Chesapeake VA County Real Estate

Welcome to Chesapeake, Virginia – a hidden gem nestled in the heart of Hampton Roads! Known for its rich history, lush landscapes, and vibrant community, Chesapeake offers a unique blend of urban convenience and rural charm, making it an ideal place to call home.

With a population exceeding 240,000, Chesapeake is the third-largest city in Virginia and boasts a diverse array of neighborhoods, each with its own distinct personality. From the tranquil waters of the Great Dismal Swamp National Wildlife Refuge to the bustling shopping hubs of Greenbrier and Oak Grove, there’s something for everyone in this dynamic city.

Chesapeake is renowned for its excellent schools, making it a family-friendly destination. The city prides itself on its commitment to education, with top-rated public and private institutions that foster a nurturing environment for students of all ages. Additionally, the city’s extensive parks and recreational facilities provide ample opportunities for outdoor activities, whether it’s hiking, biking, or enjoying a leisurely day by the water.

For those who love the arts and culture, Chesapeake is home to a thriving arts community, with galleries, theaters, and annual festivals celebrating local talent. The city’s proximity to Norfolk and Virginia Beach also means residents can easily access a wide range of entertainment options, from live music to fine dining.

Whether you’re looking for a peaceful suburban retreat or a vibrant community filled with activities, Chesapeake, VA, offers an inviting atmosphere that welcomes you home. Discover the charm of Chesapeake and explore the possibilities that await you in this beautiful city!

Newest Listings in Chesapeake VA County

$324,500

3 Beds ⋅ 2 Baths ⋅ 10646111 MLS

Beautiful home ready for its new owner! Recently renovated with modern finishes, including a new kitchen, updated bathrooms, stylish lighting fixtures, new flooring, and brand-new appliances. Featuring a large detached garage, this home offers both comfort and convenience. Schedule your tour today and see all the fantastic features for yourself!

4006 Hamilton Street, Central Chesapeake

$256,900

2 Beds ⋅ 1 Baths ⋅ 10646087 MLS

WELCOME TO THIS BEAUTIFUL HOME, WHETHER YOUR LOOKING FOR YOUR FIRST HOME OR DOWNSIZING THIS PROPERTY SITUATED IN THE WELL KEPT NEIGHBORHOOD OF DEEP CREEK. SET ON A HUGE LOT WITH DETACHED PRIVATECY FENCED PATIO FOR RELAXING AND AN OVERSIZED GARAAGE/WORK SHOP WITH GARAGE DOOR OPENER. THE HOME ALSO OFFERS SPACIOUS LIVING ROOM AND A BEAUTIFUL KITCHEN THAT HAS BEEN RECENTLY RENOVATED. FRIG, RANGE, NEWER WASHER AND DRYER MATCHING SET CONVEY. REPLACEMENT WINDOWS, 3 YEAR OLD ROOF AND TERMTE LETTER PPROVIDED. TAKE A LOOK AND END YOUR SEARCH!

2312 Ferndale Road, South Chesapeake

$330,000

2 Beds ⋅ 2.1 Baths ⋅ 10646077 MLS

This end-unit townhome in the desirable Riverwalk community offers a functional layout, thoughtful updates, and exceptional amenities. Upstairs you will find two spacious bedrooms, both with ensuite bathrooms. The open-concept first floor seamlessly connects the living room, dining area, and kitchen, with durable LVP flooring throughout the main level and continuing upstairs. The kitchen is equipped with granite countertops and stainless steel appliances, while the gas fireplace adds warmth and charm to the living space. Enjoy relaxing on the screened porch overlooking your fenced backyard. Major updates have already been completed, including a new HVAC system (2025), water heater (2024), and a roof approximately seven years old. Additional highlights include an attached garage and access to Riverwalk's outstanding community amenities, including a pool, tennis courts, and clubhouse. Conveniently located near shopping, dining, and major commuter routes, make this one your next home!

312 Esplanade Place, South Chesapeake

$470,000

4 Beds ⋅ 2.1 Baths ⋅ 10646065 MLS

3404 Winterhawk Court, South Chesapeake

$215,900

2 Beds ⋅ 1 Baths ⋅ 10645553 MLS

Welcome home to the heart of Greenbrier! This charming and stylish 2-bedroom, 1-bath second-floor condo in the desirable Heather Pointe Condominiums offers the perfect combination of comfort, convenience, and updates. Conveniently located behind Greenbrier Mall, you'll enjoy easy access to shopping, dining, entertainment, and major interstates. The beautifully remodeled kitchen (2021) features granite countertops, upgraded soft-close cabinets, ceramic tile backsplash and flooring, stainless steel Whirlpool refrigerator, microwave, dishwasher, and a new electric range (2026). All appliances, including the washer and dryer, convey. Relax by the cozy gas fireplace in the spacious living room or enjoy your private balcony. New carpet throughout the home makes this condo move-in ready. Don't miss this wonderful opportunity—schedule your private showing today!

