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5 Harbor Watch Drive Unit 405, South Chesapeake
$310,000
3 Beds ⋅ 2 Baths ⋅ 10651901 MLS
Wake up to peaceful water views right from your bedroom! This spacious, well-maintained 3-bedroom, 2-bath condo offers 1,762 square feet per MLS of comfortable, single-level living and low-maintenance convenience. Featuring luxury vinyl plank flooring in the living areas. Large windows and a sliding glass door bring in plenty of natural light. The kitchen offers abundant cabinet space, newer stainless steel appliances, including a wine fridge, and a convenient pantry. The spacious primary suite features a walk-in closet, linen closet, and private bath with a double vanity, soaking tub, and separate stand-up shower. Additional features include newer windows and a sliding glass door, ceramic tile, carpeting, and plenty of storage throughout. Amenities include a pool and clubhouse. Association services also include dock maintenance, water, sewer, and trash. Deeded Boat Slip negotiable with sale

5 Harbor Watch Drive Unit 405, South Chesapeake

2100 Millville Road, South Chesapeake
$650,000
5 Beds ⋅ 2.1 Baths ⋅ 10652716 MLS
Custom 5-bedroom, 2.5-bath Chesapeake home on a huge half-acre lot, currently zoned for Grassfield High School! This beautifully updated home features an open floor plan, pickled oak hardwood floors, quartz countertops, stainless steel appliances, gas range, custom barn doors, and European-inspired lighting and fixtures. The spacious primary suite offers cathedral ceilings, dual closets, and a private deck with peaceful wooded views. The spa-like primary bath features a freestanding soaking tub and custom porcelain-and-glass shower. Outside, enjoy an expansive deck and plenty of room for outdoor living, entertaining, and recreation. If you’ve been searching for a custom Chesapeake home with space, style, updates, and a large lot, this one deserves a closer look. Schedule your tour today!

2100 Millville Road, South Chesapeake

400 Las Gaviotas Boulevard, South Chesapeake
$505,000
4 Beds ⋅ 2.1 Baths ⋅ 10652912 MLS
A rare opportunity in one of Chesapeake’s most desirable neighborhoods!! Exceptional 4-bedroom, 2.1-bath home perfectly positioned on a corner lot overlooking the fairway in highly sought-after Las Gaviotas & the Grassfield school district. The first floor offers two generous living areas, a formal dining room, and an updated kitchen featuring granite countertops, tile backsplash, gas range, and ample cabinetry. Large windows frame peaceful views of the golf course, creating a bright, inviting atmosphere throughout. Four spacious bedrooms with the primary including a walk-in closet & a beautifully finished primary ensuite bathroom with a soaker tub, separate shower, and double-sink vanity. Step outside to enjoy composite decking & a backyard that opens directly to the fairway—an ideal setting for morning coffee, evening unwinding, or hosting friends. Just minutes from top-rated schools, shopping & dining, this home blends convenience with the charm & prestige of golf-course living.

400 Las Gaviotas Boulevard, South Chesapeake

311 Lancing Way, South Chesapeake
$619,000
4 Beds ⋅ 2.1 Baths ⋅ 10652797 MLS
Welcome to 311 Lancing Way! This beautiful 4-bedroom, 2.5 bath home in Chesapeake's desirable Grassfield area features a backyard oasis with a large, 33,000-gallon lagoon-style saltwater pool, 8-ft deep end, variable-speed pump, water feature, plumbing for a future waterslide/waterfall, and a buried pool drain line with pump-controlled discharge to the street. The pool is surrounded by a beautiful stamped concrete, complemented by a spacious screened porch with dual variable-speed fans, a poolside bar shed, and a garden shed with front and rear access. Inside, enjoy programmable dual-zone A/C with independently controlled thermostats and an automatic generator transfer switch. Parking for 4 cars, including an oversized 2-car garage, PLUS additional concrete parking for a boat or 2 more vehicles! No HOA fees! Conveniently located near Grassfield schools, shopping, dining, parks, major interstates, and military installations throughout Hampton Roads. Schedule your private showing today!

