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1644 Chesapeake Drive, Central Chesapeake
$365,000
4 Beds ⋅ 2.1 Baths ⋅ 10655000 MLS
Beautiful 4 Bedroom Home with Modern Updates and Spacious Layout This stunning 4-bedroom, 2.5-bath home features fresh paint, new carpet, and stainless-steel appliances throughout. The open floor plan creates a seamless flow that’s perfect for entertaining and cooking, with large, bright rooms that feel warm and welcoming.Enjoy a formal dining room, a comfortable family room, and a charming breakfast nook. A cozy fireplace adds the perfect touch for relaxing evenings.Step outside and take your entertainment outdoors to your private, fenced-in backyard — ideal for gatherings, play, or quiet mornings.At the end of the day, retreat to the primary suite, complete with a spacious ensuite bathroom, offering comfort and privacy. LOCATED CLOSE TO BASES, MEDICAL, INTERSTATES, ENTERTAINMENT, BEACHES AND RETAIL.

1644 Chesapeake Drive, Central Chesapeake

901 Stewart Street, Central Chesapeake
$215,000
2 Beds ⋅ 1 Baths ⋅ 10655021 MLS
Welcome to 901 Stewart Street! This charming 2-bedroom, 1-bath ranch offers comfortable single-level living in the South Norfolk area of Chesapeake. With approximately 825 square feet, the home features a functional layout with plenty of opportunity to make the space your own. Enjoy a spacious yard with room for outdoor entertaining, gardening, or creating your own outdoor retreat. Conveniently located near shopping, dining, major roadways, and everyday amenities, this property offers easy access throughout Chesapeake and surrounding Hampton Roads. Whether you're looking for your next home or an investment opportunity, 901 Stewart Street is ready for its next chapter. Schedule your private showing today!

901 Stewart Street, Central Chesapeake

1713 Sanderson Road, South Chesapeake
$1,300,000
4 Beds ⋅ 2.1 Baths ⋅ 10654856 MLS
Elegant custom details and room to live the life you’ve imagined! Sweeping down a long, paved driveway, this beautiful 4-bedroom home pairs comfortable country living with a thoughtfully arranged estate. Set on over 12 pristine acres in Chesapeake, zoned for Hickory schools, this property is a rare rural sanctuary. A wraparound porch welcomes you inside to 9' ceilings, 8' doors, and reclaimed knotty pine floors. The living room features a stone fireplace, opening to a bright kitchen with soft-close cabinets, Samsung Bespoke appliances, and butler’s pantry. Outside, enjoy a saltwater pool, fire pit, and private porches within a completely fenced in yard. The farm boasts a 6-stall barn with wash station, hot water, and mini-split, plus 5 watered pastures, 3 run-ins, and a 50x42 Morton building. An additional 1.5 acres offers potential for a riding arena or agriculture gardening, while a chicken coop, fruit trees, and berries complete the setting. Enjoy southern Chesapeake's rural character, with conveniences and Route 168 nearby.

1713 Sanderson Road, South Chesapeake

435 Gallbush Road, South Chesapeake
$849,900
4 Beds ⋅ 3 Baths ⋅ 10655045 MLS
Welcome to The Ashford by Wetherington Homes -Move-In Ready! A 5-bedroom, 3-bath new construction home with over 2,700 sqft on approximately 2 acres in Hickory School District with NO HOA! Designed for todays buyer, this open-concept floorplan offers luxury finishes, designer details, outdoor entertaining, & flexible living spaces. The kitchen features quartz countertops, Frigidaire Professional appliances, custom wood hood, shaker cabinetry, & upgraded lighting. The 1st floor Primary Suite includes a tiled spa-style shower, dual vanities, & oversized walk-in closet. Two additional 1st floor bedrooms offer flexibility for guests or office space. Upstairs includes 2 bedrooms, full bath, & loft ideal for media room, playroom, or gym. Enjoy luxury new construction convenient to Edinburgh, Greenbrier, shopping, dining, & commuter routes while still offering privacy & acreage!

