Chesapeake Homes with Well Exterior features

Welcome to Chesapeake, Virginia – a vibrant city that beautifully marries the charm of suburban living with the conveniences of urban life. Nestled in the heart of the Tidewater region, Chesapeake is known for its scenic landscapes, rich history, and strong sense of community. With over 350 miles of navigable waterways, residents enjoy a plethora of outdoor activities, from boating and fishing to hiking and biking along the extensive trail systems.

Chesapeake is also home to an array of shopping, dining, and entertainment options, ensuring that everything you need is just a stone's throw away. The city boasts an excellent school system, making it a perfect place for families looking to settle down.

One of the standout features of homes in Chesapeake is their well-designed exteriors. Many properties showcase stunning curb appeal with meticulously landscaped yards, charming front porches, and durable siding that enhances the home’s aesthetic. Whether you’re drawn to traditional Colonial styles or modern architectural designs, Chesapeake offers a diverse selection of homes that cater to various tastes and preferences.

Many homes come equipped with outdoor living spaces perfect for entertaining or simply enjoying the serene Virginia evenings. Imagine hosting summer barbecues on a spacious deck or unwinding in a beautifully landscaped backyard.

In Chesapeake, you’re not just buying a house; you’re investing in a lifestyle that celebrates community, nature, and comfort. Explore the homes available in this picturesque city and discover your dream residence today!

Newest Chesapeake Homes with Well Exterior features

$664,900

4 Beds ⋅ 2.1 Baths ⋅ 10648058 MLS

Welcome to luxury living in the heart of Chesapeake! This stunning all-brick 2-story home offers over 3,000 square feet of beautifully designed living space featuring 4 spacious bedrooms and 2.5 bathrooms. Step inside to elegant marble flooring throughout the downstairs along with modern fixtures that create a sleek and upscale feel. Sitting on an impressive 1.14-acre lot, this property is built for both comfort and entertaining with a heated in-ground pool and hot tub perfect for relaxing year-round. Spacious rooms, timeless curb appeal, and a private setting make this home truly one of a kind. Seller will have house freshly painted (one color of buyer's choosing) and replace with new carpet (color of buyer's choosing) prior to closing with full price offer. Don't miss your opportunity to own this exceptional Chesapeake property. Schedule your private showing today before it’s SOLD!

748 Greenwing Drive, Chesapeake

$330,000

4 Beds ⋅ 1.1 Baths ⋅ 10647753 MLS

Enjoy the best of both worlds with this charming brick rancher offering country living in the heart of the city! Gleaming hardwood floors and abundant natural light create a warm, inviting atmosphere throughout. The eat-in kitchen features stainless steel appliances and flows into the spacious family room with recessed lighting—perfect for everyday living and entertaining. The primary suite includes a convenient half bath, while the oversized laundry room provides plenty of storage and workspace. Come outside to a large fenced backyard with endless possibilities, including room for an addition, gardening, or creating your own mini homestead. Bring your chickens, ducks, dogs, and other animals—there's plenty of space to enjoy the country lifestyle without sacrificing city convenience!

805 Portland Street, Chesapeake

$670,000

5 Beds ⋅ 3 Baths ⋅ 10647695 MLS

Welcome to this beautifully maintained, one-owner custom home tucked away on a quiet cul-de-sac lot with breathtaking landscaping and water access. Situated on approximately .75 acres, this quality-built brick home offers 5 bedrooms and 3 full baths, including a desirable first-floor bedroom and full bath for guests, multigenerational living, or a home office. The oversized finished room over the garage provides endless flexibility as a potential 6th bedroom, media room, playroom, or gym. Inside, you’ll find spacious rooms, abundant storage, and exceptional craftsmanship throughout, all reflecting the pride and care of the original owners who built the home. Outside, enjoy stunning mature landscaping, stone walkways, colorful flowering shrubs, and a peaceful backyard setting along a scenic creek that leads directly to the river. A rare opportunity to own a truly special property in an established neighborhood.

