Chesapeake, VA Real Estate | Chesapeake, VA Properties between $500,000 and $600,000 for Sale

Luxury End Unit 2 story townhome condo w/two car front load garage in a 3 unit building! Luxury LVP throughout, wood steps, 1st floor: Open floor plan, Kitchen GE Matt Black appliances w/refrigerator, Stainless farm sink, pantry, center island w/shiplap, dining area, living room w/ linear fireplace w/shiplap & built ins, covered side entry w/mudroom and 1/2 bath, covered back patio. 2nd floor: Primary w/ceramic floor & shower-2 shower heads, dual sinks, 2 closets, 2 bedrooms & full bath, linen closet, laundry. Quartz tops kitchen & all baths, covered entry, fenced back yard. 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.

709 Flatrock Lane, South Chesapeake

$575,000

4 Beds ⋅ 2.1 Baths ⋅ 10645079 MLS

Welcome to this practically brand new 4BR/2.5BA single family home in Chesapeake that still has that new home smell! Model home level upgrades. This is not builder grade. This home was built with extensive upgrades comparable to the builder's model home, giving the next owner a highly upgraded home without the cost and wait. Immaculate and move-in ready, this home shines with crisp finishes and thoughtful design. The chef friendly kitchen features a large island, soft-close cabinetry, beautiful countertops, a stylish backsplash, and plenty of space for cooking, gathering, and entertaining. Upstairs, the spacious primary suite offers both a walk-in closet and an additional oversized closet, while the generously sized secondary bedrooms all feature large closets. A versatile flex space provides room for a home office, playroom, or cozy sitting area. The 2-car garage includes an EV charger, and the manageable backyard offers just the right amount of outdoor space to enjoy without the upkeep. Conveniently located near restaurants, breweries, coffee shops, shopping, and interstate access, this home combines modern comfort with everyday convenience. This is one you won't want to miss. Welcome HOME!

933 Brenner Road, South Chesapeake

$600,000

4 Beds ⋅ 2.1 Baths ⋅ 10645717 MLS

BACK ON MARKET, SUBJECT TO RELEASE, NO FAULT OF SELLER ~ WATERFRONT LIVING IN GREAT BRIDGE! Welcome to “The Lake House,” a waterfront retreat tucked away on a quiet cul-de-sac in the sought-after Great Bridge school district. Offering nearly 3,000 square feet, 4 bedrooms and 2.5 baths, this home was made for enjoying life on the water—with peaceful views from many of the rooms throughout the home. Start your morning overlooking the water from the kitchen and breakfast area, gather in the spacious living areas, or enter the screened porch and simply slow down. The backyard stretches to the water’s edge, creating a beautiful setting for entertaining, relaxing, or enjoying an evening outside. Upstairs, the spacious primary suite feels like a true retreat with vaulted ceilings, a fireplace in the bedroom, water views and a soaking tub—the perfect place to unwind at the end of the day. Inside, fresh paint, LVP flooring throughout the first floor, updated lighting, a refinished staircase and a convenient built-in drop zone add to the move-in-ready feel. Major improvements include HVAC (2023), water heater (2022) and an encapsulated crawlspace. Washer and dryer convey. NO HOA .

705 Turnbuckle Court, South Chesapeake

$525,000

4 Beds ⋅ 2.1 Baths ⋅ 10645295 MLS

Located in the highly sought-after Grassfield High School district, this home offers an incredible opportunity to make a home of your own in one of Chesapeake's most desirable areas. Inside features a spacious, functional floor plan boasting nearly 2700 square feet of living space. The living areas are generous with comfortable bedrooms and plenty of room to personalize. Head outside to the home's standout feature -- an expansive backyard and large deck with endless possibilities for entertaining or creating a private outdoor retreat. Conveniently located near shopping, dining, parks, and major interstates!

963 Speight Lyons Loop, South Chesapeake

$518,048

4 Beds ⋅ 3.1 Baths ⋅ 10645609 MLS

Ready Now: End Unit townhome condo w/rear load 2 car garage. 19 x 12 deck. Luxury LVP floor in select living areas, 2nd floor: Kitchen w/ GE Cafe Matt Black appliances includes refrigerator, center island w/shiplap, pantry, living room linear fireplace w/shiplap, dining area, office/flex room, covered Deck off dining area. 3rd floor: Primary w/ceramic shower-2 shower heads, tile floor, dual sinks, 2 closets, 2 bedrooms w/dual entry bath, linen closet, laundry.1st floor: bedroom/flex room w/full bath, mudroom. Quartz tops kitchen & all baths, covered entry, fenced front & Side yard w/gate to multi trail. 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, 2-10 home warranty, master insurance, trash pick up, private streets, city water/sewer, guest parking, multipurpose trails with lake and fountain. Only 56 homes. Central Greenbrier location. Generous incentives.

