Chesapeake VA Homes with Oscar Smith High school

Welcome to Chesapeake, Virginia, a vibrant city nestled in the heart of Hampton Roads. Known for its rich history, diverse culture, and stunning natural beauty, Chesapeake offers a unique blend of urban conveniences and serene landscapes. With its sprawling parks, extensive waterways, and family-friendly neighborhoods, it’s no wonder that this charming city is a sought-after destination for homebuyers.

One of the standout features of Chesapeake is its exceptional educational opportunities, particularly for families with school-aged children. Homes located within the Oscar Smith High School district offer not only a quality education but also a strong sense of community. Oscar Smith High School is renowned for its commitment to academic excellence, a wide range of extracurricular activities, and a supportive environment that fosters student growth and achievement. Living near this esteemed institution means your children have access to top-notch educational resources, dedicated teachers, and a vibrant school spirit.

The surrounding neighborhoods are equally appealing, featuring a variety of home styles that cater to different tastes and budgets. From charming single-family homes to modern townhouses, there’s something for everyone in this delightful area. Residents enjoy convenient access to shopping, dining, and recreational activities, all while being just a short drive from the beautiful beaches of the Atlantic Ocean.

In Chesapeake, you’ll find not just a place to live, but a community to thrive in. Explore the homes available near Oscar Smith High School and discover the perfect setting for your family’s next chapter in this lovely Virginia city!

Newest Chesapeake VA Homes with Oscar Smith High school

$280,000

3 Beds ⋅ 1.1 Baths ⋅ 10653026 MLS

Welcome home to this well-maintained 3-bedroom, 1.5-bath townhome! All major systems have been replaced within the last 8 years, including the roof, offering valuable updates already taken care of. The home features a functional layout with comfortable living spaces and plenty of potential to make it your own. Best of all, there are NO HOA, giving you the benefits of townhome living without the added monthly expense. Whether you're a first-time homebuyer or simply looking for a place to call home, this property is ready for its next owner. Schedule your showing today!

1208 Basswood Court, South Chesapeake

$574,900

4 Beds ⋅ 2.1 Baths ⋅ 10653018 MLS

Located in Oak Bridge Forest, this 4-bedroom, 2.5-bath home offers a spacious layout, an oversized 2-car garage, and a large backyard made for enjoying the outdoors. Inside, a two-story foyer welcomes you into a light-filled floor plan featuring new laminate flooring, installed in 2025, throughout most of the home. The custom-designed kitchen received a complete makeover in 2025 and opens to the family room, creating an easy flow for everyday living and entertaining. Upstairs, the spacious primary suite features a private bath with a double vanity, walk-in shower, and jetted tub, with three additional bedrooms and a second full bath completing the level. Out back, mature landscaping and trees surround an in-ground pool with a new liner installed in 2024 and new pool heater added in 2025. A Trex deck provides additional space to relax or entertain. Additional features include a tankless water heater, sprinkler system, smart-home capabilities, Ring doorbell and exterior security cameras, plus an Invisible Fence encompassing the front and backyard. No HOA! With generous indoor and outdoor space, thoughtful updates, and a backyard ready for pool days and entertaining, this Oak Bridge Forest home has plenty to offer. Incentives may be available through preferred partners. Contact listing agent for details and eligibility.

733 Dissdale Lane, South Chesapeake

$410,000

3 Beds ⋅ 2 Baths ⋅ 10653003 MLS

Welcome to this well-maintained 3-bedroom, 2-bath ranch home in the gorgeous Riverwalk community! Proudly offered by its original owner, this charming one-story home offers 1,600 square feet of comfortable living with the convenience of a first-floor primary bedroom. The inviting layout provides plenty of space for everyday living, entertaining, or simply relaxing at home. Step outside to enjoy the back deck and create your own peaceful outdoor retreat. Riverwalk residents enjoy fantastic amenities including a clubhouse, swimming pool, playgrounds, tennis courts, scenic trails, and a boat ramp and dock with access to the Elizabeth River. Conveniently located to access bases, beaches, dining, entertainment, restaurants, shopping, and more. Well cared for and ready for its next chapter—come see all this wonderful home and community have to offer. Call now for your personal tour.

