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4-Bedroom Houses for Sale in Chesapeake, VA with Private Pool

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  • /43

    $725,000

    • 4 Beds
    • 3.5 Baths
    • 3,096 Sq Ft

    621 Briarwood Dr, Chesapeake, VA 23322

    Don't miss this opportunity—bring your offer and make this home yours! Welcome to 621 Briarwood Dr—a beautifully maintained Colonial-style home with modern upgrades and timeless charm. Sunlight fills the open layout, enhanced by custom wood trim and a cozy wood-burning fireplace, perfect for chilly evenings. The remodeled gourmet kitchen (2021) boasts high-end appliances, including a premium

    Natalie Carrier Redfin Corporation

    621 Briarwood Dr, Chesapeake, VA 23322
  • /42

    $575,000

    • 4 Beds
    • 2.5 Baths
    • 2,900 Sq Ft

    2005 Columbo Ave, Chesapeake, VA 23321

    Located in the desirable Chittum and Western Branch school districts, this beautifully updated home sits on a quiet cul-de-sac and offers everything you need—and more! Step into a freshly painted interior featuring new LVP flooring, plush carpet upstairs, and a spacious open-concept layout perfect for modern living. The updated kitchen flows seamlessly into the main living area, creating a warm,

    Nate Carl Keller Williams Realty Town Center

    2005 Columbo Ave, Chesapeake, VA 23321
  • /50

    $670,000

    • 4 Beds
    • 3 Baths
    • 2,752 Sq Ft

    312 Wisdom Path, Chesapeake, VA 23322

    Welcome home to 312 Wisdom Path in the highly sought after neighborhood of Viridian Reserve! This gorgeous home is sure to please from inside to outside with beautiful curb appeal and a generous sized front porch to the backyard with a two year old fiberglass salt water pool with a generous stamped concrete patio. Inside walk into the foyer and enjoy a full bath plus a front flex room with

    Tom Busciglio Howard Hanna Real Estate Services

    312 Wisdom Path, Chesapeake, VA 23322
  • /49

    $630,000 Open Sat 12PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,874 Sq Ft

    718 Beckley Ln, Chesapeake, VA 23322

    Make plans to view this beautiful traditional style home in the sought after community of Etheridge Woods in the Great Bridge are of Chesapeake. Offering nearly 2900 square feet of living space, this home features 4 BR's, 2.5 baths, glowing wood laminate floors on 1st floor, large, bright and well ventilated sunroom overlooking the manicured back yard, 20' X 20' deck & gazebo. Take advantage of

    Michael Steverson Warrant Realty Inc.

    718 Beckley Ln, Chesapeake, VA 23322
  • /49

    $675,000

    • 4 Beds
    • 3.5 Baths
    • 3,092 Sq Ft

    4421 Tartan Arch, Chesapeake, VA 23321

    Welcome home to this beautifully updated 4-bedroom, 3.5 bath brick ranch in the desirable Miar's Plantation neighborhood! Step inside this immaculate home featuring a spacious open floor plan ideal for every day life and entertaining, updated kitchen, and primary suite with jacuzzi tub. Upstairs, the finished room over the garage with a full bathroom is perfect for a media room, guest suite, or

    Rebecca Perkins Howard Hanna Real Estate Services

    4421 Tartan Arch, Chesapeake, VA 23321
  • /36

    $699,900

    • 4 Beds
    • 3.5 Baths
    • 3,322 Sq Ft

    3500 Douglas Rd, Chesapeake, VA 23322

    Peaceful country living on 5 partially wooded acres—just 10 minutes from city amenities! This spacious 4 bed, 3.5 bath home offers room to grow and incredible potential with a little TLC and updating. Inside you'll find multiple bonus rooms and a dedicated office space, perfect for work, hobbies, or additional living space. Relax or entertain on the large screened-in porch overlooking the

