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2420 Payne Road, South Chesapeake
$245,000
3 Beds ⋅ 1 Baths ⋅ 10642992 MLS
Charming ranch nestled on a spacious lot in Chesapeake! This 3 bedroom, 1 bath home offers a warm and inviting layout that’s ready for you to make your own. Enjoy the convenience of a detached two-car garage, plenty of driveway parking, and a large yard with endless possibilities for entertaining, gardening, or simply relaxing. There’s even room to park your boat, RV, trailer, or recreational toys! Whether you’re a first-time homebuyer, downsizing, or looking for a property with space to spread out, this home offers the perfect blend of comfort, functionality, and outdoor living. Conveniently located with easy access to shopping, dining, schools, and major highways, this is one you won’t want to miss! * Some photos are virtually enhanced or staged*

2420 Payne Road, South Chesapeake

744 Hunters Quay Quay, South Chesapeake
$300,000
3 Beds ⋅ 2.1 Baths ⋅ 10642912 MLS
Welcome to this beautifully maintained end unit townhome nestled in a small, quaint neighborhood that offers both charm and convenience. Enjoy direct access to Oak Grove Lake Park from a fenced connected walking trail. Make sit easy to take scenic strolls, exercise, or spend time outdoors. Perfectly located with quick access to the interstate, this home is ideal for commuters while still providing a peaceful place to unwind. Inside and out you will appreciate the spacious yard, built-in storage shed, well maintained HVAC system, roof (2018), and fresh carpet and paint (2021). With thoughtful updates, extra privacy as an end unit, and and unbeatable blend of comfort, convenience, and outdoor access this move in ready home is one you wont want to miss.

744 Hunters Quay Quay, South Chesapeake

1214 Loose Strife Place, South Chesapeake
$230,000
2 Beds ⋅ 2 Baths ⋅ 10642377 MLS
Bright and inviting, this well-maintained 2-bedroom, 2-bath condo is located in the desirable Willow Point community. A welcoming first-floor foyer with soaring cathedral ceilings leads upstairs to an open, airy living space featuring beautiful oak hardwood floors. Step outside to your private balcony overlooking the community pool - the perfect spot to enjoy your morning coffee or unwind at the end of the day. Ideally situated just minutes from major highways, shopping, dining, military bases, and more, this low-maintenance community also includes pool access, landscaping, and exterior maintenance. Offering the perfect blend of comfort, style, and convenience, this home is ready to welcome its next owner!

1214 Loose Strife Place, South Chesapeake

5213 Winery Drive, West Chesapeake
$349,900
3 Beds ⋅ 2.1 Baths ⋅ 10642280 MLS
Welcome home to this beautifully maintained 3-bedroom, 2.5-bath home located in the highly sought-after Western Branch area of Chesapeake! Built in 2008 and offering over 1,500 square feet of comfortable living space, this charming residence features an inviting open layout with spacious living areas perfect for everyday living and entertaining. The kitchen flows seamlessly into the dining and family room areas, while the oversized backyard provides endless possibilities for gatherings, pets, play, or relaxing evenings outdoors. Upstairs, the generous primary suite includes a private bath and ample closet space, accompanied by two additional bedrooms and a full bath. Additional highlights include an attached garage, central air, utility room, and convenient access to shopping, dining, schools, and major commuter routes. Don't miss this opportunity to own a move-in ready home in the heart of Western Branch!

5213 Winery Drive, West Chesapeake

669 Mill Creek Parkway, South Chesapeake
$355,000
3 Beds ⋅ 2.1 Baths ⋅ 10642119 MLS
Nestled in popular Culpepper Landing, this spacious townhouse is sure to impress! With its beautiful stone accents and well-appointed landscaping, this home has instant curb appeal. The first floor can make a great office or playroom and includes a large walk-in closet. Upstairs, the open concept kitchen and living area make a fantastic space for entertaining. The kitchen includes stainless steel appliances, granite counters, tiled backsplash, a pantry and tons of cabinet space. Sliding doors open to the balcony, providing another great place to relax. In addition to the kitchen, you'll find an eat-in dining area and a sizeable living space that lets in a ton of natural light. The third floor includes three bedrooms. The primary bedroom features raised ceilings, an attached bath with double vanity and a walk-in closet. Washer and dryer are also conveniently located on the bedroom level. The attached 2-car garage offers excellent storage space. Enjoy neighborhood amenities such as the pool, clubhouse, exercise room, dog parks, and playgrounds! New elementary school coming Fall 2027!

