Pleasant Grove Real Estate

Welcome to Pleasant Grove, a charming subdivision nestled in the heart of South Chesapeake, Virginia. This picturesque community is the perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, retirees, and professionals alike.

Pleasant Grove boasts a variety of beautifully designed homes that cater to diverse lifestyles, from cozy single-family residences to spacious multi-level properties. Each home is thoughtfully situated on tree-lined streets, offering a sense of privacy while fostering a warm neighborhood atmosphere. Residents enjoy well-maintained lawns and gardens that enhance the overall appeal of this inviting community.

One of the key highlights of Pleasant Grove is its proximity to essential amenities. Just a short drive away, you'll find a variety of shopping centers, restaurants, and recreational facilities. For outdoor enthusiasts, the nearby parks and nature trails provide ample opportunities for hiking, biking, and enjoying the great outdoors. Families will appreciate the highly-rated schools in the area, ensuring that children receive a quality education close to home.

Pleasant Grove is also conveniently located near major highways, making commuting to neighboring cities a breeze. Whether you're heading to downtown Chesapeake or exploring the vibrant cultural scene of Norfolk, you'll find that Pleasant Grove offers easy access to all that the region has to offer.

In this delightful community, neighbors become friends, and every day feels like a retreat. Discover the charm of Pleasant Grove – where your dream home awaits!

Newest Listings in Pleasant Grove

$325,000

10650830 MLS

Great opportunity on 11.811 acres of cleared land in southern Chesapeake. This is a flag lot and comes with 25' of road frontage going south to the remaining 11.3 acres of cleared crop land. The bulk of this lot is located approx. 800 feet off the paved city road and will allow for a relaxed setting for that custom homesite you have been wanting. Sit on the back porch and watch the sun set while enjoying the expansive view across almost 600 acres of open crop land. Hickory school district and just minutes from the 168 bypass. Convenient to all of Hampton Roads and Chesapeake Genera Hospital. Zoned A1 presently. Sale subject to existing farm lease.

11.8 Acres Ballahck Road, South Chesapeake

$799,900

4 Beds ⋅ 2.1 Baths ⋅ 10650499 MLS

The Aspen Barndominium! Customize this 4b/ 2.5b barndo with your style, colors and finishes with the builder. Stunning Covered Front Porch leads to the Open Great Room designed with 18ft vaulted ceiling for the perfect open Living, Dining and Kitchen space. Kitchen with Stainless Steel Appliances, granite counters, tile backsplash, and walk-in pantry. Large Primary with huge walk-in closet and Spa-like Bathroom. Large laundry room, mudroom with lots of storage space and wash area. Bedrooms 2, 3, 4 share a bathroom with rec/bonus space. Best spot may just be the huge covered back porch with lovely nature views and access from the kitchen great room. Pics of previously built Aspen and may show upgrades. Listing price includes Turn-Key Cost to build with a Construction Loan including cost of Land, Well, Septic, and Land Development.

2907 Seven Eleven Road, South Chesapeake

$250,000

10649275 MLS

Discover the possibilities on 9.37 acres in desirable Pleasant Grove! This spacious parcel offers plenty of room to build your dream home while enjoying privacy, open space, and the peaceful feel of country living. Bring your builder, your vision, and create the home you've always wanted. A wonderful opportunity to own acreage and make it your own!

9.37AC Douglas Road, South Chesapeake

$1,699,000

4 Beds ⋅ 3.1 Baths ⋅ 10649536 MLS

Rare luxury estate on 23.10 private acres in Chesapeake. This 3,224 sq ft, 4-bedroom custom home combines high-end finishes, acreage privacy, and a massive 30x80 climate-controlled detached building. Premium kitchen with 10-ft island, Electrolux refrigerator/freezer with trim kit, double wall oven with sous-vide, gas cooktop, microwave drawer, quartz surfaces, pot filler, and 45-inch sink. Primary suite features vaulted ceiling, Brazilian White Santorini leathered quartzite, freestanding Kohler tub, and oversized 6x4 tiled glass shower with rain, wall, handheld heads, and built-in ledge. Upgrades include Everlast siding, GAF Ultra HDZ roof, 2-zone dual-fuel Trane heat pumps, two Rinnai tankless water heaters, 1,000-gal propane tank, generator transfer setup for future Generac, black aluminum fencing, premium insulated cedar-tone garage doors, Ring security, French White Oak flooring, and wooded trails. Rare turnkey luxury with land, privacy, flexibility, and premium infrastructure.

