South Chesapeake Homes with City View

Welcome to South Chesapeake, Virginia, where the charm of suburban living meets the vibrant pulse of city life! Nestled in the heart of Chesapeake County, this picturesque community offers a unique blend of natural beauty, convenience, and a strong sense of community. With its lush parks, scenic waterways, and friendly neighborhoods, South Chesapeake is an ideal place for families, young professionals, and retirees alike.

One of the standout features of South Chesapeake is its stunning homes that boast breathtaking city views. Imagine waking up each morning to panoramic vistas of the bustling city skyline, all while enjoying the tranquility of suburban living. These homes are designed to maximize the beauty of their surroundings, featuring expansive windows and spacious balconies that invite the outside in. Whether you are entertaining guests or enjoying a quiet evening at home, the captivating views are sure to enhance your living experience.

In addition to its beautiful residences, South Chesapeake is conveniently located near a wealth of amenities. Residents have easy access to shopping centers, dining options, and recreational activities, making it a perfect spot for those who appreciate both leisure and convenience. The area is also home to top-rated schools and community parks, ensuring that families have everything they need to thrive.

If you’re looking for a place that combines the best of both worlds—serene suburban life with stunning city views—South Chesapeake is the perfect destination. Come explore the possibilities and discover your dream home in this charming Virginia community!

Newest South Chesapeake Homes with City View

$450,000

4 Beds ⋅ 2.1 Baths ⋅ 10653149 MLS

Welcome home to Greenbrier! This beautifully maintained, move in ready home is tucked away on a desirable cul-de-sac in the heart of Chesapeake. Featuring numerous recent updates, you can move in with confidence and enjoy! The kitchen was updated in 2023 with new cabinets, countertops, and appliances. All bathrooms were refreshed in 2024 with new vanities, sinks, tubs, toilets, flooring, and paint. Major updates include a roof (2017), fence (2021), HVAC furnace (2025), condenser(2026), and water heater (2026). The first floor offers a spacious foyer, open living and dining areas, plus flexible bonus space great for a home office or playroom. Upstairs features a large primary suite with private bath and walk-in closet, three additional bedrooms, and a spacious shared bath. Conveniently located near Greenbrier shopping, dining, interstates, and local attractions. Don't miss your opportunity to make this home yours!

1914 Keeter Run, South Chesapeake

$369,000

3 Beds ⋅ 1.1 Baths ⋅ 10652758 MLS

Open House - Sunday, Sept 13, 1-3 PM. Have you been searching for a home with a large garage and a no-tree lot? This is it. The kitchen has been completely renovated with a new gas stove, dishwasher, and refrigerator. A new mini-split system keeps the sun-filled Florida room (with its wall of windows) comfortable year-round. The oversized garage is a standout - wired with a 240V outlet, cooled by a window AC unit, and offering plenty of room for whatever organizing system you need. A small outdoor shed keeps lawn equipment tucked away, and the carport is a nice bonus.

1333 Boxwood Drive, South Chesapeake

$545,000

4 Beds ⋅ 2.1 Baths ⋅ 10652777 MLS

Exceptional opportunity in the sought-after Etheridge Lakes community located in the highly desirable Hickory High School district! This well-maintained 4 Bedroom, 2.5 Bath home offers comfort, space, and peace of mind with a NEW ROOF installed in 2026. The home features a functional layout perfect for everyday living and entertaining, with spacious bedrooms and plenty of natural light throughout. Versatile room downstairs for office needs or additional living area. All appliances convey, making this home truly move-in ready. Fenced yard offering privacy, yard space for pets or entertaining. 3 TVS convey! Enjoy the benefits of a well-established neighborhood with NO HOA fees or restrictions. Conveniently located near shopping, dining, parks, and major commuting routes, this home combines value, location, and pride of ownership in one outstanding package!

716 Tallahassee Drive, South Chesapeake

$534,900

4 Beds ⋅ 2.1 Baths ⋅ 10652341 MLS

One owner. 40+ Years of Care and Memories. Now it’s YOUR turn! This lovingly maintained 2,477 square foot Great Bridge Home offers 4 Bedrooms, 2 1/2 Baths & wonderfully distinctive architecture & floor plan. A true Sunken Living Room features a Soaring Brick Accent Wall & Wood Stove, while the oversized kitchen offers Abundant Cabinetry, Island & Sunny Bay Window dining area. Formal dining room, main-level Primary Suite + Additional 1st-floor Bedroom provide great flexibility. Upstairs, 2 Bedrooms share a Jack-and-Jill bath, plus an ENORMOUS Walk-in Attic provides exceptional storage & possibilities for future use! Enjoy a Corner lot, large Patio, Shed & 2-car Garage. Roof replaced 2022 and new water pump for geothermal HVAC installed 7/2026. All Great Bridge schools! A home with character and personality is a rare find in today’s “cookie cutter“ world. * Ask about the “secret hatch!” Bring your own vision to its classic spaces and make the next chapter yours!

716 Montebello Circle, South Chesapeake

$287,000

2 Beds ⋅ 2.1 Baths ⋅ 10651614 MLS

Come fall in love with this beautiful move-in ready corner unit in sought-after Greenbrier. You will be impressed by this spacious & bright open-concept layout connecting the living & dining areas, the updated kitchen with granite countertops & SS appliances. Kitchen & half bath grouted tile. New flooring downstairs in 2025. Home features 2 large bedrooms with 2 full en-suite baths & 2 large walk-in closets. Enjoy private enclosed patio with additional storage. Appl. working, but convey "as is". Condo fees include inground pool, trails with park benches, water, sewer, trash, grounds maintenance & master insurance policy. Minutes from shopping, dining & entertainment. Easy access to VAB oceanfront. Schedule a tour today!

