Chesapeake Homes with Well Exterior features

Welcome to Chesapeake, Virginia – a city where southern charm meets modern living! Nestled in the heart of Hampton Roads, Chesapeake is a vibrant community that boasts picturesque landscapes, rich history, and a plethora of recreational opportunities. With its convenient access to both the bustling cities of Norfolk and Virginia Beach, Chesapeake offers the perfect blend of suburban tranquility and urban excitement.

One of the standout features of homes in Chesapeake is their well-designed exteriors. Many properties showcase stunning architectural styles that reflect the region’s heritage, from classic colonial designs to contemporary masterpieces. Imagine coming home to a picturesque façade adorned with lush landscaping, charming front porches, and inviting outdoor spaces perfect for entertaining family and friends.

The homes in Chesapeake are not just about aesthetics; they are built to enhance your lifestyle. Many residences feature spacious yards, ideal for gardening, play, or simply enjoying the serene Virginia weather. With an array of options available, from cozy single-family homes to expansive estates, you’re sure to find a property that suits your needs and desires.

Living in Chesapeake means embracing a community rich in amenities. Explore the lush parks, scenic waterways, and vibrant local shops and restaurants. Whether you’re a nature enthusiast, a foodie, or someone who enjoys cultural events, Chesapeake has something for everyone.

Discover the charm of Chesapeake, VA, and find your dream home with a well-crafted exterior that reflects your style and welcomes you home. Experience a community where comfort, beauty, and convenience come together seamlessly!

Newest Chesapeake Homes with Well Exterior features

$719,900

5 Beds ⋅ 4 Baths ⋅ 10653264 MLS

Nestled on a cul-de-sac in Saddle Ridge Estates with NO HOA, 804 Wakedale Arch offers 3,720 square feet of spacious living with five bedrooms and four full baths. New hardwood floors, new carpet, and fresh paint throughout make this home move-in ready. An expansive sunroom just off the eat-in kitchen provides additional space for entertaining or relaxing. The generously sized primary suite features a sitting area, walk-in closet, and private bath with dual vanities, a separate shower, and soaking tub. A first-floor bedroom and full bath offer flexibility for guests or multigenerational living. Enjoy practical extras, including ample built-in garage shelving and a backyard shed with electricity. Space, comfort, and convenience come together in this beautifully refreshed home!

804 Wakedale Arch, South Chesapeake

$850,000

4 Beds ⋅ 3 Baths ⋅ 10653178 MLS

All brick ranch in the sought-after Hickory school district, set back from the road on almost 4 acres offering exceptional privacy, great curb appeal and mature plantings. This spacious home offers an open floor plan, 4 bedrooms, 3 full baths and an oversized 3 car attached garage. The kitchen features hardwood floors, walk-in pantry and a bay window in the breakfast area. Spacious family room with fireplace, plus formal living and dining rooms and a separate study/office. The primary suite features a jetted tub with skylights above, separate shower, double sinks and its own water heater. Enjoy the screened porch overlooking the expansive property. Additional features include a high crawl space, replacement windows and architectural roof replaced in 2015. A rare combination of acreage, privacy and space in Hickory!

2329 Centerville Turnpike S, South Chesapeake

$775,000

5 Beds ⋅ 2.1 Baths ⋅ 10653033 MLS

Welcome to 3708 Riverwood Crescent! Situated on approx. 3 acres in sought after Chesapeake 23322, this nearly 3,000 sq. ft. home offers space, privacy & extensive updates! Enjoy a private backyard retreat with pool, screened porch & updated deck. Inside features a remodeled kitchen with quartz countertops, mostly stainless steel appliances, soft-close cabinetry, recessed lighting, hardwood & luxury vinyl plank flooring, plus new carpet upstairs, and solar hallway lighting. Updated baths include new countertops, toilets, fixtures, ceramic tile, tub/shower & an enlarged porcelain-tiled primary shower. Major improvements include dual-zone HVAC (2019/2021), 2024 water heater, water softener, encapsulated crawl space with pump & dehumidifier, replaced exterior/garage doors, vinyl windows & 2011 roof with 50-yr warranty. Shed and lawn tractor conveys! A rare combination of acreage, updates, pool & location; come see it!