435 Gallbush Road, South Chesapeake

3208 Pineridge Drive, West Chesapeake
$525,000
5 Beds ⋅ 3.1 Baths ⋅ 10654949 MLS
Classic character meets seriously usable space. Tucked beneath the trees in the highly desirable Silverwood neighborhood, this 5 bedroom, 3.5 bath Dutch Colonial brings together original character and thoughtful updates without losing its charm. Natural light fills the rooms and plays across the original refinished hardwood floors, bringing warmth throughout the 2,602 square foot home. The brand-new kitchen brings new cabinetry, countertops, appliances and LVP, while the stunningly updated bathrooms add a fresh, polished finish. A gas fireplace adds another touch of original character to the living room, and the finished room over the garage offers flexible space for whatever the home needs. The EZBreeze porch takes outdoor living a step further, with heat and air conditioning that keep the space comfortable throughout all the seasons. Whether enjoying a mild morning or settling in on a cooler evening, this is outdoor space with the comfort to make it genuinely usable year-round. A home with the kind of character you notice right away, paired with a fresh kitchen, beautiful updates, and spaces that make you want to stay awhile. Move in with nothing to do!

3208 Pineridge Drive, West Chesapeake

1514 Myrtle Avenue, Central Chesapeake
$339,900
3 Beds ⋅ 2 Baths ⋅ 10654924 MLS
The possibilities are endless with this spacious ranch-style home! Offering a flexible layout ideal for multi-generational living, the home features two separate living areas and bathrooms with a shared kitchen and laundry. A separate side entrance leads to the rear living space with a large bedroom, walk-in shower and private living area, offering great potential for an in-law suite or extended family. The large kitchen offers a pantry and tons of cabinet space, with neutral colors and updated windows throughout. Major improvements include a new roof, newer HVAC, 2026 furnace, encapsulated crawl space with dehumidifier and new sewer line from the home to the street. Enjoy a fenced backyard, storage shed and fantastic detached garage with plenty of room for vehicles, workshop, hobbies or storage. Convenient to shopping and everyday amenities. Seller will be holding an estate sale; some listing photos have been AI-enhanced to digitally remove personal belongings and estate sale items to better showcase the rooms and space.

1514 Myrtle Avenue, Central Chesapeake

552 Saddlehorn Drive, South Chesapeake
$575,000
3 Beds ⋅ 2 Baths ⋅ 10654878 MLS
Set on approximately 1.5 beautiful acres, this well-maintained brick ranch offers comfortable living with room to enjoy the outdoors, pursue hobbies, and make it your own. Priced $10k under recent appraised value of $585k! Closing cost assistance and/or interest-rate buydown are negotiable with acceptable offer. Inside you’ll find 3 bedrooms and 2 full baths, custom closet systems, a thoughtfully designed kitchen with a large island and abundant cabinet storage, and a newly renovated mudroom/laundry room! A climate-controlled two-story attached 2-car garage/workshop provides space for vehicles, projects, and hobbies, with upstairs flex space for more options. Step outside and the property truly comes to life. Entertain, relax or just enjoy the privacy of your own space on the new deck. A raised bed garden, chicken run, grape arbors, barn, and storage shed add character and functionality. Located in desirable Hickory School District, just 20 minutes from Redmill and Landstown commons!

552 Saddlehorn Drive, South Chesapeake

1824 Lancing Crest Lane, South Chesapeake
$1,100,000
5 Beds ⋅ 4.1 Baths ⋅ 10654932 MLS
Welcome to an exceptional 4,800 sq. ft. all-brick home in Chesapeake's sought-after Grassfield area! Offering 5 bedrooms and 4.5 baths, this spacious home features a private primary wing designed as its own retreat, complete with an incredible oversized walk-in shower that truly has to be seen. Each additional bedroom is a suite with access to its own bath, providing privacy and comfort for family and guests. Enjoy outdoor living on the screened porch overlooking the inground pool with a fountain perfect for relaxing or entertaining. The community offers its own boat ramp and marina area with water access to the Elizabeth River. Conveniently located near shopping, dining, and interstate access, this home combines space, privacy, recreation, and an outstanding Chesapeake location.