1064 Mesa Loop, South Chesapeake

$554,718

4 Beds ⋅ 2 Baths ⋅ 10645495 MLS

A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch-style living with 4 bedrooms, including a large finished room over the garage. From the front porch to the Family Room also open to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, a community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your doorstep in an exciting new homes community! Builder is offering 3% CCA (See listing agent for details, as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5 pm at 5023 Annapolis Drive.

2207 Hampton Roads Parkway, West Chesapeake

$574,900

4 Beds ⋅ 2.1 Baths ⋅ 10645491 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

$575,000

4 Beds ⋅ 2.1 Baths ⋅ 10645393 MLS

Premium location in one of Western Branch’s most sought-after neighborhoods & schools. Beautiful, manicured homes w/large lots & no homeowner’s association. Just minutes to 664 & ALL of Hampton Roads Military bases, shopping & entertainment and medical facilities. Step inside to a welcoming foyer that leads to a formal dining room, living room and a custom kitchen with an Island. The sunken den features a gas fireplace which exits to a multi-level deck for cookouts and entertaining. The upstairs features a primary suite for a private retreat with an en-suite bath, a large walk-in closet for keeping all your items organized, while two additional bedrooms (all with walk-in closets) provide versatility for guests or even a game (flex) room. In addition, a 4th bedroom is located over the 576 SQFT. Attached garage. New interior paint and carpet, move in ready. Some rooms virtually staged.

1416 Pine Grove Lane, West Chesapeake

$584,900

5 Beds ⋅ 2.1 Baths ⋅ 10645337 MLS

A versatile floor plan with ample space for entertaining! Tha Palm offers 5 Bedrooms , 2.5 Baths, a large Family room, open to the kitchen, all BR's on 2nd floor, large patio space for outdoor living. A desirable Primary Suite bath & walk-in closet.The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, a community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your doorstep in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details, as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5 pm at 5023 Annapolis Drive.

2202 Wilmington Avenue, West Chesapeake

$577,740

3 Beds ⋅ 3 Baths ⋅ 10645211 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. Taxes are estimated and will be updated after county assessment.

2166 Edwin Drive, South Chesapeake

$568,000

4 Beds ⋅ 2.1 Baths ⋅ 10645016 MLS

*Seller to contribute an amount of $7K toward the Buyer's allowable closing costs and prepaid expenses subject to lender guidelines with an acceptable offer.* Welcome to this beautifully maintained 4-bedroom, 2.5-bath home offering an open-concept floor plan designed for comfortable everyday living and effortless entertaining. Conveniently located near shopping, dining, and with easy interstate access, this home combines comfort with convenience. Relax and unwind on the spacious deck while enjoying peaceful views of the pond and the surrounding wildlife. The generous primary suite features a large walk-in closet, providing plenty of storage space. The well-appointed kitchen includes a gas range, a large pantry, and ample workspace for cooking and gathering. Located in the highly sought-after Chesapeake School District, this home also offers numerous valuable upgrades, including a new roof (2024), HVAC system (2024), and water heater (2021). Additional features include solar panels for energy efficiency, an irrigation system with a dedicated well, a security system, and the washer and dryer, all of which convey with the home.

1311 Piedmont Arch, South Chesapeake

$599,999

4 Beds ⋅ 2 Baths ⋅ 10644979 MLS

Welcome to this beautifully remodeled all-brick ranch tucked into the peaceful Hickory area of Chesapeake, where country charm meets modern comfort on approximately 3 sprawling acres. This 4-bedroom, 2-bath gem has been thoughtfully updated from top to bottom, featuring luxury vinyl plank flooring, tiled showers, granite countertops, and stainless steel appliances throughout a bright, open layout made for both everyday living and easy entertaining. Step outside and fall in love with the lifestyle this property offers: relax on the covered front porch, host gatherings on the expansive rear deck, or unwind on your own private deck just off the primary suite. Dreaming of homegrown eggs? The property includes chicken coops, ready for you to raise your own flock and enjoy farm-fresh living right in your backyard. A newly poured driveway and a 50-AMP power pole with RV hookup round out the practical upgrades, making this move-in-ready retreat as functional as it is charming. With updated finishes, room to roam, and space to grow your own little homestead, this Chesapeake beauty is ready to welcome you home.

