Pleasant Grove Real Estate

Welcome to Pleasant Grove, a charming neighborhood nestled in the heart of South Chesapeake, Virginia. Known for its serene surroundings and friendly atmosphere, Pleasant Grove offers a delightful blend of suburban tranquility and convenient access to urban amenities.

As you stroll through the tree-lined streets, you’ll discover a community that prides itself on its welcoming spirit and neighborly connections. The neighborhood features a variety of well-maintained homes, ranging from cozy single-family residences to modern townhouses, catering to diverse lifestyles and family sizes. With lush green parks and recreational spaces nearby, Pleasant Grove is perfect for outdoor enthusiasts, offering plenty of opportunities for picnics, jogging, and leisurely walks with family and friends.

One of the standout features of Pleasant Grove is its proximity to excellent schools, making it an ideal choice for families. The area boasts a selection of highly-rated public and private educational institutions, ensuring that children receive a quality education in a nurturing environment.

Shopping, dining, and entertainment options are just a stone's throw away, with the bustling city of Chesapeake offering a variety of local boutiques, eateries, and larger retail centers. Whether you’re in the mood for a casual dining experience or a fun night out, you’ll find plenty to satisfy your cravings.

With its blend of community spirit, natural beauty, and convenient access to amenities, Pleasant Grove is not just a place to live; it’s a place to thrive. Come and discover the charm of this delightful neighborhood, where every day feels like home.

Newest Listings in Pleasant Grove

$775,000

5 Beds ⋅ 2.1 Baths ⋅ 10653033 MLS

Welcome to 3708 Riverwood Crescent! Situated on approx. 3 acres in sought after Chesapeake 23322, this nearly 3,000 sq. ft. home offers space, privacy & extensive updates! Enjoy a private backyard retreat with pool, screened porch & updated deck. Inside features a remodeled kitchen with quartz countertops, mostly stainless steel appliances, soft-close cabinetry, recessed lighting, hardwood & luxury vinyl plank flooring, plus new carpet upstairs, and solar hallway lighting. Updated baths include new countertops, toilets, fixtures, ceramic tile, tub/shower & an enlarged porcelain-tiled primary shower. Major improvements include dual-zone HVAC (2019/2021), 2024 water heater, water softener, encapsulated crawl space with pump & dehumidifier, replaced exterior/garage doors, vinyl windows & 2011 roof with 50-yr warranty. Shed and lawn tractor conveys! A rare combination of acreage, updates, pool & location; come see it!

3708 Riverwood Crescent, South Chesapeake

$534,900

4 Beds ⋅ 2.1 Baths ⋅ 10652341 MLS

One owner. 40+ Years of Care and Memories. Now it’s YOUR turn! This lovingly maintained 2,477 square foot Great Bridge Home offers 4 Bedrooms, 2 1/2 Baths & wonderfully distinctive architecture & floor plan. A true Sunken Living Room features a Soaring Brick Accent Wall & Wood Stove, while the oversized kitchen offers Abundant Cabinetry, Island & Sunny Bay Window dining area. Formal dining room, main-level Primary Suite + Additional 1st-floor Bedroom provide great flexibility. Upstairs, 2 Bedrooms share a Jack-and-Jill bath, plus an ENORMOUS Walk-in Attic provides exceptional storage & possibilities for future use! Enjoy a Corner lot, large Patio, Shed & 2-car Garage. Roof replaced 2022 and new water pump for geothermal HVAC installed 7/2026. All Great Bridge schools! A home with character and personality is a rare find in today’s “cookie cutter“ world. * Ask about the “secret hatch!” Bring your own vision to its classic spaces and make the next chapter yours!

716 Montebello Circle, South Chesapeake

$674,500

5 Beds ⋅ 3 Baths ⋅ 10647461 MLS

Qualified buyers may be able to assume the Seller's existing VA Loan - Grassfield High School Zone | Outdoor Oasis with In-Ground Pool | Renovated Kitchen & 1st Floor Bedroom Welcome to 1076 Scenic Blvd, located on nearly half an acre with NO HOA! This spacious 5 bedroom home features a main-floor bedroom with a full bath, new LVP flooring, fresh Paint, and a fully remodeled 2026 kitchen with smart Appliances. Step into your private outdoor oasis complete with an in-ground pool surrounded by an extended concrete deck, plus a cozy fire pit for entertaining. Convenient to local bases, shopping, and dining. Schedule your tour today!

