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1420 Chestnut Street, Central Portsmouth
$2,500,000
10658206 MLS
Income producing property. Current owner is interested in a sale-leaseback transaction. The income comes from the office buildings plus a 65 space parking lot for big rigs. The owner is prepared to rent the office space for $112,970 per year and the current income from parking revenue is $132,000 per year. Excellent investment opportunity or a Section 1031 Exchange. Property is located close to the port and has been used for parking big rigs for many years. A 6-foot fence surrounds this rear parking lot and is accessed 24/7 by a remote control gate. Owner has been operating a business in this location for the past ten years.

1420 Chestnut Street, Central Portsmouth
1601 Marshall Avenue, Central Portsmouth
$1,700,000
10546046 MLS
This property is being SOLD AS IS.

1601 Marshall Avenue, 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
3736 Turnpike Road, Central Portsmouth
$1,000,000
10606072 MLS
Due to confidentiality of the residents, only pre-qualified buyers for showings please! Assisted Living facility approved for 32 beds! Located at the intersection of Turnpike Rd and Utah St., this property sits on .8 acres. Large corner lot has potential for expansion. Please do not disturb the tenant!

3736 Turnpike Road, Central Portsmouth
400 Broad Street, Central Portsmouth
$904,500
10657213 MLS
Discover the possibilities in this 7949-square foot mixed-used building in the Port Norfolk section of Portsmouth. Featuring (3) one-bedroom and (1) two-bedroom renovated apartments upstairs along with a large, shared laundry room and three commercial spaces downstairs, this property offers opportunities for the investors and business owners alike. Property highlights: 7949 SF historic mixed-use asset; Built 1922 - Fully modernized; Two-Story structure plus 4 residential units. Capital Improvements: Over $550K in completed renovations, new electrical, plumbing, HVAC and more, restored brick facade, new storefronts, and concrete pad, new roof, framing, bathrooms, ceilings, ALL WORK PERMITTED AND APPROVED BY HISTORICAL SOICETY. With residential and commercial space under one roof, this versatile property offers multiple potential income streams and room to bring your plans to life. Qualifies for cost segregation and bonus depreciation. Schedule your showing and explore the possibilities.

400 Broad Street, Central Portsmouth
3235 Clover Hill Drive, Northwest Portsmouth
$890,000
2 Beds ⋅ 1.1 Baths ⋅ 10622848 MLS
***TO BE SOLD IN CONJUNCTION WITH THE FOLLOWING UNITS****Total of 5 units3227, 3229, 3231, 3235- 1024sqft. each. Current tenants with valid leases through March 20273233- 1024sqft. Recently renovated, move in ready. No current tenants. Excellent income producing property in Westmoreland! This is a House Hacker's dream! Move into one unit while collecting rent for the others, or rent out the vacant unit for even more monthly income! Calling all investors, make this your first and last stop!

3235 Clover Hill Drive, Northwest Portsmouth
1520 Prentis Ave Avenue, Central Portsmouth
$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
12 N Eleanor Ct N Court, Central Portsmouth
$729,900
4 Beds ⋅ 3 Baths ⋅ 10652054 MLS
Discover lakefront living in desirable Crystal Lakes! This impressive all-brick home offers over 5,000 sq. ft. with 4 bedrooms plus a spacious loft. Enjoy an updated kitchen with modern appliances newer flooring, a bright sunroom, and a private deck off the bedroom. Outdoor living shines with a pavilion, expansive concrete patio, and direct lake access—Great for entertaining, relaxing, and enjoying beautiful waterfront views. A rare opportunity!

12 N Eleanor Ct N Court, 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
455 Riverside Drive, Central Portsmouth
$725,000
5 Beds ⋅ 2.1 Baths ⋅ 10652239 MLS
STILL SHOWING!!! FIRST RIGHT OF REFUSAL ATTACHED TO CURRENT OFFER, 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
2001 Azalea Avenue, Central Portsmouth
$650,000
10659101 MLS
RARE NEW-CONSTRUCTION INVESTMENT OPPORTUNITY! Two spacious, attached, three-story townhomes on Azalea Avenue offered together as ONE purchase—not available individually. Ideal for investors seeking two rental properties in one acquisition or an owner-occupant who wants to live in one home and rent the other to help offset ownership expenses. Each residence offers approximately 2,500 square feet of thoughtfully designed living space, for approximately 5,000 square feet combined. Highlights include 9-foot ceilings, two primary suites per residence, granite countertops, upgraded lighting, ceiling fans, a private garage, and driveway parking. A second-story deck adds desirable outdoor living space—perfect for unwinding, entertaining, or enjoying fresh air without leaving home. The three-level floor plans offer flexibility for a range of living arrangements, with ample space for residents, guests, or work-from-home needs. Separate homes side by side provide the convenience of nearby ownership while preserving the independence of each residence. Looking for an owner-occupied investment opportunity? Make one townhome your personal residence and explore renting the neighboring home for supplemental income. Prefer a fully investment-focused purchase? Rent both townhomes and build a two-property portfolio with new construction. Either approach offers options for long-term ownership and potential income generation. A compelling opportunity for buyers who value spacious floor plans, modern finishes, garage parking, driveway parking, outdoor living space, and the versatility of two residences sold together. Purchase both, choose your strategy, and make the most of this distinctive new-construction offering!

