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625 Briarwood Dr, South Chesapeake
$669,999
5 Beds ⋅ 3.1 Baths ⋅ 10634984 MLS
Welcome to this beautifully updated 5-bedroom, 3.5-bath home in the heart of Great Bridge, where timeless character meets modern comfort. Stunning curb appeal begins with lush landscaping, a welcoming front porch, and an oversized driveway. Inside, custom tongue-and-groove plank ceilings and exposed wood beams bring warmth and architectural charm to the living room, anchored by a gas fireplace and enhanced by crown molding and chair rail throughout. The chef’s kitchen features custom white maple cabinetry, granite countertops, under-cabinet lighting, and newer stainless appliances. Stylishly updated baths and flexible living space, including an in-law suite, offer versatility for today’s lifestyle. Outside, your private backyard retreat awaits with a sparkling saltwater pool, gazebo, and paver patio designed for entertaining and quiet relaxation. This is the kind of home that simply feels right the moment you walk in.

625 Briarwood Dr, South Chesapeake

569 River Gate Road, South Chesapeake
$669,000
4 Beds ⋅ 3 Baths ⋅ 10610169 MLS
Fantastic ALL BRICK 4 Bdr, 3 Full Bath located directly on the Lake in desirable Carriage House Estates! This beauty has many updates & is truly ready for new owners! New Arch Roof to be installed. New carpet & paint throughout, two new A/C units 10/25, several light fixtures. The lovely updated eat-in kitchen features new Gas Range, Refrigerator, Microwave, backsplash. Unobstructed water views from eat in kitchen. Primary boasts huge WI closet w/window, en-suite bath w/ jetted tub, shower & dual vanities. Walk up attic provides lots of storage. FROG is large and could double as 4th bedroom, media room/playroom & as a full bath at bottom of stairs. The real showstopper are the expansive lake views which can be enjoyed from all back windows, patio or private dock on the Lake. The lake provides gorgeous views & privacy & the land extends on the back right (Est. 335 ft) along the waterfront w/ a wooded private trail on the property! 1.75 acre lot extends into water.

569 River Gate Road, South Chesapeake

109 Agave Court, South Chesapeake
$666,990
4 Beds ⋅ 2.1 Baths ⋅ 10585770 MLS
Welcome to the Denton at Riverview Landing, Chesapeake’s premier new home community! This beautifully crafted single-story home offers seamless open-concept living with luxury finishes, including a gas fireplace and a smart home package. The spacious living area flows effortlessly into the gourmet kitchen—complete with a large center island, stainless-steel appliances, and premium quartz countertops-making it perfect for entertaining. Retreat to the oversized primary suite featuring a spa-inspired bath with a frameless shower, a private water closet, and a huge walk-in closet. With three additional bedrooms, a second full bath, tankless water heater, and durable Hardiplank siding, this home is designed for comfort and efficiency. Enjoy the friendly, amenity-rich community with walking trails, a fire pit, and easy access to Chesapeake’s vibrant waterfront, festivals, and nearby beaches.

109 Agave Court, South Chesapeake

645 Crestfield Drive, South Chesapeake
$666,615
4 Beds ⋅ 2.1 Baths ⋅ 10615164 MLS
Up to $10K closing cost assistance all when seller's preferred lender is used for financing, see agent for details. This beautiful Wells plan is backing a mature tree line, featuring 4 spacious upstairs bedrooms, including an owner’s suite with a tiled shower and quartz double vanity. Bright, open kitchen boasts a large island, quartz countertops, stainless steel appliances, and generous pantry. Enjoy an inviting front porch, welcoming foyer with ample storage, and a fenced backyard. Additional highlights include 2-car garage & custom wood shelving in large closets. Buyer must register agent on or before first visit or first substantial communication with listing agent and Agent must accompany Buyer on 1st visit, see Listing Agent for details. Photos & video are of previously completed home, finishes and upgrades vary.

