5 Bedroom homes for sale & real estate in Chester, VA

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Chester, VA
Welcome to 2803 Jolly Lane! This spacious 5-bedroom, 3-bath Chester home offers 2,674 square feet of comfortable living space and a functional floor plan designed for everyday living and entertaining. The beautifully updated kitchen features refinished cabinetry and granite countertops, creating a fresh and inviting space for preparing meals and gathering with family and friends. Home has a downstairs primary bedroom with bath, main primary is upstairs with 3 other bedrooms, there is plenty of room for family, guests, a home office, or flex space. A convenient 2-car garage provides ample parking and storage. Located in a desirable Chester area with convenient access to shopping, dining, sch

$429,000

5 beds3 baths2,674 sq ft

2803 Jolly Ln, Chester, VA 23831

Convenient access • Refinished cabinetry • Updated kitchen

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chester, VA
Charming Cottage Cape with Space, Character & Endless Possibilities! Fall in love with the charm and versatility of this inviting Cottage Cape, offering spacious living areas and room for everyone! The first floor features a living room, dining room, and family room, all with beautiful hardwood flooring, along with a galley kitchen and separate utility room. The first-floor primary bedroom includes a full bath for added convenience. Upstairs, you'll find two additional bedrooms with walk-in closets, a full bath, and hardwood flooring. The basement offers even more possibilities, featuring a kitchenette with sink, two additional bedrooms, and a separate family room—ideal for ext

$335,000

5 beds3 baths2,508 sq ft

15500 Richmond St, Chester, VA 23836

Utility room • Galley kitchen • Living room

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chester, VA
NEW PRICE — MOTIVATED SELLER LOOK BEYOND THE TREES — YOUR PRIVATE FAMILY OASIS AWAITS! Some homes reveal everything from the street. 14500 Happy Hill Road is different. Tucked behind mature trees on 1.59 private acres, this spacious Chester home offers approximately 3,600± square feet, 5 bedrooms, 2.5 baths, renovated kitchen and bathrooms, and large rooms throughout. But beyond the trees, you’ll also find two garages, an in-ground pool, a screened porch, plenty of room to spread out, and NO HOA. The seller is motivated, and this is a property you need to experience in person. DON’T JUST DRIVE BY — COME SEE WHAT’S BEYOND THE TREES.

$627,500

5 beds2.5 baths3,598 sq ft

14500 Happy Hl, Chester, VA 23831

In-ground pool • Renovated kitchen • Screened porch

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chester, VA
Wonderful quality built colonial on an acre and a quarter in a sought after neighborhood. 5 bedrooms including one that could be a separate suite. Hardwood floors in all rooms on the firstfloor and primary bedroom. New LVT flooring in the other 3 bedrooms. The comfortable family room opens to the breakfast and kitchen area for good traffic flow on the first floor. Large Primary bedroom has it's own fireplace. Large mud room with adjacent full bath for the sportsman in the family. Plus a large sunroom opening to the private deck. The garage doubles as a "man cave" with full kitchen possibilities and large floored attic accessed by stairway for plenty of convenient storage. Located

$425,000

5 beds3 baths2,544 sq ft

11716 Ivywood Rd, Chester, VA 23831

Private deck • Large floored attic • New lvt flooring

FLOOR PLAN

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chester, VA
Welcome to Meadowville Landing! This beautifully maintained Corsica by Ryan Homes offers spacious, flexible living in a sought-after community along the James River. Featuring 10' ceilings, a 3-car side and front entry garage, wide level lot, and a thoughtfully designed floor plan. This home is move-in ready and built for everyday living and entertaining. The main level features a welcoming foyer, formal dining room, spacious great room, and a first-floor bedroom ideal for guests, multigenerational living, or a home office. The gourmet kitchen offers quartz countertops, stainless steel appliances, abundant prep space, and a large island, opening to a bright great room with a stone fireplace

