Refine Search
Sort by
544 Wickwood Drive, South Chesapeake
$574,900
4 Beds ⋅ 2.1 Baths ⋅ 10660561 MLS
Welcome home to comfort, connection, and room to make lasting memories! Nestled in the desirable Briarwood neighborhood, this inviting home offers the perfect blend of everyday comfort and spaces designed for gathering with family and friends. Fresh paint downstairs and in the FROG adds a fresh touch, while the lovely kitchen features solid-surface countertops and a cozy breakfast area, perfect for morning coffee, family meals, and everyday moments. Step outside and discover your own backyard retreat! The oversized composite deck and inground pool with a new pool cover create the perfect setting for summer fun, weekend gatherings, or simply relaxing and enjoying the sunshine. Inside, you'll find a spacious primary suite featuring a second fireplace, an impressive walk-in closet, and generously sized guest bedrooms that offer plenty of room for family, visitors, or a home office. A convenient walk-in attic provides additional storage to help keep everything organized. You'll also appreciate the added peace of mind that comes with recent updates including a new water heater in 2025 and one HVAC unit replaced in 2026.

544 Wickwood Drive, South Chesapeake

720 Paula Drive, South Chesapeake
$670,000
5 Beds ⋅ 3.1 Baths ⋅ 10659692 MLS
Endless possibilities on over 3 acres! Bring your vision and transform this spacious 5-bedroom, 3.5-bath home your own! Offering both upstairs and downstairs primary suites and approximately 3,900 square feet of living space, this property is bursting with potential and features multiple living and entertaining areas, providing plenty of room to spread out and create your dream home. Situated on over 3 acres of beautiful wooded land, the possibilities are endless! The expansive property features the footprint of a former swimming pool, along with an existing brick pool equipment building, offering potential for a future backyard oasis. A separate 320-square-foot workshop with electricity provides excellent space for hobbies, projects, or additional storage. Whether you envision a private wooded retreat, space for gardening, agricultural pursuits, potential livestock use, or simply room to roam and explore, this unique property offers an incredible opportunity to bring your ideas to life. With abundant space both inside and out, this is your chance to create something truly special!

720 Paula Drive, South Chesapeake

1909 Chesapeake Drive, Central Chesapeake
$419,000
5 Beds ⋅ 3 Baths ⋅ 10660548 MLS
This beautifully maintained, one-owner home offers complete peace of mind and total move-in readiness. You can bypass immediate major expenses since the roof, HVAC, and water heater are all less than ten years old, while the included solar panels provide the added convenience of lower monthly energy bills. Inside, the kitchen features stainless steel appliances, granite countertops, and the pantry space you have been dreaming about. The spacious living room serves as a perfect gathering space, complete with great built-ins and a cozy electric fireplace for chilly winter nights. Notably, this versatile layout boasts a highly desirable first-floor bedroom and full bathroom. Upstairs, the secondary bedrooms are generously sized and offer exceptional closet storage. The principal suite serves as a true retreat, highlighting a fantastic ensuite bathroom and an extra-large walk-in closet. Outside, the backyard transforms into a private oasis, beautifully bordered by lush woods behind for maximum seclusion. The property is ideally located just moments from nearby schools, parks, the public library, dining, and local entertainment. For an easy commute, the home sits roughly three miles from the Norfolk Naval Shipyard, five miles from the Portsmouth Naval Hospital, and just over twelve miles from Naval Station Norfolk.

1909 Chesapeake Drive, Central Chesapeake

1312 Woodview Lair, South Chesapeake
$715,000
4 Beds ⋅ 3.1 Baths ⋅ 10660380 MLS
Welcome to 1312 Woodview Lair a beautiful all-brick home in Chesapeake's desirable Grassfield area! This spacious home offers an open floor plan with hardwood flooring throughout the first floor, a formal dining room with butler's pantry, private office with French doors, and a welcoming family room with custom built-ins and gas fireplace. The kitchen features granite countertops, stainless appliances, center island, breakfast bar, and new refrigerator and stove. The primary suite offers a sitting area and completely remodeled bathroom. Additional bedrooms include a Jack & Jill bath and second primary suite with private bath. Recent improvements include fresh paint throughout most of the interior and a new pool liner, salt cell, and pump in 2025–2026. Enjoy the backyard saltwater pool, stamped concrete patio, and nearby walking trails. Convenient to shopping, dining, and major commuter routes!

1312 Woodview Lair, South Chesapeake

4016 3rd Street, Central Chesapeake
$387,000
4 Beds ⋅ 3 Baths ⋅ 10660417 MLS
Welcome home to this spacious and beautifully maintained 4 bedroom, 3-bath residence offering nearly 2,000 square feet of comfortable living space. Built in 2014, this modern home combines style, functionality, and convenience in one desirable package. Highlights You'll Love: 4 generously sized bedrooms,3 full bathrooms, Open and inviting floor plan used for entertaining, Cozy fireplace for relaxing evenings, Modern construction with contemporary finishes, Spacious kitchen and living areas, Private backyard with room for gatherings and outdoor enjoyment, Convenient parking and low-maintenance lot, Easy access to shopping, dining, schools, military installations, and major highways Whether you're looking for more space or a move-in-ready home in Chesapeake, this property offers the comfort and convenience you've been searching for. Request a tour today!!!