2001 Azalea Avenue, 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
1205 Airline Boulevard, Central Portsmouth
$625,000
10649494 MLS
Rare opportunity to own an automobile repair business. Equipment included. Has been in business for over 40 years. Located on a quarter-acre with three bays and approx. 15,000 vpd. Please do not disturb the tenant! Zoned C-2. Owner will consider carryig 2nd mortgage

1205 Airline Boulevard, 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
1601 Elm Avenue, Central Portsmouth
$599,999
10651878 MLS
Fully rented quad offering immediate cash flow with total rental income of $5,550 per month. The property underwent an extensive top-to-bottom rehab approximately 5 years ago, with improvements including stainless steel appliances, granite countertops, new cabinetry, updated flooring, bathtubs, toilets, and more. Rents total $5,625 total monthly and tenants are responsible for paying all utilities. Building sqft per tax records, apt sqft. est

1601 Elm Avenue, Central Portsmouth
3905 Colony Road, Northwest Portsmouth
$574,900
4 Beds ⋅ 2.1 Baths ⋅ 10657211 MLS
Social Butterfly or Private Home Lover...this home has your name on it. Beautiful Brick home in desirable Briarwood with an outdoor oasis you'll never want to leave. This home features several living spaces, downstairs including 3 fireplaces indoors and one outside. Two car, two story garage is on a designated breaker. Exposed brick kitchen is open with room for a large farm style table, beside fireplace and sitting area with custom mosaic tile floors and french doors that lead to an outdoor paradise. Fall, winter football parties with outdoor fireplace, granite counter outdoor kitchen entertainment room, with tv, oven, gas range, sink, beverage refrigerator and ceiling fans. Backyard is stunning with a 22,000 gallon salt water pool, with accent lights and dolphin fountain, maintenance free lawn with firepit area, and pavers. Firepit area has gazebo and benches.

3905 Colony Road, Northwest Portsmouth
4533 Wake Forest Road, Northwest Portsmouth
$550,000
4 Beds ⋅ 4 Baths ⋅ 10657834 MLS
Discover boundless possibilities in this beautifully renovated 4-bedroom, 4-full-bath home located in the heart of Portsmouth's Pinehurst neighborhood! Offering a versatile floor plan ideal for multigenerational living, this spacious home features a private entrance, providing added flexibility and privacy. Extensive renovations throughout include beautifully updated bathrooms with custom tiled walk-in showers and a stunning kitchen featuring quartz countertops, upgraded appliances, and an abundance of cabinet space. Enjoy a spacious family room with fireplace, dedicated office, formal dining room, and a thoughtfully designed layout offering great flow throughout. The inviting four-season room opens to a raised stamped concrete patio overlooking the backyard enclosed by PVC privacy fencing, perfect for relaxing or entertaining. Previously operated as a group home, this property offers potential for continued use, subject to applicable approvals and requirements. With its extensive updates, flexible living spaces, and numerous possibilities, this exceptional property is truly a must-see!

4533 Wake Forest Road, Northwest Portsmouth
200 Park Road, Northwest Portsmouth
$549,000
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
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
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
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
4700 Norman Road, Northwest Portsmouth
$490,000
4 Beds ⋅ 3 Baths ⋅ 10656560 MLS
Space, character, and room to make it your own in Churchland’s established Green Acres neighborhood! Situated on approximately 1.15 acres, this spacious 4-bedroom, 3-bath home offers approximately 4,038 square feet, hardwood floors, abundant natural light, and charming details throughout. Multiple living areas provide flexibility for gathering, working from home, or creating your own quiet retreat. A generous kitchen offers ample cabinetry, while built-in storage adds to the home’s character. Outside, enjoy an expansive lawn, mature trees, and a substantial attached garage with room for vehicles, hobbies, and storage. Take the opportunity to bring your vision to a distinctive property with impressive space inside and out. Come explore the possibilities at 4700 Norman Road!

4700 Norman Road, Northwest Portsmouth
13 Aft Court, Northwest Portsmouth
$465,000
3 Beds ⋅ 2.1 Baths ⋅ 10656182 MLS
Welcome home to this fully renovated solid brick tri-level on a corner lot with 3 bedrooms and 2.5 baths! The brand-new kitchen shines with sealed butcher block countertops, new cabinets, and a sleek vent hood. Upstairs, both updated baths feature elegant Carrara marble. Unwind in the primary suite with its own fireplace, sitting area, stone resin soaking tub, and separate shower. The family room opens to a bright sunroom addition with access to the 2-car garage. Fresh paint, new doors, updated plumbing, new main-floor flooring, Spanish tile, new lighting, semi-custom closets, two-zone HVAC, and two sheds complete this move-in-ready gem. Schedule your showing today!

