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421 North Street, Portsmouth
$725,000
5 Beds ⋅ 3.1 Baths ⋅ 10654294 MLS
Step into 1879 with all the perks of today. This grand Victorian in the heart of Olde Towne pairs soaring 12 foot ceilings, original hardwood floors & stained glass windows with modern conveniences. There was a 2022 top-to-bottom refresh. Full interior repaint, renovated kitchen & a fully built-out attic that's now the ultimate hangout: pool table area, bar & movie space all in one. The kitchen is a showstopper with large island, 8 gas burner stove, & dual chef stations. There are 5 bedrooms and 3.5 baths spread across a floorplan made for entertaining, with huge, light-filled rooms including a formal parlor, a library & a large dining room. The primary suite features heated bathroom floors, and a porch and second floor balcony give you your pick of outdoor space. The lot is generously sized for Olde Towne, a rare find alongside so much historic character!

421 North Street, Portsmouth

5105 Deep Creek Boulevard, Portsmouth
$275,000
2 Beds ⋅ 1 Baths ⋅ 10653874 MLS
Move-In Ready Bungalow with Metal Roof & Modern Updates! Welcome home! This charming fully refreshed bungalow on the boarder of Chesapeake & Portsmouth blends modern upgrades with classic character. From the street, you will immediately notice the durability and sleek look of the brand-new metal roof, offering peace of mind for years to come. Step inside to find a blend of original hardwood flooring and all new flooring throughout the rest of the house. The kitchen has been beautifully updated with modern finishes, making meal prep a breeze. All appliances convey. Enjoy a fresh, updated bathroom with contemporary ceramic tile. Natural gas heating and central AC will keep you comfortable all year long. The backyard sits on a generous 0.35 acre lot perfect for pets, gardening, entertaining, or future expansions. Super convenient access to local schools, parks, major roadways and all dining and shopping Portsmouth and Chesapeake have to offer.

5105 Deep Creek Boulevard, Portsmouth

1407 Ekstine Drive, Portsmouth
$304,999
3 Beds ⋅ 2 Baths ⋅ 10653957 MLS
Welcome to this beautifully updated 3-bedroom, 2-bathroom home offering 1,225 square feet of comfortable living space in a quiet, established neighborhood. Thoughtfully renovated from top to bottom, this property blends classic charm with contemporary convenience. Natural light pours through the oversized picture window in the family room, creating a bright and airy atmosphere throughout the main floor. The completely renovated kitchen boasts brand-new quartz countertops, brand-new sleek stainless steel appliances, a gas range and soft-close cabinetry. New luxury vinyl flooring runs throughout the entire home, complemented by fresh neutral paint and abundant natural light. The primary suite offers a private retreat with an updated en-suite bathroom featuring a walk-in tile shower and 2-sink vanity, making getting ready easier and more functional. Step outside to a partially fenced backyard with a screened in porch and built-in brick bbq grill, great for weekend barbecues, hosting family and friends, and outdoor play. The previously converted garage seamlessly connects to the home just off the kitchen and offers you a multipurpose bonus space that can be used as a dining room, flexible family room, additional bedroom, home office suite, home gym, or creative studio. The options are endless! Conveniently located just minutes from local schools, parks, and shopping centers. Schedule your private tour today!

1407 Ekstine Drive, Portsmouth

120 Sandpiper Drive, Portsmouth
$340,000
4 Beds ⋅ 2 Baths ⋅ 10653910 MLS
Step into the privacy of your new charming cape cod surrounded by scenic water views on a quiet street. Get away with your canoe at high tide or relax at the fire pit as majestic herons and eagles take flight. As the kids play in the custom playhouse with loft, slip away into a gardener's dream courtyard and rose garden. This desirable four-bedroom two bath home boasts meticulous, custom details that can be found throughout by a master craftsman and artist. You will find gleaming hardwood floors, a spacious kitchen, a large laundry room with custom cabinetry, a 20x20 garage with a 100-amp subpanel, and so much more. Pride of ownership is evident in the mature landscaping and upgrades. Use the sizeable bonus room upstairs overlooking the creek as a fifth bedroom. You will fall in love with the natural lighting as you watch the sunset from your backyard each evening. Don't miss your chance on this sought-after home.

