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

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.

2154 Edwin Drive, South Chesapeake

$574,777

5 Beds ⋅ 3 Baths ⋅ 10638985 MLS

Move in Ready! Stunning new construction home built by experienced and award-winning builder! The spacious Swan model features an open-concept first floor with a generous living room, gourmet kitchen with custom cabinets and crown molding, a large granite island, stainless steel appliances, and a dining area made for entertaining. You'll also find a versatile bedroom or study and a full bathroom downstairs. Upstairs, the luxurious primary suite boasts two walk-in closets and a spa-inspired bath with LVT flooring, a soaking tub, tiled shower, double vanity, and private water closet. Three additional large bedrooms, a full hall bath, and a convenient laundry room round out the upper level. With upscale finishes throughout—9-foot ceilings, elegant LVT and carpet flooring, and an electronic fireplace with mantle—this home delivers comfort, beauty, and modern flair.

2515 Deal's Creek Court, South Chesapeake

$599,900

4 Beds ⋅ 3 Baths ⋅ 10638728 MLS

Come see this solid, all brick 2 story home sitting on a quiet cul-de-sac lot with almost half an acre. This well maintained home offers 3,444 sq. feet with 4 bedrooms and 3 full baths. On the first floor you will find a desirable, massive primary bedroom and second bedroom with hallway full bath. The first level also features a large foyer, dining room, family room and gorgeous living room with built in bookshelves, pocket doors, fireplace & cathedral ceilings looking into an upstairs loft area. Walk into a large kitchen with breakfast area that leads to a 4 seasons sunroom overlooking a newer fully fenced backyard with newer above ground salt water pool. Windows galore with tons of natural light throughout the home. Downstairs laundry room completes the first floor. Upstairs, a spacious 3rd bedroom with full bath and walk-in closet. You will find the 4th oversized bedroom over the garage that feels a separate area. Spacious 2 car garage. This home has a whole house backup generator, tankless water heater, storage shed and well irrigation system. Fresh paint within the last few years. Minutes from all Western Branch Schools, baseball field, interstate and military bases.

3120 Deans Court, West Chesapeake

$575,000

4 Beds ⋅ 2.1 Baths ⋅ 10638907 MLS

$10,000 IN CLOSING COST ASSISTANCE OFFERED - use it to lower your interest rate or reduce your cash to close! Built in 2022 and move-in ready, this meticulously maintained Culpepper Landing home offers modern finishes and an open-concept layout. The gourmet kitchen features quartz countertops, a large island with seating, gas cooktop, double ovens, stainless steel appliances, under-cabinet lighting, walk-in pantry, and breakfast area. The family room features a gas fireplace with granite surround. LVP flooring, a private office, and drop zone complete the main level. Upstairs, the spacious primary suite includes a sitting area, two walk-in closets, double vanity, and Roman shower. Three additional bedrooms, a full bath, and laundry room with utility sink provide plenty of space. Enjoy the covered patio, tankless water heater, and two-car garage. Community amenities include a pool, playgrounds, dog park, golf-cart-friendly streets, and year-round events. Schedule your showing today!

776 Big Bear Lane, South Chesapeake

$599,900

4 Beds ⋅ 2.1 Baths ⋅ 10638501 MLS

Stunning 4-BR Home on Large Lot – No HOA! Experience modern living in this 2 year built, 4-bedroom, 2.5-bathroom gem located in the highly desirable Centerville Commons neighborhood. Combining exceptional curb appeal with an expansive layout, this property sits on an oversized lot offering rare privacy and freedom. Main Level Highlights: Grand Entrance: A welcoming foyer leads to an elegant formal dining room featuring a sophisticated tray ceiling. Open-Concept Great Room: Bright and airy with massive windows, premium Luxury Vinyl Plank (LVP) flooring, and a cozy central gas fireplace. Chef’s Kitchen: Features crisp white cabinetry, stainless steel appliances, a pantry, and an enormous quartz island over contrasting gray accent cabinets. Sunlit Dining: An attached eat-in area boasts large windows overlooking the sweeping backyard. Upper Level & Amenities: Architectural Details: A gorgeous stained staircase with wrought-iron spindles leads to the second floor. Spacious Bedrooms: Generous layouts.