311 Lancing Way, South Chesapeake

1808 Ashlar Lane, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10652753 MLS
This is the kind of home that makes you want to unpack and stay awhile! Conveniently located for access to major Hampton Roads military installations, commuter routes, shopping, and dining, this beautifully maintained property in the highly sought Fieldstone neighborhood of Chesapeake offers 2,559 sq ft of living space, 4 bedrooms, and 2.5 baths. Brand new LVP flooring on the main level and fresh carpet upstairs create an inviting, move-in-ready feel. The open kitchen features granite countertops, abundant cabinetry, and pantry storage, flowing seamlessly into the living and dining areas with a cozy gas fireplace. A dedicated first-floor office adds exceptional flexibility for remote work, study, or hobbies. Upstairs, spacious bedrooms include a generous primary suite with a private bath and walk-in closet. Outside, enjoy a fully fenced backyard and patio, wonderful for outdoor relaxation and summer gatherings. Some photos were virtually staged using AI.

1808 Ashlar Lane, South Chesapeake

620 Estates Way Unit 120, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10652230 MLS
Surrounded by trees, this 2006 townhome-style condo offers a quieter setting with shopping, dining, parks & interstate access close by. The open main level features flexible living spaces anchored by a gas fireplace. The adjoining kitchen offers granite counters, stainless appliances, & an efficient layout open to the living areas. Upstairs are comfortably sized bedrooms, including a spacious primary suite w/ ensuite bath, double sinks, tiled shower & generous storage. Enjoy a shaded rear deck overlooking the wooded setting plus an oversized attached garage. Major updates include a high-efficiency York heat pump/HVAC installed 12/2025 (includes 10 yr parts/3 yr labor warranty) & architectural-shingle roof estimated at 2–5 years old. Pre-list inspection completed 9/2026; report available.

620 Estates Way Unit 120, South Chesapeake

2052 Charwood Drive, South Chesapeake
$720,760
4 Beds ⋅ 3.1 Baths ⋅ 10652698 MLS
Beautiful lot backing to mature tree line. Experience the perfect blend of comfort and functionality in this versatile ranch home. The heart of the residence features an expansive open-concept living area, overlooking the kitchen with oversized island. Retreat to the spacious owner’s suite, a private sanctuary complete with a generous walk-in closet & a spa-like ensuite featuring a soaking tub & separate walk-in shower. Two additional bedrooms offer flexibility for guests or a home office. A large finished room over garage adds a 4th bedroom & full bath, included in list price, plus attic storage. Seller to pay up to $10,000 in closing cost assistance when using preferred lender, see agent for details. Buyer must register agent on or before first visit or first communication w/ listing agent & Agent must accompany Buyer on 1st visit, see Listing agent for details. Photos & Video are of previously built homes, finishes vary.

2052 Charwood Drive, South Chesapeake

152 Mann Drive, South Chesapeake
$460,000
3 Beds ⋅ 2 Baths ⋅ 10652558 MLS
Welcome to 152 Mann Drive in the heart of Great Bridge! This well-built brick ranch offers the perfect blend of charm and modern updates. Nearly every major improvement was completed in 2023, including luxury vinyl plank flooring, a fully updated kitchen, renovated bathrooms, HVAC system, and roof—giving you peace of mind for years to come. You’ll appreciate the seamless flow of the floor plan, designed for both everyday living and easy entertaining. Just off the kitchen, a cozy wood-burning fireplace creates a warm and inviting ambiance—perfect for relaxing evenings at home. With solid construction, stylish updates, and plenty of potential to make it your own, this is one you won’t want to miss!

152 Mann Drive, South Chesapeake

641 Edgewood Arch, South Chesapeake
$550,000
4 Beds ⋅ 3.1 Baths ⋅ 10652602 MLS
This beautiful traditional style home nestled in the sought-after Cheshire Forest community of Chesapeake is ready for its next chapter. It offers comfortable living spaces inside and out. The family room is great for movie nights and entertaining, featuring a 120-inch projection screen and projector that conveys with the home. Go outside to enjoy your private screened-in porch, wonderful for morning coffee or relaxing evenings, with an attached trex deck offering even more space for gatherings to unwind. A new fence adds privacy to the backyard, while the partial house generator provides peace of mind. Living in Cheshire Forest means enjoying more than just a beautiful home. The community offers an impressive collection of amenities including a clubhouse, swimming pool, tennis courts and more. This property is more than a home, it's a community.