120 Sandpiper Drive, Portsmouth

2210 Chestnut Street, Portsmouth
$389,900
5 Beds ⋅ 3.1 Baths ⋅ 10653734 MLS
Welcome home to this spacious 5-bedroom, 4-bath residence offering space and flexibility, including TWO primary suites—one upstairs and one downstairs. The first-floor PBR features two closets, private bath, dbl sinks and walk-in shower; upstairs primary has dbl sinks for added convenience. Beyond the five bedrooms, this home features a separate large dining room, dedicated office, and a spacious loft—could be used as a second family room, game room, playroom, media space, or additional lounge area. Additional highlights include a tankless water heater, dual-zone HVAC with the downstairs system replaced in 2022 and the upstairs system replaced in 2024, plus laminate, vinyl, and carpet flooring throughout. With multiple living spaces and a versatile floor plan, Multigenerational living, growing households, entertaining, or anyone who simply wants room to spread out. NNSY, military bases, entertainment and shopping nearby.

2210 Chestnut Street, Portsmouth

408 Court Street, Portsmouth
$399,900
4 Beds ⋅ 3 Baths ⋅ 10653765 MLS
Live in the heart of historic Olde Towne Portsmouth at 408 Court Street. Enjoy stunning historic details including original Victorian wavy cylinder glass windows, soaring ceilings, and authentic period millwork. The interior boasts gorgeous pocket doors, gas radiant heat, dual-zone high-velocity central air, and a unique library with a ladder and backlit panels. A bright kitchen features a Dacor professional gas range and anchors a layout ready for your personal updates. Outside, a primary suite deck with a spiral staircase leads to a fully fenced backyard with a large workshop and shed. Experience the peak of Olde Towne living moments strolling along the waterfront. Spend weekends at the Saturday farmers market, catching Pavilion concerts, visiting the local brewery and new winery. This premier location offers an effortless commute to the Naval Hospital, USCG installations, and regional bases. Plus, the Elizabeth River Ferry is nearby for seamless access to Norfolk.

408 Court Street, Portsmouth

2314 Chestnut Street, Portsmouth
$260,000
3 Beds ⋅ 2 Baths ⋅ 10653439 MLS
Welcome to modern, worry-free living in this beautifully updated 3-bedroom, 2-bathroom home! Discover a bright, inviting layout highlighted by gorgeous luxury vinyl plank flooring and upgraded finishes that flow seamlessly throughout the space. The heart of the home is a stunning kitchen, boasting crisp Shaker-style cabinetry, beautiful granite countertops, and sleek stainless steel appliances. Imagine preparing meals here while entertaining friends or family! You will enjoy incredible peace of mind knowing the major systems were completely redone in 2022, including a brand-new roof, a new HVAC system, and a fully revamped crawl space. Located perfectly for ultimate convenience, you are just minutes away from excellent shopping, fantastic restaurants, and easy interstate access. This turnkey gem is truly a must-see and ready for its next chapter!

2314 Chestnut Street, Portsmouth

2123 Greenwood Drive, Portsmouth
$313,900
4 Beds ⋅ 2 Baths ⋅ 10653274 MLS
Welcome home to this spacious 4-bedroom, 2 full bath property offering 1900 sq ft of living space on a generous .35-acre lot. This well-maintained home features major updates completed within the last 5 years including hvac, flooring and roof. The updated kitchen offers a fresh, functional space with a walk-in pantry and plenty of room for cooking and entertaining. An oversized utility room that provides excellent additional space for laundry and storage.A major feature of the property is two large, detached garages that offer plenty of room for vehicles, tools, equipment, hobbies, storage or workshop space.The property provides a spacious .35-acre lot with plenty of room for outdoor entertaining, gardening, pets, or just relaxing. With the major updates already completed, generous living space and an updated kitchen this home offers an excellent combination of comfort, functionality, storage and value. Schedule your showing today and see everything this property has to offer.

