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805 Helmsdale Way, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10650654 MLS
Welcome home to this charming ranch offering plenty of space to spread out and enjoy! Inside, you’ll find a formal living room and dining room, along with a cozy living area featuring a wood-burning fireplace. The kitchen offers new flooring and opens to a breakfast nook with convenient backyard access. Just off the back of the home is a versatile bonus room, currently used as a playroom, that would also make a great sunroom, home office, or flex space. The primary bedroom features a private bath and two closets, and both bathrooms feature new flooring. Step outside from either the breakfast nook or bonus room to a fully fenced, private backyard complete with a storage shed, playset, cozy patio, and firepit area, patio for entertaining or relaxing outdoors. A comfortable floor plan with flexible spaces inside and a backyard ready to enjoy!

805 Helmsdale Way, South Chesapeake
3016 Aaron Drive, South Chesapeake
$375,000
4 Beds ⋅ 2.1 Baths ⋅ 10649682 MLS
Welcome home to waterfront living! Solar panels will be paid off at closing! Completely renovated in 2019, this stunning home offers the feel of new construction with modern finishes throughout. Enjoy fishing or kayaking right from your own backyard! Located in a quiet community with convenient access to the interstate, NMCP, USCG, shopping, and more. Major 2019 updates include the roof, windows, siding, and HVAC system. Move-in ready, beautifully updated, and waterfront—this home is ready for you!

3016 Aaron Drive, South Chesapeake
173 Harbor Watch Drive, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10645496 MLS
Don't miss out on this waterfront Penthouse condo in the heart of Great Bridge. Relax on one of two huge decks overlooking your own private boat slip offering the epitome of coastal living. Once inside, you will find a light-filled open space great for indoor-outdoor living and entertaining. The updates, including the HVAC, low-maintenance LVP flooring, and fresh paint mean you can pack your backs (and life jackets) and move right in! The ample storage indoor and out (don't miss the walk-in attic inside the primary closet) adds practicality and function. The resort-style condo amenities are not to be missed- not only is trash, water, and sewer covered, but you also have a community pool, clubhouse, and ground maintenance to leave all of your free time to enjoy your new coastal lifestyle. The sellers are open to selling the new boat and floating dock for an additional cost.

173 Harbor Watch Drive, South Chesapeake
905 Shillelagh Road, South Chesapeake
$375,000
4 Beds ⋅ 2 Baths ⋅ 10643554 MLS
Welcome home to this charming four-bedroom ranch featuring a spacious, open floor plan designed for comfortable living. The inviting living room is anchored by a classic brick fireplace and flows seamlessly into the dining area and kitchen, complete with a cozy breakfast nook. An oversized utility room provides additional storage and everyday convenience. The home offers four generously sized bedrooms, including a primary suite with a private ensuite bathroom. Outside, enjoy the deck and patio overlooking the large backyard. The detached garage is accompanied by a substantial bonus room, creating endless possibilities for a workshop, hobby space, home gym, recreation room, studio, or additional storage. With its functional layout and versatile spaces, this home offers wonderful opportunities both inside and out

905 Shillelagh Road, South Chesapeake
1089 Saint Julian Drive, South Chesapeake
$375,000
4 Beds ⋅ 2 Baths ⋅ 10643138 MLS
Wonderfully updated and absolutely meticulously maintained and spotless ranch style home with 4 bedrooms 2 baths a 2 car DETACHED GARAGE in this lovely Chesapeake waterfront neighborhood! Modest sized home that comes to life with an open concept lover's dream!! This is the perfect house for entertaining! Sprawl out on the kitchen island and enjoy hosting- make sure to invite all your friends; the driveway and backyard can hold just about anyone and anything! Exclusive access to a public boat ramp—perfect for weekend adventures on the water!! Enjoy the convenience of a dedicated laundry room, and take full advantage of the expansive, fully fenced backyard—perfect for pets, play, and outdoor gatherings. Everything in the home has been updated in the last few years. Roof, hvac, water heater, flooring, kitchen, bathrooms and all new appliances. It’s all virtually new. All that’s missing is YOU!

1089 Saint Julian Drive, South Chesapeake
2839 Lambert Trail, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10640055 MLS
Welcome home to this charming ranch tucked away on a quiet street, offering comfort, functionality & an incredible backyard retreat. Designed for relaxing & entertaining, the backyard features lush banana trees, tranquil koi pond w/ waterfall, hot tub, paver patio ideal for grilling, fire pit area w/ pavers & space for seating - all surrounded by a full privacy fence. Impressive 2 story detached garage complete w/power, workbenches & upstairs storage. Featuring 3 bedrooms & 2 full baths the layout provides spacious living. Oversized kitchen w/ abundant counter space, large eat-in area w/backyard views. Converted garage creates second den, flex space, laundry, attic storage access. Expanded driveway offers plenty of parking. Relax on the welcoming front porch, unwind in the backyard, enjoy the comforts throughout the property.