3012 Golden Hind Road, Chesapeake

$1,200,000

4 Beds ⋅ 3.1 Baths ⋅ 10647623 MLS

Rare opportunity for true multi-generational living with exceptional flexibility, privacy, and space! This beautifully updated ranch offers one-level living with a finished room over attached 2-car garage, soaring ceilings, formal dining, first-floor laundry, and a luxury granite kitchen featuring KitchenAid appliances, built-in desk and a sun-filled eat-in. Relax year-round in the vaulted sunroom with a wood-burning fireplace or step outside to your private resort with a an inground saltwater pool, luxury landscaping, and expansive patio. The standout feature is the detached 3-car garage with a separate 3-bedroom, 1-bath apartment complete with kitchen, laundry, and private living space. Additional highlights include RV storage/hangar, workshop, Tesla charger, whole-house water filtration and softener, geothermal HVAC, encapsulated crawl space, buried drainage, sprinkler system, high-speed Cox WiFi, oversized walk-in attic, and extensive updates throughout.

1717 Long Ridge Road, Chesapeake

$525,000

5 Beds ⋅ 3 Baths ⋅ 10646864 MLS

Charming & lovingly updated farmhouse in heart of Deep Creek on 1.2 acres includes all modern conveniences while respecting historic heritage w/features like original hardwood floors, crown molding, chair railing w/both welcoming front porch & screen porch. Beautiful kitchen w/SS appliances, granite counters, peninsula w/gas range, prep sink, SS wine fridge, oversized breakfast bar & pendent lighting. Bright & airy upstairs w/3 beds 2 w/walk-in closets, linen closet & updated hall bath w/beaded board wainscoting. 4th bed downstairs w/ensuite bath. Fantastic laundry room w/cabinetry, counter space, shelving & utility sink. Updates include: newer HVAC, ductwork & insulation, hardy plank siding & vinyl replacement windows. Spacious backyard 2 sheds & irrigation. Detached garage boasts almost 1500 sq feet split between the 2 levels. Upstairs living area has a full bedroom, bathroom and bonus closet/storage area. Great for your guests!

3248 Galberry Road, Chesapeake

$634,900

4 Beds ⋅ 3.1 Baths ⋅ 10646890 MLS

Beautifully maintained 4 Br 3.5 bath home on 1/2 acre lot located in the Grassfield area of Chesapeake. 2 large primary suites 1 upstairs and 1 downstairs. 2 additional bedrooms upstairs that share a Jack n Jill. Theater room located downstairs that you will absolutely love. Some other upgrades include gourmet kitchen, granite countertops, stainless steel appliances, hard wood/LVP flooring, full privacy fence and beautifully maintained landscaping. The roof was replaced 2018.

2308 Angler Lane, Chesapeake

$609,000

5 Beds ⋅ 3 Baths ⋅ 10646979 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.

789 Caddie Street, Chesapeake

$599,000

4 Beds ⋅ 2 Baths ⋅ 10646894 MLS

This is the one you’ve been waiting for! Beautifully updated & filled w/ character, this 2,800-square-foot ranch delivers 4 bedrooms, 2 baths and an incredible blend of indoor comfort & outdoor resort-style living. Covered front porch welcomes you to a light-filled interior where floor-to-ceiling windows surround the sunroom, while the family room showcases a fireplace, built-in bookcase & extensive molding. The spacious primary suite offers walk-in closets plus a versatile sitting area perfect for a home office, reading retreat or private escape. Outside, prepare to be wowed! The expansive backyard is your own private oasis with a 26,000-gallon saltwater pool (new pump 2025, salt cell 2026), deck, gazebo, fire pit, hammocks, pool house, sheds, fish pond with fountain, weeping willow, mature Japanese maple, peach tree and lush gardens. Smart-home features and Wi-Fi irrigation add modern ease. Finished room over garage, expansive attic, numerous updates & low traffic dead-end street.

