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1217 Willow Lakes Court, West Chesapeake
$565,000
4 Beds ⋅ 3 Baths ⋅ 10644284 MLS
Immaculate, move-in ready 4BR/3BA ranch nestled on a quiet cul-de-sac offers a perfect blend of comfort & functionality with an open floor plan and easy one level living! Rare in-law suite is great for multigenerational living, guests, or private home office. Spacious living area opens to kitchen with large island and new appliances! Primary Bedroom offers walk-in closet, ensuite with double sinks with shower & soaking tub! Relaxing screen porch overlooks peaceful, private backyard & patio is ready for summer cookouts! Peace of mind with upgraded appliances, water heater, and HVAC components being replaced within past 3 years! Pride of ownership shines throughout! Outside bonus features extended parking pad for RV, boats, etc...Combining immaculate condition, flexible living spaces, and desirable private setting, this beauty is a rare find! Conveniently located minutes to 664 for easy access to all of Hampton Roads with nearby dining, shopping, Western Branch schools!

1217 Willow Lakes Court, West Chesapeake

1527 Jolliff Road, West Chesapeake
$565,000
4 Beds ⋅ 3.1 Baths ⋅ 10608307 MLS
This one-of-a-kind, well-cared-for home—originally built in 1900—offers timeless charm, vintage details, and thoughtful modern updates in the heart of Western Branch. Nestled on 3.5 private, tranquil acres in the well-established Jolliff Woods neighborhood, this classic 4-bedroom, 3.5-bath home is both spacious and inviting. Enjoy a built-in saltwater pool, patio, deck, and open porch—perfect for relaxing or entertaining. Property features two wells, septic system, Generac generator, and a large 2-car garage with full bath and extra storage. Fruit trees—apple, pear, pecan, and blueberry—add to the property’s natural beauty. With a peaceful, charming setting close to top-rated schools, shopping, dining, medical, and major interstates, this rare Western Branch gem perfectly blends history, comfort, and convenience.

1527 Jolliff Road, West Chesapeake

5039 Annapolis Drive, West Chesapeake
$565,000
4 Beds ⋅ 2.1 Baths ⋅ 10602873 MLS
Quick close available / 30 days or sooner / 100% complete. Upgrades include: LVP flooring, gas range, ceramic tile shower/tub surround in PBTH w/granite top vanity. Welcome to the Bayberry II, offering open-concept living without compromising comfort. Features include a large gourmet kitchen with w/granite countertops & stainless steel appliances. Walk-in closets in 3 bedrooms, family room with open loft, fireplace, downstairs primary bedroom and so much more. 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 w/a resort-style in-ground swimming pool. Seller is offering up to 4% CCA Buyer incentive when using one of our trusted lenders. Model home open daily 12-5pm at 5023 Annapolis Drive

5039 Annapolis Drive, West Chesapeake

2231 Captiva Lane, West Chesapeake
$564,690
4 Beds ⋅ 2 Baths ⋅ 10594839 MLS
Welcome to The Dogwood, our most popular ranch model! This highly desired floor plan offers 4 bedrooms, 2 baths, and 2335 sq ft. Perfect first home or forever home! 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. There is truly no better place to feel at home in a floor plan that has all your needs in an exciting new home community! Model Home Open 12-5 PM Daily at 5023 Annapolis, Chesapeake, VA 23321. Builder is offering partial CCA & $15,000 buyer incentive (used at buyer's discretion) when using one of our preferred lenders.

2231 Captiva Lane, West Chesapeake

2072 River Pearl Way, West Chesapeake
$563,500
4 Beds ⋅ 3.1 Baths ⋅ 10648135 MLS
Welcome to 2072 River Pearl Way in well-established Waterstone; two-story home featuring 2,800 sqft, 4 bdms, 3.5 baths, giving you room to grow, host, and settle in. A fireplace warms the main living area, while exotic wood, carpet, and ceramic tile carry through the floor plan. Upstairs, the spacious primary suite offers a peaceful retreat complete with a private en suite featuring heated tile floors for a touch of everyday luxury. Step outside to a deck featuring composite decking materials designed for longevity overlooking the backyard, made for morning coffee or evening gatherings, with a long driveway providing ample parking. Waterstone is known for its tree-lined streets and community pond, where residents can paddle a kayak, canoe, or paddleboard right in their own neighborhood. Book your showing now!