    Courtney Myers Own Real Estate LLC

    3500 Douglas Rd, Chesapeake, VA 23322
  • /50

    $612,000

    • 4 Beds
    • 2.5 Baths
    • 3,007 Sq Ft

    833 Copper Stone Cir, Chesapeake, VA 23320

    Welcome to this spacious 4-bedroom, 2.5-bath home offering 3,007 square feet of comfortable living space. Step outside to a large deck overlooking the inground pool and fenced-in backyard—perfect for entertaining or relaxing in privacy. The home also features oversize gutters with leaf guards for low-maintenance care, plus a storage shed for added convenience. Inside, you’ll find a dedicated

    Ron Sawyer RE/MAX Prime

    833 Copper Stone Cir, Chesapeake, VA 23320
  • /45

    $569,000

    • 4 Beds
    • 2.5 Baths
    • 2,219 Sq Ft

    805 Saddleback Trail Rd, Chesapeake, VA 23322

    WELCOME TO SOUGHT AFTER COUNTRY ROADS. THIS STUNNING UPDATED COLONIAL HAS A CHEF'S DESIGNER KITCHEN WITH GRANITE COUNTERS, SS APPL, AND CUSTOM CABNIETRY, WITH HUGE OPEN SPACES. LARGE FAM RM W/ FIREPLACE AND BULIT INS. OPEN DINING ROOM. RESORT-STYLED SPARKLING SWIMMING POOL, HOT TUB AND COVERED PATIO, PERFECT FOR LARGE FAM GATHERINGS. PRIM SUITE WITH WALK IN AND UPDATED LUXURY BATH WITH DOUBLE

    Jason Dodd RE/MAX Alliance

    805 Saddleback Trail Rd, Chesapeake, VA 23322
  • /50

    $615,000

    • 4 Beds
    • 2.5 Baths
    • 2,849 Sq Ft

    2000 Kelsey Bay Ct, Chesapeake, VA 23323

    Welcome to the Mill Creek Harbor neighborhood! This MOVE-IN ready home is located in the highly sought-after Grassfield section of Chesapeake, zoned for Grassfield schools. This nice sized corner lot is in a cul-de-sac with a beautifully maintained landscape offering a welcoming curb appeal. As you step inside, this home immediately shows off its' nice sized square footage with high ceilings and

    Richard Febus Next Chapter VA Realty Inc

    2000 Kelsey Bay Ct, Chesapeake, VA 23323
  • /50

    $849,900

    • 4 Beds
    • 3 Baths
    • 3,029 Sq Ft

    1076 Taft Rd, Chesapeake, VA 23322

    This gracious 2 story Cape Cod style Home boasts classic and exceptional details throughout! Situated on a serene and park like setting of 2+ acres, you will appreciate the backyard oasis with inground pool with large deck and patio. The 28 x 32 2 car Detached Garage offers plenty of room for extra cars, boats, and more and even has an additional 12 x 14 workshop and a large unfinished 2nd floor!

    Rachael Kraft Turner GreenTree Realty Inc.

    1076 Taft Rd, Chesapeake, VA 23322
  • /50

    $557,900

    • 4 Beds
    • 3 Baths
    • 2,362 Sq Ft

    1300 Saint Brides Rd W, Chesapeake, VA 23322

    Beautiful brick ranch on almost 1/2 acre of land! Vaulted ceilings in Primary bedroom and family room. This home also features formal Dining room and Living room. Chefs delight of a kitchen with eat in breakfast area with bay window! Lots and lots of decking in your oasis of a back yard w privacy fence. You will enjoy entertaining 16X36 lazy L Aegean pool. Attached 2 car garage + a huge, detached

    Toni Minnis Wainwright Real Estate

    1300 Saint Brides Rd W, Chesapeake, VA 23322
  • /39

    $516,000

    • 4 Beds
    • 2.5 Baths
    • 2,319 Sq Ft

    1248 Saint Brides Rd W, Chesapeake, VA 23322

    Enjoy peaceful country living in this spacious 3-bed, 2.5-bath brick ranch on nearly half an acre in sought-after Chesapeake. This home features cathedral ceilings, hardwood floors, a cedar closet, and a dual-sided gas fireplace (owned propane tank). Recent updates include a 30-year architectural roof (2023), new HVAC system with attic and exterior units (2024), cleaned ducts, and a dehumidifier