1076 Scenic Boulevard, South Chesapeake

$589,699

4 Beds ⋅ 2.1 Baths ⋅ 10646302 MLS

Beautifully maintained all-brick transitional corner lot in Great Bridge. 4 bedroom/2 bath. 1st floor MB with en suite. Open floor plan with huge kitchen and stainless steel appliances, breakfast area. Wood-burning fireplace for cozy evenings. Walk out of family room door onto a TREX deck and large backyard. Award winning Cheshire Forest community. Amenities include clubhouse, pool, tennis/pickleball court, parks and playground. Shed sold as-is.

746 Yorkshire Trail, South Chesapeake

$355,000

3 Beds ⋅ 1 Baths ⋅ 10645994 MLS

Welcome to 944 Bells Mill Road, a beautifully updated Craftsman-style bungalow in the highly desirable Great Bridge area of Chesapeake. This home blends timeless character with modern updates, featuring fresh paint throughout, brand-new kitchen countertops, new luxury vinyl plank flooring in the kitchen and laundry room, and a refreshed bathroom. Situated on a spacious 0.36-acre lot, the property offers a detached garage/workshop, a welcoming front porch, a newer HVAC system, energy-efficient windows, and a durable metal roof. This charming home is just minutes from shopping, dining, parks, and major commuter routes. If you're looking for character, thoughtful updates, and an unbeatable location, 944 Bells Mill Road is ready to welcome you home.

944 Bells Mill Road, South Chesapeake

$664,000

4 Beds ⋅ 2.1 Baths ⋅ 10644422 MLS

Welcome to peaceful country living without sacrificing convenience, this 4 bed 3 bath home is situated on 3 beautiful acres in the desirable Hickory area of Chesapeake. Enjoy the privacy and open space you’ve been looking for while remaining close to shopping, restaurants, and movies in the Edinburgh shopping area. Solar panels add significant savings on electricity bill every month and will be paid off by sellers at closing. Choose your own adventure, take route168 down to the Outer Banks in NC or go north to Virginia Beach. Get all of this with no HOA restrictions!!

1924 Land Of Promise Road, South Chesapeake

$399,900

4 Beds ⋅ 2 Baths ⋅ 10633925 MLS

Step into a timeless sanctuary nestled on a serene 1-acre lot, this charming 4-bedroom, 2-bathroom home offers the perfect blend of tranquility and convenience. Enjoy the privacy and peace of country living while still being within easy reach of city amenities. Step inside to find spacious interiors filled with natural light and cozy ambiance. Originally built circa 1898, this property exudes character and warmth. The four generously sized bedrooms provide ample space for everyone, while the two bathrooms ensure comfort and convenience. Outside, your private oasis awaits. Imagine spending your days enjoying the outdoors, gardening, or simply unwinding on your expansive property. The possibilities are endless! Don't miss this opportunity to make this peaceful retreat your own. Schedule a showing today and experience the lifestyle you've been dreaming of.

1400 Fentress Road, South Chesapeake

$275,000

10623777 MLS

Centrally located. QUIET, SECLUDED LIVING on 4.87 ACRES IN THE COUNTRY PART OF CHESAPEAKE. Located off RT 17 near the North Carolina line in a growing area. Less than 10 minutes to GREAT BRIDGE and minutes from I-64 for access to all S Hampton Roads and the Peninsula. PRIVACY, SECLUDED LOCATION. THE CITY OF CHESAPEAKE TAX RECORDS DOCUMENT LAND USE AS RESIDENTIAL ACREAGE. THIS IS A GOOD TIME TO PURCHASE AND BUILD.

3725 Cornland Road, South Chesapeake

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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.