2072 River Pearl Way, West Chesapeake

3029 Crossings Drive, West Chesapeake
$560,000
5 Beds ⋅ 3.1 Baths ⋅ 10630413 MLS
Well-maintained home on a corner lot in the heart of Western Branch. This centrally located property showcases a L-shaped Grecian-style pool and offers 5 spacious bedrooms and 3.5 bathrooms, including 2 ensuites. The layout is ideal for multi-generational living, with a primary ensuite on each floor. The 1st floor suite serves perfectly as an in-law suite, featuring a separate entrance and dry bar, while both suites include jetted tubs and expansive walk-in closets. The 2nd-floor primary suite adds a touch of warmth with a gas fireplace and a generous bathroom w/dual sinks. The open and airy main level is designed for both everyday living and gatherings, offering 2 large living areas, a dining room, a well-equipped eat-in kitchen, vaulted ceilings with skylights, and a cozy gas fireplace. Step outside to your private pool oasis that elevates the outdoor experience, creating a serene backyard retreat ideal for both relaxation and entertaining. Don't forget about the neighborhood park!

3029 Crossings Drive, West Chesapeake

2119 Seastone Trace, West Chesapeake
$560,000
4 Beds ⋅ 2 Baths ⋅ 10608310 MLS
Back on Market No Fault of seller. Set on a 0.27-acre lot in the Waterstone community. Enjoy serene lakefront living with your own private stationary dock, double bulkhead, and Trex deck perfect for fishing, kayaking, and outdoor gatherings. This beautifully updated ranch offers nearly 2,500 sq. ft. of living space with 4 bedrooms, 2 baths, including a versatile finished room over the garage. The layout features a wide-open foyer leading to a formal living/dining area, a family room with gas fireplace, and a modern kitchen with granite counters, white cabinetry, and black stainless-steel appliances. The primary suite includes dual vanities, a soaking tub, and tiled shower. Upgrades include Interior paint, HVAC 2018, most windows 2018, gutters and roof and H20 heater 2025. with Access to a 93-acre park with playgrounds, dog park, tennis/pickle ball court and easy access to interstate.

2119 Seastone Trace, West Chesapeake

4744 Sunray Avenue, West Chesapeake
$559,999
4 Beds ⋅ 2 Baths ⋅ 10628510 MLS
A slice of country charm—agricultural zoning welcomes chickens, horses, and goats alike. Completely updated ranch home located in desirable Western Branch. situated on just over six acres of land. Major improvements include a fully updated kitchen (2022), updated primary bath (2024), new flooring (2022), new windows (2022), roof (2018), HVAC (2022), and hot water heater (2022). As you enter the home, you are welcomed by a spacious dining room featuring beautiful hardwood floors, a cozy fireplace, and charming bay window. The family rm also offers hardwood flooring, bay window, and opens seamlessly to the stunning eat-in kitchen, which uniquely features its own fireplace, creating a warm and inviting space for everyday living and entertaining. The primary bedroom is generously sized with two closets and a beautifully updated en-suite bath. Three additional bedrooms provide ample space and flexibility, including one with a built-in Murphy bed. Truly a rare find in Western Branch.

4744 Sunray Avenue, West Chesapeake

4704 Wood Stork Drive, West Chesapeake
$555,000
4 Beds ⋅ 2.1 Baths ⋅ 10642654 MLS
Welcome to this elegant Craftsman-style home in highly sought after Lakes of Jolliff! Perfectly situated on an oversized privacy-fenced lot, this beautiful 2 story home offers 4 bedrooms, 2.5 baths, a 2-car garage and inviting covered front porch. Inside, discover 10' ceilings, new luxury vinyl plank flooring, Craftsman-style doors, zoned HVAC w/Nest thermostats, & Rinnai tankless Wtr Htr. The bright, open layout is designed for both everyday living & entertaining, featuring an expanded living room w/gas fireplace & sunroom, private dining rm, dedicated office, and transom windows that fill the home with natural light. The gourmet kitchen boasts granite counters, stainless appliances, breakfast bar, chef's gas range w/split oven, and a casual dining area. Upstairs offers 3 large bedrooms, a dedicated laundry w/cabinets & gas/electric hookups, plus an oversized primary suite w/walk-in closet & spa inspired bath w/dual sinks & jetted tub. Conv to Military Bases, Shopping & Dining!