645 Crestfield Drive, South Chesapeake

528 Belem Drive, South Chesapeake
$665,000
4 Beds ⋅ 3 Baths ⋅ 10633498 MLS
Welcome to Las Gaviotas in South Chesapeake, where golf course views, cul-de-sac living, and custom details come together in all the best ways. Sitting at the end of a quiet street overlooking the wooded backdrop and the 7th hole, this home offers the kind of setting people wait years for. The gorgeous kitchen features tons of countertop space, a huge island with room for everyone to gather, and a beautiful wine rack detail opening into the living room. The living area flows right out to a screened-in porch overlooking the backyard and golf course views that feel like vacation every day. Upstairs, the primary suite steals the show with a private balcony great for coffee or evening unwinding. The oversized FROG, not counted as a bedroom, features 10-foot ceilings, bar area, sink, refrigerator, ice maker, and the ultimate entertaining setup. Offering 4 bedrooms, 3 baths, and over 3,100 square feet, this home combines functionality, character, and lifestyle all in one.

528 Belem Drive, South Chesapeake

940 Painted Lady Place, South Chesapeake
$665,000
6 Beds ⋅ 3 Baths ⋅ 10614633 MLS
This well cared for one owner home offers 6 bedrooms, 3 full baths, and 3,732sqft of living space in desirable Dominion Meadows, zoned for Grassfield High. The thoughtful layout includes a first-floor bedroom and bath, a FROG for play or entertaining, a bright sunroom, and a cozy fireplace. Recent updates include a new refrigerator, newer outdoor compressor, fresh paint throughout. Outside, enjoy the long front porch and a community known for annual events like a chili cook-off, turkey trot, Santa visits, and food trucks. With size, functionality, and location, this home offers comfort and lifestyle. Easy access to highway, shopping and restaurants. An additional finance opportunity, through seller preferred lender offering a 1-0 temporary rate buy down at no cost to the buyer. Receive a 1% lower interest rate for the first year with the cost covered by our preferred lender. Contact agent for full details on financing opportunities and updates that have been made! Welcome HOME!

940 Painted Lady Place, South Chesapeake

5031 Annapolis Drive, West Chesapeake
$664,184
4 Beds ⋅ 3.1 Baths ⋅ 10573232 MLS
PRE-SOLD | Our Aspen model offers spacious living at its finest. This 4 bedroom, 3.5 bathroom two-story home is designed for comfort, convenience, and luxury. The main floor features a thoughtfully designed living room and an open-concept kitchen and dining area. Upstairs - four generously sized bedrooms, each designed with your comfort in mind. The primary suite is a true retreat, offering a spacious layout, a walk-in closet, and a tranquil ensuite bathroom. The additional three bedrooms are equally impressive, each offering ample closet space and large windows that allow natural light to pour in. Whether you need extra bedrooms for family or guests, these spaces offer ultimate flexibility. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, a community playground, water features, a sports field, bike paths, and a resort-style community clubhouse.

5031 Annapolis Drive, West Chesapeake

815 Angel Wing Drive, South Chesapeake
$664,000
5 Beds ⋅ 2.1 Baths ⋅ 10645285 MLS
Welcome home to a beautiful one owner home in the highly sought after neighborhood of Dominion Meadows, and Grassfield High School District. Built in 2020, this home offers a bright open-concept design, with 5 spacious bedrooms, and 2.5 baths. Versatile living room or home office, formal dining room, gourmet kitchen with large island, custom cabinetry, granite countertops, stainless appliances, and pantry flows into the spacious family room. Upstairs you will find a laundry room, and generously sized bedrooms. Luxurious primary suite with tray ceiling, spa bath, oversized custom closet. Outside unwind in the screen porch, or the large patio enjoying privacy in the fenced backyard while spending time with family or entertaining with friends. Easy commute to all military bases, and a few minutes away from shopping, restaurants, and entertainment.

815 Angel Wing Drive, South Chesapeake

704 Crestfield Drive, South Chesapeake
$662,015
4 Beds ⋅ 2.1 Baths ⋅ 10623451 MLS
11,500 square foot lot with August delivery. Elegant two-story home with approx. 2,652 square feet of meticulously designed living space. The main level boasts an open-concept layout with soaring 9-foot ceilings throughout. The heart of the home is the large kitchen, equipped w/tons of storage & countertops for meal prep & entertaining. A flex space on the first floor provides versatility for a home office, playroom, or den, catering to your household's needs. Upstairs, 4 spacious bedrooms ensure comfort for everyone & the large, upstairs laundry room simplifies household chores. Fenced backyard on larger lot. Seller to pay up to $10,000 in closing cost assistance when using preferred lender, see agent for details. Buyer must register agent on or before 1st visit or 1st communication with listing agent & Agent must accompany Buyer on 1st visit, see agent for details. Photos & video are of other Everett's completed, not actual home, finishes vary.

