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Chesapeake, VA Houses for Sale with Private Pool

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  • /50

    $549,990

    • 5 Beds
    • 2.5 Baths
    • 2,581 Sq Ft

    1751 Emerald Sea Dr, Chesapeake, VA 23323

    Updated single family home in the highly sought Grassfield school district. Nice layout and space. New cabinets with polished granite counters & vanities, new carpet & luxury vinyl plank flooring, and upgraded stainless steel appliances. Primary bedroom has walk-in closet and large bath with new tiled shower, luxurious jetted tub, and extra vanity space. Located in a quiet family-friendly

    Agent Photo

    Stacy Potts

    Focus Realty LLC

    (757) 514-8694

    1751 Emerald Sea Dr, Chesapeake, VA 23323
  • /25

    $499,900

    • 3 Beds
    • 2 Baths
    • 2,159 Sq Ft

    517 Vicksdell Crescent, Chesapeake, VA 23322

    Located in the Bridgefield neighborhood where homes rarely come available, this 3-bedroom, 2-bathroom property offers endless potential. With newer flooring, roof, and HVAC, it's a solid foundation just waiting for your personal touch.The kitchen features a generous footprint, offering plenty of space to reimagine and customize to your style—whether you're dreaming of an island, expanded storage,

    Agent Photo

    Maureen Montealegre

    Iron Valley Real Estate Hampton Roads

    (757) 794-4602

    517 Vicksdell Crescent, Chesapeake, VA 23322
  • /48

    $639,900 Open Sun 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,750 Sq Ft

    704 Danali Ct, Chesapeake, VA 23322

    Don't miss this GREAT Home in Sought after Grassfield High School Zone. Built in 2015,tucked away on a large Private Cul-de-Sac. This home offers space & privacy inside & out. Wood flooring in foyer, dining room & great room areas. Ceramic tile in Kitchen & Baths. Large kitchen w/ Pantry, Stainless Appliances, Granite Counters & Breakfast Bar opens to large family room w/fireplace & 1/2 bath for

    Chrissy Wilkins Howard Hanna Real Estate Services

    704 Danali Ct, Chesapeake, VA 23322
  • /29

    $600,000

    • 5 Beds
    • 3 Baths
    • 3,300 Sq Ft

    617 Saint Brides Rd W, Chesapeake, VA 23322

    Welcome to this 5-bedroom, 3-bath farm-style home located in the desirable Grassfield School District. With over 3,300 sq. ft. of living space, this home blends comfort with charm and offers plenty of room to grow. On the main floor, you'll enjoy hardwood floors, adding warmth and character to the space. The home also features a partially wooded lot behind, providing privacy and space for outdoor

    Chrissy Hagler Coastal Towne Realty

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

    $595,000

    • 4 Beds
    • 3 Baths
    • 3,018 Sq Ft

    4017 Middleburg Ln, Chesapeake, VA 23321

    Premium location in one of Western Branch’s most sought-after neighborhoods & elementary schools. Beautiful, manicured homes w/large lots & no homeowner’s association. Just minutes to 664 & ALL of Hampton Roads bases, shopping & entertainment. Bring your swimsuit & take a dip in the refreshing saltwater pool, toast marshmallows over the fire or just enjoy relaxing on the deck. Formal living &

    Tracie Gaskins Howard Hanna Real Estate Services

    4017 Middleburg Ln, Chesapeake, VA 23321
  • /49

    $680,000

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    1016 Fox Trail, Chesapeake, VA 23323

    Welcome to 1016 Fox Trail in Chesapeake, VA – a stunning blend of elegance and modern living. Built in 2018, this beautifully designed home offers over 2,500 sq. ft of thoughtfully crafted living space on a spacious 0.48-acre lot. Inside, the open-concept layout seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere ideal for both entertaining and

    Steve Marable Iron Valley Real Estate Hampton Roads

    1016 Fox Trail, Chesapeake, VA 23323
  • /36

    $605,000

    • 5 Beds
    • 2.5 Baths
    • 2,798 Sq Ft

    1225 Veranda Way, Chesapeake, VA 23320

    Welcome to Eagle Lake Plantation North! This charming home offers 5 bedrooms, including a spacious room above the garage, and a well-designed layout featuring a formal living room and a cozy family room that flows into your kitchen with a generous breakfast space. You'll also find a formal dining room perfect for entertaining. Relax in your private backyard oasis, complete with an in-ground pool