4704 Wood Stork Drive, West Chesapeake

5521 White Swallow Way, West Chesapeake
$555,000
4 Beds ⋅ 2.1 Baths ⋅ 10638772 MLS
Beautifully maintained transitional-style home set on a fully fenced .35-acre lot in Chesapeake's Lakes of Jolliff. Downstairs, distinct spaces blend seamlessly to create an inviting layout. The main level features a formal dining room with tray ceilings, a spacious family room with a gas fireplace, and a well-appointed kitchen with granite countertops, shaker-style cabinetry, and stainless-steel appliances. Upstairs, the expansive primary suite includes dual vanities, a soaking tub, separate shower, and walk-in closet. A large FROG offers flexible use as a bedroom, home office or media room. Two additional bedrooms and shared hall bath complete the second floor. Outside, enjoy a 16x32 Latham fiberglass saltwater pool with gas heater, cartridge filter, new pump ('25), new salt cell ('26), and recently replaced chlorinator. Conveniently located near shopping, dining, and military bases.

5521 White Swallow Way, West Chesapeake

2044 Columbo Avenue, West Chesapeake
$553,000
4 Beds ⋅ 3 Baths ⋅ 10656145 MLS
WESTERN BRANCH HOME WITH A DETACHED 2-CAR GARAGE, SPACIOUS FENCED YARD, AND FLEXIBLE LIVING SPACE! Welcome to 2044 Columbo Avenue, set on a generous .34-acre lot in Chesapeake’s Western Branch area. This well-maintained home is an excellent fit for buyers who need room for vehicles, tools, hobbies, storage, a home business setup, or recreational equipment. In addition to the attached 1-car garage, the property offers an oversized detached 2-car garage with a finished second floor. Built approximately 2009, it includes insulation, drywall, electrical, and a Wi-Fi-controlled mini-split HVAC system—ideal for a workshop, office, studio, recreation room, hobby space, or conditioned storage. Inside, the kitchen features granite countertops, black stainless appliances, a breakfast bar, and an open connection to the great room for easy everyday living and entertaining. A formal dining room, first-floor flex room, full bath, and enlarged laundry room add valuable versatility. Upstairs, the spacious FROG serves as the fourth bedroom with a full bath nearby, while the primary suite includes a refreshed bath. Recent improvements include a Trane dual-zone Wi-Fi HVAC system approximately four months old, vinyl siding, metal exterior wrap, newer front and sliding rear doors, screened porch, LVP/laminate flooring, rear windows, and gutters. Natural gas serves the heat and hot water. Enjoy the large fenced backyard with a deck, screened porch/patio, and hot tub—plenty of room to relax, entertain, play, garden, or let pets roam. Seller is replacing carpet before closing.Convenient to I-664, military installations, tunnels, shopping, dining, and destinations throughout Hampton Roads.

2044 Columbo Avenue, West Chesapeake

2229 Captiva Lane, West Chesapeake
$551,055
4 Beds ⋅ 2.1 Baths ⋅ 10594846 MLS
Welcome to the Bayberry, which offers open-concept living without compromising comfort. With features like a large gourmet kitchen with granite countertops & stainless steel appliances. Walk-in closets in 3 bedrooms, family room with open loft, fireplace, downstairs master bedroom and so much more. You also have the option to build any variety of our models and completely customize them to suit your lifestyle. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, tree-lined sidewalks, lush gathering spaces, a community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. Builder is offering up to 3% CCA (see listing agent for details) when using one of our preferred lenders. Model home open daily from 12-5 pm at 5023 Annapolis Drive.

2229 Captiva Lane, West Chesapeake

2905 Drum Point Crescent, West Chesapeake
$550,411
5 Beds ⋅ 3.1 Baths ⋅ 10634081 MLS
Welcome to the highly sought-after Hunters Cove community in the Western Branch School District! This spacious and beautifully updated home offers 5 bedrooms and 3.5 baths, including a first-floor in-law suite with its own private entrance, full bath, bedroom, and kitchenette, making it great for multi-generational living or guests. The bright and open living room features a cozy fireplace and flows into the updated kitchen complete with silestone-quartz countertops, updated appliances, pantry, eat-in area, and newer flooring. Formal dining and living rooms plus a laundry room complete the first floor. Upstairs 4 additional bedrooms, including a massive primary suite with soaking tub, walk-in shower, double vanity, and walk-in closet. Beautiful hardwood floors run throughout. Major updates include roof (2020), tankless water heater, high-efficiency furnace, newer windows, and fresh paint within the last few years. Minutes from interstate/bases/shopping and more!

