Chesapeake Homes with Jolliff Middle Middle school

Welcome to Chesapeake, Virginia – a vibrant city that perfectly blends suburban charm with a rich tapestry of history and modern conveniences. Nestled in the heart of South Hampton Roads, Chesapeake is celebrated for its lush landscapes, extensive parks, and a strong sense of community. With its picturesque waterways and miles of scenic trails, it’s a haven for outdoor enthusiasts and families alike.

One of the highlights of Chesapeake is its commitment to quality education. Homes located within the Jolliff Middle School district benefit from a strong educational foundation, making it an ideal choice for families. Jolliff Middle School is known for its dedicated staff, innovative programs, and a supportive environment that encourages students to thrive both academically and socially. Living in this area means that your children will have access to excellent educational opportunities right in their neighborhood.

The real estate market in Chesapeake offers a diverse range of homes, from charming single-family residences to modern townhouses, catering to various lifestyles and budgets. Many of these homes are situated in friendly neighborhoods, where community spirit thrives, and residents enjoy local amenities such as parks, shopping centers, and dining options.

Chesapeake is not just a place to live; it’s a place to call home. With its welcoming atmosphere, strong educational institutions like Jolliff Middle School, and a wealth of recreational activities, it’s easy to see why so many families choose to settle down in this beautiful city. Explore the possibilities and discover your perfect home in Chesapeake, where community and comfort come together!

Newest Chesapeake Homes with Jolliff Middle Middle school

$396,900

3 Beds ⋅ 2.1 Baths ⋅ 10647620 MLS

Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This Laurel plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ soft-close cabinetry & drawers, upgraded granite countertops, & subway tile backsplash. Easily maintained & durable luxury vinyl plank flooring throughout the 1st level & secondary baths. Crown molding featured throughout 1st level. Lighted tray ceiling & WIC in primary, & en-suite w/ glass-enclosed shower & double upgraded granite vanity. Enjoy exceptional amenities, including state-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Model home located at 4968 Breck Lane.

2015 Guava Lane, Chesapeake

$292,000

4 Beds ⋅ 2 Baths ⋅ 10647346 MLS

4 bedroom ranch offering an open layout. This home features a converted garage that provides additional living space. Come check this home out, it wont last long!

3931 Port Road, Chesapeake

$575,000

4 Beds ⋅ 2.1 Baths ⋅ 10647147 MLS

Welcome to this beautifully updated home featuring a spacious yard and a sparkling saltwater pool, for relaxing or entertaining. Inside, you'll find freshly refinished hardwood floors, fresh interior paint, and a stunning new light fixture that adds a modern touch. The kitchen boasts custom cabinetry, while the bathrooms have been updated with new vanities. Major improvements include a new HVAC system (2025), a new fence (2024), and a tankless water heater for added efficiency. Additional features include a whole-house water filtration system, offering comfort and peace of mind. This move-in-ready home combines timeless charm with thoughtful upgrades inside and out.

4712 White Owl Crescent, Chesapeake

$335,000

3 Beds ⋅ 1.1 Baths ⋅ 10647019 MLS

Beautifully updated home in the heart of Western Branch, situated on a spacious corner lot with a newly installed privacy fence enclosing the backyard. The interior features a custom kitchen with shaker-style cabinetry, granite countertops, stainless steel appliances, and upgraded lighting and finishes throughout. Both bathrooms have been completely renovated with stylish fixtures and modern details. Additional improvements include a new roof, updated HVAC, replacement windows, garage door, front entry door, and low maintenance exterior trim. This move-in-ready home offers attractive curb appeal, a private backyard, and convenient access to area military installations, naval bases, shipyards, shopping, dining, and major commuter routes. Ai staging used for marketing purposes.