669 Mill Creek Parkway, South Chesapeake

505 Shadow Brooke Drive, South Chesapeake
$695,000
5 Beds ⋅ 3.1 Baths ⋅ 10639316 MLS
Set on a gently elevated lot is this gorgeous Colonial-style all-brick home offering 5 upstairs bedrooms, 3.5 baths, and 3,330 square feet in a convenient Chesapeake location! Beautiful landscaping and well-maintained curb appeal welcome you inside to a spacious layout featuring formal living and dining rooms, dual staircases, and new flooring throughout much of the home. The updated kitchen includes stainless steel appliances and offers a great space for everyday living and entertaining. Multiple updated bathrooms. Additional highlights include a 2-car garage with a separate storage room, providing extra space for projects, storage, or hobbies. Easy access to the bypass, shopping, dining, and other nearby conveniences. Don't miss this one!

505 Shadow Brooke Drive, South Chesapeake

1537 Waterway Circle, South Chesapeake
$580,000
3 Beds ⋅ 3 Baths ⋅ 10641081 MLS
Enjoy low-maintenance living in this beautifully updated brick ranch with vinyl-wrapped soffits and fascia, plus oversized gutters and downspouts. The open-concept layout is filled with natural light and features 3 bedrooms, 3 updated baths with custom tile, modern vanities, and upgraded fixtures. A private third bedroom offers an ideal in-law suite or student retreat. Flexible living spaces include a first-floor bonus room perfect for an office, playroom, or hobby room, plus a finished room over the garage with a closet and window that can serve as a fourth bedroom. The upgraded kitchen showcases newer cabinetry with lighting, quartz countertops, and updated appliances. A breakfast bar overlooks the sunken great room, creating the perfect space for entertaining. Located in the sought-after Hickory/Butts Road school district with easy access to the Great Bridge Bypass and major interstates. A rare find that won't last long!

1537 Waterway Circle, South Chesapeake

2708 Horseshoe Drive, South Chesapeake
$485,000
4 Beds ⋅ 2 Baths ⋅ 10640735 MLS
Completely renovated all-brick ranch offering timeless charm & modern updates throughout! Recent improvements include a new roof, HVAC system, gutters, carpet, interior & exterior paint, shutters, well pump & sealed crawlspace w/dehumidifier, providing peace of mind for years to come. The updated kitchen features modern cabinetry, countertops & appliances, while both bathrooms have been tastefully renovated with stylish tile, vanities, toilets & fixtures. Bright, inviting living spaces showcase fresh paint, updated flooring & a functional layout designed for comfortable everyday living. The durable brick exterior offers lasting curb appeal & low-maintenance ownership. With major system upgrades & cosmetic improvements already completed, this move-in-ready home is the perfect blend of quality, comfort, & convenience. Simply unpack & enjoy all this beautifully updated property has to offer!

