Chesapeake VA Homes with City View

Welcome to Chesapeake, Virginia—a captivating blend of suburban charm and urban convenience. Nestled in the heart of Hampton Roads, Chesapeake is a vibrant city known for its rich history, lush landscapes, and a strong sense of community. With its scenic waterways, expansive parks, and a variety of recreational activities, Chesapeake offers residents a serene lifestyle while being just a stone's throw away from the bustling cities of Norfolk and Virginia Beach.

One of the most alluring features of Chesapeake is its diverse housing market, particularly homes with stunning city views. Imagine waking up to a picturesque skyline, where the sun rises over the horizon, casting a warm glow on your home. These properties not only provide breathtaking vistas but also offer a unique vantage point to enjoy the vibrant energy of the city below. Whether you’re sipping your morning coffee on a sun-drenched balcony or hosting friends for a sunset dinner, these homes elevate your living experience to new heights.

Chesapeake is also known for its excellent schools, thriving local businesses, and a plethora of dining and entertainment options. From outdoor adventures at the Great Dismal Swamp National Wildlife Refuge to family-friendly events at the Chesapeake City Park, there’s always something to explore.

If you're seeking a home that combines the beauty of city views with the tranquility of suburban living, Chesapeake, VA, is the perfect place to call home. Discover your dream property today and embrace the lifestyle that awaits you in this charming city!

Newest Chesapeake VA 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

$499,900

5 Beds ⋅ 3 Baths ⋅ 10653261 MLS

BRAND-NEW CONSTRUCTION IN AN ESTABLISHED CHESAPEAKE NEIGHBORHOOD! Welcome to 3705 Davis Avenue, where modern design and the ease of new construction come together in an established community. Offering approximately 2,550 square feet, this spacious home features 5 bedrooms, 3 full baths, and a thoughtfully designed open floor plan with flexibility for today's lifestyle. A standout feature is the oversized first-floor bedroom with direct access to a full bath, also conveniently accessible from the hallway. This versatile space is ideal for multigenerational living, an in-law suite, overnight guests, a private home office, or anyone seeking comfortable first-floor accommodations. Davis offers the opportunity to enjoy a fresh, modern home without giving up the character and convenience of an established neighborhood.

3705 Davis Avenue, Central Chesapeake

$509,900

4 Beds ⋅ 2.1 Baths ⋅ 10653139 MLS

Welcome to 508 Schaefer Avenue, a beautifully maintained 2018-built home in Chesapeake’s Deep Creek area! With 4 bedrooms, 2.5 baths, and 2,398 square feet, this home offers the space today’s buyers are looking for. The main level features an open flow between the kitchen, dining, and living areas, along with a separate front flex room ideal for a home office, playroom, or sitting room. The bright kitchen includes white cabinetry, granite countertops, a large island with seating, and stainless steel appliances. Upstairs, the spacious primary suite includes a separate sitting area and an ensuite bath with dual vanities, a soaking tub, and a separate glass shower. Three additional bedrooms and an upstairs laundry room add everyday convenience. Outside, enjoy a level backyard, concrete patio, wooded backdrop, and attached two-car garage. Potential 5.75% assumable loan opportunity for qualified buyers, subject to lender/servicer approval, underwriting, applicable terms, and buyer qualification. Schedule your private showing today!! THIS ONE IS A STEAL!!!

508 Schaefer Avenue, West 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

$225,000

3 Beds ⋅ 2 Baths ⋅ 10652708 MLS

NEW PLUSH CARPET THROUGHOUT. Open concept living room eat in kitchen with breakfast nook. 1st Floor Primary Bedroom with bathroom that opens to laundry room. 2 bedrooms upstairs with a full bath. 1 larger bedroom upstairs features a seating area that could be used as an office or additional multi use space. Large sheds in the back for storage. Covered front porch for relaxing on crisp fall days.

1310 Hoover Avenue, Central Chesapeake

$385,000

4 Beds ⋅ 2.1 Baths ⋅ 10652567 MLS

This all-brick ranch is just waiting for you to call it home! Featuring 4 bedrooms & 2.5 baths, this spacious home has been thoughtfully updated throughout the years. Major improvements include a roof and water heater updated in 2020, HVAC replaced in 2022 & windows approximately 12 years old. Inside, you’ll find a large kitchen with expansive countertops, stainless steel appliances, a formal dining room, and a generously sized living room complete with a cozy gas fireplace. Primary bedroom has a walk-in in closet while the other bedrooms are generous in size. The outdoor space is just as impressive! The back deck overlooks the large, fully fenced backyard. 2 concrete driveways offer plenty of parking & the 2nd driveway extends to a double gate into the backyard, providing convenient access for trailers, boats, recreational vehicles, or additional parking. Come see everything this home has to offer and make it yours! Some photos have been virtually staged.

909 Portland Street, Central 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

$299,900

3 Beds ⋅ 2 Baths ⋅ 10652386 MLS

3536 Dunedin Drive, West 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

$360,000

3 Beds ⋅ 2 Baths ⋅ 10652237 MLS

Welcome home to this beautifully updated brick rancher! This one is truly move-in ready, with LVP flooring throughout and a fresh, updated kitchen featuring soft close cabinets, granite countertops and new appliances. Major updates are already taken care of, too, with a new roof and HVAC in 2026. Outside, you’ll love the fenced-in backyard and the spacious deck, complete with a retractable awning that makes it a great spot to relax or entertain. And the detached garage is an added bonus — it has electricity and plenty of room for a workshop, hobbies, storage, or whatever you need. Comfortable, updated, and easy to love, this is one you’ll want to see in person!

405 Villanova Avenue, Central 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.