978 properties for sale in Holley Square At Westbury

Historic charm meets spacious living! This beautifully maintained three-story home offers the character and craftsmanship of a historic property with the space today's buyers are looking for. Featuring generously sized living areas and large bedrooms, there is plenty of room to spread out, relax, and entertain. The inviting exterior features a covered front porch, white columns, detailed trim, and a fenced yard. Inside, the spacious living room showcases hardwood floors, an ornate fireplace with detailed mantel, decorative molding, and abundant natural light. The updated kitchen features white cabinetry, stainless steel appliances, granite countertops, tile backsplash, and recessed lighting. Additional architectural details throughout add to the home's distinctive character. On the second floor, you will find 3 substantial bedrooms and an office. The third floor is finished with new carpet installed. Great for a 4th bedroom, bonus room, or storage. Schedule your private showing today!

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

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!

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!

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

This charming 4-bedroom, 2-bath Cape Cod–style home offers a bright and spacious open floor plan designed for comfortable living. The beautifully updated kitchen is a standout feature, complete with luxury vinyl plank flooring, stainless steel appliances, granite countertops, and classic shaker cabinetry—perfect for cooking and entertaining alike. A deep walk-in pantry and separate utility room provide ample storage and convenience. Recent upgrades, including new carpet and fresh paint, give the home a clean, move-in-ready feel. Whether you're looking for a private residence or a smart investment opportunity, this property offers versatility and value. Ideally located just moments from the interstate, commuting throughout the Tidewater area is quick and easy. You’ll also enjoy being minutes away from the scenic Elizabeth River waterfront, as well as the dining, shopping, and charm of Olde Towne. *this property has a tenant on a rental lease to expire june 30, 2027

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

This beautifully maintained 3-bedroom, 1.5-bath Dutch Colonial in the quiet West Park View neighborhood offers the perfect blend of classic charm and modern updates. Tucked away on a peaceful dead-end street near Scotts Creek, this character-filled home features a spacious floor plan, dedicated laundry room, generous attic storage, and a fully fenced backyard with storage shed. Thoughtful improvements include renovated bathrooms (2022), an updated kitchen with new flooring (2023), a new roof and water heater (2024), and a screened feature low-maintenance Trex decking (2025). Conveniently located near shopping, dining, and other local amenities, this home is ready for its next owner

Charming 3-bedroom, 2.5-bath home offering 1,592 sq ft in Portsmouth’s Prentis Park area. Situated on a corner lot, this two-story property features a welcoming covered front porch, classic exterior details, and established landscaping. The main level offers a functional layout with comfortable living spaces, while the upper level provides three bedrooms and two full baths. Enjoy outdoor living from the spacious rear deck overlooking the yard. Conveniently located in Portsmouth with easy access to nearby shopping, dining, parks, and major roadways. A great opportunity to own a home with character, outdoor space, and a desirable corner-lot setting

This is a beautiful ranch situated on a quiet street in Shea Terrace. Many notable upgrades including: addition of second bathroom, lead-free copper piping throughout the home, tub reglazed, updated Electrical throughout, new refrigerator, new dish washer, and new deck. Roof, flashing and gutters all under 10 years old. AC & Furnace recently refurbished. This is a wonderful home with several updates that you aren't going to want to miss!

Discover this modern 3-bed, 3-bath home built in 2019, offering comfortable two-story living on a spacious 5,009 sq ft lot. Located in a quiet Portsmouth neighborhood, this home features contemporary construction, a practical and inviting layout, and low-maintenance living throughout. With newer finishes and a convenient location close to local amenities, it’s a great opportunity for anyone seeking a move-in-ready home with modern comfort

Very roomy 3 bed 2.5 bath home located on a large fenced in lot with recent systems and cosmetic updates. Beautiful granite kitchen. Great condition and ready today. Close to military bases, hospitals, universities, and shipyards

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!

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

High ceilings, gleaming hardwood floors, old world charm with all the right upgrades! Kitchen features stunning maple cabinets double basin sink, huge island and ceramic tile floors. Pantry/storage room and door to the cute backyard are conveniently located off the kitchen. Enjoy vibrant downtown living! Downtown Portsmouth features the regions largest farmers market every Saturday. Blocks to the Commodore Theatre, restaurants, the waterfront, and the ferry to Norfolk where there are more restaurants and the nationally recognized Elizabeth River Trail. Condo living without the condo fee. Very close to Naval Medical Portsmouth, Coast Guard headquarters and Portsmouth Marine Terminals. Very quick access to I-264, downtown/midtown tunnels and 164 to Suffolk/Newport News

Discover the charm of a beautifully restored 121-year-old home at 14 Parkview. Blending historic character with modern updates, this home features original architectural details, a brand-new roof, new HVAC system, new windows, and a completely remodeled interior. The updated kitchen includes an installed stove and microwave, while the finished third floor provides additional living space and versatility. Conveniently located near Naval Hospital, shopping, dining, and major interstates, this home offers character, comfort, and everyday convenience. Schedule your private showing today!

This is what you have been waiting for! Gorgeous renovated 4 bedroom 3.5 bath home, boasts of laminate flooring, granite countertops, new roof, new duct work and some new plumbing & electrical. 2 master bedrooms. 1st floor master can be in-law suite or flex room. All bedrooms are great in size. Seller offering 2 year home warranty. This is a must see!