641 Edgewood Arch, South Chesapeake

712 Appalachian Court Court, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10652632 MLS
Welcome to 712 Appalachian Court in Centerville Commons! Move right into this detached single-family home featuring a second-floor loft converted into a true, spacious 4th bedroom! Built in 2014, this 2,389 sq ft home perfectly pairs classic charm with an inviting, modern layout optimized for comfortable living and entertaining. Main Level Highlights: Step into a bright, open-concept floor plan with natural light, custom blinds, and wood/laminate flooring. The expansive living room offers a cozy electric fireplace, flowing into an updated kitchen with stainless steel appliances, modern tile backsplash, crisp cabinetry, large pantry, and sunlit breakfast area. Upper Level Retreats: Features 4 bedrooms, highlighted by the newly converted 4th bedroom and a primary suite with an en suite bath and large walk-in closet. Outdoor Living & Efficiency: Relax on the rear deck overlooking a fenced backyard with peaceful local farm views. Large modern playset is negotiable. Capital updates include a 2025 HVAC system, tankless water heater, smart home features, and energy-efficient window tinting. Attached 2-car garage is ideal for parking, storage, or a home gym. Centrally located near bases and interstates. Bonus: Seller's preferred lender is offering closing cost assistance if utilized—ask LA for details!

712 Appalachian Court Court, South Chesapeake

213 Maggie Bell Ln., South Chesapeake
$608,900
3 Beds ⋅ 2.1 Baths ⋅ 10652577 MLS
Low Loan Rate, No PMI! Visit SITE: GPS 369 Scotland Ln. Chesapeake OPEN S/S 12-4. Nestled in Greenbrier come visit the newest community by renowned local builder. Primrose Cottage welcomes you with an inviting full front porch, soaring two-story foyer and family room, and beautiful hardwood flooring throughout the main living areas. First-floor primary suite with custom walk-in closet and spa bath with quartz dual vanity, tiled shower, and private laundry.Designed for easy living and entertaining with open layout connects the family room, dining area, and HGTV-inspired chef’s kitchen featuring oversized quartz island, custom hood & floating shelves, and designer finishes. Upstairs two spacious bedrooms, tons of storage and 2nd laundry room and Opt. for 4th BR/Loft and/or add'l full bath. Professionally managed grounds for a low-maintenance lifestyle, giving you more time to enjoy the comfort, quality, and craftsmanship of your Primrose haven.

213 Maggie Bell Ln., South Chesapeake

1836 Bancroft Road, South Chesapeake
$735,000
3 Beds ⋅ 2 Baths ⋅ 10652410 MLS
Welcome to 1836 Bancroft! Immaculate, barely lived-in, and loaded with upgrades, this home truly feels brand new. Thoughtful improvements throughout make it as functional as it is beautiful. The open and inviting interior features ceiling fans in every room, including remote-controlled fans in the primary bedroom and living room, plus a spacious flex room offering endless possibilities as a home office, playroom, media room, or potential 4th bedroom. The home is exceptionally well-equipped for modern living, with Ethernet connections in every room and a central Ethernet relay in the coat closet, upgraded HDMI and cable connections in the living room, and prewiring for an electric vehicle. Smart-home conveniences continue with a Kwikset electronic lock, Wi-Fi connected refrigerator and dishwasher, and a Wi-Fi capable all-in-one washer/dryer. The kitchen features exterior-vented cooking ventilation, while both bathrooms have grab bars and walk-in showers—including the second full bath. A tankless water heater adds efficiency and convenience. Endless natural light, no short in thanks to the LARGE oversized sliding door installed off of the living room. Outside, enjoy a very spacious screened-in back porch perfect for relaxing or entertaining, a rear gas connection ready for your outdoor cooking setup, and an installed sprinkler system to help keep the yard looking its best. Meticulously maintained and thoughtfully upgraded from top to bottom, 1836 Bancroft offers the rare opportunity to enjoy the feel of a brand-new home without waiting for new construction. Simply move in and enjoy!