704 Crestfield Drive, South Chesapeake

4415 Mccaan Quay, West Chesapeake
$662,000
5 Beds ⋅ 3.1 Baths ⋅ 10626008 MLS
Welcome home to Miars Plantation, Western Branch, Chesapeake. This gorgeous brick marsh front home features an open floor plan, entry way, formal dining room, gourmet kitchen, eat in kitchen, breakfast bar and pantry. The den has gas fireplace and is wired for surround sound with direct access to screened porch & deck. Formal living room can be used as an office or flex room. Primary suite features a walk in closet, jetted tub, shower and double vanity & a private Bonus Room. Refinished hardwood floors, ceramic and newer carpet upstairs. Finished room over garage and fifth bedroom with full bath, upstairs near kitchen and laundry room. 5th Bedroom/Mother in law suite with walk in closet and private bathroom with tub. Marsh view from screened back porch and deck for grilling or relaxing. 2 car side entry garage with pedestrian door. 1/10 of a mile to the Park!

4415 Mccaan Quay, West Chesapeake

603 Marjorie Lane, South Chesapeake
$661,000
4 Beds ⋅ 3 Baths ⋅ 10613473 MLS
Rare opportunity to live in the Woods of Whitehurst! This sought after neighborhood is tucked back and private but close to EVERYTHING! Located in the heart of Greenbrier. It offers a very open floor plan with a kitchen of your dreams that opens to the spacious living room. The kitchen has tons of counter space, is very open, lots of cabinets, gas stove, etc) The 1st floor primary bdrm is so large the current owners have a work out area and a full sauna in the room and there's still a ton of space! It has a spacious walk in closet and a huge bathroom with separate sinks, a jetted tub and shower. As you enter there is a formal dining room to your left and a perfect room for an office to the right. All the bdrms are large and the finished room above the garage has a full bathroom attached, perfect for your company to have their own private area for their stay. The backyard is a dream! Large back deck, perfect for entertaining! This home has so much to offer!! Schedule your showing today!

603 Marjorie Lane, South Chesapeake

105 Lenwil Drive, Central Chesapeake
$661,000
4 Beds ⋅ 3.2 Baths ⋅ 10599126 MLS
Experience grand-scale living in this exquisite multigenerational estate, offering over 4,500 sq ft of thoughtfully designed space behind a gated brick paver driveway. With garage parking for up to 7 vehicles and even more outside, this rare gem blends luxury, functionality, and versatility. The home features 4 spacious bedrooms, 3 full and 2 half baths, a first-floor primary suite, and an entertainer’s dream with an in-ground pool that has a half bath and wet bar right next to it, also don't miss the fully equipped theater room. A private in-law suite with its own entrance, full kitchen, and bath provides the perfect setup for extended family or guest accommodations. From the elegant interiors to the expansive outdoor living areas, every detail has been curated for comfort, privacy, and style. A true haven for those seeking luxury and space in one stunning package.

105 Lenwil Drive, Central Chesapeake

2219 Captiva Lane, West Chesapeake
$660,415
6 Beds ⋅ 3 Baths ⋅ 10608812 MLS
PRE-SOLD | The Magnolia is a grand floor plan with a 2-story foyer as you enter! Large family room that opens to the Kitchen and Eating Area. Downstairs utility space that allows for the perfect 'Mudroom.' 4 spacious bedrooms & 2 baths on the 2nd floor with a finished room over the garage. The 3rd-floor walk-in attic can be upgraded to an additional bed/bath. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, a community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

2219 Captiva Lane, West Chesapeake

1337 Barbara Court, South Chesapeake
$660,000
4 Beds ⋅ 2.1 Baths ⋅ 10639495 MLS
BACK ON MARKET! Welcome home to this beautifully maintained ranch located on over an acre in the highly desirable Hickory area. Situated on a quiet cul-de-sac, this 4-bedroom, 2.5-bath home offers the perfect combination of space, comfort, and modern efficiency. Major updates include a newer geothermal heating and cooling system, new water heater, whole-home water filtration system, and a roof that is approximately 5 years old. Additional features include a generator hookup and a dedicated 30-amp outdoor RV/camper plug, providing convenience and preparedness for a variety of lifestyles. The oversized 3-car attached garage offers ample storage and workspace with an unfinished room over the garage. As well as an additional 2 car garage for extra storage! Relax on the conditioned porch and enjoy the privacy of the yard backing to mature trees. Inside, you'll find spacious living areas, a family room with a fireplace, large dining room and an inviting eat-in kitchen with new cabinets and quartz counter tops. A rare opportunity to own a one story, country-style living, well-maintained home in one of Chesapeake's most sought-after communities and school districts.