    Leah Rybak The Real Estate Group

    1225 Veranda Way, Chesapeake, VA 23320
  • /49

    $695,000

    • 4 Beds
    • 3.5 Baths
    • 3,117 Sq Ft

    1020 Pernell Ln, Chesapeake, VA 23322

    Move into luxury living in this stunning home built in 2019, it's where elegance meets carefully curated interior design. This space features an outdoor oasis with a covered attached patio overlooking a sparkling salt water pool and the pavers surrounding it add to paradise vibes. Receipts prove approx. $83,000 in upgrades. Neighborhood has no through traffic. Primary bedroom on first floor away

    Cheri Bass-Wozniak BHHS RW Towne Realty

    1020 Pernell Ln, Chesapeake, VA 23322
  • /41

    $649,900

    • 5 Beds
    • 2.5 Baths
    • 2,897 Sq Ft

    1849 Sunsprite Loop, Chesapeake, VA 23323

    Experience luxury living in this lovely 5-bedroom home, perfectly designed for comfort and entertainment. The main floor boasts elegant bamboo flooring, a spacious bedroom, and an open-concept living area. The gourmet kitchen includes a wine refrigerator, great for hosting. Step outside to your private oasis featuring a heated saltwater pool, large deck, hot tub, and hard-wired landscape

    Paul Gitlin Redfin Corporation

    1849 Sunsprite Loop, Chesapeake, VA 23323
  • /50

    $615,000

    • 5 Beds
    • 3 Baths
    • 2,612 Sq Ft

    3657 Kathys Way, Chesapeake, VA 23323

    Spacious 5-bed, 3-bath home in sought-after Deep Creek! Enjoy a backyard oasis with a stunning saltwater pool, tanning ledge, child safety fencing, stamped concrete, & serene wooded views. Inside, a stylish home office features a barn door and built-in book shelves. Whole-house water purification & reverse osmosis system in the kitchen. Added perks: Solar Panels, 11x16 shed, alarm system, FiOS

    Bridgette Hamm The Real Estate Group

    3657 Kathys Way, Chesapeake, VA 23323
  • /43

    $905,000

    • 4 Beds
    • 2.5 Baths
    • 4,082 Sq Ft

    1500 Blade Ct, Chesapeake, VA 23320

    This gorgeous home is located in the heart of Chesapeake near many shopping centers and restaurants. This lovely home features four bedrooms and two full and one half bathrooms. The master bedroom is very large with two walk in closets. The master bath features a jetted tub with double vanity. The recently remodeled kitchen is very spacious. The fenced back yard is very large for entertaining

    Mark Gatling Keller Williams Coastal Virginia Chesapeake

    1500 Blade Ct, Chesapeake, VA 23320
  • /50

    $875,000

    • 6 Beds
    • 4 Baths
    • 4,118 Sq Ft

    517 Peaceful Rd, Chesapeake, VA 23322

    Welcome home! Enjoy 6 bedrooms, 4 full baths, beautiful updates, and tranquility surrounded by nature. This gorgeous 3 acre property offers ample parking with a large circular driveway, carport, and oversized garage. The primary suite features a private balcony overlooking the pool and wooded backyard. The suite boasts a fireplace, walk-in closet, and bathroom with a double-sink, tub, and tile

    Reagan Feuerhahn Prodigy Realty

    517 Peaceful Rd, Chesapeake, VA 23322
  • /28

    $799,900

    • 5 Beds
    • 3.5 Baths
    • 3,300 Sq Ft

    3801 Pine Grove Cir, Chesapeake, VA 23321

    Deep water access! Inground pool! Hot tub! New deck! New carpet! Look no further -- this gorgeous all brick home has it all. First floor primary with walk in closet and spa bath. Formal living and dining rooms and a large kitchen with breakfast room. Family room with fireplace and soaring ceilings. Beautiful hardwood flooring. Four full bedrooms with jack-n-jill baths upstairs. But the

    Lisa Richardson-Smith Fathom Realty

    3801 Pine Grove Cir, Chesapeake, VA 23321
  • /50

    $667,000

    • 5 Beds
    • 2.5 Baths
    • 2,831 Sq Ft

    312 White Dogwood Dr, Chesapeake, VA 23322

    This stunning home in Chesapeake Colony Estates is ready for you! Featuring beautiful flooring throughout, an open-concept eat-in kitchen that flows seamlessly into the bright and inviting living space, and a versatile downstairs bedroom—perfect as a rec room, home theater, or fitness area—the possibilities are endless. Step outside to your backyard oasis, complete with a spacious deck for