1824 Lancing Crest Lane, South Chesapeake

1013 Baydon Lane, South Chesapeake
$550,000
4 Beds ⋅ 2.1 Baths ⋅ 10654935 MLS
Extremely well maintained home featuring a standout family room addition w/ floor to ceiling windows, vaulted ceilings, & a gas stove that creates a warm setting for winter days. This space overlooks the beautiful yard, established gardens, & a soothing water feature, offering a seamless connection to the outdoors. The living room includes a coved ceiling and a gas fireplace, with Brazilian walnut floors extending through to all bedrooms, the guest bath, and the primary bath. The eat in kitchen offers ceramic tile flooring and quartz countertops. The updated hallway bath serves two additional bedrooms. The primary bedroom includes a walk in closet, updated ensuite bath, and a flexible bonus space suitable for an office, nursery, or second closet. Outdoor highlights include a newer Trex deck with direct access to the newer hot tub, perennial landscaping that returns each year, and a private yard designed for relaxation. Updates include HVAC (2021) and a mini split in the FROG (2020).

1013 Baydon Lane, South Chesapeake

1228 Laurel Avenue, Central Chesapeake
$349,000
3 Beds ⋅ 2 Baths ⋅ 10654920 MLS
Step onto the front porch and into this modern 3-bedroom, 2-bath bungalow in the Norfolk Highlands neighborhood of Chesapeake! The updated kitchen features shaker-style cabinets, granite countertops, stainless steel appliances, and a convenient breakfast/dining area. The home also offers a second family room with coffered ceilings, providing plenty of space to relax or entertain. All three bedrooms are spacious and feature walk-in or oversized closets. The primary bedroom includes an ensuite bathroom with a modern shower and granite vanity. Outside, enjoy a fully fenced backyard with a covered patio, wood-burning fireplace, and storage shed. Conveniently located near Greenbrier and Acredale shopping, dining, entertainment, and major roadways.

1228 Laurel Avenue, Central Chesapeake

708 Colony Drive, South Chesapeake
$465,000
4 Beds ⋅ 2 Baths ⋅ 10654846 MLS
Buyer may receive a lender credit of up to 1.25% of the loan amount toward eligible closing costs with the use of the sellers preferred lender. Hickory schools, no HOA, and a quiet Chesapeake neighborhood, 708 Colony Drive has a lot to love before you even step inside. This updated 4-bedroom, 2-bath home offers primarily one-level living with three bedrooms on the main floor and a true fourth bedroom with a closet above the garage. The open layout flows from the spacious living and dining areas into an updated kitchen featuring quartz countertops, brass fixtures, a large sink, stainless steel appliances, and modern finishes. Both bathrooms have also been beautifully updated with tile and fresh finishes throughout. Outside, enjoy a fully fenced backyard with a deck that’s perfect for entertaining, relaxing, or pets. An attached one-car garage, two-car driveway, and additional parking provide plenty of space. Located in an established, quiet neighborhood with no HOA and sought-after Hickory schools, this move-in-ready home offers the updates you want with the freedom and location that can be hard to find in Chesapeake.

708 Colony Drive, South Chesapeake

4212 Bainbridge Boulevard, Central Chesapeake
$349,800
4 Beds ⋅ 3 Baths ⋅ 10654898 MLS
Love the home, need a lower rate? A 5% rate may be possible with a seller-paid buydown, ask us how! Now offering CCA or Rate buy down up to $10k. Discover the freedom of space at 4212 Bainbridge Boulevard! This 4-bedroom, 3-bath home offers 1,588 square feet of comfortable living on an expansive 0.45-acre lot. Enjoy the convenience of city living without the close-neighbor feel of a great neighborhood. With plenty of room for RVs, boats, trailers, work vehicles, and large equipment, this property is amazing for anyone who needs extra space to live, work, park, and play. The neighboring home at 4210 Bainbridge Boulevard is also available, presenting a unique opportunity to purchase two homes side by side—good for multigenerational living, extended family, or living in one home while renting the other. Don’t miss this rare chance to enjoy privacy, flexibility, and room to spread out in Chesapeake!