644 Appalachian Court, South Chesapeake

$509,900

4 Beds ⋅ 2.1 Baths ⋅ 10638582 MLS

This beautifully maintained four-bedroom home blends modern living with traditional style comfort. It features updated 2.5 bathrooms (2025), a new fireplace mantel, and sleek new LVP flooring that flows seamlessly throughout the main living areas. The updated kitchen offers both style and functionality while fresh paint throughout gives every room a bright, move-in-ready feel. Step outside to enjoy the brand-new backyard deck, perfect for relaxing or entertaining. Located close to highways, military bases, and shops - the only thing missing is you!

1204 Elverton Court, West Chesapeake

$580,000

4 Beds ⋅ 3.1 Baths ⋅ 10638478 MLS

Spacious Huntington Woods Home with Pool! Located in the desirable Huntington Woods neighborhood, this expansive home offers over 3,500 square feet of living space and endless potential. Featuring vaulted ceilings, generous living areas, and a two-car garage, there is plenty of room to spread out and make this home your own.Step outside to enjoy the large in-ground pool, perfect for relaxing, entertaining, and making the most of warm summer days. Conveniently situated just minutes from Greenbrier Country Club, you'll enjoy easy access to golf, dining, shopping, and more. With its spacious layout, sought-after location, and opportunity to add your personal touch, this Huntington Woods property is ready for its next owner. Don't miss your chance to call it home!

1340 Danielle Court, South Chesapeake

$550,000

5 Beds ⋅ 3.1 Baths ⋅ 10638408 MLS

Looking for space? This spacious home offers over 3,000 sq ft of living space 5 bedrooms and 3.5 baths. There is a first-floor primary suite and an oversized bonus room which could be a 6th bedroom. The downstairs flooring and carpet was installed in 2024. The family room has a cozy stone gas fireplace. The large eat-in kitchen features stainless steel appliances and plenty of cabinet space. Enjoy outdoor living on the expansive deck overlooking the fully fenced backyard with gazebo and storage shed. Attic and crawl space are encapsulated and home is listed under appraised value.

1113 Crystalwood Circle, South Chesapeake

$569,900

4 Beds ⋅ 2.1 Baths ⋅ 10638424 MLS

Located in the highly sought-after Grassfield School District, this spacious home offers over 2,400 square feet of comfortable living space with 4 bedrooms, a dedicated study, and 2.5 bathrooms. The thoughtfully designed floor plan features a bright and inviting sunroom sitting area just off the kitchen. Continue outside to enjoy the large backyard, offering plenty of room for gardening, pets, or future entertaining. Recent updates provide added value and peace of mind, including a new hot water heater (2026), new air conditioner condenser (2025), new living room carpet (2026), updated downstairs toilet (2026), and new primary bathroom faucets (2026). Outdoor improvements include a back patio (2020), new back porch (2023), and new front porch/deck steps (2024), creating welcoming spaces to enjoy both the front and backyard.

1916 Orangewood Road, South Chesapeake

$582,000

5 Beds ⋅ 3 Baths ⋅ 10637811 MLS

One owner home which was custom designed and built in 1991. Situated in the heart of Great Bridge. 5 bedrooms, (1 downstairs is currently used as an office). 3 full baths, downstairs bath has ceramic tile and a shower. Primary bath was remodeled in 2024. Manufactured Hardwood floors were installed in the den and foyer in 2021 and in the LR, DR, and Kitchen in 2016. The Den has a cathedral ceiling, 2 skylights, a gas FP, built in cabinets and has a pass thru from the kitchen. Stainless steel appliances installed in 2018. There is a gorgeous and peaceful screened in back porch and a brick paver patio. Painted custom crown molding throughout the downstairs. A new concrete driveway and sidewalk was poured in 2021. Back yard is fenced but three different sections are owned by the 3 neighbors.

