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$577,740
3 Beds ⋅ 3 Baths ⋅ 10639726 MLS
Welcome to The Charleston at Retreat at Edinburgh—a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more—all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections.

2156 Edwin Drive, South Chesapeake
$324,900
4 Beds ⋅ 2 Baths ⋅ 10639636 MLS
Four bedroom ranch with thoughtful updates throughout. The home features a freshly painted interior, new lighting, new interior doors, and updated laminate and carpet flooring. A spacious living room welcomes you inside, while a cozy den with a fireplace offers a great place to unwind. The kitchen has been refreshed with new granite countertops and stainless steel appliances. Each bedroom is well-sized, and the bathrooms have been fully updated with a clean, modern feel. Situated on a sizeable lot, the property offers plenty of space for outdoor activities or simply relaxing.

2833 Candlewood Circle, Central Chesapeake
$820,000
5 Beds ⋅ 4.1 Baths ⋅ 10639536 MLS
Well maintained and loved home nestled on a prime corner lot in the beautiful Riverwalk community, 700 Harbor Quay delivers nearly 5,000 square feet of refined living, where luxury and functionality come together effortlessly. Featuring 5 bedrooms, 4 full bathrooms, and 1 half bath. Designed for those who love to entertain, the expansive floor plan offers elegant gathering spaces, abundant natural light, and exceptional flow throughout. Whether hosting holiday celebrations, welcoming overnight guests, or simply enjoying everyday life, every detail of this home was thoughtfully crafted to accommodate it all. Roof replaced in 2021 and some windows have been updated. Encapsulated crawlspace. Beyond this front door awaits a lifestyle few communities can match. Residents enjoy access to resort-style amenities including a clubhouse, swimming pool, tennis courts, and close proximity to the beautiful Elizabeth River. Seller to provide a 1 year home warranty of buyer's choice up to $600. Seller to provide concession toward window upgrades with acceptable offer.

700 Harbor Quay, South Chesapeake
$450,000
10639627 MLS
Well-established, highly profitable Mediterranean restaurant generating $700K+ in annual gross sales with strong, consistent cash flow. This is a turnkey operation situated in a prime, high-traffic location with a deeply loyal local customer base. The favorable lease is secured through 2030 at $3,900/month. Multiple flexible purchasing options are available to fit your investment goals: Purchase the established brick-and-mortar Restaurant Business alone for $300,000. Acquire the complete mobile expansion assets, including a brand-new, fully branded food trailer and dedicated Ford tow vehicle, for an additional $150,000. Purchase the entire comprehensive package (Restaurant + Trailer + Tow Vehicle) for $450,000. This is an incredible turnkey opportunity perfectly suited for an owner-operator or an investor looking to immediately capitalize on established dine-in, catering, and lucrative mobile/festival revenue streams. Complete financial records (POS data and tax returns) and an equipment inventory list are available upon request with a signed NDA. Seller is relocating. Please do not disturb employees or discuss the sale on-site. All showings are strictly by appointment only. Serious, qualified buyers only.

1437 Sam's Drive, South Chesapeake
$444,000
3 Beds ⋅ 3.1 Baths ⋅ 10639592 MLS
Juniper Model built in 2021. 1st floor has flex room, can be used as office, mud room, or rec room. Also, separate bedroom with full bath. 2nd floor has huge open floor plan. Kitchen has large island, SS appliances, lots of cabinets, and large pantry. Great room with gas electric fireplace. Deck off front. Lots of windows for natural lighting. Please call night before to see.

450 Asuza Street, South Chesapeake
$450,000
4 Beds ⋅ 2.1 Baths ⋅ 10639464 MLS
Beautiful brick ranch in Western Branch with gorgeous updates! Remodels/refreshes include a new roof (2020), dining and living rooms (2019), and kitchen/den/bathrooms (2016). Three bedrooms are on the first floor, and a finished room over the garage can be your home office or even a home gym. Enjoy a quiet evening on the screened-in back porch while dinner cooks on the grill on the adjacent patio. Call today for your private showing!