913 Long Ridge Road, South Chesapeake

$524,500

4 Beds ⋅ 3 Baths ⋅ 10644867 MLS

Welcome home to this beautiful Craftsman-style ranch in highly desirable Culpepper Landing! This spacious 4-bedroom, 3-bath home offers approximately 2,380 square feet of thoughtfully designed living space with an open floor plan, soaring 10-foot ceilings, hardwood floors, upgraded trim, and surround sound in the living room. The gourmet kitchen features granite countertops, custom cabinetry, a large center island with bar seating, and ample storage—perfect for large families or entertaining. The first-floor primary suite offers a tray ceiling, walk-in closet, and an ensuite bath with double vanities, a garden tub, and a tiled walk-in shower. A finished room over the garage with a full bath and walk-in closet provides the perfect guest suite, home office, or flex space. Enjoy relaxing on the inviting front and side porches or entertaining on the rear deck. Additional features include a two-car attached garage, sprinkler system, and garage door opener with a transferable warranty and MyQ smart access for convenient remote operation and secure package delivery. Inground Sprinkler System has recently been inspected, a new back flow preventer was added and sprinkler heads relocated to accommodate a future fence. Interior professionally painted, new easy open window blinds installed thoughout w/4 yr warranty (2025). Located across from the neighborhood dog park, Culpepper Landing offers outstanding amenities including a clubhouse, community pool, fitness center, playgrounds, and walking trails, all with convenient access to shopping, dining, military bases, and major interstates.

3209 Dodd Drive, South Chesapeake

$539,900

4 Beds ⋅ 3.1 Baths ⋅ 10644619 MLS

Welcome to your home in the highly sought after Grassfield Meadows community of Chesapeake, zoned for the desirable Grassfield school district! This beautiful townhome features custom accent walls that add warmth and character throughout. With 4 spacious bedrooms and 3.5 bathrooms, the flexible layout is perfect for today's lifestyle. The first floor offers an ideal space for guests, a home office or an in-law suite. The open concept main living area is bright and inviting, great for entertaining or everyday comfort. Go out onto your private balcony to enjoy morning coffee or evening relaxation. The third-floor hosts three more bedrooms and two full baths, including a tranquil primary suite. Community amenities include a covered pavilion with grilling area, dog park, fitness park and playground for year-round enjoyment. Conveniently located near shopping, dining and major commuter routes, this move-in- ready home offers the perfect blend of style, comfort and convenience.

1837 Honey Milk Road, South Chesapeake

$539,999

4 Beds ⋅ 2.1 Baths ⋅ 10644558 MLS

Located in the highly sought-after Jolliff Landing neighborhood of Western Branch, this like-new home has tons to offer! Backing to a protected preserve, you’ll have added privacy with no future construction behind you. Featuring an open floor plan with a versatile bonus/flex room and beautiful LVP flooring throughout the main living areas. The gourmet kitchen is equipped with stainless steel appliances, a gas range, quartz countertops, and a custom tile backsplash. A large center island makes entertaining easy, while the cozy gas fireplace adds warmth and charm to the living space. Additional upgrades include smart blinds, smart ceiling lighting in the living room, and an updated primary walk-in shower with a glass door. The community provides amenities such as a pool, walking trails, parks and plazas with outdoor seating, a playground, natural preservation areas, and a state-of-the-art clubhouse with kitchen, conference room, and fitness center. New construction without the wait! Schedule your showing today! Open to a 1-year lease at $3,600 per month. If you're interested in leasing or would like more information about this option, please contact the listing agent.

2216 Hampton Roads Parkway, West Chesapeake

$599,000

5 Beds ⋅ 3 Baths ⋅ 10644309 MLS

Tired of expensive water and sewer bills, HOA restrictions, or dealing with the stress and cost of a fixer upper? Then this brand new home is exactly what you have been waiting for. Welcome to this stunning 2,600 sq. ft. open concept residence built by local award winning builder. Featuring 5 spacious bedrooms, including a first floor bedroom great for guests or multi generational living, and 3 full baths with upscale designer finishes throughout. Enjoy luxury features including granite countertops, ceramic tile, luxury vinyl plank flooring, a cozy fireplace, and a beautiful standalone soaking tub. With NO HOA, this property is superb for boat owners, campers, trailers, or anyone wanting freedom and flexibility without extra fees or restrictions. Located in a highly sought school district with flexible spaces wonderful for entertaining and everyday living. Everything is brand new, offering peace of mind and low maintenance living.

785 Caddie Street, South Chesapeake

$500,000

5 Beds ⋅ 3 Baths ⋅ 10644216 MLS

Situated on a corner lot in sought after Culpepper Landing, this spacious home is ready for new owners to make it their own. A formal living and dining room, both with hardwood floors greet you as you enter. A large living room with gas fireplace opens to the spacious kitchen that includes tons of cabinet space and granite counters. The eat-in kitchen provides access to the large fenced-in backyard, great for entertaining. A bedroom and full bath are also located on the first floor. Upstairs, the primary bedroom includes an attached bath with double vanity, soaking tub and walk-in shower. Three more bedrooms and an impressive laundry room complete the second level. The attached 2-car garage provides excellent additional storage space. Neighborhood amenities include a clubhouse, exercise room, playgrounds, pool and more!