605 Foxgate Quarter, South Chesapeake

$550,000

5 Beds ⋅ 2.1 Baths ⋅ 10638238 MLS

Welcome to your ultimate retreat in the heart of Grassfield! Situated in a cul-de-sac in the highly sought-after Sawyers Mill community, this expansive 5-bedroom, 2.5-bath home features vaulted ceilings with a bright open floor plan. The large open kitchen is equipped with granite countertops, white shaker soft-close cabinets and drawers, stainless steel appliances, kitchen island and tile backsplash. Step through the relaxing sunroom onto a sprawling backyard deck serving as an outdoor oasis designed for grand-scale entertaining, summer barbecues, or peaceful evenings under the stars. The bedrooms are spacious, while the primary bedroom features tray ceilings, big walk-in closet, a large & elegantly designed en-suite bathroom. Conveniently located near shopping, dining, and major commuter routes while still enjoying the privacy of a cul-de-sac setting. This home offers interior comfort, plenty of outdoor entertaining space, privacy, modern updates, & community. This is a must see!

402 Undershot Court, South Chesapeake

$599,500

5 Beds ⋅ 4 Baths ⋅ 10638098 MLS

Welcome home to this spacious and well maintained home located on a corner lot in the desirable Grassfield School district! With 5 bedrooms and 4 full bathrooms, this home provides space for every day living and entertaining. The upstairs primary suite provides two closets, double vanity, stand up shower, and relaxing garden tub. The downstairs bedroom with en suite bathroom is perfect as a guest room or in-law suite. And you'll enjoy the kitchen which includes granite countertops, breakfast bar, updated appliances, and opens to the living room with fireplace and sunroom. Plus the wooded backyard provides plenty of privacy. Hurry and schedule your showing today!

705 Creekwood Drive, South Chesapeake

$599,900

3 Beds ⋅ 2.1 Baths ⋅ 10638060 MLS

ONE SPECIAL PRICE! First Time Buyer 5.5 rate, low down, NO PMI! 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 (A) welcomes you with an inviting full front porch, soaring two-story foyer and family room, and beautiful hardwood flooring throughout the main living areas. 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, designer finishes, and mudroom. The first-floor primary suite offers a custom walk-in closet, spa-like bath with quartz dual vanity, tiled shower, and private laundry. 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 Lane, South Chesapeake

$525,000

4 Beds ⋅ 2 Baths ⋅ 10637966 MLS

WOW! This backyard is an entertainer's dream! From the spacious vaulted den to the relaxing screened-in porch, you'll enjoy an incredible amount of living and entertaining space both inside and out, with .56 of an acre. The above-ground pool, partially recessed into the ground and only three years old, provides the look and feel of an inground pool without the added expense. The beautiful curb appeal sets the tone for this charming all-brick ranch. Inside, you'll find hardwood flooring throughout the main living areas, vinyl replacement windows, and a brand-new water heater. Don't miss this opportunity to own a home with great bones, fantastic outdoor living spaces, and room to make it your own! You can keep the dining room now set up as an office, including furniture, or convert back.

1103 Northmoor Court, South Chesapeake

$537,900

3 Beds ⋅ 3.1 Baths ⋅ 10637835 MLS

First Time Buyer 5.5 rate, low down, NO PMI! GPS 369 Scotland Ln. for site location.. see model home 910 Bernard Ln. open S/S 12-4. Coveted award-winning builder unveils newest neighborhood with sophisticated row homes and UPGRADES galore! 10’ midlevel ceilings, 9' other floors, oversized windows, and extensive hardwood flooring. First-floor BR w/ensuite bath for multi-generational living. Midlevel seamlessly connects Dining and Great Room w/fireplace for easy entertaining leading to covered screened porch overlooking nature. Chef’s kitchen w/10’ island, quartz counters, custom hood w/GE Cafe drawer microwave, 6-burner gas range and dishwasher. Luxurious primary retreat custom closet, spa bath oversized tiled shower, dual heads & large niche, dual vanities, and private water closet. laundry room. Secondary petite suite w/huge closet & ensuite bath. Nat. Gas Tankless water heater and 2 car garage. Professional ground and management services. Minutes to Greenbrier.