4005 Terry Drive, West Chesapeake
$794,740
5 Beds ⋅ 3.1 Baths ⋅ 10639533 MLS
The Tillman offers 3,226 sq. ft. of stylish and flexible living - great for multigenerational living! This spacious home includes 5 bedrooms, 3.5 baths, and a 2-car garage. The first-floor primary suite provides the perfect retreat with a massive walk-in closet, dual vanities, and a private water closet. Upstairs, you’ll find a second primary-style bedroom with direct access to a full bath, offering comfort and privacy. Three additional bedrooms (each with walk-in closets), a large loft, and a convenient laundry room complete the second floor. The open-concept main level features a welcoming dining room, expansive kitchen with an oversized island and two pantries, including a Costco pantry, and a bright family room. Photos and renderings are from builder's library, actual finishes and features may vary.

911 Intracoastal Way, South Chesapeake
$1,150,000
6 Beds ⋅ 3.1 Baths ⋅ 10639257 MLS
Nestled in the heart of Great Bridge a fully remodeled home in a coveted 12 house cul de sac neighborhood. This custom built home redefines elevated living. The grand staircase entrance flows seamlessly into the dining and living spaces. The kitchen featuring a 12 foot quartz island and new stainless appliances is any chefs dream. The primary suite is a private retreat with spa-inspired bath featuring two walk in closets. Access the second living level from either of the two staircases. Home has five upstairs bedrooms and two full bathrooms. There is room for everyone. Parking is a breeze with the 3 car attached garage and extended driveway. Book your private showing today.

520 Youngstown Court, South Chesapeake
$75,000
10639494 MLS
Imagine the possibilities! This vacant lot offers the flexibility to build your dream home and create a space designed to fit your needs.

4999 Clifton Street, West Chesapeake
$195,000
2 Beds ⋅ 1.1 Baths ⋅ 10639351 MLS
Affordable home in Great Bridge minutes to Greenbrier mall $10K+ below fair market for TLC. Central heat pump less than 5 years old. Stainless appliances with new counter-depth energy saving refrigerator. Home has Living room, large combo Family room and dining room, a laundry room and a half bath on first floor. 2nd floor has 2 over-size bedrooms and a full bath.

509 Harbour North Drive, Central Chesapeake
$899,900
5 Beds ⋅ 4 Baths ⋅ 10638532 MLS
Premium fountain-view homesite in the highly desirable Woodford Estates community! Located in the award-winning Hickory School District, this immaculate home, built in 2024 and completed in 2025, offers 5 bedrooms, 4 full baths, 3,393 square feet, and a 3-car garage. Thoughtfully designed with an open-concept layout, gourmet kitchen, spacious living areas, abundant natural light, and a first-floor bedroom with a full bath. Features include natural gas heating, HVAC, a tankless water heater, gas fireplace, and brick and fiber cement exterior. Enjoy peaceful fountain views from your backyard while benefiting from the quality and efficiency of newer construction. Move-in ready without the wait of building new!

150 Hessian Loop, South Chesapeake
$755,425
5 Beds ⋅ 3.1 Baths ⋅ 10639256 MLS
10,000 square foot lot, ready early 2027, still time to customize. The Hawthorne floor plan offers flexibility & spacious living, making it the largest & most adaptable 2-story home at Crestfield. With an impressive 3,089 square feet, this open-concept home offers 5 bedrooms, including dual owner’s suites & 3.5 baths. The kitchen features quartz countertops, stainless steel appliances, and a generously sized island for seating & casual dining. Both levels boast 9-foot ceilings, enhancing the sense of space & light throughout the home. The front porch invites you to relax & enjoy the neighborhood, & the 2-car garage provides ample storage and parking. Fenced yard. Buyer must register agent on or before first visit or first substantial communication with listing agent and Agent must accompany Buyer on 1st visit, see Listing Agent for details. Photos & Video are of previously built home for illustrative purposes, finishes & upgrades will vary in home to be built.

2039 Charwood Drive, South Chesapeake
$780,425
5 Beds ⋅ 3.1 Baths ⋅ 10639250 MLS
Location backing mature tree line, ready early 2027, still time to customize. The Hawthorne floor plan offers flexibility & spacious living, making it the largest & most adaptable 2-story home at Crestfield. With an impressive 3,089 square feet, this open-concept home offers 5 bedrooms, including dual owner’s suites & 3.5 baths. The kitchen features quartz countertops, stainless steel appliances, and a generously sized island for seating & casual dining. Both levels boast 9-foot ceilings, enhancing the sense of space & light throughout the home. The front porch invites you to relax & enjoy the neighborhood, & the 2-car garage provides ample storage and parking. Fenced yard. Buyer must register agent on or before first visit or first substantial communication with listing agent and Agent must accompany Buyer on 1st visit, see Listing Agent for details. Photos & Video are of previously built home for illustrative purposes, finishes & upgrades will vary in home to be built.