322 Holyoke Lane, South Chesapeake

$549,900

4 Beds ⋅ 2.1 Baths ⋅ 10651217 MLS

Welcome to 2809 Cistern Circle! This beautifully maintained home offers spacious living areas, abundant natural light and a flexible floor plan for everyday living, entertaining and working from home. Dedicated space offers room for a home office, study, flex room or workspace. Smart Home Ready with Samsung SmartThings potential and compatible lighting, locks, cameras, thermostats, sensors and more. The living room features built-in surround sound, while the garage offers two additional 240V outlets. Enjoy a large fenced backyard, deck, patio and fire pit area. Community amenities include a pool, clubhouse, playground, picnic areas and green space. With a home office option, smart-home features, outdoor living, storage, flexible living space and neighborhood amenities, this move-in ready home is ready for its next owner!

2809 Cistern Circle, South Chesapeake

$415,000

4 Beds ⋅ 2 Baths ⋅ 10651469 MLS

Come Fall In-Love With This Gorgeous Ranch Home Nestled in the Beautiful Sought After Area Of Chesapeake. This is like a Private street with No Through Traffic. Enjoy Cookouts and Gather around the Firepit in the Huge Fenced Backyard. Lots of Extra storage in the Multiple Sheds. Bask in the Beauty of the Famous Cherry Blossom Tree. Come inside and Feel the Elegance of the Vaulted Ceilings and Grand Open Room. Cozy Up next to the Gas Fireplace and Have your Favorite Beverage. Lots of Room for Cooking in the Beautiful Kitchen with the Stainless Appliances including a Gas Range. Relax in the Big Primary bedroom with Private Ensuite Bathroom and Walk in closet. Includes 3 additional bedrooms and even a Big 2 car attached Garage. This Beautiful Well Maintained Home is Ready to Move Right In. Close to TOP SCHOOLS, Shopping and Entertainment. Come See this Lovely Home Today:)

2460 Broadnax Circle, South Chesapeake

$614,000

4 Beds ⋅ 2.1 Baths ⋅ 10650661 MLS

Welcome home to 1912 Merano Lane in Chesapeake’s desirable Hickory Manor community! This beautiful Bentley model is move-in ready and offers four spacious bedrooms with a bright, open floor plan designed for comfortable everyday living and entertaining. Enjoy a well-appointed kitchen, generous living spaces, and a relaxing primary suite. Conveniently located near shopping, dining, interstate access, and sought-after Chesapeake schools. The seller will pay six months of HOA fees with an acceptable offer. Don’t miss this opportunity to own a beautifully maintained home in the heart of Hickory

1912 Merano Lane, South Chesapeake

$290,000

3 Beds ⋅ 2 Baths ⋅ 10650500 MLS

Welcome home to this charming 1,224-square-foot home with a comfortable layout and plenty to offer. Inside, you'll find an updated kitchen and bathrooms, inviting living spaces, and a home that's been freshly cleaned and is ready for its next chapter. A little fresh paint gives the new owner an easy opportunity to add their own style. Outside, enjoy a manageable yard and convenient driveway parking. Whether you're buying your first home, downsizing, or looking for an investment, this one is worth a look!

2502 Livesay Road, South Chesapeake

$269,000

3 Beds ⋅ 2.1 Baths ⋅ 10649987 MLS

Move in condition Freshly painted. New carpets, flooring and kitchen cabinets. Close to interstate Close to Oak Grove Park

1250 Corkwood Circle, South Chesapeake

$464,900

3 Beds ⋅ 2.1 Baths ⋅ 10648866 MLS

Experience low-maintenance living at its finest in this beautifully appointed home in the heart of Chesapeake. Built in 2019, this 3-bed, 2.5-bath residence offers a modern, open-concept design w/stylish finishes and thoughtful details throughout. The spacious main living area flows seamlessly into a well-designed kitchen. A first-floor primary suite provides comfort and convenience, while additional bedrooms offer flexibility for guests, a home office, or hobbies. Enjoy the ease of a low-maintenance lifestyle with community amenities that elevate everyday living, all in a sought-after location near shopping, dining, and top conveniences. This is the perfect blend of comfort, style, and simplicity, great for those ready to enjoy more and maintain less.

419 Heartfield Drive, South Chesapeake

$749,900

4 Beds ⋅ 3.1 Baths ⋅ 10649237 MLS

Welcome to Riverwalk, a beautifully maintained community offering an exceptional blend of comfort, style, and amenities including a pool, tennis courts, and playground! This updated spacious home features an amazing first-floor primary suite and bath w/ 2 huge walk-in closets, soaring 9-foot ceilings, and a bright, inviting Florida room. The interior includes NEW paint throughout, NEW hardwood flooring in the den, NEW carpet upstairs, NEW bathrooms, and NEW light fixtures. The kitchen, primary bath, and half bath showcase beautiful custom cabinetry and quality finishes. With 4 bedrooms plus a FROG, there is plenty of space for guests, and work-from-home needs. Major HVAC systems replaced in 2017 and 2023. Dual staircases. Outside, enjoy the low-maintenance lifestyle of a tumbled-brick exterior and wrap, Trex deck, and a dedicated gas line for the grill—perfect for entertaining! It also features an encapsulated crawlspace w/2 dehumidifiers, providing added peace of mind. Just beautiful!

745 Seagrass Reach, South 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.