2839 Lambert Trail, South Chesapeake
1073 Scenic Boulevard, South Chesapeake
$375,000
3 Beds ⋅ 1 Baths ⋅ 10639800 MLS
Closing cost assistance! Welcome to 1073 Scenic Boulevard! This beautifully updated ranch-style home offers modern finishes, flexible living space, and a private setting on approximately .4 acres in the desirable Great Bridge area. Step inside to an open and inviting floor plan featuring updated flooring, fresh paint, modern fixtures, and a stunning kitchen w/ white shaker cabinetry, granite countertops, stainless steel appliances, and a large breakfast bar for entertaining. The spacious living and dining areas flow seamlessly together, creating a bright and comfortable atmosphere. The updated bathroom adds a fresh, contemporary touch, while the screened porch provides the perfect place to relax and enjoy the peaceful, wooded backdrop. Outside, you'll find a detached garage with electricity, additional storage shed, ample parking, and a large backyard offering endless possibilities for recreation, gardening, or gatherings. Conveniently located near top-rated schools, shopping, dining, and more!

1073 Scenic Boulevard, South Chesapeake
1321 Hamill Lane, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10637304 MLS
Beautifully updated and move in ready home featuring an open floor plan with fresh paint and hard surface flooring throughout. Light and bright interior with a vaulted ceiling and cozy fireplace in the spacious great room. Tucked away in a quiet cup-de-sac in the heart of Greenbrier, this home offers convenience to shopping, dining and local restaurants. Enjoy outdoor living with a nice patio and privacy fenced backyard, for relaxing or entertaining. The perfect combination of comfort, style and location!

1321 Hamill Lane, South Chesapeake
612 Tuskegee Avenue, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10636616 MLS
Move-in ready and beautifully updated, this Chesapeake home in the desirable Crestwood area has it all—new carpet, fresh paint, new LVP flooring, renovated bathrooms, and a remodeled kitchen featuring new stainless steel appliances. The convenient first-floor primary suite offers a walk-in closet, while two additional bedrooms upstairs provide plenty of space for family or guests. A finished walk-in attic adds easy-access storage. Enjoy the outdoors on the refinished wood deck for grilling, entertaining and relaxing. Additional features include a Ring doorbell, and a wheelchair-accessible ramp for added convenience and mobility.

612 Tuskegee Avenue, South Chesapeake
2418 Fieldsway Drive, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10635457 MLS
Enjoy stylish, comfortable living in this beautifully maintained Goldenrod model with 3 bedrooms, 2.5 baths, and ~1,750 sq. ft. of thoughtfully designed space. The open floor plan is great for everyday living and entertaining, featuring a spacious primary suite, oversized pantry, and new carpet throughout. Relax or host in the private, fenced backyard with patio. Located in Coleman Farms, Chesapeake's premier luxury townhome community, just 1.5 miles from Greenbrier and minutes from I-64. Community amenities include a clubhouse, fitness center, and resort-style pool. Seller Will Cover 1 Year of Condo Fees to Make Your Move Effortless! Move-in ready and showing true pride of ownership

2418 Fieldsway Drive, South Chesapeake
2205 Wildwood Road, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10632858 MLS
Welcome to your new home in Chesapeake, beautifully updated on a quiet, tree-lined street. This move-in-ready property features 3 bedrooms and 2 full baths, including a spacious primary suite with en suite bath, walk-in closet, and direct access to a large, fenced backyard—perfect for relaxing or entertaining. Enjoy an open-concept layout with seamless flow between living spaces. Recent updates include brand-new LVP flooring, new carpet in bedrooms, and fresh paint throughout. Major systems have been updated with a newer roof, windows, HVAC, and water heater (all 2016). Just minutes from the Shipyard and bases, making for an easy, hassle-free commute. A perfect blend of comfort, style, and peace of mind—don’t miss this one!

2205 Wildwood Road, South Chesapeake
908 Hornswaggle Way, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10629972 MLS
Beautiful 3 bedroom, 2.5 bath located in the desirable Grassfield community of Bryans Cove. Main level offers open floor plan, large kitchen with granite counter tops and stainless steel appliances, lots of natural light and access to the balcony. Third level consists of 3 bedrooms with walk-in closet and double sinks in en suite, primary bathroom. Lower level could be used as a gym, office or playroom. private cove with beach, clubhouse, pool, boat dock, gym, playgrounds and dog park.

