Olde Towne Real Estate

Welcome to Olde Towne, a charming neighborhood nestled in the heart of Central Portsmouth, Virginia. This historic enclave is a hidden gem that beautifully marries the rich tapestry of the past with the vibrancy of modern living. As you stroll through the tree-lined streets, you'll be captivated by the stunning architecture, featuring beautifully preserved 18th and 19th-century homes that tell the story of a bygone era.

Olde Towne is not just about its picturesque homes; it's a community that thrives on connection and culture. The neighborhood boasts a variety of local shops, art galleries, and delightful eateries that showcase the best of Portsmouth's culinary scene. Whether you're in the mood for a cozy café or a gourmet dining experience, Olde Towne has something to satisfy every palate.

Nature enthusiasts will appreciate the proximity to waterfront parks and recreational areas, where you can enjoy scenic views of the Elizabeth River. The area's rich history is further celebrated through local events and festivals, providing residents with a sense of belonging and community spirit.

Families will find Olde Towne to be an ideal place to call home, with excellent schools and safe, welcoming streets. The neighborhood's vibrant community engagement ensures that there are always activities and gatherings to partake in, making it easy to forge lasting friendships.

In Olde Towne, you’ll discover not just a place to live, but a lifestyle steeped in history, community, and charm. Come explore the magic of this enchanting neighborhood and see why so many have chosen to call Olde Towne home!

Newest Listings in Olde Towne

$289,900

3 Beds ⋅ 1.2 Baths ⋅ 10652878 MLS

Don’t Miss This Rare Opportunity! Condos in this sought-after community rarely hit the market—especially one of this size! The last comparable condo to come available was in Spring 2024. With a prime waterfront location and low condo fees, it’s easy to see why owners don’t want to leave! Live in the heart of Portsmouth’s revitalized waterfront district, just blocks from the Naval Medical Center, marina, ferry service to Norfolk Waterside, incredible dining and entertainment, museums, cruise ship docks, street vendors, fireworks, and concerts. Conveniently located near the Norfolk Naval Shipyard and three major interstate connectors, making travel throughout Hampton Roads a breeze. Inside, enjoy fresh paint and new flooring, creating a bright, move-in-ready space you’ll be proud to call home. Rare. Convenient. Affordable. Don’t wait—this one won’t last!

306 Worthington Square, Central Portsmouth

$149,900

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

$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

$499,000

4 Beds ⋅ 4 Baths ⋅ 10651236 MLS

reasure 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.

400 Court Street, Central Portsmouth

$650,000

5 Beds ⋅ 3 Baths ⋅ 10648856 MLS

Step into Portsmouth history on Marsh Row in Historic Olde Towne. This 1910 charmer greets you with a gracious front porch and an extensively landscaped side lot with raised flower beds and brick patios, perfect for relaxing or entertaining. Inside, original hardwood floors, elegant interior columns, and rich woodwork showcase the craftsmanship of a bygone era. The first floor offers a large foyer, formal living and dining rooms, and an eat in kitchen with breakfast bar and dining area, plus adjacent full bath and flexible office/bedroom. A grand staircase leads to 3 bedrooms, 2 full baths, and a porch overlooking the gardens on the second level. The finished third floor adds a bedroom and an oversized entertainment room. Modern comforts include a double driveway and garage, well and pump, storage shed, and full house generator—historic character with everyday convenience in the heart of Olde Towne. Fireplace as-is.

535 Hampton Place, 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

$179,000

1 Beds ⋅ 1 Baths ⋅ 10646275 MLS

Rare opportunity! 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. Seller will pay 1 year of condominium dues with acceptable offer.

One Crawford Parkway Unit 1107, 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

$625,000

10638682 MLS

Rare opportunity to acquire a well-maintained 5-unit multifamily property in the heart of Portsmouth's highly sought-after Olde Towne Historic District. The property consists of two 2-bedroom, 1-bath units and three 1-bedroom, 1-bath units, offering an attractive unit mix that appeals to a broad tenant base. Positioned in one of Hampton Roads' most desirable neighborhoods, the property is just blocks from the Elizabeth River waterfront, Portsmouth-Norfolk Ferry, restaurants, coffee shops, museums, parks, and entertainment venues. Surrounded by major employment centers including Naval Medical Center Portsmouth, Norfolk Naval Shipyard, and Rivers Casino Portsmouth, the asset benefits from strong and consistent rental demand. Select units convey furnished, creating additional upside through furnished, mid-term, or executive rental strategies. Combining stable cash flow, a proven rental history, limited local multifamily inventory, and long-term appreciation potential, this turnkey asset presents an exceptional opportunity for investors seeking both current income and future growth in a supply-constrained waterfront market.?

367 Middle Street, Central Portsmouth

$239,900

2 Beds ⋅ 2 Baths ⋅ 10635673 MLS

Beautiful 2 bedroom/2 bath condo in the iconic One Crawford. Extraordinary harbor views for all your windows; amazing sunsets and moon rises at Mile Marker Zero on the Intracoastal Waterway! Centrally located with easy access to military bases, medical facilities, arts and entertainment in Southside and Peninsula. Easy proximity to Interstate access and mass transit for work or leisure activities. Arts, antiques, farmer's market, the Commodore theater, restaurants at your virtual door. Catch a cruise ship from Half Moon-Nauticus! Call today for your personal tour and see what an historic seaport has to offer - you won't be disappointed and join this great community. Welcome home!

1 Crawford Parkway Unit 1301, Central Portsmouth

$525,000

10633770 MLS

Impressive 1880 Victorian duplex in Olde Towne - a charming mix of original exterior and interior features and modern conveniences. Enjoy single story living downstairs. Lovely floorplan, large rooms, hardwood floors, tall windows, working fireplaces, and 12ft ceilings. Primary suite features an arched turret sitting area, fireplace, large open concept bathroom, walk in closet/dressing room/laundry area. Elegant living room has original moldings and fireplace. Real cook's kitchen has sitting and dining areas which open onto a deck overlooking the large rear garden with brick patio, large side deck + storage shed. Upstairs, 1450 sf of living space, features an arched turret sitting area, two decorative fireplaces, a covered porch to sit and enjoy Elizabeth River views, a large bonus room with washer/dryer. Short distance to the ferry, Portsmouth Naval Hospital &the Naval Shipyard. Suitable for live-in owner, multi-generational living or investment property.

318 Court 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.