130 Lenas Way, South Chesapeake

$545,900

3 Beds ⋅ 3.1 Baths ⋅ 10637715 MLS

First Time Buyer 5.5 rate, low down, NO PMI! End Unit Fall delivery! Modern Design UPGRADES GALORE! Built by award-winning builder. Stunning home with curated features uniquely designed in this home. Extensive Mohawk flooring mid-level with Gourmet Kitchen with Custom hood, 10’ island, Quartz counters, GE Cafe 6 Burner Gas range, GE Cafe Dishwasher, and GE Cafe Microwave Drawer. 10' ceilings main, 9' First & Third Floors, Nat. Gas Tankless water heater, 2-zone HVAC. Primary bedroom with 2 custom closets and Spa ensuite bath. Second Petite Suite with ensuite bath and large walk-in closet. Large laundry room w/linen closet. First floor bedroom with ensuite bath! Extend your living on oversized Screened covered porch with composite decking. 2-car garage! LOW $95 condo fee- Cabana, Fire pits, Bocce ball and Professional landscape and lawn maintenance for easy living! Legacy is waiting for you!

908 Jennings Ln, South Chesapeake

$565,000

4 Beds ⋅ 4 Baths ⋅ 10636627 MLS

Private 4-bedroom, 4-bath home on a wooded corner lot in Inland Colony with .96 acre! Walk into the open kitchen with white cabinets, breakfast area & attached sunroom. Large living room with fireplace with separate porch and entrance. 2 bedrooms with a shared hallway bath. Circle around into another open living space with built in shelves and vaulted ceiling, attached back porch, full bathroom and large utility room. Primary bedroom is upstairs w/balcony, walk in closet & full bath. Loads of windows and natural light from every side. Full In-law suite with living room, kitchen, fireplace, bedroom, full bath and separate entrance making it great for multi-generational living or guests. Large fully fenced backyard. 2023 roof. RV hookup. Leafguard on gutters. U-shaped driveway for multi-car parking. Two sheds with electric for extra storage. Conveniently located near top-rated schools, shopping, dining and nearby water access along the Elizabeth River. Seller is offering 2.75% VA assumption to VA buyers with substitution of eligibility.

1137 Inland Road, South Chesapeake

$545,900

4 Beds ⋅ 2.1 Baths ⋅ 10637350 MLS

The beautiful 4 bdrm Buxton model features a downstairs primary bedroom! Throughout this charming, tree-lined neighborhood are an assortment of exceptional amenities including a resort-style pool, community trails, pocket parks & plazas w/ outdoor seating, a playground, natural preservation areas & state-of-the-art clubhouse w/ kitchen, conference room, & fitness center. This homes gourmet kitchen features an upgraded appliance package, including gas range, upgraded granite countertop, & glass subway tile backsplash. 9 foot ceilings on both 1st & 2nd levels & durable LVP flooring in select areas of 1st level. The primary bdrm, w/ lighted tray ceiling, has an en-suite that includes double vanity w/ granite tops, a soaking tub, & 5' glass-enclosed shower. Gas heat & tankless hot water heater.

5025 Duxbury Road, West Chesapeake

$589,900

4 Beds ⋅ 2.1 Baths ⋅ 10637132 MLS

Welcome to this beautifully maintained 4 bedroom, 2 and a half bath, all-brick ranch in the Grassfield School District of Chesapeake. This home features updated eat-in kitchen to include granite counter tops, stainless steel appliances (KitchenAid Refrigerator), gas range, shaker cabinets, and fresh paint. Enjoy an open layout with a very spacious great room, vaulted ceilings and a gas fireplace. French doors offer privacy to the formal dining, living room/office. Stunning bamboo floors throughout the kitchen and living areas. The large finished bedroom over the garage offers new LVP flooring, lighting, shelving, built in reading nook or can be used as a bed. Major system upgrades include TRANE HVAC system installed in 2021 with duct work replaced and system zoned in 2025. RainSoft reverse osmosis, enclosed crawl space with dehumidifier, insulated garage doors, updated vents and a newer gas water heater. Half bath located next to the mudroom/laundry room, washer & dryer to convey. New carpet in all main floor bedrooms. Enjoy outdoor living on your covered front porch or in your private fenced in backyard and deck. Expansive attic space for storage and extended driveway for additional parking. A truly move-in-ready Chesapeake home, minutes to shopping, dining, and interstate access. Please ask for the detailed upgrade list of extensive repairs and improvements. The home has been meticulously maintained with major system updates throughout.

