5 Bedroom Homes for Sale in Chesapeake, VA

Welcome to your dedicated resource for 5 bedroom homes for sale in Chesapeake, VA. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Chesapeake, VA agent, Barn Door Homes specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the 5 bedroom properties currently available below, or contact a local agent to discuss the details that matters most to your search.

< Back to all Homes for Sale in Chesapeake, VA

Be the First to Know About New Chesapeake Homes

Stay ahead with real-time updates — no searching required.

See Homes Before Everyone Else

Chesapeake Real Estate Map Search

Search Chesapeake by Bedrooms

Advanced Search Market Reports Home Value Connect

All 5 Bedroom Homes for Sale in Chesapeake, VA

$645,500

5 Beds ⋅ 3 Baths ⋅ 10650640 MLS

Over 3,200 sq ft beautifully maintained 5br brick ranch in the heart of Riverbend/ Western Branch area. Situated on a spacious 0.756 acre lot. This multigenerational layout offers 4 generously sized bedrooms on the main level, including a primary suite w/ a stunning custom-modeled bath. The flexible fourth main-level bedroom off the kitchen can easily function as an in-law suite with walk in closet & a full bath conveniently located off the kitchen. The home features three full baths, plus an additional large bd over the garage, for guests, bonus room, or home office. The expansive kitchen opens seamlessly to the family room and showcases stainless steel appliances and granite countertops, great for everyday living & entertaining. Spacious formal living & dining room. Additional highlights include, large laundry room, three-zone HVAC system, gas water heater replaced in 2021, newer gutters & electric fence. Two-car garage & a wonderful backyard w/ tree house complete this rare Riverbend opportunity. NO HOA

1432 Pine Grove Lane, West Chesapeake

$595,000

5 Beds ⋅ 4 Baths ⋅ 10650611 MLS

This meticulously maintained home in the sought-after Grassfield area of Chesapeake is waiting for you! Featuring 5 bedrooms and 4 full bathrooms, this spacious home offers plenty of room for everyday living and entertaining. The upstairs primary suite provides a relaxing retreat with two closets, a double vanity, stand-up shower, and garden tub. Three additional bedrooms and two full bathrooms complete the upstairs living space. The downstairs bedroom with an en-suite bathroom offers flexibility for guests, an in-law suite, or home office. The well-appointed kitchen features granite countertops, a breakfast bar, and updated appliances. The spacious living room is warmed by a gas fireplace, creating a cozy gathering space. A bright sunroom offers peaceful views of the wooded backyard, where mature trees create a private and tranquil setting. Don't miss the opportunity to make this home in the desirable Grassfield area your next home! Come see today!

705 Creekwood Drive, South Chesapeake

$1,500,000

5 Beds ⋅ 3.1 Baths ⋅ 10650552 MLS

A builder's own estate — private, impeccable, and set on approximately eight wooded acres at the end of a quiet Chesapeake cul-de-sac. Custom-built by the builder for his own family, this brick-and-stone home reflects a level of care you rarely find. Nothing here has been left untouched; it lives like new construction. A long gravel drive winds past mature trees to the home, where a sweeping front porch offers multiple entries and room to linger. Deer, turkey, and other wildlife are frequent visitors. Inside, a grand open floor plan rises to cathedral ceilings, finished with updated tile flooring, crown molding, and Hunter ceiling fans. The living area anchors around a dramatic stone fireplace and flows into an eat-in kitchen with rustic cabinetry, updated KitchenAid appliances, an electric cooktop, and a large center island with bar seating. The first floor holds a spacious primary suite, generously sized baths, and a well-placed Jack-and-Jill. Upstairs, brand-new carpet runs through bedrooms of exceptional size, and the primary closet is fitted with extensive custom built-ins. The two-story garage apartment is a standout, two bedrooms, 1.5 baths, multiple living areas, and a full eat-in kitchen, great for guests, multigenerational living, or income potential. The garages themselves have been freshly painted white, bright and spotless. Recent improvements include fresh paint throughout, LED lighting, updated kitchen and bath fixtures, two new HVAC units, a mini-split serving the room over the garage, smoke detectors, smart locks, and an on-demand propane water heater. Estate infrastructure is equally serious: 600-amp electrical service, a four-inch private well with pump house, a new water-softening system, hard-ducted HVAC, an illuminated crawl space, and a septic system serviced in 2026. A concrete parking pad completes the property. Privacy, craftsmanship, and acreage — a genuinely distinctive Chesapeake estate.