1337 Barbara Court, South Chesapeake

660 Margaret Drive, South Chesapeake
$660,000
3 Beds ⋅ 3 Baths ⋅ 10632675 MLS
3.12 acres bordered by a 50-acre tree farm — the homestead you've been dreaming of. This 1979 modern farmhouse blends character with thoughtful updates: new metal roof, HVAC, custom black-framed windows, remodeled kitchen, gleaming hardwoods, gas fireplace, dual-zone climate, whole-house water filtration with UV + sulfide removal, and smart garage. A four seasons room and massive upper deck off the primary suite bring the outdoors in. Outside, a working homestead awaits — bougie chicken coop with auto doors, rabbit hutch, greenhouse, raised beds, two paddocks, fully fenced yard, plus plum, apple, blackberry, raspberry, grapes, asparagus, and pollinator plantings. Two powered, LED-lit outbuildings include a barn with finished space and deck above — guest suite, gym, or office. Well, septic, low-voltage lighting. Private, productive, and ready for the sanctuary you've been picturing. Call today to schedule your private showing.

660 Margaret Drive, South Chesapeake

928 Jodi Lynn Trail, South Chesapeake
$660,000
4 Beds ⋅ 3 Baths ⋅ 10631832 MLS
This is the kind of home you enter and immediately feel the care behind it. Immaculately maintained, beautifully finished, and full of thoughtful details, this 3-bedroom, 2-bath home stands out in all the right ways. The spotless plantation shutters, rich hardwood floors, stainless steel appliances, and remote-controlled gas fireplace create a clean, classic feel with just the right touch of comfort and convenience. Outside, the fully fenced backyard is just as impressive, featuring a remote-controlled electric awning that makes the patio feel like an extension of the home. Major updates include a roof replaced in 2021 and a gas furnace replaced in July 2025. The detached garage, built in 2008, adds even more function and flexibility. Homes this well cared for are hard to find. Polished, inviting, and even better in person. Schedule your private showing today.

928 Jodi Lynn Trail, South Chesapeake

700 Angel Wing Drive, South Chesapeake
$660,000
4 Beds ⋅ 2.1 Baths ⋅ 10631528 MLS
Welcome to highly sought after Dominion Meadows in the Grassfield area of Chesapeake. First time offered by the original owner, this beautifully maintained home sits on a premium corner lot backing into a park and wood preserve. This spacious four bedroom 2 1/2 bath home features an open concept floor plan filled with natural light and hardwood flooring throughout the first floor. The private, fully fenced backyard offers serene views~perfect for entertaining with an oversized patio and charming gazebo. Additional highlights include solar panels, tankless water heater for efficiency and oversized 20' X 12' detached shed/workshop. The two car garage is fully insulated with its own mini split HVAC system. Dominion Meadows offers five neighborhood parks with pavilions, scenic lakes with fountains and a vibrant calendar of community events. Move-in ready and meticulously maintained. A blend of style, comfort and convenience.

700 Angel Wing Drive, South Chesapeake

2138 Tall Pine Drive, South Chesapeake
$660,000
5 Beds ⋅ 2.1 Baths ⋅ 10626983 MLS
Located in the highly sought-after Grassfield school district, this move-in-ready 5-bedroom, 2.5-bath home offers the perfect blend of space, function, and style. The open-concept floor plan features a spacious living area and a stunning kitchen with a huge center island, ideal for entertaining and everyday living. The primary suite showcases a tray ceiling, dual vanities, a soaking tub, and a large walk-in closet. The FROG serves as the 5th bedroom, game room, or flex space. Enjoy the added convenience of a central vacuum system. Step outside to a private backyard backing to woods with no rear neighbors, complete with a paver patio perfect for outdoor living. Conveniently located near shopping, dining, and major highways, this home offers privacy, comfort, and modern living in one of Chesapeake’s most desirable communities.