318 Rio Drive, Chesapeake

$599,000

4 Beds ⋅ 2.1 Baths ⋅ 10646504 MLS

Welcome to this beautifully maintained 4-bed, 2.5-bath home tucked away on a quiet cul-de-sac in the desirable Waterstone community of Western Branch. This home combines thoughtful updates with exceptional outdoor living. The backyard is your own private retreat, featuring a sparkling in-ground pool with concrete surround —ideal for relaxing or entertaining all summer long. The fully irrigated yard is supported by a new well and controls, helping keep the landscaping lush while reducing water costs. Inside, you'll find granite countertops, stainless appliances, new range, and spacious living and dining areas designed for everyday comfort. Major improvements provide peace of mind, including carpets, hardwood in den, concrete driveway, Leafguard Gutters, well and irrigation system, newer composite decking and rails, professionally restored crawlspace with new Insulation, vapor barrier, and sand, and newer pool filter and cover. Located in the sought-after Chittum school district of Western Branch, Waterstone offers an exceptional neighborhood lifestyle with scenic walking trails that connect directly to Western Branch Park, providing convenient access to playgrounds, athletic fields, tennis and pickleball courts, disc golf, and miles of outdoor recreation just minutes from your doorstep. With convenient access to shopping, dining, military bases, and major commuter routes, this move-in-ready home offers the perfect blend of comfort, functionality, and outdoor enjoyment. Schedule your private showing today!

4709 Feldspar Quay, Chesapeake

$829,900

4 Beds ⋅ 3 Baths ⋅ 10646857 MLS

Stunning all brick home features 4 bedrooms, 3 full bath, spacious 4 season sunroom, in ground pool in sought after Great Bridge School District. Living room/office & dinning room with hardwood floors. The large main living area offers an open floor plan featuring vaulted ceiling, gas fireplace flowing into the kitchen. Updated kitchen showcases SS appliances, New solid surface counters w/single sink & new faucet, two-tone cabinetry, bar for additional seating and flows directly into the dining room and eat-in breakfast for easy meals and entertaining. Large primary bedroom with trey ceiling, walk-in closet, remodeled ensuite bathroom with spa-like features, including a soaking tub, water closet, double vanity and, separate shower & tub. Additional downstairs bedrooms are generously sized, with hard wood floors. Large private 4th bedroom is located upstairs offers a full bath. The laundry room includes cabinetry and shelving for ample storage. Walk-in attic for additional storage. Beautiful landscaped back yard has all the amenities for entertaining show casing vinyl fencing, a solar panel heated in-ground L shape salt water pool with fountain, stone pavers throughout, trek decking and a 4 season sunroom to enjoy the view. New: carpet in family room, mini split in 4 season room, SS gas stove/microwave/refrigerator, coretec flooring in 4th bedroom, fixtures, 2023 pool liner, 2021 tankless water heater, 2015 gas furnace. 2015 Roof replacement, Mr Rogers Windows and Door, gutters with gutter guards, vinyl trim wrapped. Ask agent for a full list of home improvements. THIS IS A MUST SEE!

825 Waterfall Way, Chesapeake

$675,000

5 Beds ⋅ 3 Baths ⋅ 10646878 MLS

Welcome home to this spacious 5-bed, 3-bath home offering 3,842 sq ft of beautifully designed living space on a generous .84-acre lot. With multiple living areas, a HUGE bonus room over the garage, plus a formal living room, dining room, family room, and bright sunroom, there's plenty of space to spread out. The open kitchen flows seamlessly into the family room and sunroom. Upstairs, the spacious primary suite boasts a spa-like bath with a jetted tub, separate shower, and dual vanities. Brand-new carpet was installed upstairs. Step outside to your private backyard retreat featuring a Trex deck, outdoor kitchen, stamped concrete patio, and an expansive fenced yard with a newer vinyl privacy fence with four gates. A storage shed with power provides plenty of extra storage. Additional highlights include stunning curb appeal, a stamped concrete driveway, epoxy-coated garage floor, EV charger, and easy access to military bases, major highways, shopping, dining, and entertainment.

3204 Hearring Way, Chesapeake

$674,900

5 Beds ⋅ 3.1 Baths ⋅ 10646835 MLS

If you've been searching for a spacious, move-in-ready home with a private in-law suite on a large lot in the heart of Chesapeake, your search is over! This one-of-a-kind property offers the blend of comfort, flexibility, and space. The traditional in-law suite features its own multiple entrances, full kitchen, living room with a cozy gas fireplace, recently remodeled bathroom, bedroom, and dedicated laundry area—use for multi-generational living or extended guests. Step outside to a large backyard for relaxing or entertaining, complete with a recently built gazebo with electricity and a storage shed for all your gardening and outdoor needs. Located in a neighborhood with sought-after schools, you'll enjoy convenient access to shopping, dining, parks, and more. Don't miss this rare opportunity to make this exceptional Chesapeake home yours!

1307 Channing Way, Chesapeake

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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.