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$850,000
10653977 MLS
Investment opportunity in the Prentis Park area of Portsmouth. This quadplex offers approximately 5,324 sq ft across 4 units with a total of 12 bedrooms, 4 full baths, and 2 half baths. Each unit features 3 bedrooms, 1.5 baths on the main level, and 1 full bath upstairs. Each unit is individually metered for electric and water. Improvements include roof replaced ~2021, a new crawl space fan, moisture barrier, and dehumidifier, all-new hot water heaters, new siding, front door, front porch with railings, a new electrical panel, and an insulated attic. Newer Carpet and flooring. All units include stackable front-loading washer/dryers. Unit 2 remodeled with new kitchen appliances, cabinets, granite countertops, flooring, and bathroom tub and vanity. Section 8 approved. Estimated expenses include trash ~$76/month, homeowners' insurance ~$4,700/year, and property taxes ~$4,200/year (buyer to verify). Conveniently located near major roadways, public transportation, and local amenities.

1520 Prentis Ave Avenue, Central Portsmouth

$749,000
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, Central Portsmouth

$725,000
5 Beds 2.1 Baths 10652239 MLS
Welcome to your ultimate waterfront sanctuary on the scenic Elizabeth River. Perfectly combining timeless 1925 architectural character with a comprehensive modern renovation. This extraordinary three story Classic Colonial offers a rare blend of historic charm, contemporary luxury, and an uncompromised coastal lifestyle. Expansive front porch for prime evening sunset viewing. 5 Bed 2.5 Baths and 3 floors of versatile living space. Private extended pier featuring a 10,000 lb boat lift and 2 jet ski lifts. Detached 1.5 car garage and custom paver patio are additional highlights of the classic gem. New roof in 2026 and detailed service records for all systems provides a carefee transition into making this house your new HOME! Call to schedule your private tour today.

455 Riverside Drive, 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

$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

$599,000
3 Beds 2.1 Baths 10653451 MLS
Glensheallah is calling you home. Welcome to 200 Park Road, a beautifully preserved midcentury modern gem positioned on a prominent corner lot. This custom-built, one-owner residence offers approximately 2,600 square feet of timeless character and thoughtful detail. Refinished original hardwood floors flow throughout, complemented by fresh paint, a marble foyer, recessed lighting, and abundant storage. Distinctive vintage lighting includes a crystal dining room chandelier and handcrafted Venetian chandeliers in the breakfast area and primary bedroom. The kitchen retains its original cabinetry and features double L&G/Thermador wall ovens, a Sub-Zero refrigerator, and a convenient pass-through ideal for entertaining. A fully floored attic, slate front walkway and rear porch, plus a roof and HVAC less than five years old complete this truly one-of-a-kind home.

200 Park Road, Northwest Portsmouth

$585,000
2 Beds 2 Baths 10638223 MLS
Historic Waterfront Cottage Retreat! Nestled on 1.69 acres with expansive frontage on Lake Jean and the spillway to the Western Branch of the Elizabeth River, this one-of-a-kind property offers a lifestyle few will ever experience. Originally part of a hunting lodge estate dating back to the 1800s, the quality-built home was built in 1955 and thoughtfully updated over the years. Enjoy panoramic water views, abundant wildlife, and majestic magnolias in this bird watcher's paradise. Fish from the shore, relax in the gazebo, or entertain on the expansive outdoor living areas. Features include geothermal HVAC, hardwood and ceramic tile floors, 2 bedrooms, 2 baths, potential for a 3rd bedroom, private well, sprinkler system, shed, and detached 2-car garage with electricity, cable, heated/cooled bonus space, and plumbing; an idea for an in-law suite, studio, office, or guest retreat. A rare waterfront sanctuary where memories are made for generations. Includes both parcels, 2904 & 2906 Tanbark Ln, totaling 1.69 acres (PINs 07710110 & 07710120).