908 Hornswaggle Way, South Chesapeake
3104 Knight Road, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10629478 MLS
Welcome to this beautifully updated 3-bedroom, 2-bath home offering 1,898 sq ft of comfortable living, tucked away on a quiet cul-de-sac! Home renovated in 2018 with updated features throughout. Open floor plan that creates the perfect flow for both everyday living and entertaining. The home features a modernized kitchen with granite countertops, stainless steel appliances, upgraded tile, fixtures, and soft- closed cabinetry giving you plenty of storage and style. Major updates include roof, water heater, laminate flooring, carpet, and paint (2018), plus new HVAC with mini split installed (2025). Outside, you will love the spacious backyard, complete with a wood privacy fence and patio, perfect for relaxing, entertaining, or pets. Plus, a storage shed. Conveniently located near interstates, shopping, restaurants, military bases, beaches, and more.

3104 Knight Road, South Chesapeake
428 Rock Drive, South Chesapeake
$375,000
4 Beds ⋅ 2 Baths ⋅ 10627238 MLS
Welcome to this 4-bedroom, 2-bathroom classic brick ranch in the Deep Creek part of Chesapeake. Inside, you'll find new laminate flooring throughout and a functional layout featuring a formal dining room and comfortable living space with a wood burning fireplace. Major upgrades include a brand-new HVAC system and ductwork, an updated hall bathroom, and a new refrigerator, making this home truly move-in ready. Venture outside to enjoy the new privacy fence and large yard, made even more wide open thanks to recent tree removal. With gravel sitting area around a firepit, this yard is great for relaxing or entertaining. Conveniently located near shopping, dining, and major commuter routes, this home offers both comfort and accessibility. This home is the move-in ready house in Chesapeake, you've been looking for.

428 Rock Drive, South Chesapeake
3204 Bruno Drive, South Chesapeake
$375,000
4 Beds ⋅ 2 Baths ⋅ 10623637 MLS
Make this your first stop! This beautiful brick ranch blends modern updates with classic charm. Roof and windows are less than 7 years old, and the freshly painted interior features LVP flooring in the bedrooms. The modern kitchen shines with updated soft-close cabinets, granite countertops, and a matching backsplash. Enjoy two full bathrooms, a spacious primary suite with oversized closets, and a dedicated laundry room. The open family room flows seamlessly into the foyer and living area. Outside, you’ll find a fenced backyard and detached rear garage. Easy access to the interstate, shopping, and dining with NO HOA!

3204 Bruno Drive, South Chesapeake
2552 Roundtree Circle, South Chesapeake
$375,000
4 Beds ⋅ 2 Baths ⋅ 10621302 MLS
Spacious all-brick ranch in Oak Manor situated on a generous .54-acre lot! This 4-bedroom, 2-bath home offers over 1,700 square feet of primarily single-level living, with vaulted ceilings in the living room and FROG adding light and openness. Enjoy a large fenced backyard, deck for entertaining, attached garage, and city water/sewer. Conveniently located in South Chesapeake with easy access to schools, shopping, and major routes. A solid home with space inside and out!

2552 Roundtree Circle, South Chesapeake
1508 Debbs Lane, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10620904 MLS
Located on the edge of Greenbrier and Virginia Beach, this 3 bedroom home offers the blend of convenience and comfort. Enjoy easy access to shopping, dining, and major highways while tucked away in a quiet neighborhood with a low-fee HOA. Recent updates provide peace of mind, including a new roof (2025), HVAC system (2024), and water heater (2021). A fantastic opportunity for buyers seeking location, value, and low-maintenance living.

1508 Debbs Lane, South Chesapeake
1017 Scarlet Oak Court S, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10608928 MLS
This charming lakeview home offers the perfect blend of comfort, updates, and location. Tucked away in a peaceful cul-de-sac with direct access to scenic community trails and the lake, it’s ideal for those who love both privacy and nature. Tastefully remodeled in 2015, the home features a 30-year architectural roof, vinyl windows, and a beautifully updated kitchen with modern cabinetry, a decorative backsplash, stainless steel appliances, and a convenient breakfast bar. The converted garage provides a flexible space that can serve as a third bedroom, home office, or media room—whatever fits your lifestyle best. You’ll also enjoy ample storage with both an attic and a backyard shed. Conveniently located with quick access to the interstate, shopping, and local eateries.

