Olde Towne Real Estate

Welcome to Olde Towne, a charming neighborhood nestled in the heart of Central Portsmouth, Virginia. Rich in history and character, Olde Towne is a delightful blend of quaint streets, stunning architecture, and a vibrant community spirit that makes it a truly special place to call home.

As you stroll through Olde Towne, you'll be captivated by the beautifully preserved 18th and 19th-century homes, many of which showcase intricate details and unique designs that tell the story of the area’s storied past. The tree-lined streets are perfect for leisurely walks, and you'll often find neighbors engaging in friendly conversations or enjoying the picturesque parks that dot the landscape.

Olde Towne is not just about its historical charm; it also boasts a lively arts scene and a variety of local shops, galleries, and restaurants. Whether you’re in the mood for a cozy café, a gourmet dining experience, or a unique boutique, you’ll find it all within walking distance. The neighborhood hosts numerous events throughout the year, from art walks to seasonal festivals, fostering a strong sense of community and connection among residents.

For families, Olde Towne offers access to quality schools and recreational facilities, making it an ideal place to raise children. With its proximity to the waterfront and easy access to major highways, residents can enjoy the tranquility of suburban living while being just a short drive away from the bustling city life in Norfolk and beyond.

Experience the charm and warmth of Olde Towne, where history meets modern living, and discover why so many are proud to call this neighborhood home.

Newest Listings in Olde Towne

$399,000

5 Beds ⋅ 3 Baths ⋅ 10646044 MLS

Come live in this Historical, Victorian Home in Olde Towne Portsmouth. It is elegant, spacious and filled with gorgeous details. The graceful front porch leads to a lovely foyer with a soaring ceiling and original hardwood floors. The spacious kitchen overlooks a lovely garden that was dedicated to the memory of a Virginia First Lady. A separate living, dining and full bathroom complete the 1st floor. The 2nd floor has 4 generous bedrooms (1 with a balcony), a large full bath with shower and clawfoot tub. The large laundry room leads to 2nd balcony. The 3rd floor has a large room with sink, full bath, a storage space/small bedroom and a larger bedroom with closet.-useful as a guest suite or possible income opp. Centrally located in the walkable downtown, it is less than a mile from the local coffee shops, movie, restaurants, churches, a concert pavilion, NMCP, & USCG East District, and the ferry to Norfolk - and its restaurants, Tides games, Waterside & Town Point Park.

357 Dinwiddie Street, Portsmouth

$189,000

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.

One Crawford Parkway Unit 1107, 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, 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, Portsmouth

$147,900

2 Beds ⋅ 1.1 Baths ⋅ 10638250 MLS

Carefree living at its best in Olde Towne! You're going to love this beautifully updated, move in ready condo featuring gleaming quartz countertops and soft close cabinets. Complete with spacious rooms and large closets and a condo building full of amenities. Near to downtown restaurants, ferry to Norfolk, interstates, and Portsmouth Naval Hospital. Condo fee includes nearly ALL your utilities including electric, water, gas, trash, cable TV, sewer and security, pool, plenty of off street parking, event/party room, and lobby area. Come see what makes One Crawford so special!

1 Crawford Parkway Unit 1306, Portsmouth

$254,500

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, Portsmouth

$549,900

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, Portsmouth

Start Your Search

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.