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420 Dundee Lane, South Chesapeake
$532,500
3 Beds ⋅ 2.1 Baths ⋅ 10647647 MLS
Welcome home to easy, low-maintenance, luxury living in Eagle Pointe, Chesapeake’s premier 55+ community! This move-in-ready Hamilton plan features brand-new flooring, a new water heater, and TWO spacious primary suites - one on each level - perfect for guests or multi-generational living. The eat-in granite kitchen offers an island and stainless steel appliances and opens to a bright, sunny morning room. A formal dining room features a box-bay window and tray ceiling. The 1st-floor primary includes two closets, a ceramic shower, and a double vanity. Enjoy generous finished walk-in storage, too! At the heart of Eagle Pointe is the Bay Club with indoor & outdoor pools, hot tub, fitness center, billiards, library, game rooms, grand celebration room, catering kitchen, and so much more. Come experience the Eagle Pointe lifestyle! Call today to schedule your personal tour. Some pics digitally staged.

420 Dundee Lane, South Chesapeake

451 Seahorse Run, South Chesapeake
$275,000
2 Beds ⋅ 2 Baths ⋅ 10647569 MLS
Welcome home to easy living and modern comfort! This home features two spacious bedrooms, each with its own private en-suite bath, including one thoughtfully renovated for enhanced accessibility. Also, there is a third floor flex room with balcony! The open-concept living and dining area is filled with natural light, highlighted by soaring vaulted ceilings and a gas fireplace that creates the perfect gathering space. Step onto the private balcony overlooking the peaceful marsh, where abundant wildlife and tranquil views provide a serene backdrop and exceptional privacy. Enjoy year-round comfort and energy efficiency with a newer HVAC system. Residents also have access to outstanding community amenities, including a swimming pool, tennis courts, and a playground. If you’ve been searching for a low-maintenance lifestyle in a peaceful setting, this is the home you’ve been waiting for. Schedule your private showing today or view the virtual tour! Virtually staged.

451 Seahorse Run, South Chesapeake

4936 Oriole Drive, West Chesapeake
$520,000
4 Beds ⋅ 2.1 Baths ⋅ 10647434 MLS
Welcome to this beautifully maintained home in Jolliff Woods! Offering approx 2,400 square feet of living space, this spacious 4-bedroom, 2.5-bath residence combines comfort, style, and functionality. Step inside to a beautiful two-story foyer filled with natural light, creating a bright and inviting first impression. The main level features engineered hardwood flooring, a well-appointed kitchen with stainless steel appliances, and a spacious family room highlighted by a cozy gas fireplace and custom built-in cabinetry—perfect for everyday living and entertaining. Situated on a generous 0.63-acre lot, the backyard is an entertainer's dream, featuring a large new deck with in-ground pool and expansive yard, providing the ideal setting for summer gatherings, outdoor dining, or simply relaxing in your own private retreat. Upstairs, you'll find four generously sized bedrooms with abundant closet space. The impressive primary suite offers a walk-in closet ,a spa-inspired ensuite bath with a jetted soaking tub, separate walk-in shower, and plenty of room to unwind. Additional features include ceiling fans throughout, elegant dining room light fixtures, and ample storage. Don't miss this incredible opportunity to make it yours!

4936 Oriole Drive, West Chesapeake

3909 Bruce Road, West Chesapeake
$759,900
5 Beds ⋅ 3 Baths ⋅ 10647712 MLS
New Home by Custom Builder in Martin’s Point (Western Branch) main floor living, 4 or 5 bedroom plan. First floor primary bedroom with luxury bath- zero entry tiled shower & free standing tub, Open floor plan with Huge Gourmet Kitchen w/ Quartz counter tops, 36” gas cooktop with built-in microwave/oven, Cathedral Ceiling Family Room w/ Beamed ceiling, amazing stone fireplace with built-in bookcases, expansive covered porch (29’x10’) overlooks a privately wooded backyard & scenic view .42 acre. 3 Bedrooms & Study with French doors on 1st floor with 2 add'l large rooms on the second floor, 3 baths. Excellent location, easy access to I-664, near schools, shopping, Custom Builder is a member of Southern Living Custom Home Builder Program (since 1993). Superior quality features include Trane HVAC system, tankless hot water heater, custom cabinetry, large utility room/drop zone, Hardie Plank exterior, quality upgrades throughout. Fully sodded and irrigated yard.