1017 Scarlet Oak Court S, South Chesapeake
1406 Otterbourne Court, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10608371 MLS
This beautifully maintained 3-bedroom, 2.5-bath home offers exceptional comfort and convenience, currently the largest available home in the neighborhood. Tall ceilings and an open layout create a bright, airy atmosphere throughout the living spaces. Featuring two bedrooms with en-suites, one on the first floor and another upstairs, this home provides flexible living options for guests or multi-generational living. The eat-in kitchen flows seamlessly into the main living area, great for both everyday meals and entertaining. Outside enjoy a private patio great for relaxing or enjoying a quiet morning coffee. The attached one-car garage and low-maintenance community make this home as practical as it is inviting. Located in the highly desirable Greenbrier area of Chesapeake, you’ll be near shopping, dining, parks, and major roadways, everything you need right at your fingertips.

1406 Otterbourne Court, South Chesapeake
1316 Debbs Lane, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10607301 MLS
Gorgeous updated ranch in Greenbrier! Kitchen updated in 2023 with new cabinets, granite countertops, newer appliances, update floors throughout, windows and sliding glass door all replaced in 2020-2021. The inviting floor plan features a cozy living room with a fireplace, a well appointed kitchen with plenty of cabinet and counter space, and three spacious bedrooms with two full bathrooms. Head outside to a sizable backyard with a trex deck allowing for relaxing or entertaining. Conveniently located near shopping, restaurants, and so much more, this home offers comfort, charm, and convenience all in one.

1316 Debbs Lane, South Chesapeake
411 Prince Michael Court, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10607046 MLS
Beautiful Split-Level Detached Condo in the heart of Chesapeake!This 3-bedroom, 2.1-bathroom home offers a versatile layout with two bedrooms, a full bath, laundry, and a large rec room with pool table (conveys) on the first floor. Upstairs features an open living space, kitchen (stove 2024), family room, and primary suite with walk-in closet. Enjoy indoor-outdoor living with a private backyard oasis featuring a hot tub & a water feature —perfect for unwinding after a long day. Roof 5-9 years old, Water Heater 2024. Detached condo living - low-maintenance with the privacy of a single-family home. Conveniently located near shopping, dining, and major routes—this home has it all!

411 Prince Michael Court, South Chesapeake
1108 Mill Lake Quarter, South Chesapeake
$375,000
4 Beds ⋅ 2.1 Baths ⋅ 10606849 MLS
Welcome to 1108 Mill Lake Quarter, a spacious 4-bedroom, 2.5-bath home with just over 2,100 sq. ft. located in the heart of Chesapeake’s highly desirable Greenbrier community. This property offers a flexible floor plan great for families or those needing extra space for guests or a home office. The seller is also offering allowances, giving buyers the rare opportunity to personalize updates and finishes to truly make the home their own. Living in Greenbrier means enjoying the best of Chesapeake—just minutes from Greenbrier Mall, dining, the newly developed Summit Pointe, and entertainment, plus easy access to parks, libraries, and top-rated schools. With quick routes to Virginia Beach, Norfolk, and all of Hampton Roads, you’ll have convenience at your doorstep while still enjoying the warmth of a welcoming neighborhood. Whether you’re looking for everyday comfort or a home to grow into, this property is the perfect blend of location, lifestyle, and potential.

1108 Mill Lake Quarter, South Chesapeake
1308 Boxwood Drive, South Chesapeake
$375,000
4 Beds ⋅ 2.1 Baths ⋅ 10604799 MLS
Welcome to this spacious four-bedroom home located in the heart of Deep Creek. This property offers ample room for family and guests, with features designed for comfortable living and entertaining. The home is ideal for entertaining, featuring a screened porch, a deck surrounding the above-ground pool, and a dedicated fire pit area for relaxing evenings with friends and family. Moisture barrier installed 2025.

1308 Boxwood Drive, South Chesapeake
317 Shadowlake Drive, South Chesapeake
$375,000
4 Beds ⋅ 2.1 Baths ⋅ 10602412 MLS
This spacious 4-bedroom, 2.5-bath home with over 2,500 square feet of living space is waiting for your personal touch! With some updating and TLC, this home has incredible potential to truly shine. Featuring a generous floor plan with large living spaces. Situated on a spacious lot, there’s plenty of room to create your own outdoor oasis! The attached garage allows for the potential of additional parking or storage. Conveniently located near dining, shopping, the Interstate, and more! Call today for more information and to schedule your tour!