    Rosalind Levy Triumph Realty

    312 White Dogwood Dr, Chesapeake, VA 23322
  • /44

    $847,500

    • 4 Beds
    • 3.5 Baths
    • 3,644 Sq Ft

    331 Greens Edge Dr, Chesapeake, VA 23322

    Don’t miss this beautiful all-brick home in the sought-after Cahoon Plantation golf community. Inside, you’ll find a bright, open layout with a spacious first-floor primary suite featuring a remodeled bath with double vanities, a soaking tub, and a walk-in closet. The great room boasts soaring ceilings, a cozy fireplace, and a wall of windows that fill the space with natural light. The updated

    Lorenzo Goganious Realty Specialists

    331 Greens Edge Dr, Chesapeake, VA 23322
  • /21

    $409,999

    • 4 Beds
    • 2.5 Baths
    • 2,154 Sq Ft

    2408 Crown Ct, Chesapeake, VA 23325

    Come check out this beautiful 4 bedroom, 2.5 bath ranch style home minutes away from Greenbriar in a cul-de-sac. Mother-in-law suite/detached apartment has two bedrooms and an additional bathroom with AC/Heat. Sunroom overlooks the Tropical Oasis Back Yard with Large inground Pool and, Koi Pond! Double Drive Way entries on Both Sides of the House with Fenced RV Parking. Primary bedroom with walk

    Rashad Felton Iron Valley Real Estate Hampton Roads

    2408 Crown Ct, Chesapeake, VA 23325
  • /37

    $420,000

    • 3 Beds
    • 2 Baths
    • 1,480 Sq Ft

    1019 Chattanooga St, Chesapeake, VA 23322

    Updated 3BD/2BA ranch in the heart of Great Bridge! Kitchen was remodeled a few years ago and features custom cabinetry, granite counters & stainless steel appliances. All windows in the house were replaced in 2016. 178 sqft sunroom is included in the square footage. Large detached garage with unfinished room over it. 30amp RV hookup, with ample space to park it! New fully fenced backyard with

    Bessie Ostrander Fathom Realty

    1019 Chattanooga St, Chesapeake, VA 23322
  • /18

    $450,000

    • 4 Beds
    • 2.5 Baths
    • 2,103 Sq Ft

    500 Landmark Ct, Chesapeake, VA 23322

    BEAUTIFUL SOUGHT AFTER DETACHED CONDO HAS LARGE CORNER LOT GRANITE COUNTERTOP, SS APPLIANCES, VAULTED CEILINGS, CROWN MOLDING, WOOD BURNING FIREPLACE, HARDWOOD FLOORS DOWNSTAIRS, HVAC RECENTLY SERVICED, BOX RENEWED, NEW BLINDS UPSTAIRS, STAIRWAY CARPET TO BE REPLACED AS WELL AS THE STAIR RAILS, PATIO DOOR TO BE REPLACED, MASTER SHOWER REDONE, TILE FLOORS IN KIT, GAZEBO & LAWN FURNITURE STAY, LOTS

    Iris Cauldwell Coldwell Banker Premier

    500 Landmark Ct, Chesapeake, VA 23322
  • /30

    $280,000

    • 3 Beds
    • 1.5 Baths
    • 1,044 Sq Ft

    909 Mayfield Ave, Chesapeake, VA 23324

    Welcome to 909 Mayfield Avenue—a well-cared-for 3-bedroom, 1.5-bath ranch that blends comfort with thoughtful upgrades. The home features added laminate flooring in the hallway and living room, offering a clean, modern touch. Key updates include a new HVAC system, windows, and doors in 2021, plus a new dishwasher and backyard fencing in 2023,& fully renovated full bathroom in 2024. Solar panels

    Ricardo Moreno Iron Valley Real Estate Hampton Roads

    909 Mayfield Ave, Chesapeake, VA 23324
  • /50

    $559,000 Open Sun 12PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,853 Sq Ft

    3601 Gretna Ct, Chesapeake, VA 23321

    Beautiful, Move-In Ready Home Packed with Upgrades! Too many to list here. This stunning, low-maintenance home features a sleek exterior and an upgraded kitchen complete with stainless steel appliances (all convey), pantry, and modern finishes. The spacious primary suite offers two closets—including a large walk-in—and a private ensuite bath. Enjoy year-round relaxation in the sunroom, which