700 Canoe Street, South Chesapeake

$577,740

3 Beds ⋅ 3 Baths ⋅ 10644251 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.

2164 Edwin Drive, South Chesapeake

$506,990

2 Beds ⋅ 2 Baths ⋅ 10644247 MLS

The Asheville, one of our quad-style homes, features two bedrooms and two 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. $10,000 closing cost incentive with use of preferred lender! Photos and renderings are from builder's library, actual finishes and features may vary.

2150 Edwin Drive, South Chesapeake

$545,000

4 Beds ⋅ 2.1 Baths ⋅ 10643841 MLS

Welcome to this remarkable Pines of Warrick home in highly sought-after Great Bridge—affectionately touted by locals as "The Promised Land!" : ) … also known for it's highly acclaimed Great Bridge school district. This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of timeless charm and thoughtful updates. The renovated kitchen features gorgeous custom high-end cabinetry, granite countertops, THE PRETTIEST backsplash with beautiful beveled ceramic subway tile, and a perfect breakfast nook. Rich hardwood flooring and crown moulding, formal living spaces include dining room and private library/office with French doors providing flexibility for working from home or entertaining. The inviting family room features a wood-burning fireplace (gas line remains if desired) and opens to a great sunroom overlooking the spacious deck and large fenced backyard. The first floor primary suite offers double closets and a beautifully remodeled en-suite bath, while the secondary bedrooms are exceptionally large! The finished room over the garage with custom built-ins makes an ideal media room, playroom, 4th bedroom or hobby room. Extensive recent improvements provide peace of mind, including TWO new zoned HVAC heat pump systems (inside and out) installed March 2025, condensate drain pump with alarm (April 2025), crawlspace encapsulation with new vapor barrier, dehumidifier, lighting, extended access door, and sump system to divert gutter and HVAC condensate drains (2020). Additional updates include a new garage door and opener (2021) and newer dishwasher. Pride of ownership shines throughout this lovely home—don't miss this beauty!

424 Pines Of Warrick Drive, South Chesapeake

$525,000

4 Beds ⋅ 2 Baths ⋅ 10643319 MLS

Over $42,420 in Renovations! Beautiful Ranch with screened porch, detached garage, and circular driveway. Open Floor plan, spacious, ready for New Owners! Please see attached upgrade sheet.

858 Waters Road, South Chesapeake

$570,000

4 Beds ⋅ 2.1 Baths ⋅ 10643685 MLS

Stunning 4 bedroom beautifully maintained home in Hickory Manor, a sought-after neighborhood known for its desirable schools and many amenities offered by the association. The home offers modern comfort and style throughout. The recently updated upstairs bathroom features sleek finishes and contemporary design, adding a fresh, luxurious touch. With its like-new condition, open living spaces, and thoughtful upgrades, this home is move-in ready and perfect for today’s lifestyle. Ideally located near shopping, dining, and the interstate. This home shows like new and is beautifully maintained throughout. The wonderful HOA offers fantastic amenities including a pool, grounds maintenance, trash pickup, gym, clubhouse/pool room, and monthly community events.

1910 Bexley Lane, South Chesapeake

$539,999

4 Beds ⋅ 2.1 Baths ⋅ 10643469 MLS

Experience refined living in the sought after Western Branch area, where timeless design meets today's comfort. This well maintained 4-bedroom, 2.5-bath home offers over 2,500 Sqft of beautifully appointed living space with soaring cathedral ceilings that create an open, light-filled atmosphere from the moment you enter. Kitchen upgrades include granite countertops, and ample storage providing both style and functionality. The spacious primary suite serves as a private retreat, complete with a beautifully renovated bathroom. Step outside to your own backyard oasis, where a spacious deck and patio overlook a fully fenced enclosed yard, perfect for outdoor entertaining, or simply relaxing. Additional highlights include an attached two-car garage and a whole-home water filtration system. Conveniently located near I-664. Local shipyards, medical facilities, military bases, shopping and restaurants. Best of all, enjoy the freedom of no HOA!

2720 Deerfield Crescent, West Chesapeake

$565,000

5 Beds ⋅ 2.1 Baths ⋅ 10642758 MLS

COMING SOON-TWO CAR GARAGE! The sellers are converting the garage back to its original two-car setup with two new garage doors. Inside, the biggest updates are already done. The kitchen features quartz countertops and a tile backsplash, and the primary bathroom has been fully renovated. Major updates include roof 2018, HVAC and water heater 2021, primary bath 2021, and kitchen/appliance package 2025, along with additional flooring updates throughout much of the home. HOME WARRANTY AVAILABLE.