4212 Bainbridge Boulevard, Central Chesapeake

4210 Bainbridge Boulevard, Central Chesapeake
$284,800
3 Beds ⋅ 2 Baths ⋅ 10654894 MLS
Love the home, need a lower rate? A 5% rate may be possible with a seller-paid buydown, ask us how! Now offering CCA or Rate buy down up to $10k. Welcome to 4210 Bainbridge Boulevard! This charming 3-bedroom, 2-bath home offers 900 square feet of thoughtfully designed living space with a versatile front flex room—great for a home office, playroom, or cozy sitting area. Enjoy the convenience of living in Chesapeake without the close-neighbor feel of a traditional subdivision. The neighboring property at 4212 Bainbridge Boulevard is also available, creating a rare opportunity to purchase both homes—amazing for extended family, multigenerational living, or living in one home while renting the other. Don’t miss this unique and flexible opportunity!

4210 Bainbridge Boulevard, Central Chesapeake

933 Brenner Road, South Chesapeake
$565,000
4 Beds ⋅ 2.1 Baths ⋅ 10654848 MLS
Built in 2024 and loaded with model home upgrades, this move in ready 4 bedroom, 2.5-bath home stands apart from the standard build. The open concept kitchen and living area showcases soft close cabinetry, stainless steel appliances, quartz countertops, and an oversized island: great for cooking, entertaining, and casual dining. Retreat to the spacious primary suite featuring a spa inspired bath with a soaking tub, double vanity, and beautifully upgraded custom shower. Additional features include an upstairs laundry room, tankless water heater, whole-home surge protection, two-car garage with EV charger, beautiful front porch, landscaped lot, and fully fenced backyard with white vinyl fencing. Conveniently located near shopping, dining, and major interstates. Make this your first stop! Easy to show, easy to love!

933 Brenner Road, South Chesapeake

1300 Oregon Crossing, South Chesapeake
$549,900
4 Beds ⋅ 2 Baths ⋅ 10654828 MLS
Remarkable brick ranch situated on a corner lot overlooking the community pond! Meticulously maintained and beautifully updated, this home offers exceptional style and comfort throughout. Recent improvements include gorgeous flooring, fresh paint, and updated fixtures that create a warm, inviting atmosphere. The spacious room over the garage serves as a fourth bedroom and offers additional space perfect for a home office, hobby room, or flex area. The well-appointed kitchen features gas appliances, while the cozy gas fireplace adds charm to the living space. Step outside to your private backyard retreat featuring a sparkling in-ground pool, captivating landscaping, and multiple deck areas designed for relaxing and entertaining. Every detail has been thoughtfully maintained, making this home truly move-in ready. A rare opportunity, don't sit on this one

1300 Oregon Crossing, South Chesapeake

728 Angel Wing Drive, South Chesapeake
$715,000
6 Beds ⋅ 3 Baths ⋅ 10654725 MLS
Your weekends just got an upgrade at 728 Angel Wing Drive! Located in the sought-after Grassfield school district, this meticulously maintained home offers 5 bedrooms, 3 full baths, and a media room that could serve as a 6th bedroom. A first-floor bedroom and full bath are ideal for multigenerational living or guests, while a space for a home office and formal dining room add flexibility. Your private backyard oasis features a heated saltwater pool, spacious patio, and pergola overlooking peaceful woods with no rear neighbors. Perfect for poolside afternoons and football Sundays! The oversized garage includes shelving and a dedicated workspace. Freshly painted inside and out within the past 3 years and cared for by just two owners, this home also features a whole-house water softener, separate drinking water system, and 32 fully paid-off solar panels for potential monthly energy savings. Thoughtful upgrades, exceptional outdoor living, and room for everyone. Your next chapter starts here!