    Dusty Thayer Own Real Estate LLC

    1248 Saint Brides Rd W, Chesapeake, VA 23322
  • /50

    $550,000

    • 4 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    137 Waterfront Dr, Chesapeake, VA 23322

    Welcome to this beautifully updated 4-bedroom, 2.5-bath home on a prime corner lot in Inland Colony! Enjoy serene views of the Elizabeth River from this beautiful home nestled in a neighborhood with convenient water access. Inside, you'll find an updated kitchen complete with granite counter-tops and stainless steel appliances. Updated bathrooms throughout. A large bonus room over the garage

    Brian Wurst A Better Way Realty Inc.

    137 Waterfront Dr, Chesapeake, VA 23322
  • /50

    $990,000

    • 4 Beds
    • 3.5 Baths
    • 3,589 Sq Ft

    1149 Beaver Dam Rd, Chesapeake, VA 23322

    Welcome to Southern chesapeake “Hickory,” an exquisite custom-built residence in Southern Chesapeake, set upon 3.3 secluded acres. This gracious four-bedroom, three-and-a-half-bath home unfolds more than 3,500 square feet of serene rural elegance. Equestrian amenities abound—fenced pastures await your horses—while the expansive deck overlooks a shimmering pool and lush, private gardens. Inside,

    David Allison Atlantic Sotheby's International Realty

    1149 Beaver Dam Rd, Chesapeake, VA 23322
  • /50

    $499,000

    • 4 Beds
    • 2.5 Baths
    • 2,245 Sq Ft

    1116 Fairhaven Rd, Chesapeake, VA 23322

    Welcome to 1116 Fairhaven Road—a home offering both comfort and style! Featuring a recently renovated primary bathroom with a luxurious soaking tub and an oversized walk-in closet, designed for escape and relaxation! Frustrated with a lack of hot water...fret not, this home has a tankless water heater which provides endless hot water for any family! Step outside to your private oasis backyard

    Daniel Goffigan Own Real Estate LLC

    1116 Fairhaven Rd, Chesapeake, VA 23322
  • /32

    $480,000

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft

    701 Merle Ct, Chesapeake, VA 23322

    Spacious 4-bedroom, 2-bath ranch tucked away on a quiet cul-de-sac, offering the perfect blend of comfort and functionality. The inviting living room features a charming wood-burning fireplace and flows effortlessly into the dining and kitchen areas—ideal for everyday living and entertaining. The primary bedroom includes its own private en-suite for added convenience and relaxation. Outside,

    Kris Weaver Atlantic Sotheby's International Realty

    701 Merle Ct, Chesapeake, VA 23322
  • /33

    $519,000

    • 4 Beds
    • 2 Baths
    • 2,585 Sq Ft

    4252 Raleigh Rd, Chesapeake, VA 23321

    Fully renovated 4-bedroom, 2.5 bath home blending style and function! Enjoy peace of mind with a new roof, plumbing, electrical, HVAC, and more. Inside, you'll find new flooring, a sleek modern kitchen, updated baths, fresh lighting, and open living spaces. Outside features two new decks, a fresh driveway and walkway, plus a sparkling upgraded pool. Bonus: Finished room over the garage and a

    Naty Horev BHHS RW Towne Realty

    4252 Raleigh Rd, Chesapeake, VA 23321
  • /50

    $550,000

    • 4 Beds
    • 2.5 Baths
    • 2,202 Sq Ft

    543 Stillwater Dr, Chesapeake, VA 23320

    Welcome to your updated stunning summer oasis home situated on a cul-de-sac with plenty of parking! This home features an open floor plan with formal dining room, office/living room, large den with custom built ins that opens to beautiful kitchen with high end stainless appliances, granite, glass backsplash, bay window, bar area, and much more. The second story offers oversized bedrooms and a