2708 Horseshoe Drive, South Chesapeake

1068 Scenic Boulevard, South Chesapeake
$1,089,000
4 Beds ⋅ 3.1 Baths ⋅ 10639310 MLS
This incredible all-brick, nearly 5,000SF custom-built home is the kind of home dreams are made of. 4 bedrooms PLUS a FROG(finished room over garage), and 3.5 baths in the main house alone! Thoughtfully renovated in recent years with exceptional attention to comfort, craftsmanship, and the way life is actually lived. 4bedrooms each offer their own private retreat w/ ensuite baths. The primary suite bath is a true retreat, with heated tile floors, a soaking tub, and a dual-head shower. Kitchen was made not just for cooking but for gathering: double ovens, gas range, pot filler, under-cabinet lighting, and custom Closet Factory pantry that makes Home Edit dreams come to life. Set on 0.73 acres and no HOA, the outdoors is an extension of the home. Heated saltwater pool, covered patio, lush landscaping, irrigation& room for boats, RVs, and whatever comes next. Detached garage has fully equipped apt wonderful for guests, extended living, creative pursuits, and even rental income. It makes a wonderful private inlaw suite and already has a chair lift installed. There are truly too many features to list. Every detail has been considered! This one is a must see!

1068 Scenic Boulevard, South Chesapeake

809 Grantham Lane, South Chesapeake
$525,000
4 Beds ⋅ 2 Baths ⋅ 10639060 MLS
Welcome home to this beautifully updated ranch in the highly desirable Hickory School District! This 4-bedroom, 2-bath home offers a welcoming front porch, attached 2-car garage, and a spacious floor plan designed for comfortable living. The renovated eat-in kitchen features ample cabinetry, pantry storage, and plenty of room for gathering. Recent updates include white shaker cabinets, quartz countertops, updated flooring throughout the main living areas, and refreshed bathrooms. Continue outside to enjoy the expansive deck overlooking the fully fenced backyard, complete with a storage shed and plenty of space for entertaining, pets, or play. This move-in ready home combines modern updates with classic ranch-style charm.

809 Grantham Lane, South Chesapeake

608 September Lane, South Chesapeake
$712,900
5 Beds ⋅ 3.1 Baths ⋅ 10637525 MLS
Rare attached private in-law suite with a full kitchen! Need multi generational living, it truly doesn't get better than this one! Welcome to this beautifully updated home in the heart of Great Bridge, offering a blend of space, comfort, and versatility. Located on a private lot with wooded views in the desirable Stonegate neighborhood. This exceptional home offers a spacious 4-bedroom, 2.5-bath main residence, plus an additional 500-square-foot attached guest suite featuring 1 bedroom and 1 full bath making the home a total of 5 bedrooms and 3.5 baths. What truly sets this property apart is the fully attached private in-law/guest suite An added 500 square feet of living space unlike anything else currently on the market. Designed for independence and comfort, this exceptional suite features its own HVAC system, full kitchen with granite counters, stainless steel appliances, living room, separate stackable washer and dryer, spacious bedroom, and full bath with a large walk-in shower. With a separate entrance and direct access to the patio and pool area, it offers endless possibilities for multi-generational living, extended family, home office or whatever your current needs are. Inside the main home, you'll find updated finishes, LVP flooring, newer carpet, newly installed wine fridge, granite counters, a gas fireplace. and a freshly updated primary bath featuring a brand new vanity with double sinks, lighting, granite counters, freestanding soaking tub, and a beautiful separate shower. Step outside to your own backyard oasis featuring a sparkling saltwater pool, expansive backyard, private wooded view, full vinyl fence, designed for easy outdoor living and entertaining. Exterior features also include an in-ground sprinkler system and concrete patio improvements. Combining modern updates, exceptional outdoor living, and a one-of-a-kind in-law suite, this Chesapeake home offers a level of flexibility and value that is truly hard to find.

608 September Lane, South Chesapeake

2217 Edwin Drive, South Chesapeake
$571,990
3 Beds ⋅ 3 Baths ⋅ 10637360 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 beautiful 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 and renderings are from builder's library, actual finishes and features may vary. Photos are to be used as an example and do not represent exact listings selections.