$654,950

5 beds3 baths3,527 sq ft

12044 Almer Ln, Chester, VA 23836

Quartz countertops • Owner’s suite • Gourmet kitchen

Property at 4104 Birchleaf Ct, Chester, VA 23831, 5 beds, 3.5 baths

$479,000

5 beds3.5 baths3,520 sq ft

4104 Birchleaf Ct, Chester, VA 23831

Property at 12621 Green Garden Ter, Chester, VA 23836, 5 beds, 2.5 baths

$465,000

5 beds2.5 baths2,516 sq ft

12621 Green Garden Ter, Chester, VA 23836

Property at 1506 White Mountain Dr, Chester, VA 23836, 5 beds, 3.5 baths

$699,950

5 beds3.5 baths3,036 sq ft

1506 White Mountain Dr, Chester, VA 23836

Property at 4512 Forrestal Rd, Chester, VA 23831, 5 beds, 4.5 baths

$615,000

5 beds4.5 baths4,217 sq ft

4512 Forrestal Rd, Chester, VA 23831

Property at 5042 Lorkimwood Rd, Chesterfield, VA 23832, 5 beds, 3 baths

$589,990

5 beds3 baths3,059 sq ft

5042 Lorkimwood Rd, Chesterfield, VA 23832

Property at 13446 Bradley Bridge Rd, Chester, VA 23831, 5 beds, 4.5 baths

$1,780,000

5 beds4.5 baths4,444 sq ft

13446 Bradley Bridge Rd, Chester, VA 23831

Property at 13601 Green Spire Cir, Chester, VA 23836, 5 beds, 3.5 baths

$499,950

5 beds3.5 baths3,100 sq ft

13601 Green Spire Cir, Chester, VA 23836

Property at 2526 Channelmark Pl, Chester, VA 23836, 5 beds, 3 baths

$660,000

5 beds3 baths3,341 sq ft

2526 Channelmark Pl, Chester, VA 23836

Property at 5301 Ashton Creek Rd, Chester, VA 23831, 5 beds, 4 baths

$895,000

5 beds4 baths4,732 sq ft

5301 Ashton Creek Rd, Chester, VA 23831

Property at 4313 Poplar Village Dr, Chester, VA 23831, 5 beds, 3 baths

$495,950

5 beds3 baths2,624 sq ft

4313 Poplar Village Dr, Chester, VA 23831

Property at The Potomac Plan, Chester, VA 23831, 5 beds, 2.5 baths

$454,950

5 beds2.5 baths2,232 sq ft

The Potomac Plan, Chester, VA 23831

Listing provided by Zillow

Property at The Cordova Plan, Chester, VA 23831, 5 beds, 2.5 baths

$464,950

5 beds2.5 baths2,599 sq ft

The Cordova Plan, Chester, VA 23831

Listing provided by Zillow

Property at 4042 Hiddenwell Ln, Chester, VA 23831, 5 beds, 2.5 baths

$484,000

5 beds2.5 baths2,480 sq ft

4042 Hiddenwell Ln, Chester, VA 23831

(571) 292-5377

Property at 610 Rivers Bend Cir, Chester, VA 23836, 5 beds, 3 baths

$554,900

5 beds3 baths3,131 sq ft

610 Rivers Bend Cir, Chester, VA 23836

(571) 292-5377

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Chester, VA
Set on almost one acre in The Highlands, 11700 Braystone Lane offers the space to spread out, entertain, and unwind in privacy at home, along with access to the neighborhood's pool, golf course, tennis courts, and clubhouse. With 5 bedrooms, 3.5 baths, and 3,384 square feet, this freshly renovated home delivers generous living spaces, distinctive design choices, and an atmosphere that feels anything but ordinary. Hardwood flooring flows throughout, and rich finishes, statement lighting, and abundant natural light create a warm, elevated feel. The kitchen features leathered granite countertops, a center island, and breakfast nook, while the adjoining living room is anchored by a fireplace an