4308 Galston Court, West Chesapeake

$570,000

4 Beds ⋅ 2.1 Baths ⋅ 10642996 MLS

Welcome to luxury, low-maintenance living in the highly sought-after Westfield at Hickory Manor! This beautifully upgraded Galloway Model, built in 2018, offers 2,059 sq ft of stylish, thoughtfully designed living space with quality finishes throughout. The open-concept layout is superb for everyday living and entertaining, featuring spacious, light-filled rooms, an upgraded kitchen, a private primary suite, and flexible additional bedrooms. Enjoy resort-style amenities including a pool, 24-hr fitness center, clubhouse/community center, and playgrounds. Located in the sought-after Hickory School District with easy access to shopping, dining, military bases, major interstates, and more, this move-in ready home offers comfort, convenience, and lifestyle. Schedule your private showing today!

508 Cavendish Way, South Chesapeake

$524,900

3 Beds ⋅ 2.1 Baths ⋅ 10643243 MLS

Beautifully maintained 55+ condominium in the desirable Greenbrier area. Built by Stephen Alexander Homes, this elegant residence blends historically inspired architecture with timeless craftsmanship, featuring 10-foot ceilings, transom windows, custom crown moulding and trim work, and hardwood floors. Offering 3 bedrooms plus a spacious room over the garage, this home provides exceptional flexibility for guests, hobbies, or a home office. The gourmet kitchen with double ovens is designed for everyday living and entertaining. An interior private elevator provides effortless access to both levels. Additional features include an attached two car garage with overhead storage and utility sink, brand-new dual-zone HVAC, a Rinnai tankless water heater, and a freshly painted exterior. Relax on the spacious front porch or entertain on the private tiled patio with a SunSetter retractable awning. Whole-house audio and family room surround sound add comfort and ambiance throughout. Move in ready!

1016 Briars Landing, South Chesapeake

$599,000

6 Beds ⋅ 4.1 Baths ⋅ 10642445 MLS

Rare opportunity to own a beautifully updated 6-bedroom, 4.5-bath home featuring a private, fully equipped in-law suite for multigenerational living, extended family, guests, rental income, or a private home office. The main residence offers 5 spacious bedrooms, 3 full baths, and a stunning remodeled kitchen with quartz countertops, sleek high-gloss cabinetry, stainless steel appliances, and space for a large center island. The separate in-law suite lives like its own home, complete with an open loft-style bedroom, 1.5 baths, walk-in closet, full-size laundry, upgraded kitchen with quartz counters and stainless appliances, and generous living space. Recent upgrades include renovated baths, new windows, patio doors, and Nest thermostats. Step outside to your backyard oasis featuring an 8-foot in-ground pool with newer liner, filter, and pump, plus a built-in deck bar ideal for entertaining. Conveniently located near shopping, dining, schools, military bases, beaches, and major commuter routes.

501 Thornloe Ln Lane, South Chesapeake

$550,000

5 Beds ⋅ 3 Baths ⋅ 10642122 MLS

Rare find in sought after neighborhood. Spacious and flexible floor plan features 5 bedrooms and 3 full baths, 4 closets in primary bedroom, huge family room and a flex room with fireplace that would be perfect for an office, library or study. Large back bedroom has its own entrance with easy, close access to full bath. Workshop has electricity. Well maintained by original owners. Make an appointment today to view this treasure and update to make it your own.

1213 Lakeford Place, South Chesapeake

$524,900

3 Beds ⋅ 2 Baths ⋅ 10642197 MLS

Recently appraised at $600k, opportunities for instant equity like this are rare. Situated on 5 acres in Chesapeake's Grassfield High School district, this move-in-ready 3-bed, 2-bath home features a 720 sq. ft. detached, fully powered workshop—great for a contractor or hobbyist. Located near Deep Creek Park and the Dismal Swamp Canal Trail, enjoy peaceful surroundings, deer sightings, and views of sailboats on the Intracoastal Waterway. A 2012 renovation opened the layout, updated the kitchen and baths, and added central duct HVAC. Recent improvements include a new 3-ton heat pump (2023), whole-house paint (2024), new carpet (2025), and new utility room vinyl flooring, plus upgraded electrical, plumbing, and replacement windows. Outdoors features a fenced yard with mature fruit and fig trees throughout the property. Motivated seller facing an unexpected military relocation (PCS). Contact agent for more information!