2217 Edwin Drive, South Chesapeake

605 Oxbow Court, South Chesapeake
$905,000
5 Beds ⋅ 3 Baths ⋅ 10637102 MLS
Rare find in Carriage House Estates in the sought-after Hickory school district! This custom all-brick 5 bedroom, 3 bath home in a quiet cul-de-sac offers space, privacy, and retreat-style living. Tucked away on over an acre, the property extends well beyond the fence. Enjoy an in-ground pool, screened back porch, raised garden, chicken coop, and room to entertain, garden, play, or unwind. The floor plan features a spacious first-floor primary suite with his and her closets and a reading nook, plus an additional first-floor bedroom or office, generous living areas, spacious kitchen, amazing storage, media room with projector to convey, climate-controlled attic storage, and whole-house water filtration. Attached 2-car garage, extended driveway area for RV parking, plus detached 2-car carriage house-style garage with second floor and full HVAC offer flexibility for storage, hobbies, office, gym or future flexible use. Convenient to major routes, schools, and shopping. Zero-turn mower to convey.

605 Oxbow Court, South Chesapeake

1103 Santeetlah Ave, Central Chesapeake
$324,998
4 Beds ⋅ 1 Baths ⋅ 10636804 MLS
Welcome home to this charming brick ranch in sought after Indian River Estates! Offering 4 bedrooms and thoughtful updates throughout, this move-in ready home blends comfort, character, and convenience. The updated kitchen features granite countertops, stainless steel appliances, and a functional layout optimal for everyday living. Natural light pours through the bay window, creating a warm and inviting living space. Step outside to your fully fenced backyard retreat featuring an extended deck, gazebo, detached garage, and an electrically powered shed great for hobbies, projects, storage, or a workshop. Conveniently located near shopping, dining, schools, and major commuter routes. Whether you're entertaining guests or enjoying a quiet evening at home, this property offers space, flexibility, and value. Schedule your private showing today before this one is gone!

1103 Santeetlah Ave, Central Chesapeake

1436 Paul Eason Drive, South Chesapeake
$1,740,000
6 Beds ⋅ 5.2 Baths ⋅ 10634528 MLS
Experience luxury country living at its finest in the heart of Chesapeake. Situated on over 4 private acres with its own pond, this stunning all-brick estate offers over 6,000 sqft of refined living space with 6 bedrooms and 7 bathrooms, including 5 bedrooms with private full baths. Every bedroom features oversized closets large enough to rival bedrooms in many homes. The fully remodeled designer kitchen blends modern elegance with timeless charm, while grand Chandeliers create a breathtaking first impression. Step outside to your private resort featuring an inground heated pool, pool house with kitchenette and half bath, outdoor grilling area, and a custom Italian pizza oven perfect for entertaining. Attached double garage plus detached double garage with finished room above. Too many exceptional features to list-this is a property that truly must be seen in person to be fully appreciated.

1436 Paul Eason Drive, South Chesapeake

713 Flatrock Lane, South Chesapeake
$569,073
4 Beds ⋅ 2.1 Baths ⋅ 10617476 MLS
Under construction End Unit 2 story townhome condo w/two car front load garage in a 3 unit building! Luxury LVP, wood steps,1st flr:Open floor plan, Kitchen GE Matt White appliances w/refrigerator,Kohler white porcelain sink,pantry,center island w/shiplap,Midnight Blue Cabinets,Champagne fixtures,dining area, living room w/ linear fireplace w/shiplap, covered side entry w/mudroom and 1/2 bath,covered back patio. 2nd flr: Primary w/ceramic floor & shower-2 shower heads,dual sinks, 2 closets, 2 br's & full bath, linen closet, laundry. Quartz tops kitch&all baths, covered entry, Large fenced backyard. Wood shelving all closets.Pet Friendly. Quiet easy lifestyle with the comfort of quality construction & name brand building materials including James Hardie Fire Retardant Fiber Cement Board. Builder 2-10 home warranty, master insurance, trash pick up, private streets, city water/sewer, guest parking, multipurpose trails with lake and fountain. Central Greenbrier location. Only 56 homes.