1120 Kathleen Lane, South Chesapeake

$688,900

5 Beds ⋅ 3 Baths ⋅ 10650242 MLS

Proudly offered by its original owner, this beautifully maintained 5-bedroom, 3 bathroom home is a rare opportunity in one of the area's most desired neighborhoods. The thoughtfully designed floor plan features a spacious downstairs bedroom and full bath, ideal for guest or multi-generational living along with a Great room, well-appointed kitchen, dining room, and flex room. Upstairs you will find 4 additional generous sized bedrooms, including the primary suite with a beautifully updated bathroom and large closet. Enjoy gathering with family and friends in the inviting family room complete with a built-in bar. Start your mornings on the welcoming front porch and unwind in the evenings on the spacious back patio, perfect for outdoor dining, entertaining, or simply relaxing. Find out why Warrington Hall is one of the most desired communities with all of its amenities including: pool, playgrounds, ball fields, and tennis courts.

816 Poquoson Crossing, South Chesapeake

$529,900

5 Beds ⋅ 2.1 Baths ⋅ 10649924 MLS

Make this your first stop! This spacious home sits in a sought-after area and offers an incredible amount of space for the price. Featuring a large custom kitchen, generous living areas, and a huge deck for entertaining, this home has plenty of room to make it your own. One of the larger homes in the area, it backs directly to a wooded portion of Oak Grove Lake Park, creating a private backyard setting with direct access to running and biking trails. With a fantastic location, tons of square footage, and endless potential, it's hard to find this much home at this price point.

1152 Crystalwood Circle, South Chesapeake

$497,500

5 Beds ⋅ 3 Baths ⋅ 10650190 MLS

4624 Westborough Drive, West Chesapeake

$624,900

5 Beds ⋅ 3 Baths ⋅ 10650063 MLS

Welcome to 3649 Kathys Way! 2.25% assumable VA loan! Balance $380,616, matures in 2050. The curb appeal immediately catches your eye with a beautifully manicured lawn and welcoming exterior. Inside, you’ll find a thoughtfully designed floor plan filled with natural light, with each space flowing seamlessly into the next. A cozy sitting area, inviting living room, and spacious dining area create plenty of room to gather and entertain. At the heart of the home is the well-appointed kitchen, featuring a center island, stylish backsplash, dedicated coffee or bar area, and stainless steel appliances, including a new wine refrigerator. The primary bedroom offers a walk-in closet and a spa like bathroom with a freestanding soaking tub and glass enclosed shower. Four additional well sized bedrooms and two more full bathrooms provide plenty of space for family and guests. Outside, enjoy the spacious fenced backyard with a paver patio and fire pit creating an inviting setting for relaxing or entertaining.

3649 Kathys Way, South Chesapeake

$446,500

5 Beds ⋅ 2.1 Baths ⋅ 10650002 MLS

Full appliance package (including washer/dryer & refrigerator) on all existing inventory! Seller will pay up to $12,000 for closing cost assistance or to be used at buyer's discretion using our preferred lender and our attorney; Stunning New Construction! Welcome to this beautiful 5-bedroom, 2.5-bath home offering 1,862 square feet of modern living space. Designed with a spacious open floor plan, it's perfect for entertaining and everyday family living. Inside, the kitchen shines with soft-close cabinets, granite countertops. Bathrooms are also appointed with granite countertops and soft-close cabinetry for a cohesive, upscale look. Throughout the home, you'll find a blend of durable LVP flooring and plush carpet. Tray ceiling in the primary bedroom and walk in closet. This home features a 1-car garage. This brand-new home is the perfect blend of comfort, style, and convenience—don't miss your chance to own it in the heart of Chesapeake!