2905 Drum Point Crescent, West Chesapeake

3619 Mardean Drive, West Chesapeake
$550,000
5 Beds ⋅ 3 Baths ⋅ 10650125 MLS
You will love this graceful, all brick 2 story transitional Home tucked away on a quiet, double cul de sac street in the Wellington neighborhood in the Western Branch community of Chesapeake. Meticulously maintained and lovingly cared for by original owners, this Gem boasts many details including a large and spacious floorplan, renovated granite Kitchen opening to the vaulted Great Room, 2 story Entry, newer architectural shingle roof, and both a Sun Room and a Screened Porch overlooking the private and lush backyard. Additional Features: 1st floor Bedroom and full bath, wide plank hardwood floors throughout 1st floor, newer carpeting, Formal Dining Room, Office, vaulted Primary Suite with sitting area, secondary bedrooms with ceiling fans, stunning double sided and stone surround gas fireplace, zoned HVAC with programmable thermostats, oversized 2 car garage and extended concrete driveway and parking pad, gutter system, and more!

3619 Mardean Drive, West Chesapeake

4827 Condor Drive, West Chesapeake
$550,000
3 Beds ⋅ 3 Baths ⋅ 10630891 MLS
This property will not disappoint! Owner updated, upgraded since purchased in 2014, including full kitchen renovation, 25.5 x 18 great room w/ real HW floors, 17.5 x 16 primary bedroom w/ 3 closets, renovated bath w/ custom-tile, low-step shower, 518 sf FROG w/ walk-in closet, 3 full baths, screen porch, composite deck overlooking backyard w/ park-like setting. 2-car garage, 648 sf w/ insulated overhead doors, mud sink, TV mount, workbench, and more! Systems/Equipment updated: polybutylene pipes REMOVED; new roof (12/2025); crawlspace well-maintained. Many more great features...see it for yourself, but don't wait! In established Jolliff Woods: No HOA, off the beaten path but less than 2 miles to I-664, zoned for desirable Western Branch schools.

4827 Condor Drive, West Chesapeake

5108 Annapolis Drive, West Chesapeake
$550,000
4 Beds ⋅ 2 Baths ⋅ 10630795 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.

5108 Annapolis Drive, West Chesapeake

2259 Jolliff Landing Parkway, West Chesapeake
$550,000
4 Beds ⋅ 2.1 Baths ⋅ 10627920 MLS
Move-in-Ready home offers modern living with high-end finishes and a versatile floor plan. Interior features include engineered hardwood flooring, plantation shutters, crown molding, and an upgraded kitchen with granite countertops, a large center island, gas range, and a bright breakfast area. The living room looks out to back patio and pergola. The flexible layout includes front flex rooms ideal for a home office or additional living space. The spacious primary suite features a tray ceiling and a spa-like en-suite bath with a soaking tub and separate shower. Highlights include upstairs laundry, a tankless water heater, and a rear-load garage. Located near I664, military installations, shopping, dining, fitness centers, coffee shops. Community amenities include a pool, parks, playground, natural areas, and a clubhouse with fitness center & gathering rooms.

2259 Jolliff Landing Parkway, West Chesapeake

3236 Bentham Lane, West Chesapeake
$549,000
4 Beds ⋅ 2.1 Baths ⋅ 10641379 MLS
Tucked in the sought-after Crossings neighborhood of Western Branch, this beautifully updated home blends modern finishes with a thoughtfully designed floor plan that works for every stage of life.The main level offers incredible versatility with a dedicated home office and a separate flex room, perfect as a playroom, formal dining space, or fifth bedroom for guests. A spacious walk-in pantry keeps the kitchen organized and clutter-free, a feature every home cook will appreciate. Upstairs, four generously sized bedrooms provide plenty of room with comfort and privacy built right in. Step outside and enjoy one of the standout features of this property, a truly spacious backyard that's ready for summer entertaining, weekend barbecues, or simply room to roam. Recent updates throughout mean you can move right in and enjoy everything without the projects. From fresh finishes to modern touches, this home has been lovingly improved and is ready for its next chapter.

3236 Bentham Lane, West 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.

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