1836 Bancroft Road, South Chesapeake

905 Washington Drive, South Chesapeake
$749,000
5 Beds ⋅ 2.1 Baths ⋅ 10652400 MLS
Welcome to this spacious 5-bedroom home set on nearly half an acre in the Grassfield school district! Designed for comfortable everyday living and effortless entertaining, the light-filled layout features soaring ceilings and generous living spaces. Kitchen showcases granite countertops, abundant cabinetry, and stainless steel appliances, opening naturally to the main living areas. A first-floor bedroom offers flexibility for guests, a home office, or playroom. Upstairs, the expansive primary suite features a sitting area with fireplace, oversized walk-in closet, dual vanities, soaking tub, and tiled walk-in shower. Outside, enjoy a large deck, hot tub, and fully fenced backyard with plenty of room to gather, play, and unwind. An above-ground pool is currently in place for buyers who would like it, with removal also an option. Oversized two-car garage, ample driveway parking, and convenient access to shopping, dining, and major roadways complete this exceptional Chesapeake home.

905 Washington Drive, South Chesapeake

661 Allery Road, South Chesapeake
$429,900
3 Beds ⋅ 2.1 Baths ⋅ 10652385 MLS
Now preselling by appointment. The Marlow plan offers three 3rd floor bedrooms with the option to add an additional 4th bedroom & full bath on 1st floor. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. 2-car rear-loading garage. Community will feature pool, playground, dog park and grilling stations, all surrounded by a protected forested area and conveniently located just 2 miles from Virginia Beach. Seller to pay up to $8,000 in closing cost assistance when using preferred lender, see agent for details. Special presale incentive: Receive a $15,000 anyway allowance to use at buyer's discretion when using seller's preferred lender, listed price reflects allowance taken off base price, see agent for details. Photos & video are of previous model, for illustrative purposes, finishes and upgrades vary in actual home to be built.

661 Allery Road, South Chesapeake

649 Allery Road, South Chesapeake
$452,900
4 Beds ⋅ 3.1 Baths ⋅ 10652383 MLS
Now preselling by appointment. This Marlow plan includes our 4th bedroom & full bath on 1st floor already spec'd and included in price. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. 2-car rear-loading garage. Community will feature pool, playground, dog park and grilling stations, all surrounded by a protected forested area and conveniently located just 2 miles from Virginia Beach. Seller to pay up to $8,000 in closing cost assistance when using preferred lender, see agent for details. Special presale incentive: Receive a $15,000 anyway allowance to use at buyer's discretion when using seller's preferred lender, listed price reflects allowance taken off base price, see agent for details. Photos & video are of previous model, for illustrative purposes, finishes and upgrades vary in actual home to be built.

649 Allery Road, South Chesapeake

322 Holyoke Lane, South Chesapeake
$287,000
2 Beds ⋅ 2.1 Baths ⋅ 10651614 MLS
Come fall in love with this beautiful move-in ready corner unit in sought-after Greenbrier. You will be impressed by this spacious & bright open-concept layout connecting the living & dining areas, the updated kitchen with granite countertops & SS appliances. Kitchen & half bath grouted tile. New flooring downstairs in 2025. Home features 2 large bedrooms with 2 full en-suite baths & 2 large walk-in closets. Enjoy private enclosed patio with additional storage. Appl. working, but convey "as is". Condo fees include inground pool, trails with park benches, water, sewer, trash, grounds maintenance & master insurance policy. Minutes from shopping, dining & entertainment. Easy access to VAB oceanfront. Schedule a tour today!

322 Holyoke Lane, South Chesapeake

2809 Cistern Circle, South Chesapeake
$539,900
4 Beds ⋅ 2.1 Baths ⋅ 10651217 MLS
Welcome to 2809 Cistern Circle! This beautifully maintained home offers spacious living areas, abundant natural light, and a flexible floor plan with space for a home office or study. Smart Home Ready with Samsung SmartThings potential and compatible lighting, locks, cameras, thermostats, sensors, and more. The living room features built-in surround sound, and the garage offers two additional 240V outlets. Enjoy a large fenced backyard, deck, patio, and fire pit area. Community amenities include a pool, clubhouse, playground, picnic areas, and green space. A VA loan at a 3% interest rate may be assumable by a qualified buyer, subject to loan servicer approval and applicable terms. Ask for details about this potential financing opportunity!