901 Railroad Avenue, Central Chesapeake

$2,495,000

6 Beds ⋅ 7.1 Baths ⋅ 10649916 MLS

Waterfront Estate situated on 2+ acres, designed for luxurious waterfront living, direct access to the Chesapeake Bay, and multigenerational flexibility. This stunning gated estate offers expansive gathering spaces with waterfront views, and elevator that services the garage to the 2nd floor for effortless access. The 1st-floor Primary Suite is a private retreat featuring a spa-inspired bath, dual walk-in closets, sitting area, and connecting outdoor covered patio. Additional bedrooms all en suites with walk-in closets. Detached 6-car garage with apartment for extended family, guests, or independent living. Outdoor amenities include a saltwater pool, fire pit, expansive terraces & gathering spaces to watch the boat go by, a true boater's paradise with premier boating facilities 2-30K lifts + 1- 20 K lift & jet ski lift, multiple floating docks, and 5 FT at low tide. The amenities for this home are extensive; include a media room, climate-controlled detached 6+ car garage, central vac and more; inquire for a full list. Call today to schedule your private tour.

4112 Mingo Trail, Central Chesapeake

$725,000

5 Beds ⋅ 3 Baths ⋅ 10649882 MLS

MM Ashbee at Riverview Landing - To Be Built. The Ashbee is a 5-bedroom home with a first-floor Owner’s Suite, four bedrooms and a loft upstairs. Open-concept kitchen with large island, high-end finishes, double ovens, pantry, and plenty of counter space. Features include first and second-floor laundry (or option to convert upstairs laundry to a full bath), mudroom, and optional rear covered porch. Standard features and design options available. Convenient to shopping, dining, healthcare, and major roadways

MM Ashbee, South Chesapeake

$839,540

6 Beds ⋅ 4.1 Baths ⋅ 10649851 MLS

Welcome to the Tillman at Riverview Landing! This Property is great for multigenerational families! This spacious home includes 6 bedrooms, 4.5 baths, and a 2-car garage. The first-floor primary suite provides the perfect retreat with a massive walk-in closet, dual vanities, and a private water closet. Upstairs, you’ll find a second primary-style bedroom with direct access to a full bath, offering comfort and privacy for guests, teens, or extended family. Three additional bedrooms (each with walk-in closets), a large loft, and a convenient laundry room complete the second floor. The open-concept main level features a welcoming dining room, expansive kitchen with an oversized island and two pantries, including a Costco pantry, and a bright family room. This house is complete with a FINISHED BASEMENT! Photos are from the builder's library, actual finishes and features may vary.

1228 Kidbrooke Street, South Chesapeake

$839,900

5 Beds ⋅ 4.1 Baths ⋅ 10649639 MLS

Discover luxury, space, and versatility all in one remarkable Chesapeake address. 3504 Riverwood Crescent delivers an extraordinary living experience, offering a total of 5 bedrooms and 5 bathrooms thoughtfully tailored for comfort and style. Every detail has been considered to provide an elevated lifestyle for you and your family.Designed with ultimate flexibility in mind, the layout includes a completely private 1-bedroom, 1-bathroom in-law suite—complete with its own dedicated amenities—making it ideal for multi-generational living, extended family, or visiting guests while ensuring complete privacy for everyone under your roof.Nestled in a peaceful neighborhood while remaining close to top-tier dining, shopping, and major commuter routes, this home truly has it all. Don't miss the opportunity to make this incredible property your own!

3504 Riverwood Crescent, South Chesapeake

Start Your Search

Prev
1
...
3
4
5
...
15
of 15
Next

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.