Chesapeake VA County Real Estate

Welcome to Chesapeake, Virginia – a vibrant city that beautifully blends the charm of coastal living with the conveniences of urban life. Nestled in the heart of Hampton Roads, Chesapeake is renowned for its picturesque landscapes, rich history, and a strong sense of community.

With over 350 miles of waterways, including the stunning Great Dismal Swamp and the tranquil Elizabeth River, Chesapeake is a paradise for outdoor enthusiasts. Whether you enjoy kayaking, fishing, or simply taking a leisurely stroll along the scenic trails, the natural beauty of this area is sure to captivate you. The city also boasts an array of parks and recreational facilities, making it an ideal place for families and individuals to stay active and engaged.

Chesapeake is characterized by its diverse neighborhoods, each offering a unique blend of suburban tranquility and modern amenities. From charming historic districts to new developments, there’s a perfect home for everyone. The city is also known for its top-rated schools, making it a desirable location for families seeking quality education for their children.

Culturally rich and community-focused, Chesapeake hosts various events throughout the year, including art festivals, farmers markets, and outdoor concerts, fostering a strong sense of belonging among residents. With easy access to major highways, commuting to nearby cities like Norfolk and Virginia Beach is a breeze, allowing you to enjoy the best of what the region has to offer.

Experience the warmth and welcoming spirit of Chesapeake, VA – a place where you can build a life you love amidst stunning scenery and a vibrant community. Discover your dream home in this delightful city today!

Newest Listings in Chesapeake VA County

$415,000

3 Beds ⋅ 2.1 Baths ⋅ 10647138 MLS

Deceptively spacious! Beautifully renovated 3-bedroom, 2.5 bathroom brick ranch in a quiet centrally located Chesapeake neighborhood. Open floor plan w/ LVP flooring, carpeted bedrooms, & 2 inviting family rooms offering endless possibilities for entertaining or relaxing. Dedicated dining room provides a warm, defined space for gatherings. Kitchen completed w/ quartz countertops, stainless steel appliances, soft-close cabinets & drawers & a cozy breakfast nook. Primary bedroom is a private retreat w/ its own flex room great for a sitting area, office, or workout space. Enjoy two walk-in closets & a breathtaking ensuite bathroom designed like a luxury spa. This standout space features dual vanity sinks & an impressive 7' x 7' dual-head shower room transforming your daily routine into a rejuvenating experience. Secluded deck & private backyard for outdoor living. Property includes a two-level workshop, abundant storage & ample workspace for hobbies, projects, or equipment. Tour it today!

357 Dexter E Street, Chesapeake

$269,900

3 Beds ⋅ 2 Baths ⋅ 10647137 MLS

AMAZING CENTRAL LOCATION FOR THIS RENOVATED BEAUTY! JUST A FEW BLOCKS AWAY FROM THE FREEWAY ENTRANCE! FRESH PAINT, LANDSCAPING, CARPETS, AND SO MUCH MORE! NEWER KITCHEN, BATHROOMS, LIGHT FIXTURES, AND PRIVACY FENCE! ADT SECURITY SYSTEM CONVEYS! ENJOY ALL THE BENEFITS OF A LOW ELECTRICITY BILL WITH SOLAR (NO MONEY OWED ON THE SYSTEM!)! BASEBALL FIELD AND LARGE ALL ABILITIES PLAYGROUND WITH A PLETHORA OF PLAY EQUIPMENT IS CATTY CORNER FROM THIS HOUSE! COME AND CALL THIS ONE HOME TODAY! WOWZER IN YOUR BROWSER! * Current temporary street closure due to city sewer line replacement

1405 Perry Street, Chesapeake

$285,000

3 Beds ⋅ 1.1 Baths ⋅ 10647127 MLS

Super convenient Chesapeake & Greenbrier location. Three bedrooms 1.5 baths plus a separate dressing area in master bedroom includes a 3rd sink. Spacious kitchen with nice counter space, all appliances, and a big front bay window. Schedule an easy showing today. 2-private parking spaces and a cul-de-sac location with no through traffic. BRAND NEW COSTCO is coming to Greenbrier Mall. Easy commute all military bases & downtown Norfolk shipyards. Easy access to beachfront and Greenbrier restaurants, shopping, NFCU & banks. YMCA includes swimming pool and activities. Buyer has ability to pick replacement carpeting. HOA approves - backyard fencing can be painted by seller. Newer heat pump unit for heating and cooling with Coolant 410A. HVAC under yearly inspection program. Seller provides Termite/Moisture clearance via Hampton Roads Warranty Program. No flood insurance required. Trash & Recycle cans provided.

1218 Cedar Mill Square, 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

$355,000

3 Beds ⋅ 2.1 Baths ⋅ 10647123 MLS

Welcome home to this charming 3 bedroom, 2.5 bath condo in the heart of Greenbrier, offering the perfect blend of comfort, convenience, and low maintenance living. The thoughtfully designed floor plan features a first floor bedroom and half bath, ideal for guests, a home office, or flexible living. The spacious kitchen is equipped with granite countertops, rich cherry wood cabinetry, abundant counter space, and a breakfast bar that's perfect for everyday living or entertaining. Upstairs, both bedrooms offer private en suites and walk in closets. The primary suite features a relaxing Jacuzzi style soaking tub, a separate shower, and plenty of space to unwind. An upstairs laundry room, complete with the washer and dryer, adds everyday convenience. Step outside to your private patio with an attached storage unit, providing additional space for your outdoor essentials. The condo association covers water, trash, landscaping, access to the community pool, and individual roof maintenance, making homeownership even easier. Conveniently located just minutes from Greenbrier Mall, golf courses, shopping, dining, schools, and major interstates, this move in ready home offers the ideal combination of location, comfort, and carefree living. Schedule your private tour today! This version is well under the MLS limit and reads naturally for buyers.