3909 Bruce Road, West Chesapeake

1928 Rockwood Drive, South Chesapeake
$645,000
4 Beds ⋅ 2.1 Baths ⋅ 10647705 MLS
Experience the perfect blend of quality, comfort, and outdoor living at 1928 Rockwood Drive in the highly sought-after Grassfield School District! Originally built by Stephen Alexander Homes, this beautifully maintained home is tucked away in a quiet neighborhood and features a dedicated office/study, second-floor laundry, and a spacious primary suite with soaring cathedral ceilings. The inviting living room showcases a gas fireplace flanked by custom built-ins. Outside, enjoy a private backyard oasis with an in-ground pool and TREX decking, installed in 2020. Additional updates include new windows and doors, installed in 2021. Complete with a two-car attached garage and driveway parking for four vehicles, this home truly has it all!

1928 Rockwood Drive, South Chesapeake

3012 Golden Hind Road, West Chesapeake
$649,900
5 Beds ⋅ 3 Baths ⋅ 10647695 MLS
Welcome to this beautifully maintained, one-owner custom home tucked away on a quiet cul-de-sac lot with breathtaking landscaping and water access. Situated on approximately .75 acres, this quality-built brick home offers 5 bedrooms and 3 full baths, including a desirable first-floor bedroom and full bath for guests, multigenerational living, or a home office. The oversized finished room over the garage provides endless flexibility as a potential 6th bedroom, media room, playroom, or gym. Inside, you’ll find spacious rooms, abundant storage, and exceptional craftsmanship throughout, all reflecting the pride and care of the original owners who built the home. Outside, enjoy stunning mature landscaping, stone walkways, colorful flowering shrubs, and a peaceful backyard setting along a scenic creek that leads directly to the river. A rare opportunity to own a truly special property in an established neighborhood.

3012 Golden Hind Road, West Chesapeake

2800 Meadow Wood Drive E, West Chesapeake
$549,900
4 Beds ⋅ 2.1 Baths ⋅ 10647633 MLS
Not finding the quiet and privacy you are looking for in a brand-new construction home? Want quiet luxury on a lot nestled in trees and neighbored by a quiet tributary instead of fences, driveways and alleys? Don’t want to have to pay for an HOA you won't benefit from? If so, then you have to see this brand-new home. This stunning new construction home offers 2,235 square feet of beautifully designed living space, featuring 4 bedrooms and 2.5 baths, with NO HOA! Perfectly situated on a tributary of the Western Branch of the Elizabeth River, this property is an absolute dream for water enthusiasts. Launch your kayak, paddleboard, or small craft right from your own backyard, or take advantage of the ultra-convenient public boat launch located just next door! Enjoy nature among the mature trees with plenty of lawn and space from your neighbors. Inside, enjoy all the modern luxuries and pristine finishes that only new construction can offer, with an open floor plan designed for effortless entertaining and everyday living. If you have been dreaming of a turnkey waterfront lifestyle where every day feels like a vacation, your search ends here!

2800 Meadow Wood Drive E, West Chesapeake

4921 Clifton Street, West Chesapeake
$460,000
4 Beds ⋅ 2.1 Baths ⋅ 10647376 MLS
Welcome home to this spacious property located in a quiet neighborhood with only one entrance, offering a peaceful setting and minimal through traffic. Situated on a large lot, this home features generous living spaces, including a large family room, formal dining room, and a versatile living room that can also serve as a home office. The open kitchen offers a center island, built-in desk, and plenty of workspace, making it suitable for everyday living and entertaining. Upstairs, the oversized primary suite provides a relaxing retreat with a large garden tub, double-sink vanity, and ample space to unwind. Recent updates include newer laminate flooring throughout the first floor, newer carpet upstairs, and an HVAC system and roof that are approximately four years old. Step outside to enjoy the large screened-in porch overlooking the spacious backyard—suitable for relaxing, entertaining, or enjoying the outdoors.

4921 Clifton Street, West Chesapeake

138 Greengable Way, South Chesapeake
$909,500
5 Beds ⋅ 4 Baths ⋅ 10647253 MLS
Exceptional all-brick custom home nestled in the heart of Great Bridge, meticulously maintained and thoughtfully designed with a floor plan you’re sure to love. Offering 5 spacious bedrooms and 4 full bathrooms, this home also features a versatile first-floor flex room with adjacent full bath ideal as a 6th bedroom, home office, playroom, or guest suite. The private, beautifully landscaped backyard creates the perfect retreat, complete with a patio and full-yard irrigation system. Built as the builder’s personal residence, the home showcases quality craftsmanship and upscale details throughout, including extensive custom trim work and abundant storage. Additional highlights include a garage loft with extra storage space, dual heat pump/HVAC systems for comfort and efficiency, a large walk-in closet, oversized pantry, generous laundry room, and spacious secondary bedrooms. A rare opportunity to Buy a truly well-crafted custom home in one of Great Bridge’s most desirable locations.