3959 Bunch Walnuts Road, South Chesapeake

$1,199,000

5 Beds ⋅ 3.1 Baths ⋅ 10648292 MLS

Welcome home!! 28.18 private acres, 3,714 sq ft, 5 bedrooms, 3.5 updated baths, TWO primary suites, a detached 4-car garage and 20x30 workshop—all in Chesapeake’s sought-after Hickory area?! Yes! Here at 509 Ballahack Rd. Extensively improved inside and out, this one-of-a-kind property delivers the space, flexibility and freedom of country living with modern comfort. Abundant natural light fills the spacious living areas, while warm finishes and thoughtful updates create an inviting feel throughout. The kitchen is complemented by a butler pantry with granite countertop, cabinetry and additional storage, adding function for everyday living and entertaining. The rare dual-primary layout offers one suite on each level, both with private ensuite baths—ideal for multigenerational living, extended guests or added privacy. The main-level primary has been refreshed with new flooring, paint, lighting and hardware. Upstairs, the second primary features a showstopping spa-inspired ensuite with an oversized wet room, rainfall shower, body jets, two-person soaking tub, porcelain tile and polished marble mosaic. All 3.5 bathrooms have been updated with fresh flooring, lighting, paint, mirrors and hardware. Outside, enjoy a nearly wraparound front porch, expansive 20x40 composite deck, outdoor kitchen setup, custom fire pit, fruit trees, grape vines and 28+ acres to explore. Proven deer and turkey hunting is literally steps from your back door, with private shooting and archery areas already in place. The detached 4-car garage provides exceptional storage, while the 20x30 workshop features concrete flooring, lighting and its own electrical panel. Additional improvements include 33 solar panels (to be paid off with acceptable offer), Level 2 EV charger, major electrical upgrades, crawlspace encapsulation, updated HVAC and a private well with NO monthly water bill. A rare combination of acreage, recreation, extensive improvements and flexible living in Southern Chesapeake. See attached Feature & Upgrade Sheet for even more! Make this an easy day and stop here first!

509 Ballahack Road, South Chesapeake

$825,000

4 Beds ⋅ 3.1 Baths ⋅ 10648270 MLS

Beautiful custom home on 3 Acres that backs up to woods! Two Primary Suites, one downstairs and one upstairs each with their own full bath! Amazing custom Kitchen with loads of storage, Pantry, plenty of counter space, center island, brand new cabinets, granite and Stainless Steel Appliances! Dual zoned central Heat/AC. Move in ready! Located in the Grassfield School district! Completely remodeled and waiting for you, be sure to come check this one out first!No HOA, bring your horses, chickens and goats!

2239 Benefit Road, South Chesapeake

$550,000

5 Beds ⋅ 3.1 Baths ⋅ 10647572 MLS

Welcome home to this beautifully updated 5-bedroom home, where thoughtful upgrades and spacious living come together perfectly. The heart of the home is the stunning kitchen featuring quartzite countertops, a Sub-Zero refrigerator, butler's pantry, and an open layout overlooking the dining area and expansive family room—great for entertaining and everyday living. A first-floor bedroom with its own private en-suite bath offers the perfect space for guests or multi-generational living. Upstairs, retreat to the impressive primary suite with vaulted ceilings, a generous sitting area, and a walk-in closet. Convenient second-floor laundry includes a granite folding counter for added functionality. Enjoy abundant parking with a half-moon driveway plus additional gravel parking. Generator conveys as-is; sellers have never used it. 3% closing cost assistance with a full priced offer!

514 Waters Road, South Chesapeake

$549,000

3 Beds ⋅ 2 Baths ⋅ 10646565 MLS

Welcome to 1928 Centerville Turnpike in the highly sought-after Hickory School District. Set on 3 acres, this 3-bedroom, 2-bath home offers 1,688 square feet of comfortable living. Enjoy the ideal balance of privacy and convenience with ample space for gardening, recreation, animals, or future expansion. There is also a barn and a work shop equip with electricity. The property provides a peaceful rural setting while still being just minutes from shopping, dining, and major commuter routes. Updates-Renovated kitchen with NEW appliances , NEW roof, New AC, Septic 4years, generator 7 years.

1928 Centerville Turnpike S, 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

$499,900

3 Beds ⋅ 2.1 Baths ⋅ 10644718 MLS

Amazing property in the heart of Hickory. Home is dated before 1850, that is when they started record keeping! 3 beds up with 2 baths, and 1/2 bath down. 2 wood burning fireplaces. Owner willing to make minor repairs with acceptable offer. Large barn/garage, that was a former auto-mechanic shop! Large, covered deck with additional open-air deck. All appliances convey. Must see to appreciate the size.

3248 Battlefield Boulevard S, South Chesapeake

$675,000

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. 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

$795,000

5 Beds ⋅ 3 Baths ⋅ 10644737 MLS

Beautiful 5 Bedroom Brick Home featuring a spacious open floor plan perfect for everyday living and entertaining. The large kitchen offers stainless steel appliances, abundant cabinetry, and ample prep space. A standout feature of the home is the custom library, complete with French doors, built-in shelving, and a rolling ladder, creating an elegant and inviting space for work, reading, or relaxation. The main level includes a guest bedroom and full bath. Upstairs you'll find a media room and an oversized primary suite with double closets and a luxurious bathroom featuring a jetted tub, separate shower, a double vanity and private toilet room. Be sure to notice the built-in light-up stairs going up to the second floor! Enjoy your own private backyard oasis with mature landscaping, an in-ground saltwater pool, hot tub, and an expansive custom paver patio, ideal for relaxing or entertaining. Extended driveway with Boat/RV pad. Located in the sought after Great Bridge school district and community, local shops and restaurants, and close to the interstate for a quick trip to OBX!

208 Leicester Court, 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.