1709 Rock Bridge Mews Unit B, South Chesapeake

$300,000

3 Beds ⋅ 1.1 Baths ⋅ 10646018 MLS

Ideally located in the heart of Greenbrier, this move-in-ready three-bedroom townhouse is the perfect find! Recently refreshed with updated flooring and renovated bathrooms, this home is ready for its new owners. Features include a spacious kitchen with plenty of counter space, a convenient laundry area, and roomy, comfortable bedrooms. Complete with a private, fenced-in backyard and patio, this home offers everything you need. Schedule your showing today!

1204 Cedar Mill Square, South Chesapeake

$575,000

5 Beds ⋅ 2 Baths ⋅ 10646017 MLS

FRESH EGGS, BIG FREEDOM, ENDLESS POTENTIAL in Chesapeake's desirable Blackwater area! Welcome to your private sanctuary—the ultimate lifestyle upgrade. Picture sipping morning coffee while collecting farm-fresh eggs from your backyard chickens, surrounded by peaceful green space. Enjoy pure, independent water from your premium 600+ ft Certified Artesian well, complete with a double tank water softener and an energy-efficient tankless electric water heater. Dream big with future-proof infrastructure: an oversized septic system is already in place to support an ADU, multi-generational living, or rental income. Built for comfort and efficiency, this ultimate hobbyist setup includes a premium dual-fuel HVAC and a sub-panel wired for a generator. Whether you envision a luxury guest cottage, a workshop, or an expanded country compound, the foundation is completely set. Schedule your tour today!

1336 Blackwater Road, South Chesapeake

$365,000

3 Beds ⋅ 1 Baths ⋅ 10645994 MLS

944 Bells Rd Road, South Chesapeake

$427,000

4 Beds ⋅ 2.1 Baths ⋅ 10645995 MLS

Welcome to your dream home in Chesapeake! This meticulously maintained end-unit condo blends modern luxury with effortless living, offers 4 bedrooms, 2.5 bathrooms, and beautifully upgraded living spaces. Go inside to an airy open-concept layout with vaulted ceilings, crown molding, and luxury vinyl flooring. Enjoy upgraded recessed lighting, pendant lights, and modern ceiling fans. The chef's kitchen, renovated in 2023, features new cabinets, granite counters, and premium stainless steel appliances. Major systems have been updated, including a water heater (2022) and HVAC (2024). The 1st floor ensuite is a private retreat with custom built-in shelves, walk-in closet, and spa-like bathroom with double sinks and a jetted tub. Upstairs, 2 additional bedrooms share a dual-entry bathroom with double sinks, offering great privacy for family or guests, and a large bonus loft area. Parking includes an attached garage and 2-space driveway. Welcome home to style, space, and convenience!

713 Tiffany Green Court, South Chesapeake

$550,000

3 Beds ⋅ 2.1 Baths ⋅ 10645963 MLS

Wonderful opportunity to get 4+ acres in high rated schools. HUGE outbuilding with 3 bays garage bays, powered, multi-level, for storage and recreational activities. Home sold as is. Part of an estate. Seller to do no repairs.

2323 Herring Ditch Road, South Chesapeake

$449,000

5 Beds ⋅ 2.1 Baths ⋅ 10645903 MLS

Full appliance package (including washer/dryer & refrigerator) on all existing inventory! Seller will pay up to $12,000 for closing cost assistance or to be used at buyer's discretion using our preferred lender and our attorney; Stunning New Construction! Welcome to this beautiful 4-bedroom, 2.5-bath home offering 1,862 square feet of modern living space. Designed with a spacious open floor plan, it's perfect for entertaining and everyday family living. Inside, the kitchen shines with soft-close cabinets, granite countertops. Bathrooms are also appointed with granite countertops and soft-close cabinetry for a cohesive, upscale look. Throughout the home, you'll find a blend of durable LVP flooring and plush carpet. Tray ceiling in the primary bedroom and walk in closet. This home features a 1-car garage. This brand-new home is the perfect blend of comfort, style, and convenience-don't miss your chance to own it in the heart of Chesapeake!

MM Railroad Ave (Trestle), Central Chesapeake

$389,900

3 Beds ⋅ 2.1 Baths ⋅ 10645889 MLS

This adorable 2-story, Townhouse-style, end-unit condo is conveniently located in sought after Hampshires @Greenbrier. The 1st floor features an open-concept layout consisting of an inviting foyer that flows into the formal dining room, Primary bedroom w/ensuite bathroom, walk-in closet, updated kitchen boasts quartz counter tops, stainless steel appliances, ample counter space, loads of cabinets for storage, family room w/cozy gas fireplace, utility closet, a powder room off the hallway for guests and access to the attached, 1- car garage & fenced-in patio area. The carpeted stairs lead to the 2nd floor that features 2 additional bedrooms, one w/an en-suite bathroom and large walk-in attic. Highlights include: some hardwood flooring, neutral carpet, lots of natural light & MORE! Neighborhood amenities include: a clubhouse, community pool & ample guest parking. Great central location adjacent to shopping, schools, parks, local beaches & highway access for an easy commute. Welcome Home!

1472 Otterbourne Circle, South Chesapeake

Start Your Search

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.