Olde Towne Real Estate

Welcome to Olde Towne, a charming neighborhood nestled in the heart of Central Portsmouth, Virginia. Steeped in history and brimming with character, Olde Towne is a delightful blend of the past and present, making it one of the most sought-after communities in the area.

As you stroll through the tree-lined streets, you’ll be captivated by the stunning architecture that reflects the rich heritage of Portsmouth. Historic homes, many dating back to the 18th and 19th centuries, showcase unique designs and craftsmanship, while modern renovations breathe new life into this picturesque neighborhood. The vibrant community spirit is palpable, with friendly neighbors who take pride in their homes and surroundings.

Olde Towne is not just about beautiful houses; it’s a hub of culture and activity. Residents enjoy easy access to an array of local shops, art galleries, and delightful eateries that serve up everything from Southern comfort food to gourmet cuisine. The waterfront is just a stone's throw away, offering scenic views of the Elizabeth River and opportunities for leisurely walks, picnics, or simply soaking in the serene atmosphere.

For families, Olde Towne is served by quality schools and community parks, providing ample recreational options for children and adults alike. The neighborhood is also conveniently located near major highways, making commuting to nearby cities a breeze.

Whether you’re looking to settle down in a historic home or simply seeking a vibrant community with a rich cultural tapestry, Olde Towne in Central Portsmouth promises a fulfilling lifestyle. Discover the charm of Olde Towne and embrace the unique blend of history, community, and modern living!

Newest Listings in Olde Towne

$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

$389,000

4 Beds ⋅ 2 Baths ⋅ 10647204 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

$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 downtown Portsmouth, 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, 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

$139,900

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, Central 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, Central 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, 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.