317 Shadowlake Drive, South Chesapeake
1417 Pamlico Boulevard, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10599824 MLS
Come see this charming 3 bedroom, 2 full bath, all brick home with 2-Car Garage on a large lot with privacy fenced backyard. Updated Kitchen & Baths with LVT floors, hardwood floors in most other areas. Near Mt. Pleasant Market Place Shops for dining, grocery, vet service & more. Near Bergey's Dairy, the Intercoastal Waterway for boating and Centerville Park. Seller motivated. House freshly painted and hardwood floors being refinished. Owner moved out. Ready for fast close. Here's your chance to live in an excellent school district in a quiet established neighborhood. Owner/Agent.

1417 Pamlico Boulevard, South Chesapeake
118 Esplanade Place, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10599534 MLS
Welcome to Riverwalk! This stunning home offers a modern open-concept layout, perfect for today’s lifestyle. The bright and airy living room is centered around a cozy fireplace, seamlessly connecting to the stylish kitchen and dining area—ideal for both everyday living and entertaining. Enjoy the sun room with skylights, adding warmth and character to the home. Step outside to the private backyard patio, perfect for relaxing or hosting gatherings. An attached garage provides convenience and extra storage. Thoughtfully designed for low-maintenance living, this home is ideally located near major interstates, military bases, and shopping.

118 Esplanade Place, South Chesapeake
906 Capstan Way, South Chesapeake
$374,900
3 Beds ⋅ 2.1 Baths ⋅ 10619735 MLS
Searching for a newer home with less exterior responsibility and access to community amenities? This tri-level townhouse built in 2023, offers low-maintenance living with an open layout connecting the kitchen, dining, and living areas. The first floor includes two additional rooms, one suitable for a study or home office and another that may be used for exercise or storage. The kitchen includes stainless steel appliances, a large center island, and access to a balcony. The primary suite features a private bath with his-her sinks for more convenient. HOA amenities including a community beach, pool, clubhouse, dog parks, playgrounds, boat ramp, kayak racks. No flood insurance is needed. Located in the Grassfield School District. Schedule a showing to see if this home meets your needs. Year Built and Sqft per Tax record.

906 Capstan Way, South Chesapeake
169 Harbor Watch Drive, South Chesapeake
$374,900
3 Beds ⋅ 2.1 Baths ⋅ 10603682 MLS
Beautifully maintained waterfront condo in the heart of Great Bridge. Enjoy water views and your private boat slip, offering ultimate coastal living. Step inside to an open, light-filled layout perfect for everyday comfort and entertaining. The spacious living and dining areas flow into a thoughtfully designed kitchen, framed by large windows and a private balcony with panoramic views of the water. Generous closets and storage add to the home's practical appeal. Upstairs, the primary suite includes a serene second private balcony; your personal retreat after a day on the water. Life at Harbor Watch offers resort-style amenities: relax by the community pool, host guests in the clubhouse, or enjoy peaceful moments at the waterfront gazebo. With ground maintenance included, you’ll have more time to enjoy the lifestyle you deserve. Whether you're a boating enthusiast, searching for a vacation getaway, or looking to settle into low-maintenance waterfront living, this condo truly has it all.

169 Harbor Watch Drive, South Chesapeake
1534 Penton Mews Unit 32, South Chesapeake
$373,500
3 Beds ⋅ 2.1 Baths ⋅ 10638220 MLS
Beautiful waterfront 3-bedroom, 2.5-bath condo in the heart of Greenbrier! This move-in-ready home features an updated kitchen with stainless steel appliances and granite countertops, new garage door, new LVP flooring, new carpet, and a new HVAC system. Enjoy spacious walk-in closets, ample storage, and a walk-in attic. Built-in surround sound speakers throughout the home add a premium touch. Relax by the water or take advantage of the community pool just steps away. Conveniently located near shopping, dining, and everyday amenities. Don’t miss this exceptional opportunity!

1534 Penton Mews Unit 32, South Chesapeake
113 Walton Road, South Chesapeake
$373,000
3 Beds ⋅ 2 Baths ⋅ 10630087 MLS
Welcome to this beautifully maintained home in the highly desirable Butts Station neighborhood! Offering 3 bedrooms and 2 full bathrooms, this home reflects true pride of ownership throughout. The updated kitchen and bathrooms provide a modern touch, while the spacious primary suite features a walk-in closet for added convenience. Enjoy the oversized backyard, perfect for entertaining, relaxing, or future possibilities, all while being ideally located near shopping, dining, and everyday amenities. This is one you don’t want to miss!

113 Walton Road, 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.