4016 3rd Street, Central Chesapeake

2517 Number Ten Lane, South Chesapeake
$859,900
4 Beds ⋅ 3.1 Baths ⋅ 10660465 MLS
Solar panels paid off. Sellers offering a 2-1 rate buy down with full price offer. Enjoy peaceful country living on 3 beautiful acres, just 5 miles from all your city favorites. This immaculate light-filled 4-bedroom, 3.5-bath home offers 9ft ceilings, detailed crown molding, custom built-ins, a main-level primary suite with a full bath, plus a convenient first-floor laundry room and mudroom. The chef's kitchen features leathered granite countertops, custom tile backsplash, SS appliances, and a center island. Upstairs offers 2 additional bedrooms, a large loft, and a second primary suite with a full bath, dual vanity and walk in closet. Outdoors, enjoy a resort-style backyard with a fenced inground saltwater pool surrounded by stamped concrete and a gazebo. The property also features solar panels, 2 barns, raised garden beds, a playset, a fire pit, and an extended driveway with ample space for an RV or boat. A rare blend of privacy, upgrades, and convenience!

2517 Number Ten Lane, South Chesapeake

303 Diamond Avenue, South Chesapeake
$325,000
3 Beds ⋅ 2 Baths ⋅ 10660367 MLS
Welcome to your new home!Offering peace of mind and modern comfort, this home features a brand-new roof, siding, HVAC system, water heater, and windows—giving you the major updates you want without the worry of costly replacements.Inside, you’ll find a comfortable and inviting layout with plenty of natural light and space for everyday living and entertaining. The spacious bedrooms and two full bathrooms provide flexibility. Situated in a desirable Chesapeake location near shopping, dining, schools, parks, and major roadways, this move-in-ready home is an excellent opportunity for buyers looking for convenience, updates, and value. Don’t miss your chance to make this beautifully refreshed home yours!

303 Diamond Avenue, South Chesapeake

208 Leicester Court, South Chesapeake
$760,000
5 Beds ⋅ 3 Baths ⋅ 10660322 MLS
Beautiful 5 Bedroom Brick Home featuring a spacious open floor plan perfect for everyday living and entertaining. The large kitchen offers stainless steel appliances, lots of counter space and cabinets. A standout feature of the home is the custom library, complete with French doors, built-in shelving, and a rolling ladder, creating an elegant and inviting space for work, reading, or relaxation. The first floor includes a guest bedroom and full bath. Upstairs you'll find a media room and an oversized primary suite with double closets and a large beautiful bathroom featuring a jetted tub, separate shower, a double vanity and private toilet room. Be sure to notice the built-in light-up stairs going up to the second floor! Enjoy your own private backyard oasis with mature landscaping, an in-ground saltwater pool, hot tub, and an expansive custom paver patio, ideal for relaxing or entertaining. Extended driveway with Boat/RV pad. Located in the sought after Great Bridge school district and community, local shops and restaurants, and close to the interstate for a quick trip to OBX!

208 Leicester Court, South Chesapeake

5037 Annapolis Drive, West Chesapeake
$579,000
4 Beds ⋅ 2 Baths ⋅ 10660299 MLS
Enjoy sought-after ranch-style living in this like-new, two-year-old Dogwood model in Estates at Joliff Landing! Located in Chesapeake's Western Branch area, this popular floor plan offers the convenience of first-floor living, with every room except the finished room over the garage on the main level. Two bedroom suites provide added flexibility, including one with a dual-entry bathroom accessible from the hallway. The upstairs bonus room offers space for a home office, media room, or guest retreat. Step outside to an oversized, fenced backyard with wooded views, a storage shed, and plenty of room to relax or entertain. Community amenities include a clubhouse, fitness room, playgrounds, and pool. Convenient to shopping, dining, military bases, and major interstates, this beautifully maintained home combines like-new appeal with an established neighborhood setting.

5037 Annapolis Drive, West Chesapeake

409 Cairns Road, South Chesapeake
$729,900
4 Beds ⋅ 2.1 Baths ⋅ 10660244 MLS
Make this your first stop! Pride of ownership shines throughout this immaculate Hickory Landing home that has been exceptionally cared for by the seller. The open floor plan offers a great flow between the living spaces, with updated flooring and fresh paint throughout giving the home a clean, move-in-ready feel. The spacious kitchen features granite countertops, a large island, gas range, butler's pantry, and plenty of cabinet space. The primary suite offers generous closet space and a beautifully tiled ensuite bath, while the additional bedrooms provide plenty of room for family or guests. Step outside to your own backyard oasis featuring an in-ground pool, putting green, quality storage shed, and plenty of space to entertain. Located in the highly sought-after Hickory School District, this home offers the space, condition, and location you've been looking for!