$774,500

5 beds3.5 baths3,384 sq ft

11700 Braystone Ln, Chesterfield, VA 23838

Clubhouse • Tennis courts • Neighborhood pool

OPEN TODAY, 1PM TO 3PMFLOOR PLAN

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chester, VA
Welcome to this well-maintained 5-bedroom 2.5 bath home in a well-connected North Chesterfield community. Sitting proudly on a corner lot, the property offers plenty of room to enjoy the outdoors, host gatherings, or simply relax in your own space. Step inside to a modern-classic interior featuring fresh paint throughout, and a roomy comfortable feel that instantly says home. Every room offers a purposeful layout that enhances comfort and flow. It's the perfect match for buyers seeking space, value, and a welcoming neighborhood vibe. The washer, dryer stove, microwave, refrigerator and shed convey AS-IS.

$448,950

5 beds2.5 baths2,120 sq ft

4023 Evelake Rd, North Chesterfield, VA 23237

0.34 acre lot • 2 garage spots • Built 2012

OPEN SUN, 1PM TO 3PM3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chester, VA
Stately brick architecture meets an exceptional waterfront setting in Woodland Pond. Positioned on just over an acre with direct water access and a dock, this home captures sweeping water views across the entire rear of the residence. Expansive windows, soaring ceilings, and beautifully proportioned gathering spaces make the setting a part of everyday living. Hardwood floors flow throughout the first floor, where formal dining room and living room flank the two-story foyer. Beyond the entry, the dramatic family room features a two-story vaulted ceiling, floor-to-ceiling windows, and beautiful built-ins surrounding one of the home’s three fireplaces. The spacious kitchen offers a large

$1,099,000

5 beds4.5 baths5,793 sq ft

11021 Merganser Ter, Chesterfield, VA 23838

Dock • Formal dining room • Hardwood floors

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chester, VA
Discover the perfect blend of timeless elegance, modern comfort, and resort-style living in the award-winning Highlands community! This stunning Normandy model welcomes you with beautiful curb appeal, a charming full front porch, double-width paved driveway, and spacious three-car garage. Step inside the grand two-story foyer, where soaring ceilings and abundant natural light create an immediate sense of warmth and sophistication. Thoughtfully designed for effortless entertaining and everyday comfort, the expansive floor plan offers inviting living spaces that flow seamlessly throughout. At the heart of the home, the gourmet kitchen impresses with granite countertops, stainless steel applia

$720,000

5 beds4 baths3,808 sq ft

11500 Amara Dr, Chesterfield, VA 23838

Main-level bedroom • Gourmet kitchen • 1.01 acre lot

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chester, VA
Fully renovated two story, 5 bedroom, 3 full bath brick and vinyl home on a double lot in Hopewell’s Battery Park neighborhood. Every major system is new: roof, thermal windows, gutters, HVAC, plumbing, and electrical with 200 amp service, plus a fully encapsulated crawl space with drainage and a sump pump. The main level offers 9 foot ceilings, LVP flooring and recessed lighting, a family room with a wood burning brick fireplace, a bright dining room, and a kitchen with new cabinets, stainless appliances and an eat in breakfast area. A first floor bedroom near a full bath works well as an office or guest room. Upstairs are three more bedrooms, a hall bath with a double vanity, and a

$394,950

5 beds3 baths2,392 sq ft

2213 W City Point Rd, Hopewell, VA 23860

Fully renovated • New hvac • Double lot

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chester, VA
Welcome to 9731 Stagpenn Road! This well-maintained 5-bedroom, 2.5-bath home offers plenty of space and thoughtful updates, including fresh interior paint, new flooring on level 1, a whole-house water filtration system installed in 2024, and an updated attic fan. The Air Handler system was also updated in 2026. Enjoy the screened-in back porch overlooking the spacious fenced backyard—perfect for relaxing or entertaining. The backyard also features a chicken coop, which can remain or be removed, plus two large storage sheds, one with electricity, offering plenty of extra storage or workspace. Conveniently located near Route 10 with easy access to Route 288. Move-in ready and waiting f

