20

5-Bedroom Homes for Sale in Chesapeake, VA with Private Pool

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  • /50

    $515,000

    • 5 Beds
    • 4 Baths
    • 2,719 Sq Ft

    3308 Michelle Ct, Chesapeake, VA 23321

    Move-in ready & full of updates! This custom Colonial sits on a quiet low traffic cul-de-sac with a large, beautifully landscaped lot. Major upgrades in June 2025 include a new roof & 4 new bathrooms. Dual-zone HVAC with new units & ductwork (2022 & 2024), all new windows (2022), updated water heater, and stainless-steel appliances (2020). Inside you'll find original hardwood floors, granite

    Agent Photo

    Laura Blackwood

    CENTURY 21 Nachman Realty

    (757) 255-7057

    3308 Michelle Ct, Chesapeake, VA 23321
  • /44

    $765,000

    • 6 Beds
    • 4 Baths
    • 3,917 Sq Ft

    1305 Turnberry Ct, Chesapeake, VA 23320

    Spacious 6BD/4BA brick home in Emerald Greens with views of the 9th tee of Greenbrier CC golf course. Enjoy morning coffee on the back patio or host summer barbecues by the in-ground pool (liner replaced in 2024). This home features a formal dining room, bonus room, FROG (possible in-law suite), and a large family room with built-ins and a gas log fireplace. The eat-in kitchen offers ample

    Robert Rogers Real Broker LLC

    1305 Turnberry Ct, Chesapeake, VA 23320
  • /50

    $674,900

    • 5 Beds
    • 3 Baths
    • 3,800 Sq Ft

    405 Briarwood Ct, Chesapeake, VA 23322

    Beautifully maintained 5BR, 3BA home with over 3,800 sq ft across 3 finished levels on a quiet cul-de-sac in Great Bridge, Chesapeake. Flexible layout includes a front room ideal as a formal living room or home office, a large family room, formal dining, and an expansive eat-in kitchen with granite, island, and sunny breakfast nook. First-floor flex room with full bath makes a perfect guest suite

    Kris Weaver Atlantic Sotheby's International Realty

    405 Briarwood Ct, Chesapeake, VA 23322
  • /50

    $990,000

    • 5 Beds
    • 5 Baths
    • 4,700 Sq Ft

    603 Stoneleigh Ct, Chesapeake, VA 23322

    Fall in love with this one of a kind all brick stunner! Former HOMEARAMA home. Large lot with backyard paradise. Saltwater inground pool, stone fountain, pool house with entertainment area, fireplace, outdoor shower, extra storage and bathroom. The ultimate entertaining space for friends and family! Inside boasts vast and open downstairs with well appointed gourmet kitchen with new black

    Amy Holloway Coldwell Banker Premier

    603 Stoneleigh Ct, Chesapeake, VA 23322
  • /47

    $775,000 Open Sun 12PM - 2PM

    • 5 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    940 Bahama Way, Chesapeake, VA 23322

    Welcome Home to this Etheridge Pines pool-property on a large corner lot located within the highly coveted Hickory School system. Large manicured yard leads to entry foyer with two story ceilings, formal living room, formal dining room and free flow to open concept den, kitchen, eat in area, and sun room! Kitchen features hardwood floors, ceramic tile backsplash, granite tops, and stainless

    Cole Hart Own Real Estate LLC

    940 Bahama Way, Chesapeake, VA 23322
  • /49

    $799,900 Open Sun 12PM - 3PM

    • 5 Beds
    • 3 Baths
    • 3,333 Sq Ft

    905 Lingale Arch, Chesapeake, VA 23322

    Luxurious & meticulously upgraded, 5 bed/3 bath home boasting elegant living space on a serene .24-acre cul-de-sac lot in the sought-after Emerald Lake neighborhood. Immediately enter through the expansive foyer to the richly appointed interior, featuring spacious gathering areas including a beautiful dining room adorned with custom lighting, & a spectacular custom kitchen that seamlessly flows

    Bethany White Keller Williams Coastal Virginia Chesapeake

    905 Lingale Arch, Chesapeake, VA 23322
  • /50

    $768,000 Open Sun 1PM - 4PM

    • 5 Beds
    • 4 Baths
    • 3,457 Sq Ft

    1117 Old Vintage Rd, Chesapeake, VA 23322

    Looking for a stunner in Chesapeake? How about one with sought after Great Bridge schools? Maybe one with a huge lot and an oasis as a backyard including an inground pool and a Tiki Bar? This one is a beautiful all brick two-story home in an upscale neighborhood! Huge kitchen with an island & lots of storage, two-story foyer, open floor plan w/9' ceilings, huge deck, encapsulated crawl, newer