2138 Tall Pine Drive, South Chesapeake

1825 Carrera Ridge, South Chesapeake
$660,000
5 Beds ⋅ 3.1 Baths ⋅ 10617389 MLS
Enter into a 5-bedroom paradise where luxury and comfort blend seamlessly. Every inch of this amazing designer home exudes style—from vaulted ceilings and updated light fixtures to a chef’s dream kitchen with butlers pantry, an inviting living and dining area. The lavish primary suite is a private oasis, and a finished room over the garage with its own bath is ideal as a guest suite or extra private office. Outside, an extended driveway adds a third parking lane, and the two-car garage doubles as a workshop with storage plus a Level 2 EV charger for your electric vehicle. Nestled in a sought-after neighborhood on a generous lot, every detail of this showpiece has been thoughtfully curated. It's like entering into a dream home show—only this time, it can be yours. Hurry, a treasure like this won’t last long!

1825 Carrera Ridge, South Chesapeake

980 Intracoastal Way, South Chesapeake
$660,000
4 Beds ⋅ 3 Baths ⋅ 10617185 MLS
Move-In Ready New Construction Home! Welcome to Riverview Landing in Chesapeake, VA, where the 2,748 sq ft Hadley model offers stylish living with open spaces, a gourmet kitchen featuring quartz countertops, stainless steel appliances, gas cooking, and a large center island, plus a bright sunroom, cozy gas fireplace, and a flexible room for a home office or playroom. This home includes a main-level guest suite, upstairs loft, luxurious primary suite with a spa-inspired bath and walk-in closet, two more bedrooms, and convenient laundry. The house is built with durable Hardie siding, a tankless water heater, and a fully sodded, irrigated yard. Enjoy a vibrant community with walking trails and a fire pit, just minutes from beaches, festivals, and everything Virginia has to offer-making it the perfect place to live, relax, and entertain. Incentives with use of preferred lender!

980 Intracoastal Way, South Chesapeake

1922 Briton Lane, South Chesapeake
$660,000
5 Beds ⋅ 3.1 Baths ⋅ 10608483 MLS
It’s time to make your home in the sought after Hickory area of Chesapeake! Built 2021, this stunner has 5 bedrooms, 3.5 Baths, 2 Primary suites with tiled showers and quartz vanity tops. Open concept living area with large kitchen, quartz counter tops, stainless appliances including GE Profile fridge and huge island w/lots of seating. 9' ceilings, walk-in closets w/ wood shelving, high-end Samsung w/d w/steam dryer, beautiful crown molding throughout home, upgraded LR lighting pkg, 2 car garage, Kinetico whole-home water filtration system, upgraded dual ecobee premium smart thermostats, in-duct air purifier, HVAC surge protector, & fenced backyard w/patio. Too many upgrades to list! Community center w/ kitchen & great room for resident use or to reserve for private party, resort-style pool w/outdoor kitchen & cabana, 24/7 fitness & playground, walking trails & 5 community lakes. Tons of perks w/low HOA! Convenient shopping & dining nearby you’re sure to find everything you need here.

1922 Briton Lane, South Chesapeake

3108 Old Rock Street, South Chesapeake
$660,000
5 Beds ⋅ 3.1 Baths ⋅ 10605539 MLS
Ask about the 2.25% assumable VA loan! Stunning 5/6 bedroom, 3.5 bath corner-lot home in sought-after Culpepper Landing. With three levels of versatile living space, this home has it all. The main floor features formal living/dining, a private office (or 6th bedroom), and an open-concept kitchen/family room perfect for entertaining. The gourmet kitchen and breakfast nook overlook a backyard with a hot tub. The second floor boasts a luxurious 536 sq. ft. primary suite with two sizeable walk-in closets and a spa-like bath. The third floor is a private retreat with a huge 26x16 bonus room, full bath, and bedroom—ideal for guests or multi-gen living. Enjoy premier HOA amenities: pool, clubhouse, gym, and trails. Unmatched space and value—plus a new neighborhood elementary school planned for 2027!

3108 Old Rock Street, South 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.