    Lesa Klauer Thrive Realty

    3601 Gretna Ct, Chesapeake, VA 23321
  • /16

    $484,900

    • 4 Beds
    • 2.5 Baths
    • 2,372 Sq Ft

    816 Shadowberry Crest, Chesapeake, VA 23320

    Beautifully renovated 4 bedroom, 2.5 bath home with large lot on the water! Newer remodeled kitchen with granite counters, gas stove, and SS appliances! Enjoy the open living room & dining room with lovely wood flooring as well as the large family room with fireplace! New upgrades include: renovated hall bath, new carpet in 2nd floor bedrooms, new wood stairs & covered back patio! Also new front

    Steven Crawford Swell Realty Co

    816 Shadowberry Crest, Chesapeake, VA 23320
  • /30

    $500,000

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

    1308 Oil Bird Ln, Chesapeake, VA 23321

    Nestled in Lakes of Jolliff neighborhood and beautifully maintained, this home offers functionality with modern convenience. White oak plank flooring can be found throughout the main living areas for durability and style. The living room features a cathedral ceiling allowing for an open and spacious feel. The primary bedroom is conveniently tucked away on the first floor - a private oasis

    Gregory Chaplain The Real Estate Group

    1308 Oil Bird Ln, Chesapeake, VA 23321
  • /41

    $575,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,503 Sq Ft

    509 Aguila Ct, Chesapeake, VA 23322

    Beautiful ranch on cul-de-sac with quality, low maintenance custom deck over looking salt water pool and pond. Owner took pride in home and updates were done with great workmanship. Updated/new items include: pool cover, fencing, exterior doors, garage door, LVP and HVAC. Windows and roof have been replaced. Cabana has power and built-in bar. Open floor plan and outdoor living space make this

    Amy Harris BHHS RW Towne Realty

    509 Aguila Ct, Chesapeake, VA 23322
  • /50

    $2,250,000

    • 4 Beds
    • 4.5 Baths
    • 5,553 Sq Ft

    1516 Peyton Ln, Chesapeake, VA 23320

    A rare gem in Emerald Forest, this stunning mid-century modern home sits on the 8th hole of the private country club, offering breathtaking golf course views. Designed for luxury living, it features a spa-like primary suite with a stainless steel tub and dual walk-in closets, a full gym, and a theater room with surround sound and a pool table. The gourmet kitchen, showcased by B&T Kitchen &

    Kandey Wilson EXIT Realty Central

    1516 Peyton Ln, Chesapeake, VA 23320
  • /43

    $484,000

    • 4 Beds
    • 3 Baths
    • 1,900 Sq Ft

    2009 Darden St, Chesapeake, VA 23322

    Are you dreaming of peaceful country living without sacrificing the convenience of being just minutes from the city? Look no further—this stunning, move-in-ready ranch-style home is exactly what you've been searching for! 4 bedrooms/ 3 baths, one level living with open concept interior. Nestled on a private half-acre lot at the end of a quiet dead-end street, this property offers unmatched

    Linda Brooks Long & Foster Real Estate Inc.

    2009 Darden St, Chesapeake, VA 23322
  • /48

    $535,000

    • 5 Beds
    • 3 Baths
    • 2,439 Sq Ft

    4528 Davids Mill Dr, Chesapeake, VA 23321

    Check out this move-in ready; brick ranch located in Davids Mill neighborhood of Western Branch. This one-story home boast 4 bedrooms, 3 full baths and a bonus bedroom over the garage. The foyer opens up to a spacious sitting room with formal dining room & eat-in kitchen. The family room gives a sneak peek at the spacious, fenced-in backyard. Enjoy the hot tub or go for a swim in the custom

    Dominique Ferguson Real Broker LLC

    4528 Davids Mill Dr, Chesapeake, VA 23321
  • /49

    $1,345,000

    • 5 Beds
    • 3.5 Baths
    • 4,110 Sq Ft

    3527 Glencoe Ct, Chesapeake, VA 23322

    Welcome to a Steven Alexander Homes at its finest! This stunning property sits on 3 acres, offering the perfect blend of luxury and space. Relax by the heated saltwater pool or unwind on the oversized porch. A sleek, new black aluminum fence adds curb appeal, both front and rear. Step inside to discover not one, but two primary suites—one on each floor—ensuring ultimate comfort for you and your