817 Doe Run Drive, South Chesapeake

$599,900

3 Beds ⋅ 2 Baths ⋅ 10636653 MLS

RARE OPPORTUNITY TO OWN A RANCH ON 3 PRIVATE ACRES IN GREAT BRIDGE. THIS SPACIOUS 3 BED, 2 BATH HOME OFFERS APPX. 2500 SQ. FT. OF COMFORTABLE SINGLE LEVEL COUNTRY LIVING WITH TIMELESS CHARM. HOME COMES WITH 2 CAR SIDE LOADING ATTACHED AND A 2 CAR DETACHED SIDE LOADING GARAGES. ENJOY THE NEARBY DINING, SHOPPING, AND TOP RATED GRASSFIELD & HICKORY SCHOOLS. THE ATTACHED/DETACHED GARAGE, FLORIDA/SUN ROOM, AND OUTDOOR SPACE PROVIDES PLENTY OF ROOM FOR ACTIVITIES. ROOF WAS REPLACED WITHIN 5 YEARS. WATER HEATER 2018, GUTTERS/VINYL/& HVAC REPLACED APPX 2009.

645 Ravenwoods Drive, South Chesapeake

$600,000

4 Beds ⋅ 3 Baths ⋅ 10636441 MLS

Home back on the market no fault of the seller's. Welcome to this beautifully upgraded Dogwood, built by Wirth, at 2307 Tybee Loop, built in 2021. The exterior impresses with premium stacked stone skirt and pillars. Inside, designed for seamless first-floor living, the main level features an open-concept eat-in kitchen with durable LVP flooring, a mosaic tile backsplash, and a sliding glass door to the screened in porch and deck. The kitchen boasts premium pull-out cabinets and a bump-out for extra storage. Convenient electric blinds service this kitchen area, the living room, and the primary. Extended by 5 feet allowing direct access to the outside, the primary suite features his-and-hers closets, an en-suite with dual vanities, and a custom tiled shower. An additional feature in the hall bathroom is the specialty walk-in jet tub. Upstairs has a spacious loft, a private en-suite, and walk-in attic space for storage. Relax on the screened porch overlooking a fully landscaped yard, backed by a whole-house 22kw Generac generator.

2307 Tybee Loop, West Chesapeake

$539,900

4 Beds ⋅ 2.1 Baths ⋅ 10636555 MLS

Some houses make you feel like a guest. This one makes you never want to leave. Spread across two spacious stories in one of Chesapeake's most sought-after communities, this home was built for people who actually use their space — whether that's splashing in the private pool on a Virginia summer afternoon, hosting a backyard cookout on the deck, or just enjoying the rare luxury of a completely fenced yard where nobody can see in. Inside, the layout flows the way life actually does: room to cook, room to gather, room to disappear into your own corner. Four generous bedrooms upstairs mean everyone has their own space. The half-bath on the main level keeps guests out of your business. And the attached 2-car garage means no fighting for the driveway. This is the kind of house that sells itself — the only question is whether someone else will schedule a tour before you do.

936 Saddleback Trail Road, South 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

$600,000

4 Beds ⋅ 3.1 Baths ⋅ 10636294 MLS

Welcome to a home that feels warm, inviting, and designed for everyday living. The stunning custom kitchen is both beautiful and highly functional, featuring floor-to-ceiling cabinetry, a huge island with quartz countertops, and hidden additional storage under the stairs. Hardwood floors flow throughout the first floor, where the gas fireplace serves as a beautiful focal point in the main living room with an open line of sight to the kitchen—perfect for entertaining. A formal dining room sets the stage for special occasion dinners, while a half bath and additional sitting room or office add flexibility. Upstairs offers 4 bedrooms, 3 full bathrooms, and a dedicated laundry room, making busy mornings easier for everyone. At the end of the day, unwind on the deck overlooking the woods and enjoy the privacy and peaceful retreat this home offers.

