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301 Grayson Street, Central Portsmouth
$410,000
3 Beds ⋅ 1.1 Baths ⋅ 10645037 MLS
This charming 3-bedroom, 1.5-bath home in Portsmouth's sought-after Waterview neighborhood blends the character of a 1940s home with modern energy-efficient upgrades. Recent improvements include new insulation, updated HVAC featuring a dual-zoned heat pump for the second and third floors and a gas pack serving the first floor. The renovated kitchen (2020) offers new cabinetry, quartzite countertops, and a gas range. Original hardwood floors preserve the home's timeless appeal, while new energy-efficient windows include a one-time transferable life time warranty. Situated on a spacious lot, the property also features a detached three-car garage and a custom storage shed, providing exceptional space for vehicles, hobbies, and storage. Historic charm meets modern comfort in this move-in-ready home.

301 Grayson Street, Central Portsmouth

433 Glasgow Street, Central Portsmouth
$329,900
3 Beds ⋅ 2.1 Baths ⋅ 10642379 MLS
Beautifully maintained two-story home ideally situated directly next to a quiet neighborhood park 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. The home is available fully furnished with an acceptable offer; offering a rare turnkey opportunity. 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. Located near waterfront, restaurants, shops, parks, entertainment, the ferry to Norfolk, and a 30-minute drive to the oceanfront in Virginia Beach. 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

271 Webster Ave Avenue, Central Portsmouth
$225,000
3 Beds ⋅ 2 Baths ⋅ 10640997 MLS
Great updated home in historical Park View - Come check out this 2 story, 3 bedroom, 2 bath move-in ready home! This home has old charm combined with modern living. It features a covered porch out front to enjoy your morning coffee and a screened in porch off the kitchen to enjoy eating outside. There's a first floor bedroom, family room, large kitchen with Corian countertops, stainless steel appliances, island with cabinet storage & overhang for bar stools. There is another room downstairs that could be used as a study. In addition there are 2 bedrooms upstairs, huge storage closet and 2nd bath. New laminate floors on first floor and new carpet upstairs. Fresh paint as well - move in ready! Centrally located to all major highways, close to the Naval Base/Hospital and the casino.

271 Webster Ave Avenue, Central Portsmouth

1909 High Street, Central Portsmouth
$329,999
10639458 MLS
Investor and owner-occupant opportunity in a designated Portsmouth Opportunity Zone. This 2-story duplex unlocks flexible income potential: run it as a traditional two-unit rental, or convert to the co-living model it was originally designed for, with up to 3 rentable rooms (2 up + 1 down). At approximately $800 per room market rent, the by-the-room scenario projects roughly $2,400 per month in gross potential income, giving an investor two paths to a strong cash-on-cash return. Three bedrooms and 2.5 baths across two stacked units. 2025 upgrades include luxury vinyl plank flooring and ductless mini-split systems, plus forced-air heat and central air. Eat-in kitchen, fireplace, covered patio, wood deck, fenced backyard, and a detached storage outbuilding. Low-maintenance vinyl and brick exterior. Public transportation is on the corner; the surrounding area is improving. All appliances convey.

1909 High Street, Central Portsmouth

367 Middle 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

161 Maryland Avenue, Central Portsmouth
$326,000
3 Beds ⋅ 3 Baths ⋅ 10636625 MLS
This charming home is full of character and unique features, from the original stained glass greeting you at the entryway to the incredible third-floor home theater room. Offering 3 bedrooms & 3 full baths, including a convenient first-floor bedroom. The beautifully updated kitchen features granite countertops, stainless steel appliances, modern lighting, a built-in breakfast nook & a stylish bar area. Cozy up by the electric fireplace or enjoy the abundance of inviting indoor and outdoor living spaces. Relax on the wraparound porch complete with a swing, unwind on the private balcony off the primary suite, or take advantage of the detached shed for additional storage. A dedicated laundry room and thoughtful upgrades throughout make this home as functional as it is inviting. This one-of-a-kind property offers warmth, personality, and space to entertain — a must-see! Short sale approved!

161 Maryland Avenue, Central Portsmouth

318 Court Street, 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

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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