138 Greengable Way, South Chesapeake

3017 Lord Bradford Court, West Chesapeake
$519,900
5 Beds ⋅ 2.1 Baths ⋅ 10647023 MLS
Beautiful 5-bedroom brick colonial in sought-after Brittany Woods, perfectly situated on a quiet cul-de-sac. This well maintained one owner home features a granite kitchen with island, eat in area, and stainless steel appliances, plus a bright year round sunroom and cozy office/loft. Updated baths include Corian countertops, and the primary bath offers duals sinks and is enhanced with a ceiling heater for added comfort on cold winter nights. Laundry room with W/D. The primary bedroom also boasts a large walk-in closet. A spacious family room has a natural gas fireplace and built-ins with gleaming hardwood floors in the living room, dining room, and foyer. Major updates include a 2021 gas furnace with 5 ton 17 SEER AC and new ductwork, 2025 exterior paint, 2023 refrigerator, newer Pella windows, and LeafGuard® gutters. Large backyard ideal for entertaining. Convenient to shopping, fine dining, medical facilities, shipyards, Portsmouth Naval Hospital, and interstates. A must-see home!

3017 Lord Bradford Court, West Chesapeake

825 Waterfall Way, South Chesapeake
$829,900
4 Beds ⋅ 3 Baths ⋅ 10646857 MLS
Stunning all brick home features 4 bedrooms, 3 full bath, spacious 4 season sunroom, in ground pool in sought after Great Bridge School District. Living room/office & dinning room with hardwood floors. The large main living area offers an open floor plan featuring vaulted ceiling, gas fireplace flowing into the kitchen. Updated kitchen showcases SS appliances, New solid surface counters w/single sink & new faucet, two-tone cabinetry, bar for additional seating and flows directly into the dining room and eat-in breakfast for easy meals and entertaining. Large primary bedroom with trey ceiling, walk-in closet, remodeled ensuite bathroom with spa-like features, including a soaking tub, water closet, double vanity and, separate shower & tub. Additional downstairs bedrooms are generously sized, with hard wood floors. Large private 4th bedroom is located upstairs offers a full bath. The laundry room includes cabinetry and shelving for ample storage. Walk-in attic for additional storage. Beautiful landscaped back yard has all the amenities for entertaining show casing vinyl fencing, a solar panel heated in-ground L shape salt water pool with fountain, stone pavers throughout, trek decking and a 4 season sunroom to enjoy the view. New: carpet in family room, mini split in 4 season room, SS gas stove/microwave/refrigerator, coretec flooring in 4th bedroom, fixtures, 2023 pool liner, 2021 tankless water heater, 2015 gas furnace. 2015 Roof replacement, Mr Rogers Windows and Door, gutters with gutter guards, vinyl trim wrapped. Ask agent for a full list of home improvements. THIS IS A MUST SEE!

825 Waterfall Way, South Chesapeake

409 Tranquility Trace, South Chesapeake
$665,000
4 Beds ⋅ 3 Baths ⋅ 10646600 MLS
LUXURY COASTAL RESORT STYLE RIVER FRONT COMMUNITY! Welden Field & Rowe Custom Home on a Premium .44-acre lot backs to Nature Preserve. Resort like lifestyle w/ waterfront Gazebo, deep water access, Kayak launch, Clubhouse, Pool, Fitness Room, Green Space, Nature Preserve w/Trails. Welcome to this meticulously maintained Craftsman-style home w/ Southern Living front porch & thoughtfully designed luxurious light-filled floor plan. Chef's kitchen w/ expansive island, bar seating, range, tile back splash tile backsplash & SS appliances. Comfortable open living spaces that flow seamlessly throughout w/fireplace, high ceilings. Spacious downstairs owner's suite w/ Spa concept bathroom, tile floors, glass shower, over-sized Garden tub + custom walk-in closet + FF guest bedroom/Home Office w/ add storage. Outdoor oasis that backs to Nature Preserves w/ spacious covered porch, irrigation system, back up generation & MORE! Easy access to I-64, Edinburgh. WELCOME HOME!

