979 properties for sale in Chestnut Street Apartments

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

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!

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

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!

Spacious 5-bedroom, 2 full-bath older home full of character and potential. This property needs some TLC, making it a great opportunity for buyers looking to add their own personal touch. Features include a cozy wood-burning stove in the living room, a nice yard with plenty of space to enjoy, and a single-car garage. A solid home with good bones and lots of upside for the right owner

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

Great opportunity to make this home your own! Featuring fresh paint, new carpet, updated bathrooms, and brand-new stainless steel appliances, this home is move-in ready and waiting for its next owner. Whether you're purchasing your first home or looking for a fresh start, this one is worth a look! Schedule your showing today!

Four bedroom two full bathrooms with tiled showers! Downstairs includes 2 bedrooms, full bathroom (with walk in shower), & laundry area. Large & open living room, dining room & kitchen with hard surface flooring throughout the main living area downstairs. All new cabinetry, counters & appliances in kitchen (including a pantry! ). Screened porch to wake up & enjoy or wind down in the evenings!

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

Welcome home to this beautifully maintained 3-bedroom, 2.5-bathroom Portsmouth home! Enjoy an inviting layout with stylish finishes, including granite countertops, stainless steel appliances, engineered hardwood flooring, ceramic tile, and crown molding. The spacious primary suite features a vaulted ceiling, double vanity, and fully tiled walk-in shower. A versatile bonus room offers flexibility for an office, nursery, or additional living space. A major highlight is the solar panel system, which will be paid off after closing, with an average utility cost of approximately $20 per month. The fully fenced backyard is perfect for relaxing or entertaining. Conveniently located near major interstates, Norfolk Naval Shipyard, Olde Towne Portsmouth, shopping, dining, and entertainment. Schedule your private tour today!

Seller incentive! Seller is offering up to $10,000 toward the buyer's allowable closing costs or mortgage interest-rate buydown, giving buyers the opportunity to reduce upfront expenses or potentially lower their monthly mortgage payment! PLUS, a one-year home warranty of the buyer's choice, up to $1,000, with an acceptable offer! Take advantage of this opportunity to save on upfront costs or potentially secure a lower interest rate! Welcome to this beautifully renovated 4-bedroom, 2-bath brick home offering approximately 1,500 square feet of updated living space. Like new construction! Totally renovated throughout with a new roof, new HVAC, upgraded plumbing and electrical, LVP flooring, soft-close cabinetry, and modern finishes. The primary suite features a walk-in closet for added storage. Outside, enjoy a fenced front and backyard, spacious rear yard, attached garage, and driveway. Located on a quiet street with several newer homes nearby. Move-in ready and beautifully updated thro

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!

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

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

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