1555 Rollesby Way Unit 5, Chesapeake

$660,000

5 Beds ⋅ 2.1 Baths ⋅ 10647099 MLS

Welcome to 2317 Angler Lane, a well-maintained home in a sought-after Chesapeake area with convenient access to shopping, dining, and major roadways. Recent updates include new vinyl front stairs (2026), an extended driveway (2024), vinyl fencing (2024), pool house (2022), water heater (2020), roof (2019), and HVAC systems (2018). The outdoor setup is a standout with a screened-in porch, in-ground pool, and approximately 250 sq. ft. detached pool house with heating and air conditioning and a full bathroom. Speakers are located in both the living room and pool house. With plenty of space to relax, entertain, and enjoy the backyard, this home offers a hard-to-find combination of indoor and outdoor living. Make sure to check out the virtual tour.

2317 Angler Lane, Chesapeake

$345,900

3 Beds ⋅ 2 Baths ⋅ 10647096 MLS

Stunning renovation in Chesapeake! This 3BR 2BA gem features a brand new roof, new HVAC, and top-to-bottom updates designed for modern living. Gorgeous LVP flooring flows throughout an open, light-filled floor plan perfect for entertaining or working from home. The fully updated kitchen boasts new stainless steel appliances and sleek finishes that will impress any home chef. Retreat to a spacious primary suite with a custom ensuite bath. Outside you will find a private fenced backyard with a new deck — the perfect space to relax and unwind. New lighting inside and out and move-in ready condition. Schedule your showing today! **Some pictures are virtually staged**

4111 Williamson Street, Chesapeake

$1,175,000

5 Beds ⋅ 3 Baths ⋅ 10646791 MLS

Rare opportunity to own a Chesapeake equestrian property offering the perfect blend of refined country living and modern convenience. This exceptional home offers 5 bedrooms, 3 full bathrooms, 3,046 square feet, and an additional 712 square feet of living space in a true in-law suite with private entrance. Equestrian enthusiasts will appreciate three fenced pastures, a riding ring with light, the run-in shed, and a three-stall stable with tack room, while the outdoor enthusiast will love the large garden, the raised garden beds, the blueberry and raspberry bushes, the gazebo, and the picturesque koi pond with fountain. Inside, the living room with beautiful stone mantle and pellet stove is open to the updated kitchen featuring gorgeous, leathered granite countertops, a large island, and an eat-in area with additional cabinetry. The spacious primary suite offers beautiful property views and includes a walk-in closet and luxurious bath with double quartz shower and dual sinks. Additional highlights include wood floors throughout, an office with French doors, a fantastic screened-in porch and a deck, a 2-car attached garage, a 3-car detached garage, a new well, reverse osmosis water system, generator hook-up, and a 400-gallon propane tank. The best of country living without sacrificing modern convenience, this country retreat is designed for both comfortable living and equestrian enjoyment.

2000 Long Ridge Road, Chesapeake

$285,000

3 Beds ⋅ 1 Baths ⋅ 10647094 MLS

3 bedroom ranch in Western Branch ready to be updated into an amazing home!

4024 Oak Drive, 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. Loft overlooks family room-great for office space. 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

$380,000

3 Beds ⋅ 2.1 Baths ⋅ 10647070 MLS

Explore the Possibilities with a Traditional Brick Ranch style home in the Washington area of Chesapeake Virginia. This 3 bedroom 2.5 bath, 2,312 sqft has spacious rooms, open floor plan, attached garage, 2 separate parking spaces, private backyard, and original character throughout the home. Come view today, add your special touch and make this house your home. Located aprox 6miles to Greenbriar Mall, shops, Chesapeake City Park, entertainment, interstate, and so much more. Seller to make no repairs. Property is being sold as is, where is.

340 Fernwood Farm Road, Chesapeake

$459,999

4 Beds ⋅ 3 Baths ⋅ 10647060 MLS

Welcome home to this beautifully maintained luxury end unit townhome in the highly sought after Great Bridge School District! Less than seven years old, this move in ready home offers stylish, low-maintenance living with thoughtful upgrades throughout. Enjoy luxury laminate plank flooring throughout the entire home, smart switches compatible with Alexa, and an upgraded custom walk in closet in the spacious primary suite. The gourmet kitchen features granite countertops, a large island, upgraded cabinetry, refrigerator only 6 months old and a flat top stove. Soaring 9-foot ceilings, multiple walk-in closets, a spacious laundry room, garage, driveway, and covered front porch add to the home's appeal. The HOA handles yard maintenance, giving you more time to enjoy nearby shopping, dining, entertainment, and quick highway access. Schedule your private showing today!

300 Sikeston Lane, 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.