2809 Cistern Circle, South Chesapeake

1441 Whittamore Road, South Chesapeake
$469,900
5 Beds ⋅ 2 Baths ⋅ 10650780 MLS
Welcome to a rare opportunity in Chesapeake's sought-after Hickory school district! Set on a full acre, this beautifully transformed 5-bedroom, 2-bath home offers the space and setting to enjoy a touch of country living while staying near the conveniences of the city. The renovation goes far beyond cosmetics, with a new roof, siding, windows, HVAC, flooring, carpet, plumbing, septic tank, appliances and more. Inside, fresh modern finishes create a bright, move-in-ready home with room for everyone. Outside, the expansive acre lot opens the door to gardens, outdoor entertaining, hobbies, animals or simply having more room to enjoy the outdoors. With golf courses nearby and easy access to everything Chesapeake has to offer, this property delivers a unique blend of space, location and modern living. Nearly everything has been refreshed or replaced- just bring your furniture and start enjoying the Hickory lifestyle!

1441 Whittamore Road, South Chesapeake

209 Springbrook Lane, South Chesapeake
$475,000
4 Beds ⋅ 2.1 Baths ⋅ 10651998 MLS
Welcome to 209 Springbrook Lane, nestled in Chesapeake’s established Wellspring community! This well-cared-for 4-bedroom, 2.5-bath home offers approximately 2,148 sq. ft. with a floor plan that flows effortlessly from room to room. The inviting living room features several windows providing plenty of natural light and flows into the adjoining dining room. The eat-in kitchen with bay windows offers an expansive view of the beautiful backyard and opens to a comfortable family room—perfect for everyday living. From the family room, step into the bonus enclosed sunroom with convenient access to the patio and backyard. Now, let’s talk about the lot—can you say gorgeous? Situated on approximately .34 acre, the property features mature trees and established landscaping, a welcoming covered front porch, expansive patio, fenced backyard, storage shed, and plenty of room to entertain, garden, or simply enjoy the outdoors.

209 Springbrook Lane, South Chesapeake

228 Country Club Boulevard, South Chesapeake
$619,000
4 Beds ⋅ 2.1 Baths ⋅ 10652285 MLS
Fantastic location close to shopping, major hwys primary and secondary schools and so much more! The already large/oversized primary suite has a large additional private flex room for office or nursery, workout room or whatever your heart desires. Complete with private bath and large walk in closet. For additional privacy the ancillary bedrooms are on the opposite side of the home. This home is a one owner former model home. New carpet just for you! The neighborhood is low turnover, well established and quiet. Beautiful foyer and open hall say "elegance" while having "cozy home" feel. 2 large sheds so you can park both cars in the garage. Smartly laid out with oversized rooms thru out. Separate zone HVAC for large sunroom with tile flooring. updated kitchen with abundant cabinets!

228 Country Club Boulevard, South Chesapeake

1509 Waitsel Drive Unit 206, South Chesapeake
$345,000
2 Beds ⋅ 2 Baths ⋅ 10650907 MLS
Welcome home to this beautiful, like-new condo in the heart of Chesapeake! Built just 2 years ago, this home offers modern finishes, an open layout, and low-maintenance living.The open-concept floor plan connects the kitchen, dining, and living areas, creating a great space for everyday living or entertaining. The kitchen features quartz countertops, stainless steel appliances, upgraded cabinetry, and a large island with plenty of room for seating. LVP flooring, updated lighting, and plenty of natural light give the home a bright, welcoming feel throughout.The spacious primary suite offers a private retreat with a beautifully finished ensuite bath and generous closet space. Conveniently located near shopping, dining, and major interstates, you’ll have easy access to everything Chesapeake and Hampton Roads have to offer.Move-in ready, only 2 years old, and beautifully maintained—this is one you’ll want to see!