409 Cairns Road, South Chesapeake

891 Bells Mill Road, South Chesapeake
$525,000
4 Beds ⋅ 3.1 Baths ⋅ 10660202 MLS
Welcome Home! Privacy, functionality, and convenience come together in this exceptional Grassfield property! Set back from the street along a private driveway, this nearly one-acre property is surrounded by mature woods and lush greenery. Inside, fresh paint and a flexible floor plan offer something for everyone. A rare find, the home features two distinct main-level suites, including an in-law suite with its own living room, great for multi-generational living, extended guests, a fifth bedroom, or home office. The primary bathroom features live-edge wood countertops, dual showerheads, and a custom walk-in closet system. Outside, enjoy a storage shed, chicken coop, separate hookups for a future pool and hot tub, and a massive detached two-car workshop/garage with carport and RV hookup. Over $17,000 in crawlspace work has been completed, and a survey is available in the listing documents. A truly unique Grassfield property offering flexibility and room to make it your own!

891 Bells Mill Road, South Chesapeake

1620 Sandy Pines Way, West Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10659944 MLS
OVER AN ACRE IN SANDY PINES—FULLY ENCLOSED BY A NEWER WOOD FENCE! Set on an expansive lot of approximately 1.10 acres, with newer wood fencing enclosing the entire property, this traditional two story home offers a standout amount of outdoor space. With approximately 1,628 square feet, 3 bedrooms, and 2.5 baths, the home pairs a generous setting with a practical layout. Enjoy a wood burning fireplace, a kitchen with a breakfast area and pantry, and a primary bedroom with an en suite bath. Walk in closets, walk in attic space, and an attached one car garage provide convenient storage. Situated on a cul-de-sac with driveway parking and 2 storage sheds, this property offers space inside and out, with the impressive fenced lot taking center stage!

1620 Sandy Pines Way, West Chesapeake

609 Edgewood Arch, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10660136 MLS
Nestled in one of the area's most desirable neighborhoods, this stunning home offers over 3000 sq ft of beautifully designed living space. Step inside to an inviting floor plan featuring a spacious living room with soaring cathedral ceilings and a gorgeous stone fireplace. The large eat in kitchen flows seamlessly to the living area with ample cabinetry, a brand-new kitchen sink, plenty of space for entertaining. This spacious 4-bedroom home also features a versatile flex room off the foyer, great for a home office or den. Retreat to the expansive primary suite through French doors, where you will find a generous walk-in closet & a en-suite bath designed for comfort and relaxation. All new windows 2024 and a new HWH. Outside, you'll love the newer deck and fenced in yard. Cheshire Forest residents enjoy exceptional lifestyle amenities including a neighborhood pool, the flying fish swim team, clubhouse, playgrounds, tennis & pickleball courts, pond for fishing & scenic walking paths.

609 Edgewood Arch, South Chesapeake

3145 Bomar Drive, West Chesapeake
$339,900
3 Beds ⋅ 2 Baths ⋅ 10660133 MLS
Welcome to this beautifully updated, move-in-ready Western Branch ranch! Designed for effortless one-level living, this home features a bright open floor plan with a warm, inviting layout that flows seamlessly from room to room. At the heart of the home is a modern kitchen beautifully equipped with stunning granite countertops and sleek stainless steel appliances, making it perfect for both daily living and effortless entertaining. Step outside to find a large, fully fenced backyard that offers excellent privacy and space for pets, play, or weekend gatherings. Parking is a breeze with the attached one-car garage and a spacious driveway that easily accommodates multiple vehicles. Location is everything, and this home delivers. You will enjoy the ultimate convenience of being just minutes from major highways, making your daily commute and getting around Hampton Roads a total breeze. When it is time to slow down, a beautiful nearby park and scenic walking areas are just moments away, while excellent local dining, shopping, and entertainment are always within easy reach.

3145 Bomar Drive, West Chesapeake

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.

Copyright 2026 NCRMLS. All rights reserved. North Carolina Regional Multiple Listing Service, (NCRMLS), provides content displayed here (“provided content”) on an “as is” basis and makes no representations or warranties regarding the provided content, including, but not limited to those of non-infringement, timeliness, accuracy, or completeness. Individuals and companies using information presented are responsible for verification and validation of information they utilize and present to their customers and clients. NCRMLS will not be liable for any damage or loss resulting from use of the provided content or the products available through Portals, IDX, VOW, and/or Syndication. Recipients of this information shall not resell, redistribute, reproduce, modify, or otherwise copy any portion thereof without the expressed written consent of NCRMLS.

How much is your home worth?

Get instant property value now!