409 Tranquility Trace, South Chesapeake

321 Riverview Road, South Chesapeake
$769,740
5 Beds ⋅ 4 Baths ⋅ 10646721 MLS
Welcome to The Summit at Riverview Landing, where you’ll discover thoughtfully designed living space across 2 luxurious floors-perfect for families of every size. The main level impresses with a versatile 1st-floor bedroom and full bath, a flexible office or formal dining room, and a sunlit great room that flows seamlessly from the gourmet kitchen, featuring a large island, quartz countertops, soft-close cabinets, premium stainless steel appliances (including double ovens and a gas cooktop),and a walk-in pantry. Upstairs, unwind in your expansive owner’s suite with a huge closet, double vanities, a relaxing bathtub, and a separate shower, while three additional bedrooms, two full baths, a laundry room, and a loft provide ample space and flexibility. Enjoy a vibrant, amenity-rich community with walking trails and a fire pit, all within reach of Chesapeake’s scenic waterways, local festivals, and easy access to Virginia’s beaches and mountains-your ideal lifestyle begins here. Photos and renderings are from builder's library, actual finishes and features may vary.

321 Riverview Road, South Chesapeake

109 Lilypad Court, South Chesapeake
$799,990
5 Beds ⋅ 3.1 Baths ⋅ 10646719 MLS
Introducing the Tillman, a spacious home that offers both comfort and style. With 5 bedrooms, 3,5 bathrooms, and a 2-car garage. Upon entering the Tillman, you'll be greeted by a large, welcoming dining room that seamlessly flows into the expansive kitchen. The kitchen features a generous center island, ideal for meal prep or casual dining, and opens to a spacious family room, creating the perfect space for entertaining. A conveniently located powder room is just off the main hallway, adding to the home's functionality. The first floor also boasts a luxurious primary suite, providing a private retreat with a massive walk-in closet, a large double vanity, and a private water closet for ultimate convenience and privacy. Upstairs, you'll find four additional bedrooms. The second floor also features two bathrooms and a large loft area that could serve as a separate lounge, playroom, or additional living space. Photos and renderings are from builder's library, actual finishes and features may vary.

109 Lilypad Court, South Chesapeake

609 Edgewood Arch, South Chesapeake
$610,000
4 Beds ⋅ 2.1 Baths ⋅ 10646683 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

821 Redleafe Circle, South Chesapeake
$995,000
6 Beds ⋅ 4 Baths ⋅ 10645935 MLS
An exceptional opportunity to own a Stephen Alexander custom home in Greystone, one of Chesapeake's premier luxury communities where homes are rarely available. This expansive executive residence blends timeless craftsmanship with the space, flexibility, and resort-style amenities today's luxury buyers seek. A first-floor bedroom with an adjacent full bath offers versatility for guests, a home office, or multi-generational living. The primary suite is a true retreat with a fireplace, sitting area, and four closets. Enjoy a private backyard oasis featuring an in-ground pool, hot tub, screened porch, gazebo, fire pit, privacy fence, irrigation well, and expanded parking for a boat or RV. Scenic walking paths enhance this sought- after community. Significant recent investments include a new roof (2026), three HVAC systems, an encapsulated crawl space, new hardwood flooring, updated bath vanities, freshly painted kitchen cabinetry, and a new oven. Schedule your private showing today!

821 Redleafe Circle, South Chesapeake

224 Wildlife Trace, South Chesapeake
$649,900
4 Beds ⋅ 3.1 Baths ⋅ 10646358 MLS
LUXURY COASTAL RIVERFRONT LIVING W/ AT IT'S FINEST! Breathtaking sunrises, sunsets & an effortless Coastal Lifestyle on the Elizabeth River. Elegant Craftsman style home w/ First Floor Primary Suite. Luxurious Chefs kitchen, expansive island w/ bar seating, granite counter tops & extended 48' wood cabinets w/ extra storage. Comfortable open living spaces w/fireplace, 8 ft doors, high ceilings & wood floor package. First Floor FLEX SPACE for 5th bedroom/Home Office. Spacious owner's suite w/ Spa Concept bathroom, tile floors, glass shower + custom walk-in closet. ENTERTAINERS DELIGHT! Screened in porch, professionally landscaped yard w/ OLP Lighting Design, fenced in yard + 2 car detached garage. All the BELLS & WHISTLES you can Dream of. Community amenities include waterfront Gazebo w/ access to deep water, Kayak Launch, Clubhouse w/ pool, Fitness Room, Green Spaces & Nature Preserves w/ private trails throughout. TURNKEY & MOVE IN READY. WELCOME HOME!

