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361 Court Street, Central Portsmouth
$379,900
4 Beds ⋅ 2 Baths ⋅ 10658880 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
1 Crawford Parkway Unit 1805, Central Portsmouth
$117,500
1 Beds ⋅ 1 Baths ⋅ 10658458 MLS
Enjoy city living with a view at this top-floor studio condo, offering a convenient location & amenities designed to make everyday living easier. Take in the views while enjoying an updated kitchen feat. SS appliances & gas stove. The thoughtfully arranged layout creates a comfortable setting for those seeking a low-maintenance lifestyle. Beyond the unit, the community offers several shared amenities: a swimming pool, grilling area, library, event room, & onsite laundry facilities. One of the standout benefits is the low monthly condo fee: includes utilities, HVAC, & water heaters. Located in the heart of Portsmouth, this condo is near local restaurants, shops, entertainment, the waterfront, and the Portsmouth Boat Club. Situated near the Naval Medical Center Portsmouth, shipyards, major interstates & the nearby Elizabeth River Ferry provides easy access to Norfolk. This condo offers a practical opportunity to enjoy all that Portsmouth has to offer!

1 Crawford Parkway Unit 1805, Central Portsmouth
1007 Green Street Street, Central Portsmouth
$1,450,000
10658154 MLS
Come and see this first! These gorgeous mostly renovated units have tons of natural light throughout and a large living room. The kitchens have newer cabinetry and stainless steel appliances. These super clean / move in ready units boast fresh paint, LVP flooring, carpet, new bathrooms, and washer / dryer hookups provided. Check this 12 plex out before its gone! 12 Units for sale, 8/12 units currently occupied / rented, 2 are currently available for rent, 2 being left needing a full turn. There is still plenty of meat on the bone here, the current plan would leave one unit needing a full rehab.

1007 Green Street Street, Central Portsmouth
449 Dinwiddie Street, Central Portsmouth
$388,000
4 Beds ⋅ 3.1 Baths ⋅ 10657598 MLS
Welcome to 449 Dinwiddie St - a beautiful, 2714 sqft home in the historic Olde Towne district of Portsmouth. With 4 bedrooms and 3.5 bathrooms, this home provides a spacious layout set over 3 levels, plus basement - a rare find! Modernly updated whilst maintaining its historic charm, it is close to shopping, dining, major interstates and schools - this home is in a prime location! Schedule your showing today!

449 Dinwiddie Street, Central Portsmouth
1 Crawford Circle Unit 906, Central Portsmouth
$220,000
2 Beds ⋅ 1.1 Baths ⋅ 10654823 MLS
Experience elevated city living in the heart of Downtown Portsmouth! Located within  walking  distance to the Naval Medical Center Portsmouth and directly across from the Elizabeth River, This oversized 9th-floor condo offers expansive views of the harbor and city skyline. Enjoy a evening concert at the Portsmouth Pavilion, or watch a film at the historic Commodore Theatre, spend an afternoon at the Children’s Museum, or explore the dozens of established restaurants just outside your door. Best of all, the condo fee covers electricity, water, sewer, gas, trash, cable, security, and pool access—no separate utility bills!

1 Crawford Circle Unit 906, Central Portsmouth
421 North Street, Central 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, Central Portsmouth
709 South Street, Central Portsmouth
$190,000
2 Beds ⋅ 2.1 Baths ⋅ 10653852 MLS
Historic charm meets modern living in this beautiful Portsmouth home! Featuring an open, light-filled layout with spacious living areas, a stylish kitchen, generous bedrooms, and brand-new carpet throughout. Enjoy relaxing on the inviting front porch or in the private backyard space. Ideally located just minutes from Olde Towne, dining, naval bases, and major highways. Perfect for first-time buyers or investors!

709 South Street, Central Portsmouth
408 Court Street, Central 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, Central Portsmouth
306 Worthington Square, Central Portsmouth
$279,000
3 Beds ⋅ 1.2 Baths ⋅ 10652878 MLS
Rare Find! Convenient Waterfront Living at an Affordable Price! Opportunities like this don’t come along often! Condos in this sought-after waterfront community rarely hit the market, especially one of this size. Fresh paint & new flooring create a bright, inviting, move-in-ready space you’ll be proud to call home. Add a prime waterfront location & surprisingly low condo fees, & it’s easy to see why owners love to stay! Enjoy the best of Portsmouth’s revitalized waterfront district, just 1 block from the Naval Medical Center, marina, & ferry service to Norfolk’s Waterside District. Head to High Street, just a few blocks away, for an exciting mix of restaurants, entertainment, museums, street vendors, concerts, fireworks, cruise ship docks, & more. Convenient access to the Norfolk Naval Shipyard & 3 major interstate connectors, getting around Hampton Roads is a breeze. Don’t miss your chance to enjoy the charm of waterfront living & the lifestyle you deserve in this terrific home!

306 Worthington Square, Central Portsmouth
111 High Street Unit 402, Central Portsmouth
$139,900
2 Beds ⋅ 2.1 Baths ⋅ 10651744 MLS
Quiant 2-bedroom, 2-bath condo in the heart of Downtown Portsmouth! This home features an open floor plan with kitchen, dining, and living areas. Building amenities include secured code access, covered parking garage, elevator, and storage. Condo fee covers water, sewer, trash, secured parking, and building/flood insurance. Conveniently located near the Elizabeth River Ferry, Downtown Tunnel, interstates, Portsmouth Naval Medical Center, shops, restaurants, and Olde Towne attractions. Easy access with the Olde Towne shuttle. Enjoy city living with comfort and convenience

111 High Street Unit 402, Central Portsmouth
320 London Street, Central Portsmouth
$385,000
10651284 MLS
Tremendous investment opportunity offered at a great price in Olde Towne Portsmouth! Ready for a buy and hold or update and dramatically increase equity. 3 Units: Building sq ft: 3,430, All units have central AC. All units have auto 1 yr renewal, 60 day renewal notice periodUnit 1A: 2 bedroom, 1 bath, sq ft. Rents for $1,500 a month*Lease end date 01/31/2025 Unit 2A: 1 bedroom, 1 bath, 700 sq ft. Rents for $800 a month (barely raised in 10 years)*Lease end date 10/31/2017 Unit 2B: 1 bedroom, 1 bath, 700 sq ft. Rents for $825 a month*Lease end date 03/31/2019Total Rental Income: $3,125

320 London Street, Central Portsmouth
400 Court Street, Central Portsmouth
$499,000
4 Beds ⋅ 4 Baths ⋅ 10651236 MLS
A teasure 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
535 Hampton Place, 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
1 Crawford Parkway Unit 1702, 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
228 North 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
One Crawford Parkway Unit 1107, Central Portsmouth
$165,000
1 Beds ⋅ 1 Baths ⋅ 10646275 MLS
Incredible Value! 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.

One Crawford Parkway Unit 1107, 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
710 Dinwiddie Street, 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
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
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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