713 Flatrock Lane, South Chesapeake

330 Kemp Lane, Central Chesapeake
$500,000
4 Beds ⋅ 3.1 Baths ⋅ 10617326 MLS
Welcome Home to this stately home which has been meticulously maintained and cared for. It has solid brick exterior. White pillars adorn the rounded front porch. Asphalt driveway has two entrances onto this private, corner lot. Established community with just one entrance/exit which is controlled by a traffic light. This timeless, hidden gem has an attached garage and a detached garage. Inside this home you will discover classic, wood kitchen cabinets with attractive glass-window doors. Elegance greets you from the foyer entrance, into the living room with wood fireplace (has not been used by current owner), into the dining area with its chandelier. There is traditional ceramic tile in bathrooms, permanent attic stairs leading to a fully-floored attic for all kinds of storage. Laundry with washer/dryer and large utility sink are located in the basement. Kitchen stove and dishwasher 3 years old. Hardwood floors under carpet! Selling as-is and seller to do no repairs.

330 Kemp Lane, Central Chesapeake

2241 Captiva Lane, West Chesapeake
$676,263
4 Beds ⋅ 3.1 Baths ⋅ 10603969 MLS
Come visit us at our model home, 5023 Annapolis Drive, Chesapeake, VA 23321. Builder is offering partial CCA + $15,000 Flex spending (buyer incentive, call listing agent for details). 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, you’ll find 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 luxurious 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.

2241 Captiva Lane, West Chesapeake

2907 Seven Eleven Road, South Chesapeake
$170,000
10572124 MLS
Your Canvas Awaits in the Trees. Tucked in sought-after Pleasant Grove this rare three-acre wooded parcel offers the kind of privacy and potential that's becoming increasingly hard to find. Whether you're ready to break ground today or prefer to hold a premium piece of land until the time is right, this property adapts to your plans not the other way around. The site has been approved by the Health Department for a four-bedroom home, giving you the confidence to move forward with your custom build without the uncertainty. Bring your own builder and design a home that's truly yours from the footprint to the finishes. The mature wooded setting creates a natural buffer of seclusion, meaning your future home will feel like a retreat even as Chesapeake's amenities remain conveniently close. Privacy and community, all on one parcel. Pleasant Grove is known for its character and quality of life. Parcels of this size and caliber in this location rarely come to market — and for good reason.

2907 Seven Eleven Road, South Chesapeake

1001 S Scarlet Oak Court, South Chesapeake
$415,000
3 Beds ⋅ 2.1 Baths ⋅ 10642085 MLS
Tucked at the end of a quiet neighborhood in the heart of Greenbrier, this home offers the perfect blend of privacy and convenience. The kitchen shines with granite countertops and stainless steel appliances, while updated bathrooms and refreshed fixtures throughout add a modern touch. Beautiful new LVP flooring flows throughout the main level, and the spacious primary suite features a private full bath. A fully fenced backyard backing to walking paths — complete with a deck and large storage shed. Smart home upgrades convey, including a Ring Camera, Ecobee thermostat, and Tesla charger! Community sidewalks make spending time outdoors easy, with playgrounds, the library, and everyday conveniences nearby. Commuters will love the quick access to military installations, top schools, major interstates, and an abundance of shopping, dining, parks, and entertainment within minutes!

1001 S Scarlet Oak Court, South Chesapeake

4513 Overlook Place, West Chesapeake
$573,000
4 Beds ⋅ 3.1 Baths ⋅ 10641448 MLS
Spacious 4-Bedroom Home in Sought-After Western Branch! Welcome to this beautifully maintained 4-bedroom, 3.5-bath home located in the highly desirable Western Branch area of Chesapeake! Step inside to find large, light-filled rooms for both relaxing and entertaining. The modern kitchen features granite countertops, stainless steel appliances, and ample cabinet space—wonderful for any home chef. The first floor primary suite offers a true retreat with a HUGE walk-in closet and a luxurious en-suite bath. Each additional bedroom is generously sized, providing comfort and versatility for family, guests, or a home office. Enjoy the convenience of being a short drive to major interstate access, shopping, restaurants, and all the best that Western Branch has to offer. This home combines style, space, and location—everything you’ve been searching for! All appliances are "as is"

4513 Overlook Place, 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.

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