    Kimberly Bedsole BHHS RW Towne Realty

    1117 Old Vintage Rd, Chesapeake, VA 23322
  • /38

    $823,000

    • 5 Beds
    • 3 Baths
    • 2,400 Sq Ft

    1305 Sanderson Rd, Chesapeake, VA 23322

    Nestled in sought-after, peaceful Hickory neighborhood. 5-bedroom, 3-bath ranch has dedicated Mother-In-Law Suite, Sits on 3.24 private acres. Long driveway loop leads to a 1-car attached garage & a 2-car detached garage with workshop. Detached garage comes with 200-amp electrical service & a 320 SF partially FROG. Great for a DIY enthusiast or man cave. Enjoy ultimate privacy with a 20x40

    Bill Loftis 757 Realty

    1305 Sanderson Rd, Chesapeake, VA 23322
  • /50

    $940,000

    • 5 Beds
    • 4 Baths
    • 3,962 Sq Ft

    1207 Masters Row, Chesapeake, VA 23320

    Stunning 5BR/4BA custom home with saltwater inground pool and brand-new horseshoe driveway, nestled next to the golf course in sought-after Emerald Greens! Grand two-story foyer with curved staircase, gorgeous hardwood floors, and fresh paint throughout. Gourmet kitchen features granite counters and sleek black stainless steel appliances. First-floor bedroom with private entry and full bath—great

    Nancy Bui Keller Williams Realty Town Center

    1207 Masters Row, Chesapeake, VA 23320
  • /50

    $595,000 Open Sun 11AM - 1PM

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

    3657 Kathys Way, Chesapeake, VA 23323

    Enjoy energy savings from day one with a PAID-IN-FULL SOLAR PANELS! The backyard is a true showstopper featuring a luxurious saltwater pool with a tanning ledge, child safety fencing, stamped concrete patio, and peaceful wooded views—perfect for both entertaining and unwinding. Inside, work from home in style in a custom home office with a sliding barn door and built-in bookshelves. The home also

    Oxana Prikhodko A Better Way Realty Inc.

    3657 Kathys Way, Chesapeake, VA 23323
  • /47

    $1,375,000

    • 5 Beds
    • 6 Baths
    • 4,387 Sq Ft

    516 Peaceful Rd, Chesapeake, VA 23322

    Tucked away on 3 private acres in Caroon Farms, this stunning all-brick estate is a rare blend of elegance, comfort, and nature. This 5-bedroom, 4 full and 2 half bath home offers a private guest, student, or in-law suite, a chef’s kitchen, spa-inspired baths, and an oversized flex space. Outdoor living is unmatched—framed by lush blooms, the 15,000-gallon, two-tier koi pond with a tranquil

    Janice Myers-Hollowell BHHS RW Towne Realty

    516 Peaceful Rd, Chesapeake, VA 23322
  • /50

    $600,000

    • 5 Beds
    • 3.5 Baths
    • 3,141 Sq Ft

    1009 Cronin Ct, Chesapeake, VA 23322

    Welcome to your dream home in Chesapeake! This spacious 5-bedroom, 3.5-bath home offers 3,141 square feet of comfortable living, including a FROG and an in-law suite with private entry off the back porch. The heart of the home is an open-concept living area with an expansive kitchen featuring ample counter space, great for everyday living and entertaining. Step out back to your own summer oasis

    Betsy Thompson The Agency

    1009 Cronin Ct, Chesapeake, VA 23322
  • /29

    $575,000

    • 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
  • /42

    $500,000

    • 5 Beds
    • 3 Baths
    • 2,648 Sq Ft

    748 Clearfield Ave, Chesapeake, VA 23320

    Welcome home to 748 Clearfield Ave—where comfort meets style. With 5 bedrooms, 3 full baths, and a flexible layout, there's room for everyone. The updated kitchen flows into cozy living spaces, and the backyard? Your personal oasis, complete with a sparkling in-ground pool. Upstairs features a vaulted master retreat (includes an en suite w/dual vanity, separate soaking tub & shower, & walk-in