224 Wildlife Trace, South Chesapeake

1548 Waterside Drive N, South Chesapeake
$700,000
6 Beds ⋅ 3.1 Baths ⋅ 10646118 MLS
Spacious 4,899 sf lakefront home offering 6 bedrooms and 3.5 baths with an exceptional floor plan designed for comfortable living and entertaining. The expansive 1st floor primary suite provides a private retreat, while a 2nd floor ensuite is great for guests or multigenerational living. A massive great room with stunning lake views serves as the heart of the home, flowing seamlessly to a large composite deck great for outdoor gatherings. The oversized 840 sf attached garage offers ample space for vehicles, storage and hobbies. A walk-up attic provides abundant storage or future expansion potential. With generous living spaces, beautiful water views and a great price, this home is ready to accommodate every lifestyle. Photos virtually staged

1548 Waterside Drive N, South Chesapeake

2205 Edwin Drive, South Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10646287 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2205 Edwin Drive, South Chesapeake

3635 Mardean Drive, West Chesapeake
$498,000
5 Beds ⋅ 2.1 Baths ⋅ 10646195 MLS
Spacious Home In The Western Branch School District! Super Neighborhood of Wellington! NO Homeowners Association Dues!!! Solar Panels Offer LOW Utilities and Is A Great Benefit to The Buyer of This Home!!This Beautiful Home Features A Fantastic Open Downstairs Floor Plan That's Perfect For Both Everyday Living And Entertaining. Spacious Primary Bedroom Suite Downstairs With A Double Vanity & Soaking Bath...Plus Separate Shower!!!~Upstairs, You'll Find Four Additional Bedrooms. Enjoy Large Closets!! Downstairs You'll Find A Formal Living And Dining Room With Brazilian Wood Floors And A Family Room With A Gas Fireplace! Just Off A Great Kitchen, Which Has A Lots Of Cabinet Space & And An Island For The Cook In The Family! Outside There's A Covered Deck With Dual Fans, Making Outdoor Entertaining Great In The Summer Time ! Large Fenced In Back Yard With Trees! Conveniently Located Near Shopping, Dining, Military Bases, And Major Highways! This Home Is A Must See !!

3635 Mardean Drive, West Chesapeake

325 Riverview Road, South Chesapeake
$791,890
5 Beds ⋅ 3.1 Baths ⋅ 10646215 MLS
Introducing the Tillman, a spacious home that offers both comfort and style. With 5 bedrooms, 3,5 bathrooms, and a 2-car garage. Upon entering the Tillman, you'll be greeted by a large, welcoming dining room that seamlessly flows into the expansive kitchen. The kitchen features a generous center island, ideal for meal prep or casual dining, and opens to a spacious family room, creating the perfect space for entertaining. A conveniently located powder room is just off the main hallway, adding to the home's functionality. The first floor also boasts a luxurious primary suite, providing a private retreat with a massive walk-in closet, a large double vanity, and a private water closet for ultimate convenience and privacy. Upstairs, you'll find four additional bedrooms. The second floor also features two bathrooms and a large loft area that could serve as a separate lounge, playroom, or additional living space. Photos and renderings are from builder's library, actual finishes and features may vary.

325 Riverview Road, South Chesapeake

1416 Pine Grove Lane, West Chesapeake
$575,000
4 Beds ⋅ 2.1 Baths ⋅ 10645393 MLS
Premium location in one of Western Branch’s most sought-after neighborhoods & schools. Beautiful, manicured homes w/large lots & no homeowner’s association. Just minutes to 664 & ALL of Hampton Roads Military bases, shopping & entertainment and medical facilities. Step inside to a welcoming foyer that leads to a formal dining room, living room and a custom kitchen with an Island. The sunken den features a gas fireplace which exits to a multi-level deck for cookouts and entertaining. The upstairs features a primary suite for a private retreat with an en-suite bath, a large walk-in closet for keeping all your items organized, while two additional bedrooms (all with walk-in closets) provide versatility for guests or even a game (flex) room. In addition, a 4th bedroom is located over the 576 SQFT. Attached garage. New interior paint and carpet, move in ready. Some rooms virtually staged.

1416 Pine Grove Lane, West Chesapeake

2166 Edwin Drive, South Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10645211 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2166 Edwin Drive, 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.