Come see this charming 4 bedroom, 2.5 bath home featuring spacious bedrooms, an attached garage, and a generous backyard with plenty of room to enjoy. Conveniently located with access to the shipyard, Downtown Portsmouth, military installations, shopping, dining, and major roadways

Rare new-construction investment opportunity! Two spacious, attached, three-story townhomes on Azalea Avenue offered together as ONE purchase—not available individually. 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—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 preservin

Welcome to this charming and spacious Victorian style home which was rebuilt from the foundation up in 2006! Set on a corner lot in a quiet neighborhood. This home features hardy plank siding, zoned heating and cooling, Corian countertops in kitchen with an open floor plan. Two primary bedrooms: upstairs ensuite is about 1000 sq ft. And has a double sized walk-in closet, huge bathroom w/ big walk-in shower for 2! Spacious primary bedroom downstairs has a big bathroom, too. Hardwood floors in most areas, tiled kitchen and baths! Enjoy quiet mornings and evenings in your screened in porch with a fenced yard. Lots of street parking. Conveniently located near Naval medical center/hospital, Olde Towne, shopping, interstates, ferry systems to Norfolk and very near Elizabeth River

Charming & Move-In Ready in Portsmouth! Welcome home to 1406 Maple Avenue! This freshly painted gem is ready for its next owner. Step onto the brand-new front porch — the perfect spot to unwind with your morning coffee or watch the sunset. New storm doors on both the front and back entrances add extra curb appeal, energy efficiency, and peace of mind. Out back, you'll find a spacious backyard ideal for entertaining, gardening, or just letting the kids and pets run free. Location can't be beat — you're close to shopping and dining, with easy access to the interstate, making commutes to the military bases and shipyard a breeze. Perfect for military families, first-time buyers, or anyone looking for comfort and convenience. Don't miss this one — schedule your showing today!

Discover an excellent investment opportunity at 1725/1- Prentis Avenue in Portsmouth! This charming over-under duplex features two spacious units, each offering 3 bedrooms and 2 bathrooms. The upstairs unit, 1725 Prentis Avenue, offers approximately 1,640 square feet of living space. Both units feature beautiful front porches, tall ceilings, updated flooring, and updated bathrooms, adding to the property's appeal. Additional conveniences include laundry hookups and street parking. The owner is responsible for water, while tenants pay for electricity. With a reported monthly rental rate of $1,350 for the upstairs unit and $1,400 for the downstairs unit, this duplex offers an attractive opportunity for investors seeking rental income in Portsmouth. Additional Investment Opportunity: This property is part of a four-duplex investment portfolio, with each property available for individual purchase. The seller will also consider package offers. Additional properties include 204 Central Avenu

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

Discover an investment opportunity at 1622 Prentis Avenue in Portsmouth! This side-by-side duplex features two spacious units, offering flexibility and potential for investors looking to expand their rental portfolio. Unit A offers 3 bedrooms, 2 bathrooms, and approximately 1,100 square feet of living space. Currently vacant and in need of turnover and updates, this unit presents an opportunity to make improvements before securing a new tenant. Unit B features 3 bedrooms, 1 bathroom, and approximately 1,000 square feet of living space. Previous rental rates were $1,500 per month for Unit A in 2023 and $1,150 per month for Unit B in 2021. Street parking is available, with the owner responsible for water and tenants responsible for electricity. A great opportunity for investors seeking a property with value-add potential! Additional Investment Opportunity: This property is part of a four-duplex investment portfolio, with each property available for individual purchase. The seller will al

Welcome to this charming brick ranch tucked away on a quiet dead-end street in Portsmouth’s Shea Terrace neighborhood! Built in 1955 and offering over 1,500 square feet, this home is filled with character and possibilities. Enjoy beautiful original hardwood floors, a cozy gas fireplace, a formal dining room with chair rail molding, and a converted garage that provides additional living space. The kitchen features granite countertops, and all appliances convey. Additional highlights include a welcoming front porch, a jetted tub, and a roof replaced in 2016. Conveniently located just minutes from the Naval Medical Center Portsmouth, Norfolk Naval Shipyard, and major interstates. The home is being sold as-is and needs a little TLC, making it a wonderful opportunity to add your personal touches and make it your own. Don’t miss out—schedule your showing today!

Welcome home to this beautifully updated, move-in-ready property situated on a large corner lot in the heart of Portsmouth! Renovated within the past five years, this inviting home offers a spacious, functional layout with modern finishes and plenty of room to fit your lifestyle. The updated kitchen features elegant granite countertops and stainless steel appliances, while luxury vinyl plank flooring and plush carpeting create a stylish, comfortable feel throughout. The generous primary suite offers a walk-in closet and private en-suite bath, providing the perfect place to unwind. A versatile bonus room adds even more flexibility, making it ideal for a home office, playroom, fitness room, or media space. Enjoy added peace of mind with major updates, including a new HVAC system installed in 2024, along with a roof, windows, and water heater all less than five years old. Outside, a spacious, vinyl privacy-fenced backyard—perfect for entertaining, relaxing, or enjoying outdoor activities.

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

This home has an open floor plan and is located in the heart of the city near I-264, Shipyard, Banks, Restaurants, Entertainment, Waterfront, and Rivers Casino. This home has many updates including updated kitchen, master bedroom and bath on first floor, with an office on the second floor. Hurry come see this home before it's gone

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! Downstairs unit now vacant, being renovated. Great opportunity for someone who wants to live in one unit and rent the other

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