317 George Washington Highway S, South Chesapeake

$543,740

2 Beds ⋅ 3 Baths ⋅ 10641942 MLS

The Asheville, one of our quad-style homes, features two bedrooms, a large bonus room and 3 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. Incentives with use of preferred lender! Photos and renderings are from builder's library, actual finishes and features may vary. Photos and renderings are from builder's library, actual finishes and features may vary.

2162 Edwin Drive, South Chesapeake

$525,000

5 Beds ⋅ 3.1 Baths ⋅ 10641817 MLS

Tucked away on a quiet end street shared by only three other homes, this brand new construction offers a rare sense of privacy while still being close to everything Western Branch has to offer. With minimal traffic and a park-like setting, it’s the kind of place where evenings are quiet, kids can play outside, and home truly feels like a retreat. Inside, this thoughtfully designed 5 bed, 3.5 bath home is built for both comfort and flexibility. The open concept living area flows effortlessly into a spacious, modern kitchen. A 1st floor primary bedroom provides the ease of main level living, while a 2nd floor owner’s suite creates the ideal private escape or multi-generational option. Additional highlights include a two car attached garage, generous bedroom sizes, and beautifully planned finishes throughout all while located within the sought after Western Branch school district. You’re not just purchasing new construction - you’re securing space, privacy, flexibility, and a lifestyle.

5041 Queen Street, West Chesapeake

$525,000

5 Beds ⋅ 3.1 Baths ⋅ 10641815 MLS

Tucked away on a quiet end street shared by only three other homes, this brand new construction offers a rare sense of privacy while still being close to everything Western Branch has to offer. With minimal traffic and a park-like setting, it’s the kind of place where evenings are quiet, kids can play outside, and home truly feels like a retreat. Inside, this thoughtfully designed 5 bed, 3.5 bath home is built for both comfort and flexibility. The open concept living area flows effortlessly into a spacious, modern kitchen. A 1st floor primary bedroom provides the ease of main level living, while a 2nd floor owner’s suite creates the ideal private escape or multi-generational option. Additional highlights include a two car attached garage, generous bedroom sizes, and beautifully planned finishes throughout all while located within the sought after Western Branch school district. You’re not just purchasing new construction - you’re securing space, privacy, flexibility, and a lifestyle.

5036 Queen Street, West Chesapeake

$569,900

4 Beds ⋅ 3 Baths ⋅ 10641728 MLS

Welcome to The Dogwood in Jolliff Landing, one of the community’s most sought after floor plans offering the perfect blend of luxury, flexibility, and everyday comfort. This beautifully designed ranch features 4 bedrooms, 3 full baths, and 2 true primary suites including a spacious upstairs FROG suite with its own private full bath ideal for multigenerational living, guests, a private retreat, office, or media space.Why wait on new construction when this move in ready home already offers the upgrades, space, and versatility buyers are searching for? The open concept design is perfect for entertaining while the resort style community amenities including a clubhouse, pool, playgrounds, sports field, and scenic sidewalks create a lifestyle buyers fall in love with.In a neighborhood full of inventory, this layout stands apart. Schedule your private tour today before this opportunity is gone.

5103 Annapolis Drive, West Chesapeake

$559,000

4 Beds ⋅ 2.1 Baths ⋅ 10641342 MLS

Spacious Riverwalk home offering over 3,372 sq. ft. with 4 bedrooms, 2.5 baths, a two-car garage, 2 decks with private views of the lake. Recent improvements include gas HVAC in 2022, roof approximate 6 years old, Anderson windows with warranty, and new kitchen appliances. Large family room and kitchen - great for everyday life and easy hosting. Enjoy Riverwalk amenities including clubhouse, pool, playgrounds, and tennis courts. A wonderful opportunity to personalize a spacious home in a sought-after Chesapeake community. Close to the Hospital, Dining, Shopping and Interstates. Home needs TLC. Buyer can make it their own.

220 Marsh Island Drive, South Chesapeake

$550,900

4 Beds ⋅ 2.1 Baths ⋅ 10641029 MLS

This traditional floor plan offers 4 Bedrooms, 2.5 Baths, and 2420 sq ft. Enjoy the grand design of the Primary Suite with a spacious Walk-In Closet from the Primary Bath. The dining room, kitchen & family room on the first floor allow for many entertaining evenings at home. The open floor plan provides ample space with room to stretch out. 2nd floor is spacious with 4 bedrooms & utility room. The Estates at Jolliff Landing will be a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and a tree-lined sidewalks. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

2206 Wilmington Avenue, West Chesapeake

$539,900

4 Beds ⋅ 2 Baths ⋅ 10641024 MLS

A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch-style living with 4 bedrooms, including a large finished room over the garage. From the front porch to the Family Room also open to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, a community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your doorstep in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details, as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5 pm at 5023 Annapolis Drive.