2123 Greenwood Drive, Portsmouth

306 Worthington Square, Portsmouth
$279,000
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, Portsmouth

117 Kelly Drive, Portsmouth
$270,000
3 Beds ⋅ 1.1 Baths ⋅ 10652881 MLS
A true gem you won’t want to miss! This immaculately maintained, all-brick ranch is move-in ready and showcases pride of ownership throughout. A brand-new metal roof, charming front fence, established landscaping, front porch, and vibrant crape myrtles create undeniable curb appeal. Inside, the open and functional layout offers seamless flow between the spacious kitchen with peninsula seating, dining, and living areas, making everyday living and entertaining a breeze. The comfortable primary suite offers a private half bath, while two additional bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy the sprawling, fully fenced backyard with a brand-new covered deck, perfect for entertaining, relaxing, or soaking up the outdoors. Two sheds provide additional storage, while the attached garage adds even more convenience and space. Generator hookup in place for peace of mind. Beautifully cared for in a setting you’ll love, this special home is ready for its next owner!

117 Kelly Drive, Portsmouth

1700 Mcdaniel Street, Portsmouth
$267,500
3 Beds ⋅ 2 Baths ⋅ 10651779 MLS
This move-in-ready 3+ Bedroom Colonial is updated & ready for you! With updated finishes and flexible space, this Colonial offers three bedrooms plus a bonus room (no closet) that would be great for a home office, guest space, or craft room. Fresh paint and new carpet create a clean, inviting interior. Enjoy a spacious family room and a separate formal living room for flexible living and entertaining. The kitchen features a gas stove and a built-in microwave, a pantry & HVAC closet. Plenty of room for a butler's pantry or baker's rack! Both full bathrooms have some updates. All the bedrooms have a ceiling fan for added comfort. Outside, sit on the porch or relax on the deck and take advantage of the oversized, spacious corner lot. A true delight for the gardener. New Off-Street Parking gravel pad. A six-month-old architectural roof adds peace of mind. Storage sheds convey As-Is - seller to pay up to 3% of buyer's closing costs as a credit.

1700 Mcdaniel Street, Portsmouth

2600 Nashville Avenue, Portsmouth
$349,999
5 Beds ⋅ 4 Baths ⋅ 10651613 MLS
This contemporary home offers convenience, comfort, and versatility. Ideally situated near major employers including Norfolk Naval Shipyard, Naval Medical Center Portsmouth, and Rivers Casino Portsmouth, this property is also just minutes from shopping, dining, and everyday conveniences such as Walmart. Featuring 5 bedrooms and 4 full bathrooms, this home provides a flexible layout great for a variety of living arrangements. Two bedrooms include private en-suite bathrooms, offering added comfort and privacy. The home showcases a contemporary style with updated appliances and modern finishes throughout. A detached garage provides creative opportunities and could be used as a workshop, home gym, studio, or additional storage. With generous living space and a prime location near Portsmouth’s largest employers and attractions, this home is a must-see opportunity.

2600 Nashville Avenue, Portsmouth

1426 Wilcox Avenue, Portsmouth
$239,000
3 Beds ⋅ 2 Baths ⋅ 10651429 MLS
Welcome to your beautifully updated dream home in the heart of Portsmouth! Enjoy the convenient carport and a large yard that offers plenty of space for outdoor activities. Enter to discover a bright and modern interior featuring three spacious bedrooms and two fully updated bathrooms. The entire home boasts fresh paint and brand-new flooring throughout, creating a seamless and contemporary feel. At the heart of the home is the beautifully renovated kitchen, which comes fully equipped with white shaker cabinets, stunning stone countertops, and sleek stainless steel appliances. Both bathrooms have been tastefully upgraded with custom tile work, adding a touch of luxury to your daily routine.Beyond the beautiful cosmetic updates, this home offers incredible peace of mind with major system upgrades. You can rest easy knowing the property features a brand-new roof, a brand-new water heater, and a highly efficient HVAC. Come see it today!

1426 Wilcox Avenue, 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.