3708 Riverwood Crescent, South Chesapeake

$665,000

4 Beds ⋅ 3 Baths ⋅ 10652967 MLS

This home truly has it all! Welcome to this beautiful 4-bedroom, 3-full-bath home in the highly desirable Las Gaviotas golf course community. Offering 3,371 square feet of thoughtfully designed living space, this home immediately impresses with beautiful flooring and an inviting, open feel. Enjoy peaceful living along a quiet tidal creek from the Elizabeth River, where changing tides, abundant wildlife, and natural beauty create a truly serene backyard setting. Relax on the updated Trex deck and enjoy the peaceful views, or take in the scenery from the inviting sitting room just off the living room, where gorgeous windows bring the beauty of the outdoors inside. The flexible floor plan includes a first-floor bedroom, dedicated home office/gym, and an upstairs bonus room—providing plenty of space for guests, work, hobbies, or entertaining. Numerous recent updates provide peace of mind, including new ductwork in attic and crawlspace (2025), roof and skylight (2024), water heater (2024), Prodigy insulated siding, fascia and rain gutters (2024), Bosch BOVA upstairs HVAC system (2022), Trex decking (2023), first-floor LVP flooring (2021), and crawlspace dehumidifier (2026). With golf-course community living, a peaceful tidal-creek setting, abundant natural light, and an impressive list of updates, this is a home you won’t want to miss.

419 Granada Drive, South Chesapeake

$575,000

5 Beds ⋅ 3.1 Baths ⋅ 10653159 MLS

A rare financing opportunity and an exceptional floor plan set this completely renovated 5-bedroom, 3.5-bath home apart. Qualified buyers may be eligible to assume the seller’s existing VA loan at an incredible 2.625% interest rate, subject to servicer approval and existing loan terms. The versatile layout provides flexibility for extended family, guests, private workspaces and everyday living. Imagine cooling your home and enjoying the pool all summer with an electric bill that is virtually nonexistent. The seller reports exceptional energy savings from the solar-panel system, which will convey free and clear at closing. Other major improvements include new vinyl siding, garage door, HVAC, tankless water heater, fresh paint and so much more. The backyard paradise features a heated saltwater above-ground pool, new privacy fence and dedicated pool room that can also serve as a workout or recreation space. A well and sprinkler system help maintain the grounds.

412 Harper Court, South Chesapeake

$998,895

5 Beds ⋅ 3.1 Baths ⋅ 10652907 MLS

Experience luxury living in this one-of-a-kind Chesapeake retreat, nestled on a 3-acre lot in the Grassfield School District. This custom-built home blends modern comfort with timeless charm, offering an open-concept first floor design for today's lifestyle. The spacious family room flows seamlessly into the remodeled 2024 kitchen, with direct access to the back deck for everyday relaxation or entertaining guests. Choose between two generous primary suites. First floor primary suite features a gas fireplace, dual closets, and a sitting/office area. Second floor primary suite privately located above 3-car garage, offering separation from the additional upstairs bedrooms. Enjoy abundant space for hobbies and storage with two powered sheds, plus peace of mind from the new encapsulated crawl space with vapor barrier. Major upgrades, including the roof, HVAC, and kitchen in 2024, ensures comfort and efficiency for years to come. This exceptional property delivers a rare combination of privacy, space, and freedom with no HOA restrictions, making it a true Chesapeake gem.

1910 Hallmark Way, South Chesapeake

$747,995

5 Beds ⋅ 3 Baths ⋅ 10651967 MLS

Gorgeous 2 story Home situated on a private and lushly landscaped lot in the Etheridge Lakes neighborhood in Southern Chesapeake. Step into the elegant 2 story foyer and be amazed by the beautiful details throughout this spacious home that has been well maintained and lovingly cared for by the original owners. The vaulted Family Room opens to the large and updated Eat in Kitchen and both offer perfect views of the privacy fenced backyard oasis boasting a stunning and resort style saltwater pool with waterfall and stamped concrete surround, deck, storage shed, and outdoor shower. Additional Details: 1st floor Bedroom and full bath, Primary Suite with walk in closet and updated full bath, Formal Dining Room, new LVP flooring on 1st floor, nice sized bedrooms with ceiling fans, dual staircases, FROG is 5th bedroom, 2nd floor Laundry Room, freshly painted interior, newer carpeting, zoned HVAC, well/sprinkler system, 2 car sideload garage, gutter system, and more! Attends Hickory schools.

1052 Stockleybridge Drive, South Chesapeake

$574,900

4 Beds ⋅ 2.1 Baths ⋅ 10653018 MLS

Located in Oak Bridge Forest, this 4-bedroom, 2.5-bath home offers a spacious layout, an oversized 2-car garage, and a large backyard made for enjoying the outdoors. Inside, a two-story foyer welcomes you into a light-filled floor plan featuring new laminate flooring, installed in 2025, throughout most of the home. The custom-designed kitchen received a complete makeover in 2025 and opens to the family room, creating an easy flow for everyday living and entertaining. Upstairs, the spacious primary suite features a private bath with a double vanity, walk-in shower, and jetted tub, with three additional bedrooms and a second full bath completing the level. Out back, mature landscaping and trees surround an in-ground pool with a new liner installed in 2024 and new pool heater added in 2025. A Trex deck provides additional space to relax or entertain. Additional features include a tankless water heater, sprinkler system, smart-home capabilities, Ring doorbell and exterior security cameras, plus an Invisible Fence encompassing the front and backyard. No HOA! With generous indoor and outdoor space, thoughtful updates, and a backyard ready for pool days and entertaining, this Oak Bridge Forest home has plenty to offer. Incentives may be available through preferred partners. Contact listing agent for details and eligibility.