435 Supplejack Court, South Chesapeake

$244,900

2 Beds ⋅ 1 Baths ⋅ 10652612 MLS

Welcome to the historic district of South Norfolk! This beautifully updated and well maintained bungalow blends modern amenities with original charm and character. The kitchen shines with high-end granite countertops, custom cabinetry, stainless steel appliances, and ample storage. Enjoy a spacious, open living area with original hardwood floors throughout, generously sized bedrooms, and a refreshed bathroom featuring stylish tile finishes. The sizable backyard is ideal for enjoying the outdoors, relaxing, or entertaining guests. The detached garage has all new electrical and offers excellent space for a workshop or additional storage. Don’t miss the expansive attic, or the nearby park! Conveniently located near interstates and military bases.

1423 Rodgers Street, Central Chesapeake

$337,000

3 Beds ⋅ 2 Baths ⋅ 10651901 MLS

Wake up to peaceful water views right from your bedroom! This spacious, well-maintained 3-bedroom, 2-bath condo offers 1,762 square feet per MLS of comfortable, single-level living and low-maintenance convenience. Featuring luxury vinyl plank flooring in the living areas. Large windows and a sliding glass door bring in plenty of natural light. The kitchen offers abundant cabinet space, newer stainless steel appliances, including a wine fridge, and a convenient pantry. The spacious primary suite features a walk-in closet, linen closet, and private bath with a double vanity, soaking tub, and separate stand-up shower. Additional features include newer windows and a sliding glass door, ceramic tile, carpeting, and plenty of storage throughout. Amenities include a pool and clubhouse. Association services also include dock maintenance, water, sewer, and trash.

5 Harbor Watch Drive Unit 405, South Chesapeake

$629,999

4 Beds ⋅ 2.1 Baths ⋅ 10652753 MLS

This is the kind of home that makes you want to unpack and stay awhile! Conveniently located for access to major Hampton Roads military installations, commuter routes, shopping, and dining, this beautifully maintained property in the highly sought Fieldstone neighborhood of Chesapeake offers 2,559 sq ft of living space, 4 bedrooms, and 2.5 baths. Brand new LVP flooring on the main level and fresh carpet upstairs create an inviting, move-in-ready feel. The open kitchen features granite countertops, abundant cabinetry, and pantry storage, flowing seamlessly into the living and dining areas with a cozy gas fireplace. A dedicated first-floor office adds exceptional flexibility for remote work, study, or hobbies. Upstairs, spacious bedrooms include a generous primary suite with a private bath and walk-in closet. Outside, enjoy a fully fenced backyard and patio, wonderful for outdoor relaxation and summer gatherings. Some photos were virtually staged using AI.

1808 Ashlar Lane, South Chesapeake

$225,000

3 Beds ⋅ 2 Baths ⋅ 10652708 MLS

NEW PLUSH CARPET THROUGHOUT. Open concept living room eat in kitchen with breakfast nook. 1st Floor Primary Bedroom with bathroom that opens to laundry room. 2 bedrooms upstairs with a full bath. 1 larger bedroom upstairs features a seating area that could be used as an office or additional multi use space. Large sheds in the back for storage. Covered front porch for relaxing on crisp fall days.

1310 Hoover Avenue, Central Chesapeake

$608,900

3 Beds ⋅ 2.1 Baths ⋅ 10652577 MLS

Visit SITE: GPS 369 Scotland Ln. Chesapeake OPEN S/S 12-4. Nestled in Greenbrier come visit the newest community by renowned local builder. Primrose Cottage welcomes you with an inviting full front porch, soaring two-story foyer and family room, and beautiful hardwood flooring throughout the main living areas. First-floor primary suite with custom walk-in closet and spa bath with quartz dual vanity, tiled shower, and private laundry.Designed for easy living and entertaining with open layout connects the family room, dining area, and HGTV-inspired chef’s kitchen featuring oversized quartz island, custom hood & floating shelves, and designer finishes. Upstairs two spacious bedrooms, tons of storage and 2nd laundry room and Opt. for 4th BR/Loft and/or add'l full bath. Professionally managed grounds for a low-maintenance lifestyle, giving you more time to enjoy the comfort, quality, and craftsmanship of your Primrose haven.