2204 Wilmington Avenue, West Chesapeake

$550,900

4 Beds ⋅ 2.1 Baths ⋅ 10641022 MLS

This traditional floor plan that offers 4 Bedrooms, 2.5 Baths, and 2400+ sq ft. Enjoy the grand design of the Primary Suite with a spacious Walk-In Closet from the Primary Bath. The dining room, kitchen & family room on the first floor allow for many entertaining evenings at home. The open floor plan provides ample space with room to stretch out. 2nd floor is spacious with 4 bedrooms & utility room. The Estates at Jolliff Landing will be a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and a tree-lined sidewalks. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

2205 Hampton Road, West Chesapeake

$553,900

3 Beds ⋅ 3 Baths ⋅ 10641052 MLS

Enjoy peaceful country living on 1.77 acres in the highly sought-after Hickory School District! This charming 3-bedroom, 3-full-bath home offers plenty of space both inside and out, making it perfect for those seeking privacy, comfort, and room to roam.Step inside and discover a welcoming open layout designed for everyday living and entertaining. The spacious heated sunroom deck provides the perfect spot to relax year-round. Huge pantry storage room off kitchen to keep those grocerie store runs to a minimum. The expansive 1.77-acre lot includes a chicken coop, large detach garage, fenced area, carport, and open fields making this property ideal for hobby farmers, homesteaders, or anyone looking to embrace a more self-sufficient lifestyle. With plenty of room for gardening, recreation, and outdoor activities, the possibilities are endless. The back half of detached garage needs work, but has lots of potential for a nice workshop, game room, mancave, apartment, etc.

2420 Mount Pleasant Road, South Chesapeake

$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

$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

$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

$575,000

4 Beds ⋅ 2.1 Baths ⋅ 10635488 MLS

Newly Built 4 Bedroom 2 & 1/2 bath home! Featuring the top of the line finishes, including granite counters in the kitchen and baths, Stainless steel appliance package, stainless farmhouse sink, and electric fireplace. Lots of kitchen storage & work space with an island & butler's pantry. The primary suite has a tray ceiling, 2 walk-in closets, and an ensuite bath with a drop-in tub and a deluxe-sized shower. All rooms are generously sized with ample closet space throughout the home. Premium LVP on the first floor and carpet upstairs. You’ll also appreciate the large 2-car attached garage with an extra wide driveway and the included whole-house water treatment system. Make an appointment today! Owner Agent.

3620 Parr Lane, South Chesapeake

$545,900

3 Beds ⋅ 2.1 Baths ⋅ 10635941 MLS

Welcome to 1251 Veranda Way! This beautiful home features 2,578 sq ft, 3 bedrooms, 2.5 baths, a 1st floor flex room with built in bookshelves that could be 4th bedroom, a bonus 2nd living room/sitting area on the second floor along with a home office. With a welcoming covered front porch, you enter into an inviting foyer area and notice the bright & open Dining Room. The kitchen features stainless appliances, tile backsplash, recessed lighting & a bar that overlooks the breakfast area & living room with gas fireplace. The 2nd floor is where you find the large Primary Bedroom with a private bath, dual sinks & dual walk-in closets. Large private wooded backyard with a view of the pond beyond the trees. New Carpet throughout bedrooms and flex room. Located minutes from the Greenbrier area of Chesapeake with easy access to shopping, restaurants & highways.

1251 Veranda Way, South Chesapeake

$599,900

4 Beds ⋅ 2.1 Baths ⋅ 10635073 MLS

Welcome to resort-style living in highly sought-after Hickory Manor! Beautifully maintained and showing like brand new, this stunning home offers the perfect blend of modern comfort and style. The bright, open-concept living spaces are highlighted by a showstopping kitchen featuring upgraded cabinets, premium countertops, and a custom backsplash added after the original build. Beyond the pristine, move-in-ready interior, you will enjoy a low-maintenance lifestyle with unparalleled HOA amenities that are truly one-of-a-kind in Hickory. Enjoy worry-free living with grounds maintenance and trash pickup included. Spend weekends at the resort-style pool with its outdoor kitchen and cabana, hit the 24/7 fitness center, or host parties in the expansive clubhouse great room. The neighborhood boasts scenic trails, 5 community lakes, a playground, and vibrant monthly community events. Schedule your tour today!