728 Angel Wing Drive, South Chesapeake

712 Woodcott Drive, South Chesapeake
$574,900
4 Beds ⋅ 2.1 Baths ⋅ 10654685 MLS
Located in the Hickory school district, the home is less than one mile from the interstate and just minutes from the shopping, dining, and everyday conveniences of Edinburgh. With its bright interior, flexible layout, generous outdoor space, and convenient location, this home is ready to welcome its next owners. Tucked along a quiet, tree-lined street, this beautifully updated home offers a light, welcoming atmosphere and plenty of space to enjoy. Natural light fills the thoughtfully refreshed interior, creating bright and comfortable living spaces throughout. At the heart of the home is an inviting kitchen featuring stone countertops, newer cabinetry, stainless steel appliances, and durable LVT flooring—perfect for everyday living and entertaining. The spacious fourth bedroom above the garage offers wonderful flexibility as a home office, gym, playroom, guest suite, or private retreat. Outside, the expansive backyard provides plenty of room for gatherings, gardening, play, or simply relaxing beneath the open sky. The home also features a long list of valuable improvements, including PEX plumbing in place of the original polybutylene, an upgraded electrical panel, replacement of most windows, updated lighting and flooring, select exterior doors, siding, and trim. A private well serves the irrigation system, and the roof was replaced in 2014.

712 Woodcott Drive, South Chesapeake

205 Thrasher Road, South Chesapeake
$299,999
3 Beds ⋅ 1.1 Baths ⋅ 10654604 MLS
Solid Bones. Endless Potential. Bring Your Vision. In the heart of Greenbrier. This all brick ranch with attached 1 car garage has a huge fenced back yard with large storage shed . Property has been very well maintained. Convenient to shopping, interstates, Hospital and restaurants. This is a rare chance to own a home with a strong, well-built structure and the freedom to make it your own. Great property for the investor, renovator, or hands-on buyer who can see what the home can become. Solid structure, a great foundation for a remodel. Needs vision and a little TLC. Room to build equity through updates. Sold strictly as-is, where-is. Seller makes no repairs or warranties. Buyers are encouraged to complete their own inspections and due diligence.

205 Thrasher Road, South Chesapeake

MM Macon, South Chesapeake
$765,000
5 Beds ⋅ 4 Baths ⋅ 10654675 MLS
The Macon Model at Riverview Landing - Master Model Listing by Wetherington Homes. Buyers may select their lot and personalize available design options. The community offers eight thoughtfully designed floor plans along with multiple exterior elevations that highlight architectural detail and curb appeal. This plan features five bedrooms, four bathrooms, a loft, and a first-floor bedroom with a full bath. The chef-inspired kitchen includes upscale finishes, a large island, and a Butler's pantry. Designed to balance functionality and craftsmanship, this home offers modern conveniences with thoughtful design throughout. Contact us today for additional information, to join the VIP interest list, and to schedule an appointment. Discover the opportunity to build in this new community with convenient access to everyday amenities!

MM Macon, South Chesapeake

1028 Livingston Ave Avenue, Central Chesapeake
$294,500
2 Beds ⋅ 2 Baths ⋅ 10654423 MLS
Charming cottage-style single-family home on a quiet street in South Norfolk! This 2-bedroom, 2-bath gem offers 1,153 sq ft of comfortable living with a spacious eat-in kitchen and formal dining room. Enjoy the covered front porch and wood deck great for morning coffee or evening relaxing. Detached 1.5-car garage provides excellent storage. No HOA! Bonus: a heated and cooled second-floor space (not included in square footage) offers exciting potential for a home office, playroom, or extra storage, original stairs are available to restore access. Convenient location near I-464 and Bainbridge Blvd. Don't miss this move-in ready opportunity! Some photos have been virtually staged to showcase the home’s potential.

1028 Livingston Ave Avenue, Central Chesapeake

1313 Parkdale Street, South Chesapeake
$700,000
4 Beds ⋅ 3 Baths ⋅ 10653628 MLS
Offering plenty of room for everyday living and entertaining, this spacious two-story home features an inviting open floor plan, a versatile flex/office space, and a HUGE upstairs loft, giving you plenty of space to spread out and make the home your own. At the heart of the home is the generously sized kitchen, complete with a large island, spacious pantry, butler’s pantry, and abundant cabinetry—great for both everyday living and entertaining. Each bedroom offers the added convenience of a walk-in closet, providing exceptional storage throughout. Outside enjoy the huge backyard, situated on a desirable corner lot with plenty of room for outdoor entertaining, play, or simply relaxing. A beautiful shed provides additional storage for tools, bikes, and more. Conveniently located near dining, parks, and major highways, this home offers the perfect combination of space, comfort, and convenience. With its well-maintained condition, this home feels practically brand new and is ready for you to make it your own!

1313 Parkdale 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.