and dryer in the unit. All separate, tenant paid utilities. New water heater and refrigerator upstairs, concrete shed in the back for owner use.

710 Dinwiddie Street, 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.

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