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$425,000
3 Beds 2 Baths 10650518 MLS
Built in 2006 on a corner lot in historic Olde Towne Portsmouth. 448 sets it's self apart with fully paid off solar panels, secret gardens, soaring 20 ft ceiling in living room w/2-story bay windows, Double sided gas fireplace that opens to both the living & dining rooms. The Modern kitchen has stainless steel appliances & tons of cabinets. 2 downstairs BR's and full bath w/granite countertop & tub/shower combo w/tile surround. Hardwood floor staircase leads to loft library office w/custom built in cabinets & with grand Fireplace with dramatic overlook to living room and bay windows. The huge primary suite has a large walk-in closet, 2 vanities w/granite, romantic soaking tub & tile shower. Utility room w/washer & dryer, newer water heater (2022), dual zone HVAC, storage shed, privacy fence. Exterior paint/trim touched up/ repaired 2026. Solar system conveys with low electric bills! Located minutes from the Naval Hospital, Coast Guard base, local restaurants, Commodore Theatre, Children's Museum of Virginia & the Portsmouth waterfront!

448 Washington 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

$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

$529,000
3 Beds 2.1 Baths 10646786 MLS
This beautifully preserved historic property blends timeless charm with modern convenience, offering more than 2,900 square feet of updated living space. A free flowing interior layout complements the home’s grand architecture, creating an inviting setting for everyday living and entertaining. The professionally updated kitchen features quartz countertops, shaker-style cabinets, sleek stainless steel appliances, and new flooring. Spacious second-floor bedrooms and an updated bath provide generous closet space, while the large third-floor flex room or third bedroom is ideal for a media room, playroom, home office, or guest space. The large fenced backyard is well-suited for entertaining, complete with a deck, patio, and greenhouse! Nestled near the Elizabeth River and just moments from High Street’s vibrant shops, restaurants, and the ferry to Norfolk Waterside, this home offers both convenience and rich local heritage Meticulously updated and maintained, this historic Portsmouth home is ready to impress. Schedule your tour today.

228 North 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

$329,900
2 Beds 2.2 Baths 10644949 MLS
Welcome to Crawford Bay Condos! Views of the Elizabeth River Harbor. This community is located along the river. Short distance to Downtown Portsmouth and the HRT ferry to Downtown Norfolk. 2 parking spots directly in front of unit. Open floor plan downstairs. New kitchen, cabinets and countertops. Real hardwood floors. NEW HVAC Units - One new unit services downstairs, and the other new unit services floors 2 and 3, enjoy the benefits of a brand new system for each floor. Windows were updated in 2022 per previous seller. Second floor features bedroom with en-suite full bath, loft/den with fireplace, balcony with views of the water. Third floor features primary bedroom with en-suite bath, large closets and plenty of storage. One of the best values in Portsmouth.

155 Crawford Parkway, Central Portsmouth

$358,900
3 Beds 2.1 Baths 10642379 MLS
Beautifully maintained two-story home in the heart of historic Olde Towne Portsmouth. Offering 1,620 square foot of well designed living space, this 3-bedroom, 2.5 bath residence blends timeless character with everyday comfort. Inside, you'll find inviting living spaces, a functional floor plan, and abundant natural light throughout. Upstairs, three spacious bedrooms provide comfort and privacy, while the 2.5 baths offer convenience for both family and guests. Step outside to enjoy the private courtyard - an ideal setting for morning coffee, outdoor dining, or relaxing after a stroll through one of Virginia's most charming historic neighborhoods. The home is available fully furnished with an acceptable offer; offering a rare turnkey opportunity. Located near waterfront, restaurants, shops, parks, entertainment, and the ferry to Norfolk. This home combines historic charm with the convenience of urban living. Don't miss the opportunity to own this Olde Towne home!

433 Glasgow 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

$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

$189,900
2 Beds 2 Baths 10633763 MLS
Welcome to Crawford Square Condominiums! This beautiful move-in ready, condo is located in the heart of Olde Town Portsmouth. The primary bedroom includes a custom closet system, high ceilings, and an en suite bathroom. The secondary bedroom includes a walk-in closet. Other features within this 2 living level condo include 2 full bathrooms, stainless steel appliances, stackable washer and dryer, pantry with extra space for additional storage, large balcony to enjoy a sunny day, and a gas fireplace for those chilly nights. Enjoy nearby locally-owned coffee shops and restaurants, or take a trip on the ferry to Downtown Norfolk. You can enjoy local festivals and concerts at the nearby Atlantic Union Bank Pavilion. Your condo fees cover master insurance policy, flood insurance policy, water, sewage, trash, common area maintenance, and cleaning, secured access to the building and parking, pest control, and a storage unit. Schedule your private showing today!

111 High Street Unit 407, Central Portsmouth

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.