2032 Charwood Drive, South Chesapeake
$506,990
2 Beds ⋅ 2 Baths ⋅ 10639109 MLS
The Asheville, one of our quad-style homes, features two bedrooms and 2 full baths. Refreshing and cottage-like, The Asheville is single level living at its finest. A welcoming covered front porch leads you to a spacious living room with fireplace. At the heart of the home, the Kitchen is within reach of the dining room, pantry, laundry room, and access to the two-car garage. The Kitchen is accented with Shaker style cabinets, quartz countertops, tile backsplash, and stainless-steel appliances. The primary bedroom with ensuite offers a spacious walk-in closet, tiled shower with glass enclosure, counter-height vanity with double sinks and a separate water closet. For guests or an office, you’ll find a secondary bedroom with an adjacent full bath. Photos and renderings are from builder's library, actual finishes and features may vary.

2152 Edwin Drive, South Chesapeake
$695,000
5 Beds ⋅ 3 Baths ⋅ 10638952 MLS
Rarely does a property like this hit the market in Great Bridge! Sitting on a gated half-acre lot, this traditional-style home offers the perfect mix of everyday comfort and incredible workshop potential. Inside, you’ll love the open-concept layout featuring a dedicated office or homeschool space with custom built-ins, a spacious kitchen with a massive center island and commercial-size refrigerator, and a first-floor primary suite complete with a custom walk-in closet, oversized bath, and versatile flex space. The showstopper? An incredible 1,400 sq ft detached commercial-style garage/workshop with three oversized bay doors and a vehicle lift: a dream setup for car enthusiasts, hobbyists, contractors, or business owners needing serious space. Conveniently located near shopping, dining, and major commuter routes, this one-of-a-kind property delivers space, functionality, and opportunity all in one.

237 Cedar Road, South Chesapeake
$274,000
10638706 MLS
Excellent development opportunity in the Hickory area of Chesapeake. This mostly wooded parcel offers the opportunity to build a custom home in a well-established area with convenient access to shopping, dining, recreation, and major commuter routes. The residence originally built in 1957 was demolished and cleared in 2020. City water is available. Buyer to perform all due diligence regarding development potential, zoning, utilities, access, lot dimensions, and building requirements. Use caution when driving onto and walking the property due to overgrowth. Do not enter neighboring properties. Old and new surveys are available.

2524 S Battlefield Boulevard, South Chesapeake
$383,000
4 Beds ⋅ 2 Baths ⋅ 10638898 MLS
Charming all brick home with major system updates already completed! Step inside to find beautiful hardwood floors and a warm, inviting layout filled with character. Enjoy peace of mind with a roof replaced in 2021, along with the durability and timeless appeal of brick construction. Outside, you'll love the expansive, fully fenced backyard perfect for entertaining, pets, gardening, or simply enjoying your own private outdoor retreat. The home also features a spacious two car attached garage, ample driveway parking, and an adorable front porch that's perfect for morning coffee or relaxing evenings. An added bonus for qualified buyers: an assumable VA loan with an attractive 3.8% interest rate. This well maintained home offers the perfect combination of charm, updates, and value.

4113 Taylor Road, West Chesapeake
$494,990
2 Beds ⋅ 2 Baths ⋅ 10638895 MLS
QUICK MOVe-IN! The Asheville, one of our quad-style homes, features two bedrooms and 2 full baths. Refreshing and cottage-like, The Asheville is single level living at its finest. A welcoming covered front porch leads you to a spacious living room with fireplace. At the heart of the home, the Kitchen is within reach of the dining room, pantry, laundry room, and access to the two-car garage. The Kitchen is accented with Shaker style cabinets, quartz countertops, tile backsplash, and stainless-steel appliances. The primary bedroom with ensuite offers a spacious walk-in closet, tiled shower with glass enclosure, counter-height vanity with double sinks and a separate water closet. For guests or an office, you’ll find a secondary bedroom with an adjacent full bath. Photos and renderings are from builder's library, actual finishes and features may vary.