    Julie Perkins Swell Realty Co

    543 Stillwater Dr, Chesapeake, VA 23320
  • /36

    $374,500

    • 4 Beds
    • 2 Baths
    • 1,929 Sq Ft

    1615 Oleander Ave, Chesapeake, VA 23325

    NEW HEAT PUMP HVAC STSTEM JUST INSTALLED ON 7/25 ALONG W/ PRICE DROP! WOW!! THIS IS THE ONE! THIS GORGEOUS HOME LOCATED IN THE WONDERFUL NEIGHBORHOOD OF NORFOLK HIGHLANDS IN CHESAPEAKE HAS IT ALL! 4 BEDROOMS, 2 FULL BATHS, 2 KITCHENS, 2 LIVING ROOMS, HUGE WALK-IN CLOSET IN PRIMARY & ITS ALMOST 2000 SQ FT. NEW 30YR ARCHITECTURAL ROOF, NEW PAINT IN & OUT, MOSTLY ALL NEW CARPET & WINDOWS. THE MAIN

    Roger McCann Atlantic Connection Real Estate

    1615 Oleander Ave, Chesapeake, VA 23325
  • /50

    $949,900

    • 4 Beds
    • 3 Baths
    • 2,532 Sq Ft

    3600 Fluridy Rd, Chesapeake, VA 23322

    Welcome to 25 acres, including pond stocked w/ largemouth bass, 3-car garage, walking trails, 52-inch deep above-ground pool w/ sand filter, & wildlife just outside. The home has 3 bedrooms on the 1st floor, including primary bedroom w/ walk-in closet, private bath, dual vanity, & walk-in tiled shower. The kitchen, dining area, & cathedral ceiling living room all overlook the vast acreage & pond.

    Daniel Patton Prodigy Realty

    3600 Fluridy Rd, Chesapeake, VA 23322
  • /2

    $514,999

    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft

    808 Loblolly Ct, Chesapeake, VA 23322

    VACATION IN YOUR OWN BACKYARD - YOU WILL LOVE THIS HOME WITH A RESORT LIKE FEEL. BEAUTIFUL HOME W/FRESH PAINT THROUGHOUT, DESIGNER LIGHTING, OPEN - AIRY KITCHEN W/EAT IN BREAKFAST BAY, DECK OVERLOOKING TROPICAL BACKYARD INCLUDING THE INGROUND SALTWATER POOL. LOCATED ON A PEACEFUL CUL-DE-SAC. UPDATES TO THE HOME INCLUDE - NEW BACKYARD SHED 2025, NEW GARAGE DOOR 2025, NEW LVP FLOORS 2024 IN DINING

    Terri Gleason Gleason & Associates Realty, Inc.

    808 Loblolly Ct, Chesapeake, VA 23322
  • /2

    $347,000

    • 4 Beds
    • 3 Baths
    • 2,552 Sq Ft

    1012 Towanda Rd, Virginia Beach, VA 23464

    Property being sold "AS IS". Appliances convey "AS IS". Contents and debris in and on the property at settlement convey. Due diligence should be completed prior to submitting offer. No contingencies please. Property is being sold by a Conservator and as a result requires approval by a Comm'r of Accounts before any offer can be ratified.

    Mike Robinson Chesapeake Bay Realty

    1012 Towanda Rd, Virginia Beach, VA 23464

Home Trends in Chesapeake, VA

Housing Trends

Median Sale Price
$521,850
Median Single Family Sale Price
$617,450
Median Townhouse Sale Price
$383,375
Median 2 Bedroom Sale Price
$228,000
Average Price Per Sq Ft
$224
Number of Homes for Sale
95
Last 12 months Home Sales
1,246
Months of Supply
0.90
Median List Price
$530,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
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