733 Dissdale Lane, South Chesapeake

$399,000

3 Beds ⋅ 2 Baths ⋅ 10652696 MLS

A Beloved Western Branch Gem! Welcome to one of Western Branch’s most cherished neighborhoods, where many homeowners have proudly called this community home for 55+ years! This spacious brick rancher offers an inviting open floor plan, multiple flexible living spaces, and a peaceful cul-de-sac location. Step outside to enjoy the huge, private backyard, surrounded by mature trees providing wonderful shade and privacy, plus a brand-new deck perfect for relaxing or entertaining. Ideally located just minutes from Hampton Roads military bases, tunnels, bridges, shopping, dining, entertainment, doctors, and hospitals, this home puts convenience at your fingertips. Recent updates include new carpet (2023), new roof (2023), remodeled hall bath (2018), and HVAC (2016). Don’t miss your opportunity to own this wonderful home in a truly special neighborhood!

4353 Shorewood Drive, West Chesapeake

$715,000

4 Beds ⋅ 3 Baths ⋅ 10652738 MLS

Wonderful home that owners have maintained in very good condition, located in cul-de-sac!4 Bedrooms, 3 Full baths, a downstairs bedroom is adjacent to a full bath. Beautiful sunroom with custom inlay tile, paver patio, kitchen with island, spacious main bedroom - full bath with dual sinks, soaking tub and walk-in shower. Large family room with natural gas fireplace, formal dining & living rooms, true 2 car garage, plenty of driveway space.Crawl space encapsulated w/dehumidifier.

812 Brookside Arch, South Chesapeake

$849,900

4 Beds ⋅ 3 Baths ⋅ 10652646 MLS

Dreaming of waterfront living? Welcome home to the Western Branch of the Elizabeth River, where mornings begin with water views, afternoons can be spent boating, fishing or kayaking, and evenings invite you to unwind by the river. Set on a picturesque, flat .80-acre lot, this expansive all-brick custom and oversize 2 car garage offers space, storage, charm and an exceptional setting for entertaining. The private pier was resurfaced last fall and provides convenient access toward the boating channel. Inside, custom details include solid doors, extensive trim and oversized rooms. Water views fill the rear of the home, including the family room with wood-burning fireplace and enclosed ceramic-tile sunroom. Flexible living includes a first-floor primary suite and three upstairs bedrooms with balcony access. Exceptional storage includes multiple walk-in attic spaces with future design potential. A whole-house generator adds peace of mind. Live, entertain and make memories on the water!

3808 Millgrove Court, West Chesapeake

$1,000,000

6 Beds ⋅ 3 Baths ⋅ 10652479 MLS

Open House Sat Sept 12 1-3pm. Modern Farmhouse Charm Meets Turnkey Living in Desirable Chesapeake! Discover the modern farmhouse you’ve been dreaming of, where peaceful country living meets thoughtful, top-to-bottom renovation. Set on serene acreage with panoramic wooded views. It embraces the natural surroundings. This beautifully refreshed home is ideal for extended family/multi generational living. Natural light fills the home, showcasing new flooring, fresh interior paint, updated lighting, and beautifully renovated bathrooms. The completely redesigned custom kitchen is the heart of the home, featuring quartz countertops, ceramic backsplash, abundant prep space, an inviting eat-in area and a KitchenAid appliance suite, ideal for everyday living and entertaining. The expansive living area offers plenty of room to gather, while the renovated wood-burning fireplace creates a cozy focal point with a new firebox, flue, chimney cap, and Buck Stove-style insert. Step onto the Trex deck with PVC railing and enjoy peaceful wooded views from the living space, primary suite or deck. The primary suite is a true retreat, featuring a custom-tiled shower with built-in bench and generous niche, deep soaking tub, double vanity and ceramic tile flooring. The expansive custom closet with built ins provides all the space you have been longing for. Additional improvements include an encapsulated crawlspace with dehumidifier, new septic system designed for 10 occupants, finished room over the garage with generous storage, updated downstairs ductwork, new interior and exterior doors and hardware, new lighting throughout, and a freshly graded crushed-aggregate driveway. The painted brick exterior adds a fresh, modern look while preserving brick’s timeless durability and character. Best of all, the home features a highly energy-efficient geothermal HVAC system. From the crawlspace to the exterior, virtually nothing has been overlooked. Renovated by New Again Houses VB. It offers the feel of quality new construction without sacrificing character, space or setting. See it today!

3132 Benefit Road, South Chesapeake

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