2213 Edwin Drive, South Chesapeake
$599,000
4 Beds ⋅ 2.1 Baths ⋅ 10638546 MLS
A Beautiful Brick Home nestled in the sought after Scotfield Woods community of Western Branch. This home offers the perfect blend of comfort, functionality, and neighborhood charm. Step inside to discover a thoughtfully renovated home featuring generous living spaces, natural lighting, and plenty of room for everyday living and entertaining. This home offers 4 bedrooms, 2.5 bathrooms, and a 2 car garage with plenty of drive way space. Updated kitchen island with quartz countertop, stainless steel gas stove top and oven. Walk in laundry room. Large primary bedroom with 3 closets with plenty of room for storage. A beautifully renovated primary en suite bathroom with 2 vanities, tiled floors and floor to ceiling tiled walk in shower with dual shower heads. (2022) Outside, enjoy the large corner lot with a fenced in backyard with endless possibilities for outdoor gatherings, gardening, play, or simply relaxing in your private retreat. The established neighborhood provides a peaceful setting while remaining conveniently located near shopping, dining, parks, major commuter routes, shipyards, military facilities and highly regarded Western Branch schools. Whether you're looking for your first home, additional space, or a place to put down long term roots, this home delivers exceptional value in one of Chesapeake's most desirable areas. Don't miss the opportunity to make this wonderful property your next home. Updated in 2022- Kitchen Island, LVP Flooring, Bathroom vanities, Primary Bathroom and Water heater.

4100 Scotfield Drive, West Chesapeake
$434,900
3 Beds ⋅ 2.1 Baths ⋅ 10638670 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.

668 Allery Road, South Chesapeake
$269,000
3 Beds ⋅ 2 Baths ⋅ 10638533 MLS
Beautifully remodeled 3BR/2BA home is ready for its new owner! Bright, open, spacious, this two-story home offers the kind of layout that feels impressive the moment you walk in. Two-story foyer, high ceilings, skylights, large windows, and open living/dining area create a light and airy feel throughout. Home was refreshed in 2026 with new water heater, new flooring on both levels, finished walls & fresh paint throughout. HVAC replaced in 2016; serviced in 2026. Kitchen features granite countertops, stainless steel appliances, pantry, great cabinet space, and a convenient bar area. Rare first-floor bedroom with full bathroom. Upstairs includes 2 additional bedrooms, including spacious primary suite with vaulted ceiling, walk-in closet, wide vanity area, and private bath with tub. You will also love the extra closets and storage throughout. Riverwalk community offers a beautifully maintained setting with ponds, green space, a community pool, a playground, and wonderful amenities. 2 assigned parking spots for your cars, with the option to obtain an extra 3rd spot if needed. Convenient to shopping, dining, interstate access, parks, and Chesapeake favorites, while still feeling tucked away and peaceful. Some photos have been virtually staged/enhanced to help buyers visualize the property’s potential. Schedule your private showing today!

1414 Loose Strife Place, South Chesapeake
$489,900
4 Beds ⋅ 2 Baths ⋅ 10638400 MLS
WELCOME HOME! to this 1.5 story waterfront home on corner lot with 1st floor master bedroom with tray ceiling & 2 closets/master bath. Former model with converted garage-unlimited possibilities: he/she cave, office, daycare, home school, playroom, sewing/craft room, media room, bedroom, in-law apartment with separate entrance. Updates: new roof, new fence,freshly painted interior & beautiful! New carpet upstairs BR, new gas fireplace igniter & cleaned, large loft, new sink/vanity/floor-master bath w/jetted tub/separate shower. Kit with open bar to dining area, open dining area with pantry and mirrored accent wall, open family room with cathedral ceiling & sliding doors overlooking deck and water with nice shade tree & storage shed. Neighborhood park, clubhouse & pool for summer fun. Dog park and soccer park nearby as well as golf driving range, campground and shopping/dining. Hurry before it is gone!

2705 Sawyers Arch, South Chesapeake
$479,900
4 Beds ⋅ 3.1 Baths ⋅ 10637985 MLS
Ready NOW-Model Home for sale!! Luxury End Unit townhome condo w/rear load 2 car garage. covered front deck and entry.Luxury LVP, 2nd Floor:Kitchen GE stainless appliances including refrigerator, pantry,center island w/shiplap, living area linear fireplace w/shiplap and built ins,office/flex room,dining area.1st floor: br/ flex room,hall bath,mudroom. 3rd floor: Primary bedroom,ceramic shower-2 shower heads, dual sinks, linen closet, laundry. Quartz tops kitch, all baths, covered entry, fenced front yard w/gate to multi trail,2nd flr front covered deck. 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, multipurpose trails with lake and fountain. Only 56 homes. Central Greenbrier location.