2904 Tanbark Lane, Northwest 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

$499,000
4 Beds 4 Baths 10651236 MLS
reasure of a home in the heart of Olde Towne Portsmouth! Dating to 1805, this historically significant English-basement residence once belonged to the British Naval Attaché before the American Revolution. Offering approximately 3,877 square feet across three levels, the home combines remarkable period character—including two beautiful stained-glass windows—with an adaptable layout. The first floor provides flexible options for remote or professional work, guest accommodations, or potential additional rental income. Spacious living areas, a fireplace, four bedrooms and four baths provide plenty of room, while the third-floor studio offers another private and versatile retreat. A rare opportunity to own a distinctive piece of Portsmouth history near the waterfront, restaurants, shops, museums and entertainment. Back on the Market Due to No Fault of the Sellers.

400 Court Street, Central Portsmouth

$499,000
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

$485,000
4 Beds 3 Baths 10650447 MLS
Stately All-Brick Home on Long Point Corner Lot Spacious 3,189 sq ft all-brick home on a premium corner lot in Churchland's sought-after Long Point! This property features incredible structural bones and major system upgrades, making it perfect for buyers looking to build quick equity. Key Highlights: System Updates: New roof (2024), brand-new water heater (2026), central AC (2018), and new garbage disposal (2025). Solid Build: Low-maintenance, durable all-brick exterior with great curb appeal. Layout: Generous 3,100+ sq ft floor plan with expansive living areas. Buyer Incentive: Sold as-is and priced below neighborhood averages for cosmetic updates. Seller offers a generous $5,000 flooring/cosmetic credit at closing so you can choose your own carpet and finishes! Outside Shed (AS IS WHERE IS). Owner/Agent.

4012 Clipper Lane, Northwest Portsmouth

$475,000
4 Beds 2.1 Baths 10650409 MLS
Welcome home... This one is for you. Don't let it slip away.....Recent upgrades throughout this beautiful home are sure to impress your clients from the moment they walk through the door. The updated kitchen, modern flooring, energy-efficient windows, and newer HVAC system make this property truly move-in ready.And just in time to enjoy the final days of summer, the backyard features an inviting in-ground pool that’s perfect for relaxing, entertaining, and ending the season with a splash!Recent upgrades include:New roof (May 2020)New windows (September 2021)New luxury vinyl plank flooring (April 2023)New AC unit (July 2024)Completely remodeled kitchen (2026)This home combines comfort, style, and major updates that today’s buyers are looking for. Don’t miss the opportunity to see this home that’s ready to be enjoyed from day one. Go Now!!

4280 Sedgewyck Circle, Northwest Portsmouth

$465,000
5 Beds 4 Baths 10646661 MLS
Happily Ever After? Step into a storybook & discover the kind of home that simply isn't built anymore. If you've ever dreamed of Bridgerton inspired Victorian elegance, afternoon tea parties, grand holiday gatherings, or curling up with a classic novel beside one of several fireplaces, this extraordinary historic masterpiece is ready to make those dreams a reality. From the moment you arrive, the iconic turret and timeless architecture set the stage for a home filled with character at every turn. Inside, you'll find breathtaking craftsmanship that's nearly impossible to replicate today, including intricate original hardware, stunning tile work, elegant pocket doors, soaring ceilings, & exquisite millwork throughout. Every room offers another reminder of an era when homes were built as works of art. The spacious butler's pantry is both charming & functional, making entertaining effortless. Multiple clawfoot tubs invite you to slow down & soak in the romance of a bygone era, while the home's numerous fireplaces create warm, inviting spaces perfect for every season. Need more room? The enormous walk in attic features impressive ceiling height & is simply begging to be transformed into additional living space, a home theater, studio, guest suite, or whatever your imagination desires. The expansive bedrooms, oversized closets, & seemingly endless square footage offer room for every chapter of life. The detached garage, large corner lot, & generous outdoor spaces provide even more flexibility for entertaining, gardening, or simply enjoying the beauty of this remarkable property. This is more than just a home. It's the place where book clubs become unforgettable evenings, tea parties become treasured traditions, holidays become magical, & every guest leaves talking about your incredible house. Homes with this level of architectural beauty, craftsmanship, & history rarely become available. Some homes check boxes. This one steals hearts. Come experience the kind of timeless elegance that modern construction simply cannot recreate. Your happily ever after starts here.