800 Aaron Culbreth Court, South Chesapeake

$585,000

3 Beds ⋅ 2.1 Baths ⋅ 10635941 MLS

Welcome to 1251 Veranda Way! This beautiful home features 2492 sq ft, 3 bedrooms, 2.5 baths, a 1st floor flex room with built in bookshelves that could be possible 4th bedroom. 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, large soaker tub, dual sinks & dual walk-in closets. The other 2 bedrooms, the hall bath, a sitting/loft area along with a room for a home office. 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

$583,740

4 Beds ⋅ 2.1 Baths ⋅ 10635609 MLS

Summer Move-In! Welcome to the Shenandoah at Retreat at Edinburgh -Chesapeake’s premier 55+ low-maintenance community! Enjoy luxury townhome living with a modern open-concept design, gourmet kitchen with quartz countertops and stainless steel appliances, and a sunlit family room perfect for entertaining. The first-floor primary suite offers a spa-inspired bathroom, featuring a walk-in shower, and oversized walk-in closet, while upstairs features three spacious bedrooms, a loft, and ample storage. Community amenities include a resort-style pool, clubhouse, fitness center, dog park, walking paths, and more. Embrace the ultimate active adult lifestyle near fine dining, shopping, and beautiful parks. Photos and renderings are from builder's library, actual finishes and features may vary.

2009 Barton Lane, South Chesapeake

$598,000

5 Beds ⋅ 3.1 Baths ⋅ 10635255 MLS

Location, Location, Location. 5 bedrooms 3.5 baths. Quick Sale Opportunity! Seller is motivated and offering a $10,000 flooring allowance or to be used at your discretion with an acceptable offer! The desired area of Kemp Bridge offers a fantastic chance to own in Chesapeake while customizing to your style. Great layout, strong value, and priced for buyers ready to move quickly. Opportunities like this don’t last—schedule your showing today!

1423 Kemp Bridge Lane, 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

$574,900

4 Beds ⋅ 2.1 Baths ⋅ 10633505 MLS

Welcome home to your brand-new waterfront retreat! This stunning new construction home offers 2,235 square feet of beautifully designed living space, featuring 4 bedrooms and 2.5 baths, with NO HOA! Perfectly situated on a canal/river, this property is an absolute dream for water enthusiasts. Launch your kayak, paddleboard, or small craft right from your own backyard, or take advantage of the ultra-convenient public boat launch located just next door! Inside, enjoy all the modern luxuries and pristine finishes that only new construction can offer, with an open floor plan designed for effortless entertaining and everyday living. If you have been dreaming of a turnkey waterfront lifestyle where every day feels like a vacation, your search ends here!

2800 Meadow Wood Drive E, West Chesapeake

$516,000

5 Beds ⋅ 4 Baths ⋅ 10632813 MLS

Welcome to your new beautiful brick home in the desirable Georgetown Colony neighborhood. This spacious home offers 3,569 square feet of living space with an in-law-suite with kitchenette. FROG has full bath. 3 bedrooms have their own bathrooms. This home is perfect for comfortable living and gourmet kitchen for entertaining. Spacious pantry with customs made barn doors. It also provides multiple living areas, spacious bedrooms, and plenty of natural light throughout the home. Solar Panels. This beautiful brick home is located near shopping, dining, schools, close to major commuting routes while still offering the charm of a quiet neighborhood in a cute cul-de-sac. The Georgetown area is known for its well-maintained homes and strong sense of community, making it a great place for you to live. So don't wait.

316 Citizen Circle, Central 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

$550,900

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 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. 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

$525,000

5 Beds ⋅ 3 Baths ⋅ 10631735 MLS

Closing Costs Assistance. The Seller may accept an offer Contingent on the Buyer selling their home. Beautiful brick home built by the seller on a large cul-de-sac. Walking in this gorgeous home is breathtaking, Large Living room w/ nice size dining rm, the home was 4 large bedrooms & could have a 5th bedroom w/ the finished room over the garage, Very large kitchen w/breakfast rm, HUGE family room with high ceiling and a fireplace, enough space for a large family to get together, 3 full bathrooms, another large room with a fireplace, and sliding glass doors that go on to a large covered patio. House sits on a LARGE lot with a firepit in backyard. Home has a lot of space for a large family or a family that is moving in together it would be ideal. Lots of storage. Unfinished attic space but could be converted into more living space if needed. Near Shopping and Interstates. Driveway could hold 8 cars easily. Seller is willing to pay Closing costs for buyer.