    Kyla Irizarry 1st Class Real Estate-Equity Group

    748 Clearfield Ave, Chesapeake, VA 23320
  • /50

    $499,900

    • 5 Beds
    • 2.5 Baths
    • 2,388 Sq Ft

    3304 Michelle Ct, Chesapeake, VA 23321

    Welcome to this beautifully upgraded 5-bedroom, 2.5-bath home nestled in one of the area's most sought-after neighborhoods. This stunning residence features rich wood floors, luxurious carpet , and ceramic tiles seamlessly flow throughout the main living spaces. A gourmet kitchen with granite countertops, stainless steel appliances, and an open-concept design that flows into the living

    Jeremy Brown LPT Realty LLC

    3304 Michelle Ct, Chesapeake, VA 23321
  • /50

    $1,700,000

    • 5 Beds
    • 5.5 Baths
    • 5,500 Sq Ft

    318 Scone Castle Loop, Chesapeake, VA 23322

    Your best life awaits in this immaculate 5-bedroom, 5.5-bath custom-built estate in elegant Edinburgh Meadows, a sought-after neighborhood in a top school district. Enjoy water views from the open-concept living area, gourmet kitchen, upstairs veranda, and covered patio. The resort-style backyard features a heated pool, built-in hot tub with waterfall, outdoor kitchen with gas fireplace, multiple

    Diane Keeley BHHS RW Towne Realty

    318 Scone Castle Loop, Chesapeake, VA 23322
  • /50

    $1,695,000

    • 8 Beds
    • 5.5 Baths
    • 6,400 Sq Ft

    2652 Benefit Rd, Chesapeake, VA 23322

    Nestled in the heart of Hickory, this one-of-a-kind equestrian estate offers the perfect fusion of historic charm and modern luxury. The fully renovated main home features structural upgrades, 2017 roof, updated electrical (2025), plumbing, HVAC, insulation, and energy-efficient windows. Enjoy marble bathrooms, custom kitchen with Wolf range, Cafe; appliances, marble counters, and brand new white

    Andrew Christie Atlantic Sotheby's International Realty

    2652 Benefit Rd, Chesapeake, VA 23322
  • /38

    $633,000

    • 5 Beds
    • 2.5 Baths
    • 3,254 Sq Ft

    832 Doe Run Dr, Chesapeake, VA 23322

    Beautiful home in the heart of Great Bridge! Rare Opportunity! In-Ground Salt Water Pool, Pool House, updated home, with gourmet kitchen that features $25,000 in renovations! Newer cabinets with auto shut, pull out shelves, granite counters, upgrade stainless steel appliance, built in table with granite counters, laminate wood floors! Wonderful Floor Plan and Spacious Bedrooms!

    Michael Miller RE/MAX Allegiance

    832 Doe Run Dr, Chesapeake, VA 23322
  • /50

    $1,779,000

    • 5 Beds
    • 3.5 Baths
    • 3,727 Sq Ft

    2801 Ballahack Rd, Chesapeake, VA 23322

    Stunning all-brick home on 4 acres with 5 bedrooms, 3.5 baths, 2 car attached garage and a 5-bay detached garage housing 7 automobiles with 1-bedroom guest quarters downstairs and a 2-bedroom apartment upstairs. The main house features hardwood floors, new quartz kitchen countertops, double oven, gas cooktop, and stainless steel appliances. 1st floor primary ensuite boasts a sizeable dressing

    Donna Johnson Long & Foster Real Estate Inc.

    2801 Ballahack Rd, Chesapeake, VA 23322
  • /47

    $1,496,000

    • 6 Beds
    • 5.5 Baths
    • 5,600 Sq Ft

    909 Two Gates Cir, Chesapeake, VA 23322

    Stunning and luxurious 5,600 square foot multi-generational home situated on a gorgeous, three acre lushly landscaped yard with an inviting swimming pool, outdoor kitchen, greenhouse and detached two car garage with a spacious in law or guest suite on the 2nd floor with a spacious living room, bedroom and kitchen. The multiple decks and patios surrounding the pool and residence are the perfect

    Susan Pender BHHS RW Towne Realty

    909 Two Gates Cir, Chesapeake, VA 23322

Home Trends in Chesapeake, VA

Housing Trends

Median Sale Price
$521,850
Median Single Family Sale Price
$619,000
Median Townhouse Sale Price
$383,187
Median 2 Bedroom Sale Price
$228,000
Average Price Per Sq Ft
$224
Number of Homes for Sale
95
Last 12 months Home Sales
1,250
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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