250 Webster Avenue, Central Portsmouth

$460,414
5 Beds 3.1 Baths 10648278 MLS
Perfect blend of historic charm and modern living in this beautifully restored 121-year-old home at 14 Parkview. Thoughtfully renovated from top to bottom while preserving its timeless character, this home offers the best of both worlds. Original architectural details have been carefully maintained and complemented by extensive updates, including a brand-new roof, new HVAC system, and new windows. Inside, you'll find beautifully updated living spaces, a completely remodeled interior, and modern finishes that enhance the home's historic appeal without sacrificing its unique personality. Conveniently located directly across from the Naval Hospital and just minutes from shopping, dining, entertainment, and major interstates, this one-of-a-kind property offers historic character with today's modern conveniences. Schedule your private showing today!

14 Parkview Avenue, Central Portsmouth

$455,000
4 Beds 2.1 Baths 10646509 MLS
Rare opportunity to own a beautifully updated four-bedroom home on one of the largest double lots in the neighborhood! Located just steps from the Portsmouth Yacht Club and minutes from the charm of Olde Towne Portsmouth, this home offers the blend of space, convenience, and modern upgrades. Inside, you'll find two walk-in closets, an expansive open top floor with endless possibilities, and a stunning second-story balcony that's perfect for relaxing or entertaining. Major improvements include new carpet (7/2026), a new HVAC system (2026), roof (2023), paid-off solar panels (2023), water heater (2020), and gas range (2021), offering both comfort and peace of mind. Enjoy easy access to dining, shopping, waterfront attractions, and the nearby ferry for a convenient commute to downtown Norfolk. With its generous lot size, flexible living space, and extensive updates, this home is truly one of a kind.

51 Armstrong Street, Central Portsmouth

$450,000
4 Beds 2 Baths 10654312 MLS
Welcome Home! Step inside and discover the perfect blend of modern style, comfort, and charm. This beautifully updated home features a spacious open concept floor plan designed for everyday living and entertaining. Enjoy an updated kitchen, beautifully renovated bathrooms, newer LVP flooring, and garage doors. Step outside and take in the beautiful water views from your renovated deck, the perfect setting for morning coffee, relaxing evenings, cookouts, and gatherings with family and friends. With thoughtful updates throughout and an inviting atmosphere inside and out, this home is truly move in ready. Homes with this combination of updates, space, and water views are hard to find. Schedule your private showing today and come see why this could be the home you have been waiting for!

3975 Long Point Boulevard, Northwest Portsmouth

$439,900
4 Beds 2.2 Baths 10654381 MLS
Modernized Brick ranch with all the charm and solid construction of a older era. The house was added on to include a large primary bedroom, fully tiled bathroom , oversized walk in closet , a spacious family room, half bathroom and utility room (with sink, deep freezer storage/shelving & laundry) There are 3 other bedrooms, one with a half bathroom and a full bathroom in the hall. The converted garage has been turned into a game room with a built in bar. The house has beautiful hardwood floors and modern recessed lighting. The backyard is fully fenced, with an extra wide & long driveway , and a 24X28 heated and cooled garage with a 450 sq ft apartment above. The apt has a full kitchen, bathroom, walk in closet and living area that could serve as additonal income . Gas water heater 3 yrs, garage electric water heater 6 yrs, Hvac 15yrs, Original part of house windows 7 yrs, Home addition 23 yrs , detached garage 20 yrs. Ages approximate. This home has so much to offer and has been meticulously maintained . Must see to fully appreciate !

1509 Hodges Ferry Road, Central Portsmouth

$435,000
4 Beds 3 Baths 10654132 MLS
Welcome to this all-brick ranch offering 4 bedrooms, 3 full baths, and exceptional versatility! Featuring two primary suites located at opposite ends of the home, this layout is ideal for an in-law suite, multigenerational living, or out-of-town guests. One suite opens directly to the back deck, while the primary suite offers an oversized closet. All bathrooms have been updated, with one featuring skylights. Enjoy the inviting den with gas fireplace and access to a side patio, plus an eat-in kitchen, dining room, living room which leads to back deck, and welcoming foyer. Outdoors, entertain with ease in both the spacious backyard and side-yard patio area, surrounded by mature trees. Additional highlights include a double-car garage, oversized driveway, shed, and new roof in 2022. Conveniently located near the Coast Guard Base, Naval Hospital, shopping, and everyday amenities.

5629 Springwood Drive, Northwest Portsmouth

$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

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.