1060 Butte Lane, South Chesapeake
$190,000
2 Beds ⋅ 2 Baths ⋅ 10638211 MLS
Move-in ready and ideally located in the heart of Chesapeake! This well-maintained home features a spacious layout, two private terraces, and convenient access to shopping, dining, and major commuter routes. Property is being sold as-is. Home could use some TLC, offering a great opportunity to make it your own in a prime location.** SOME PHOTOS ARE VIRTUALLY STAGED.

717 Inlet Quay Unit H, South Chesapeake
$1,695,000
5 Beds ⋅ 3.2 Baths ⋅ 10637839 MLS
Set within the sought-after Woodards Mill “loop,” this beautiful landscaped property blends impressive living with peaceful privacy just minutes from everyday conveniences. Originally built in 1984 and fully reimagined beginning in 2001 by professional contractors, the home has been thoughtfully expanded to over 6,000 square feet of refined, comfortable living space. Every addition and update was meticulously planned and expertly executed. The heart of the home features an expansive family and entertainment room overlooking a spacious blue stone lanai. A stunning all brick sunroom adds warmth while the main level offers a generous primary suite along with three additional bedrooms (one used as home office.) Upstairs, a private second primary suite provides an ideal retreat for guests or multi generational living. Outdoor enjoy a true gardeners paradise with mature hydrangeas, peonies, irises and much more. The fenced saltwater pool with new liner offers both relaxation and peace of mind. Life on the loop brings a unique sense of community, known for its annual parades from Jingle Bell and Horse Parade to July 4th to the famous Halloween Parade. As an added everyday convenience enjoy school bus pick up and drop at the home. Miele, Thermador and Viking appliances. This home is not like any others sold in this neighborhood, a must see.

517 Woodards Ford Road, South Chesapeake
$229,900
2 Beds ⋅ 2.1 Baths ⋅ 10637939 MLS
Affordable living in the largest condo model available in Wimbledon Chase. Easy access to I64, the Chesapeake Expressway, Greenbrier and Great Bridge. No car needed for access to shopping & restaurants; adjacent to Chesapeake Regional Medical Complex. Summertime living is easy with the community pool. All appliances convey including washer & dryer, as-is. Besides the generous ensuite, the primary bedroom features a cathedral ceiling and more closet space than many single family homes. Condo fees cover the master insurance policy, landscaping, water, trash, sewer, pool access, as well as exterior building maintenance.

401 Henley Court Unit K, South Chesapeake
$750,000
10637870 MLS
A 28-acre property is located in the Grassfield/Hickory region of Chesapeake. Whether you intend to build your dream home or utilize it for investment purposes, the property offers limitless potential. The property is sold “as is,” “where is,” and the buyer bears the responsibility of conducting their due diligence.

28 Johnstown Crescent, South Chesapeake
$1,500,000
10637558 MLS
"BUSINESS ONLY FOR SALE" Please do not disturb customers and employees. Great location. Positive cashflow. PRICE INCLUDES INVENTORY. TURN KEY OPERATION.

3116 Western Branch Boulevard, West Chesapeake
$359,900
3 Beds ⋅ 2.1 Baths ⋅ 10637408 MLS
Tucked away on a quiet cul-de-sac in Chesapeake's highly desirable Cedar Lakes community, this beautiful 3-BR + Loft, 2.5-BA end-unit townhome offers 1,621 sq ft of bright, comfortable living space. This bright & airy home offers soaring ceilings and skylights that provide lots of natural light. The versatile upstairs loft includes a closet - perfect for a home office, playroom, or extra bedroom. Lots of storage space and attached 1-car garage. Easy access to the neighborhood pool and clubhouse.

600 Windmill Point, South Chesapeake
$268,000
5 Beds ⋅ 3 Baths ⋅ 10637287 MLS
Rare to find an end unit townhome on 0.16 Acre lot in Great Bridge area minutes to freeway I-64, I-464, to Greenbrier mall features a bedroom and a full bathroom on the first floor. Like new kitchen cabinets, SS appliances. Less than 5 years old roof, heat pump central HVAC, electric water heater, vinyl windows. Second floor has a master suite with a sitting or baby room or an office with 2 separate walk-in closets and 3 good size bedrooms with a full bathroom. 3% closing cost assistance for TLC

915 Harbour North Drive, Central 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.