$405,000

5 beds2.5 baths2,034 sq ft

9731 Stagpenn Rd, Chesterfield, VA 23832

Large storage sheds • Chicken coop • 0.54 acre lot

Property at 16132 Rowlett Rd, Chesterfield, VA 23838, 5 beds, 3 baths

$495,000

5 beds3 baths2,067 sq ft

16132 Rowlett Rd, Chesterfield, VA 23838

Property at 9101 Barrows Hill Ter, Chesterfield, VA 23838, 5 beds, 3 baths

$785,000

5 beds3 baths3,423 sq ft

9101 Barrows Hill Ter, Chesterfield, VA 23838

Property at 9966 Boschen Woods Pl, Chesterfield, VA 23838, 5 beds, 4 baths

$829,500

5 beds4 baths3,982 sq ft

9966 Boschen Woods Pl, Chesterfield, VA 23838

Property at 110 N 15th Ave, Hopewell, VA 23860, 5 beds, 2 baths

$317,000

5 beds2 baths2,268 sq ft

110 N 15th Ave, Hopewell, VA 23860

Property at 1413 Walthall Creek Dr, South Chesterfield, VA 23834, 5 beds, 2.5 baths

$475,000

5 beds2.5 baths2,584 sq ft

1413 Walthall Creek Dr, South Chesterfield, VA 23834

Property at 11707 Amara Dr, Chesterfield, VA 23838, 5 beds, 3 baths

$630,000

5 beds3 baths2,708 sq ft

11707 Amara Dr, Chesterfield, VA 23838

Property at 13254 Killbarney Dr, Chesterfield, VA 23838, 5 beds, 4.5 baths

$887,944

5 beds4.5 baths4,630 sq ft

13254 Killbarney Dr, Chesterfield, VA 23838

Property at 8409 Hopkins Rd, North Chesterfield, VA 23237, 5 beds, 2 baths

$370,000

5 beds2 baths1,874 sq ft

8409 Hopkins Rd, North Chesterfield, VA 23237

Property at 11630 Barrows Ridge Ln, Chesterfield, VA 23838, 5 beds, 4 baths

$774,950

5 beds4 baths3,455 sq ft

11630 Barrows Ridge Ln, Chesterfield, VA 23838

Property at 723 Waterfront Dr, Colonial Heights, VA 23834, 5 beds, 3.5 baths

$699,000

5 beds3.5 baths4,510 sq ft

723 Waterfront Dr, Colonial Heights, VA 23834

Property at 14713 Green Summit Pl, South Chesterfield, VA 23834, 5 beds, 3.5 baths

$499,000

5 beds3.5 baths3,052 sq ft

14713 Green Summit Pl, South Chesterfield, VA 23834

Property at 8343 Shagreen Ct, Chesterfield, VA 23838, 5 beds, 3.5 baths

$625,000

5 beds3.5 baths3,625 sq ft

8343 Shagreen Ct, Chesterfield, VA 23838

Property at 11125 Lyndenwood Dr, Chesterfield, VA 23838, 5 beds, 4.5 baths

$689,900

5 beds4.5 baths3,678 sq ft

11125 Lyndenwood Dr, Chesterfield, VA 23838

Property at 13260 Killbarney Dr, Chesterfield, VA 23838, 5 beds, 3.5 baths

$853,917

5 beds3.5 baths4,297 sq ft

13260 Killbarney Dr, Chesterfield, VA 23838

5 Bedroom Homes for Sale in Chester

There are currently 19 5 bedroom homes in Chester. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chester stay on the market for 40 days and receive 8 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 25 homes have been sold in Chester. In addition to houses in Chester, there were also 5 condos, 6 townhouses, and 1 multi-family unit for sale in Chester last month. Chester is a not walkable city in Chesterfield County with a Walk Score of 11. Chester is home to approximately 20,953 people and 6,646 jobs. Find your dream home in Chester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chester. Our Chester real estate stats and trends will give you more information about home buying and selling trends in Chester. If you're looking to sell your home in the Chester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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