213 Maggie Bell Ln., South Chesapeake

$385,000

4 Beds ⋅ 2.1 Baths ⋅ 10652567 MLS

This all-brick ranch is just waiting for you to call it home! Featuring 4 bedrooms & 2.5 baths, this spacious home has been thoughtfully updated throughout the years. Major improvements include a roof and water heater updated in 2020, HVAC replaced in 2022 & windows approximately 12 years old. Inside, you’ll find a large kitchen with expansive countertops, stainless steel appliances, a formal dining room, and a generously sized living room complete with a cozy gas fireplace. Primary bedroom has a walk-in in closet while the other bedrooms are generous in size. The outdoor space is just as impressive! The back deck overlooks the large, fully fenced backyard. 2 concrete driveways offer plenty of parking & the 2nd driveway extends to a double gate into the backyard, providing convenient access for trailers, boats, recreational vehicles, or additional parking. Come see everything this home has to offer and make it yours! Some photos have been virtually staged.

909 Portland Street, Central Chesapeake

$735,000

3 Beds ⋅ 2 Baths ⋅ 10652410 MLS

Welcome to 1836 Bancroft! Immaculate, barely lived-in, and loaded with upgrades, this home truly feels brand new. Thoughtful improvements throughout make it as functional as it is beautiful. The open and inviting interior features ceiling fans in every room, including remote-controlled fans in the primary bedroom and living room, plus a spacious flex room offering endless possibilities as a home office, playroom, media room, or potential 4th bedroom. The home is exceptionally well-equipped for modern living, with Ethernet connections in every room and a central Ethernet relay in the coat closet, upgraded HDMI and cable connections in the living room, and prewiring for an electric vehicle. Smart-home conveniences continue with a Kwikset electronic lock, Wi-Fi connected refrigerator and dishwasher, and a Wi-Fi capable all-in-one washer/dryer. The kitchen features exterior-vented cooking ventilation, while both bathrooms have grab bars and walk-in showers—including the second full bath. A tankless water heater adds efficiency and convenience. Endless natural light, no short in thanks to the LARGE oversized sliding door installed off of the living room. Outside, enjoy a very spacious screened-in back porch perfect for relaxing or entertaining, a rear gas connection ready for your outdoor cooking setup, and an installed sprinkler system to help keep the yard looking its best. Meticulously maintained and thoughtfully upgraded from top to bottom, 1836 Bancroft offers the rare opportunity to enjoy the feel of a brand-new home without waiting for new construction. Simply move in and enjoy!

1836 Bancroft Road, South Chesapeake

$320,000

3 Beds ⋅ 2 Baths ⋅ 10652493 MLS

Waterfront living takes center stage in this inviting, third-floor condo in the heart of Great Bridge. Enjoy lovely views of the Intracoastal Waterway from your private balcony where you can relax and watch the boats pass by. Even better, the property includes a deep-water access boat slip - an exceptional feature for boating enthusiasts! Inside, this 3-bedroom home offers an open layout connecting the spacious kitchen, living room, and dining area. A wide hallway leads to the generous primary suite with a well-appointed bath and large walk-in closet with a custom closet organization system. Harbor Watch amenities include a pool and clubhouse, dock maintenance, water, sewer, trash, and a master insurance policy. Enjoy low-maintenance waterfront living with your boat just steps away!

7 Harbor Watch Drive Unit 221, South Chesapeake

$249,000

3 Beds ⋅ 2 Baths ⋅ 10652470 MLS

Great opportunity to own a 3 bedroom/2 bath ranch fixer upper/investment property being sold as-is. Needs updates and some TLC. Make this one your own. Large front porch and fully fenced yard. Storage shed out back.

2918 Berkley Avenue, Central Chesapeake

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