355 Middleton Way, South Chesapeake

$509,900

4 Beds ⋅ 2.1 Baths ⋅ 10634235 MLS

Welcome to this beautifully maintained condo in one of Chesapeake's most desirable 55+ communities where, comfort and convenience come together in a park-like setting. Surrounded by mature landscaping, a scenic pond, and inviting seating area with a fireplace, this neighborhood offers a relaxed lifestyle with thoughtfully designed community spaces. Inside, this spacious home offers four bedrooms and two and a half bathrooms with a layout designed for both everyday living and entertainment. The primary suite provides a comfortable retreat with generous space and privacy. An in-unit elevator adds exceptional convenience and accessibility between levels. Call today for your private tour.

925 Cranberry Drive Unit 70, South Chesapeake

$550,900

4 Beds ⋅ 2.1 Baths ⋅ 10632280 MLS

This traditional floor plan offers 4 Bedrooms, 2.5 Baths, and 2420 sq ft. Enjoy the grand design of the Primary Suite with a spacious Walk-In Closet from the Primary Bath. The dining room, kitchen & family room on the first floor allow for many entertaining evenings at home. The open floor plan provides ample space with room to stretch out. 2nd floor is spacious with 4 bedrooms & utility room. The Estates at Jolliff Landing will be a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and a tree-lined sidewalks. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

MM Sycamore, West Chesapeake

$579,005

4 Beds ⋅ 2.1 Baths ⋅ 10632324 MLS

This traditional floor plan offers 4 Bedrooms, 2.5 Baths, and 2420 sq ft. Enjoy the grand design of the Primary Suite, which features a spacious Walk-In Closet adjacent to the Primary Bath. The open floor plan provides ample space for entertaining. 2nd floor is spacious with 4 bedrooms & utility room. Upgrades include- Kitchen: Two tone cabinets, Quartz counter top, backsplash, pre-wired pendant lights. PBTH: Granite vanity top, Tile shower. LVP in Dining, Laundry & Family rooms. Recessed LED in PBR & Fam room. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and a tree-lined sidewalks. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Call for construction timeline updates. Model home open daily 12-5:00 pm at 5023 Annapolis Drive.

2211 Hampton Roads Parkway, West Chesapeake

$501,763

4 Beds ⋅ 3.1 Baths ⋅ 10631709 MLS

Ready Now: Luxury End Unit townhome condo w/rear load 2 car garage. Luxury LVP floor in select living areas, 2nd floor: Kitchen GE Cafe Matt Black appliances including refrigerator, center island w/shiplap, living room linear fireplace w/shiplap, pantry, living area w/Office/flex room, 1st floorbr/flex room, hall bath & mudroom. 3rd floor Primary w/ceramic shower-2 shower heads, dual sinks, 2 closets, 2 br's - jack & jill bath, linen closet, laundry. Quartz tops kitchen & all baths, covered entry, fenced front yard w/gate to multi trail, 2nd floor Deck off dining area. 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. 2-10 home warranty, master insurance, trash pick up, private streets, city water/sewer, guest parking, multipurpose trails with lake and fountain. Only 56 homes. Central Greenbrier location.

1070 Mesa Loop, South Chesapeake

$505,223

4 Beds ⋅ 3.1 Baths ⋅ 10631708 MLS

Ready Now:LuxuryTownhome w/2-car garage, covered entry,fenced front yard w/gate to multi trail,covered entry. 19x12 rear deck,LVP floors select areas.2nd floor:Kitchen center island w/shiplap, GE Cafe Matte Black appliances w/refrigerator,pantry,living area w/linear fireplace w/ shiplap surround w/built ins,dining area access to covered front deck.3rd flr: Primary:tile shower 2-shower heads, dual sinks, 2 closets, 2 bedrooms, full hall bath, linen closet, laundry. 1st floor flex room/bedroom dual entry bath, mudroom. Quartz tops in kitchen and baths-designer mirrors, wood shelving in 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. 2-10 home warranty, master insurance, trash pick up, private streets, city water/sewer, guest parking, multipurpose trails with lake and fountain. Only 56 homes. Central location in the Greenbrier area. .

1072 Mesa Loop, South Chesapeake

$529,900

5 Beds ⋅ 3 Baths ⋅ 10631480 MLS

This is one of those rare homes that truly supports multi gen or other uses. TRUE in law suite with kitchenette full LARGE bath, living and bedroom, private access. The roof, paint, carpet dishwasher ALL NEW to get ready to SELL ! Just a little personalization and this could be your dream home. Its just waiting for you. Full brick, masonary fireplace, oversized deck, extra driveway and a covered parking area. City and Zillow records not reflective of the current dwelling. Three generous bedrooms plus room over the garage AND the suite make this home a winner for you!

229 Fresno Drive, South Chesapeake

Chesapeake, VA Properties between $500,000 and $600,000 for Sale

Newest Chesapeake, VA Properties between $500,000 and $600,000 for Sale