    Tyler Shelton RE/MAX Allegiance

    3527 Glencoe Ct, Chesapeake, VA 23322
  • /41

    $545,000

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    4713 Jolliff Woods Dr, Chesapeake, VA 23321

    Stunning All-Brick Home Built to Last!This exceptional property offers the perfect blend of comfort, style, and durability. Enjoy resort-style living with a heated inground saltwater pool featuring an attached jacuzzi and a custom pool house, perfect for relaxation and entertaining. The 4-seasons sunroom provides year-round enjoyment with stunning views of the backyard oasis.Newly remodeled

    BK Fitz Rock Steady Group

    4713 Jolliff Woods Dr, Chesapeake, VA 23321
  • /49

    $1,260,000

    • 6 Beds
    • 4 Baths
    • 5,511 Sq Ft

    505 Woodsmere Rd, Chesapeake, VA 23322

    Step into timeless elegance with this Georgian Colonial reproduction, inspired by the historic George Reed II house in Delaware. This 6-bed, 4-bath home offers 5,511 sq ft on 3 private acres with a Circular Drive and Saltwater Pool. Inside, you’ll find 6 Gas Fireplaces and detailed custom millwork throughout. The kitchen features upgraded SS appliances, a 6-burner Thermador gas range, granite

    Diane Keeley BHHS RW Towne Realty

    505 Woodsmere Rd, Chesapeake, VA 23322
  • /50

    $974,900 Open Sun 12PM - 2PM

    • 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
  • /30

    $555,000

    • 4 Beds
    • 3 Baths
    • 2,443 Sq Ft

    2444 Johnstown Rd, Chesapeake, VA 23322

    Welcome to your dream farmhouse retreat at 2444 Johnstown Road! This beautiful four-bedroom, three-bathroom ranch-style home offers spacious living on an large wooded lot. Step inside to an inviting open-concept layout featuring vaulted ceilings and abundant natural light. The formal sitting room and dining area for entertaining, while the eat-in kitchen is great for casual meals. The large

    Samantha Janisch Own Real Estate LLC

    2444 Johnstown Rd, Chesapeake, VA 23322
  • /49

    $1,100,000

    • 7 Beds
    • 5 Baths
    • 4,500 Sq Ft

    2341 West Rd, Chesapeake, VA 23322

    Step into luxury living in this stunning one story Chesapeake home, with 6 bedrooms, 4 baths, and 3,483 sq. ft. situated on 3 acres, this home is a rare gem. Featuring two full kitchens—one in the main home and another in the spacious in-law suite—both designed with stainless steel appliances, granite countertops, and an open feel, great for entertaining! The oversized 4-car garage with living

    Betsy Thompson The Agency

    2341 West Rd, Chesapeake, VA 23322
  • /46

    $695,000

    • 3 Beds
    • 3 Baths
    • 1,755 Sq Ft

    4103 Chowan Ave, Chesapeake, VA 23325

    Priced below appraisal, this waterfront oasis offers a beautifully renovated brick ranch home on .46 acres with 175 feet of deep water frontage. Step onto the expansive deck overlooking an inviting inground fiberglass pool, framed by sweeping water views. Enjoy the added luxury of a pool house complete with a tiki bar and full bathroom, plus a dock with a 10,000 lb. boat lift—perfect for water

    Chris faircloth Swell Realty Co

    4103 Chowan Ave, Chesapeake, VA 23325
  • /48

    $373,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 2.5 Baths
    • 2,408 Sq Ft

    1510 Victory Blvd, Portsmouth, VA 23702

    Move-in ready 5-bedroom Home! This beauty features a modern kitchen with granite countertops, stainless steel appliances, updated paint, carpet, flooring, bathrooms, and finishes. The first-floor primary bedroom with a full bath is easily accessible, and the open living room and dining room provide ample space for entertaining. Upstairs, you will find generously sized bedrooms with plenty of

    Reigne Brown RE/MAX Ultra

    1510 Victory Blvd, Portsmouth, VA 23702

Home Trends in Chesapeake, VA

Home Trends

Median Price (12 Mo)
$400,000
Median Single Family Price
$440,000
Median Townhouse Price
$300,000
Median 2 Bedroom Price
$264,500
Median 1 Bedroom Price
$190,950
Average Price Per Sq Ft
$215
Number of Homes for Sale
436
Last 12 months Home Sales
3,351
Months of Supply
1.60
Median List Price
$406,000
Median Discount From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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