4624 Westborough Drive, West Chesapeake

$549,500

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

$529,999

4 Beds ⋅ 3 Baths ⋅ 10630827 MLS

Welcome Home!!! All-brick. Newly updated and designed for how you actually want to live.This 4-bedroom, 3 full bath home brings together space, clean upgrades, and a level of comfort you’ll feel the moment you walk in. The moment you walk in, enjoy New LVP flooring runs throughout including the primary, paired with fresh paint that gives the entire home a crisp, elevated finish and feel. The kitchen has been refreshed with newly painted cabinetry, creating a look that feels both modern and timeless.Skylights bring in natural light in all the right places, with the roof being 4yr. old.And then there’s the lifestyle... freshwater fishing just steps from your door. Quiet mornings. Reset evenings. No extra drive required.This isn’t just updated... it’s aligned, intentional, and ready for its next owner.

4032 Lakeview Drive, West Chesapeake

$500,000

4 Beds ⋅ 2.1 Baths ⋅ 10626438 MLS

Opportunity awaits! Whether you're an investor, renovator, or buyer looking to build equity, this property offers incredible potential. With the right updates and vision, this home could truly shine again. Great for someone ready to renovate and make it their own or transform it into a great investment property. Bring your ideas and creativity, this is a chance to add value and create something special.

1028 Ramsgate Lane, South Chesapeake

$599,000

5 Beds ⋅ 3 Baths ⋅ 10627623 MLS

Welcome to your new home nestled in this sought after area. Enjoy your open-concept kitchen with granite counters with Stainless Steel appliances. Entertain friends and family as you all enjoy the ambiance of the gas fireplace in the winter time or step out to the screened in porch with the fan blowing on you while you sip on a cold drink and observe the sights and sounds of nature. Entertain friends and family in your beautiful dinning room that is only a few steps from your gorgeous open-concept kitchen. After a hard day at work, pamper yourself by sliding into your jetted garden tub, where you can relax and soak in clean soft water from your whole house water treatment system. You'll never have to worry about losing power with your built-in generator. Don't miss this Gem! It's going to go fast!

4521 Moonlight Way, West Chesapeake

$504,990

2 Beds ⋅ 2 Baths ⋅ 10627384 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. $10,000 closing cost incentive with use of preferred lender!

2202 Edwin Drive, South Chesapeake

$599,900

4 Beds ⋅ 2.1 Baths ⋅ 10613272 MLS

Start building your custom dream home today! Exceptional new construction opportunity on a spacious half-acre lot in the heart of Western Branch. Design your own floor plan to match your lifestyle or choose from one of the builder's stunning models. This featured plan offers a modern open-concept layout. The chef's kitchen features granite countertops, custom cabinetry, stainless steel appliances, and designer lighting. A formal dining room can easily serve as a home office. Enjoy luxury vinyl plank flooring throughout the first floor and baths, plus a covered front porch and rear patio for outdoor living. Experience quality craftsmanship, thoughtful design, and the freedom to create the home you've always imagined. Ready in Spring 2026. Contact us today to start designing your custom dream home!

1530 Jolliff Road, West Chesapeake

$539,900

4 Beds ⋅ 2 Baths ⋅ 10609828 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, 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 door step 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 12-5pm at 5023 Annapolis Drive.

MM Myrtle, West Chesapeake

$600,000

10591641 MLS

This heavily wooded parcel spans over 100 acres and is zoned for residential use. Great for those seeking privacy, nature, and space to create something special. Whether you're envisioning an estate or exploring development potential, this property offers a rare combination of natural beauty and location. Just minutes from the amenities of Edinburgh, it provides convenient access while still feeling worlds away. This lot is to be sold in conjunction with the adjacent parcel on St. Brides Road (MLS# 10591677).

Lot 14 Taft Road, 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