1509 Waitsel Drive Unit 206, South Chesapeake

2037 Charwood Drive, South Chesapeake
$703,705
4 Beds ⋅ 3.1 Baths ⋅ 10652119 MLS
Experience the perfect blend of comfort and functionality in this versatile ranch home. The heart of the residence features an expansive open-concept living area, overlooking the kitchen with oversized island. Retreat to the spacious owner’s suite, a private sanctuary complete with a generous walk-in closet & a spa-like ensuite featuring a soaking tub & separate walk-in shower. Two additional bedrooms offer flexibility for guests or a home office. A large finished room over garage adds a 4th bedroom & full bath, included in list price, plus attic storage. Seller to pay up to $10,000 in closing cost assistance when using preferred lender, see agent for details. Estimated March 2027 closing. Buyer must register agent on or before first visit or first communication w/ listing agent & Agent must accompany Buyer on 1st visit, see Listing agent for details. Photos & Video are of previously built homes, finishes vary.

2037 Charwood Drive, South Chesapeake

505 Sandy Hill Way, South Chesapeake
$599,000
4 Beds ⋅ 2.1 Baths ⋅ 10652101 MLS
Perfectly situated in the heart of Great Bridge, this spacious 4-bedroom, 2.5-bath home offers nearly 2500 square feet in the established Sandy Hill neighborhood with no HOA. Enjoy the convenience of being just minutes from shopping, dining, parks, and everyday essentials while benefiting from sought-after Great Bridge schools. Inside, you'll find generous living spaces, brand-new carpet, and a room over the garage that can be a bedroom or a hang out space. Outside, the fully fenced backyard is ready for entertaining with an in-ground pool featuring a brand-new liner, an expansive paver patio, outdoor bar area, and storage shed. Offering space, flexibility, and recent updates in one of Great Bridge's most desirable neighborhoods, this home is ready for its next owners.

505 Sandy Hill Way, South Chesapeake

961 Gabion Way, South Chesapeake
$430,000
3 Beds ⋅ 2.1 Baths ⋅ 10652100 MLS
Built in 2022, this beautiful townhome in Bryan’s Cove is truly move-in ready and offers a wonderful combination of space, comfort, and convenience. With three levels of living space, there’s plenty of room for everyone. The first floor includes a flexible bonus room that would make a great home office, workout room, playroom, or guest space, along with an attached two-car garage. The main level features an open floor plan with lots of natural light. The kitchen has granite countertops, stainless steel appliances, a large island, and plenty of space for cooking and gathering. The dining area opens to a private back porch, where you can sit and relax while enjoying the view of one of the community playgrounds directly behind the home. It’s especially nice to be able to keep an eye on the kids while they play. Upstairs, the spacious primary bedroom offers a tray ceiling, walk-in closet, and a double vanity in the primary bath. The additional bedrooms provide plenty of space for family, guests, or whatever fits your needs. Bryan’s Cove has so much to offer, with a clubhouse, fitness center, swimming pool, dog parks, playgrounds, pier, and docks. The location is also incredibly convenient to shopping, restaurants, military bases, and major interstates. If you’re looking for a newer, low-maintenance home with plenty of space, great amenities, and a backyard view that’s hard to beat, this is definitely worth seeing!

961 Gabion Way, South Chesapeake

568 Waters Road, South Chesapeake
$639,000
6 Beds ⋅ 2.1 Baths ⋅ 10652034 MLS
Located in Chesapeake’s sought-after Grassfield school district, this freshly painted, move-in ready home offers space, flexibility, and room to grow. The open floor plan centers around a spacious kitchen with generous cabinet and counter space, pantry storage, and an easy connection to the main living areas, making daily life and entertaining feel natural. With multiple finished areas across three levels, the layout works well for multigenerational living, long-term guests, remote work, hobbies, a media room, playroom, or additional bedrooms. The third floor was expanded in 2021 to include two finished rooms, giving buyers even more space. Outside, the large fully fenced backyard and spacious deck are ready for cookouts, pets, play, relaxing evenings, and weekend gatherings. An expanded extra-wide driveway and EV charger add everyday convenience. Convenient to shopping, dining, highways, and Chesapeake amenities, this home brings together function, flexibility, and a location buyers love. Closing cost contribution available with acceptable offer.

568 Waters 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.