13 Aft Court, Northwest Portsmouth
4291 Hatton Point Lane, Northwest Portsmouth
$465,000
3 Beds ⋅ 2.1 Baths ⋅ 10650093 MLS
IMAGINE ENTERTAINING IN YOUR FORMAL LIVING AND DINING ROOMS THEN VENTURING OUT OF YOUR FULLY EQUIPPED KITCHEN ONTO YOUR DECK OVERLOOKING THE RIVER FOR A COOKOUT, LATER IN THE EVENING IF YOU ARE TOO TIRED TO TAKE THE STAIRS, YOU CAN HOP IN THE ELEVATOR AND RIDE UP TO THE BEAUTIFUL THREE BEDROOM, TWO BATH SECOND FLOOR. THE PRIMARY BEDROOM AND BATH IS AMAZING. THERE ARE SO MANY UPGRADES AND RENOVATIONS. THE SINGLE CAR GARAGE HAS A KEYPAD AND REMOTE OPENER , PLENTY OF STORAGE, AND A WEATHER FREE ENTRANCE INTO THE LAUNDRY ROOM. THIS IS A MUST SEE.

4291 Hatton Point Lane, Northwest Portsmouth
14 Parkview 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
1510 Parker Avenue, Central Portsmouth
$459,000
10652031 MLS
Exceptional investment opportunity in Portsmouth! This updated triplex features a spacious 3 bed, 2 bath detached home alongside a 2 bed, 1 bath unit and a 1 bed, 1 bath unit perfect for maximizing rental income or flexible living arrangements. Each unit is well appointed and separate utility meters for ease of management. The property also includes a detached garage and sits on a large lot, offering added value and potential. Ideal for investors, owner occupants, house hackers, or multigenerational living. Live in one unit while generating income from the others or lease all three for strong cash flow.

1510 Parker Avenue, Central Portsmouth
116 Sykes Avenue, Central Portsmouth
$450,000
5 Beds ⋅ 3 Baths ⋅ 10658824 MLS
This beautifully remodeled eclectic Cape Cod is the perfect blend of charm, character, and modern comfort! Featuring 5 bedrooms, 3 full bathrooms, and two spacious primary suites, this unique and special home offers a versatile layout designed to fit a variety of lifestyles. The convenience of a first-floor primary suite and a second Primary suite upstairs, providing excellent options for multi-generational living, guests, added privacy and/or even rental potential. A generously sized mudroom/sunroom and laundry room add everyday convenience and plenty of functional space to keep life organized. Enjoy the large yard, complete with privacy fencing in the backyard—great for relaxing, entertaining, gardening, or enjoying time outdoors. A detached garage provides additional storage and parking options as well as the carport that provides a covered entry into the primary bedroom area/in-law suite.

116 Sykes Avenue, Central Portsmouth
3947 Long Point Boulevard, Northwest Portsmouth
$425,000
4 Beds ⋅ 2.1 Baths ⋅ 10658641 MLS
Welcome to this immaculate, move-in ready traditional brick home located at 3947 Long Point Blvd in Portsmouth's highly sought-after Churchland neighborhood. This spacious 4-bedroom, 2.5-bathroom residence spans over 2,000 square feet of beautifully updated, bright, and clean living space. The expansive family room serves as the heart of the home, boasting dramatic vaulted ceilings and a cozy gas fireplace. Step outside onto the generous rear deck to enjoy tranquil water views overlooking a small lake on an expansive 0.39-acre lot. Built in 1992, this well-maintained one-story ranch features a functional layout, central air conditioning, pristine flooring, and an attached garage for convenient parking and extra storage. Ideally positioned with easy access to local schools and amenities, this stunning property offers the perfect blend of comfort and scenic charm

3947 Long Point Boulevard, Northwest Portsmouth
273 Elm Avenue, Central Portsmouth
$425,000
10640946 MLS
Renovated over/under duplex in the heart of Portsmouth! Located with easy access to highways, bases, shopping, and restaurants. Tenants in both units, photos from when it was vacant. Unit 1 has LVP flooring throughout the main living areas. This unit has 3 bedrooms and 1.5 bathrooms, kitchen, dining area, living room, and extra space for storage. The kitchen has beautiful quartz counters and stainless appliances. Unit 2 has LVP flooring throughout the main living areas. This unit has 3 bedrooms, 2 bathrooms, kitchen, dining area, and living room. The primary bedroom has an attached bathroom. The kitchen has beautiful quartz counters, stainless appliances, and a pantry. All appliances convey. Come see it today!

273 Elm Avenue, Central Portsmouth
416 Maryland Avenue, Central Portsmouth
$425,000
10627210 MLS
Rare opportunity to live in one and already have a GREAT tenants on the other side paying a great portion of your mortgage. This is a great addition to you Real Estate portfolio or a good way to start a new one. The vacant unit is the 3 bedrooms, 2 full bathrooms. Both units completely remodeled within the last 6 months. A lot of new construction happening around the area, 4 blocks from the bay. Don't let this one slip by.

416 Maryland Avenue, 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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