4313 Portsmouth Boulevard, Chesapeake

$599,000

4 Beds ⋅ 2.1 Baths ⋅ 10646504 MLS

Welcome to this beautifully maintained 4-bed, 2.5-bath home tucked away on a quiet cul-de-sac in the desirable Waterstone community of Western Branch. This home combines thoughtful updates with exceptional outdoor living. The backyard is your own private retreat, featuring a sparkling in-ground pool with concrete surround —ideal for relaxing or entertaining all summer long. The fully irrigated yard is supported by a new well and controls, helping keep the landscaping lush while reducing water costs. Inside, you'll find granite countertops, stainless appliances, new range, and spacious living and dining areas designed for everyday comfort. Major improvements provide peace of mind, including carpets, hardwood in den, concrete driveway, Leafguard Gutters, well and irrigation system, newer composite decking and rails, professionally restored crawlspace with new Insulation, vapor barrier, and sand, and newer pool filter and cover. Located in the sought-after Chittum school district of Western Branch, Waterstone offers an exceptional neighborhood lifestyle with scenic walking trails that connect directly to Western Branch Park, providing convenient access to playgrounds, athletic fields, tennis and pickleball courts, disc golf, and miles of outdoor recreation just minutes from your doorstep. With convenient access to shopping, dining, military bases, and major commuter routes, this move-in-ready home offers the perfect blend of comfort, functionality, and outdoor enjoyment. Schedule your private showing today!

4709 Feldspar Quay, Chesapeake

$500,000

4 Beds ⋅ 2.1 Baths ⋅ 10646861 MLS

This beautifully maintained home that offers the look and feel of new construction. . . without the wait! Thoughtfully upgraded with custom finishes throughout, this home perfectly blends modern style with everyday comfort. Step inside to discover an open, light-filled floor plan featuring a stunning custom accent wall that adds warmth and character to the main living space. The spacious kitchen flows seamlessly into the dining and living areas for entertaining or spending time with family. Retreat to the generously sized bedrooms, each offering plenty of space for relaxation, a home office, or growing families. The primary suite provides a peaceful escape with exceptional closet space and a well-appointed ensuite bath. Conveniently located near shopping, dining, schools, and major highways. Schedule your private showing today!

539 Schaefer Avenue, Chesapeake

$574,900

4 Beds ⋅ 2.1 Baths ⋅ 10646764 MLS

Meticulously maintained by its original owner, this 4-bedroom home offers a spacious, thoughtfully designed layout with an extended living room, formal dining room, and a versatile bonus area that can serve as a home office, playroom, gym, or flex space. The kitchen features newer appliances, while additional updates include a tankless water heater, updated HVAC system, and recently painted exterior. The garage has been upgraded with durable speckled flooring and built-in storage for added organization. Step outside to enjoy the in-ground pool, installed three years ago, a storage shed, and a backyard that backs to a wooded area, providing a natural backdrop and added privacy. Tucked away in the Western Branch area, the neighborhood offers connections to adjacent communities with opportunities for walking, running, biking, and golf cart access. Conveniently located near shopping, dining, major highways, military installations and hospitals.

4721 Lake Shore Drive, Chesapeake

$345,900

3 Beds ⋅ 2.1 Baths ⋅ 10646754 MLS

Beautifully updated detached end-unit condo in the desirable River Breeze community! Enjoy the privacy and feel of a single-family home with the convenience of low-maintenance condo living. This move-in-ready home features a new roof (2026), luxury vinyl plank flooring (2026), fresh interior paint, and a new privacy fence. The open, bright interior offers a welcoming atmosphere with modern updates throughout, for everyday living and entertaining. The condo association covers ground maintenance, water, sewer, and trash service, providing exceptional value and convenience. Conveniently located near shopping, dining, schools, military bases, and major highways. Whether you’re a first-time buyer, downsizing, or looking for a low-maintenance lifestyle, this well-maintained home is ready for its next owner. Schedule your private showing today!

4107 River Breeze Circle, Chesapeake

$145,000

3 Beds ⋅ 1.1 Baths ⋅ 10646471 MLS

3936 Holly Cove Drive, Chesapeake

$370,000

3 Beds ⋅ 2.2 Baths ⋅ 10645727 MLS

Welcome to this well-maintained, like-new townhome in the desirable Fairview Towns community! Enjoy low-maintenance living in this newer gated community, conveniently located in Western Branch. This spacious tri-level townhome features 3 bedrooms, 2 full bathrooms, and 2 half bathrooms, along with two family rooms providing plenty of space for entertaining, relaxing, or creating a home office or flex space. The home also offers a one-car garage, two additional assigned parking spaces, and ample visitor parking. Come experience all this beautiful townhome has to offer and make it yours today!

4122 Riverside Drive, Chesapeake

$609,000

4 Beds ⋅ 2.1 Baths ⋅ 10645393 MLS

Premium location in one of Western Branch’s most sought-after neighborhoods & schools. Beautiful, manicured homes w/large lots & no homeowner’s association. Just minutes to 664 & ALL of Hampton Roads Military bases, shopping & entertainment and medical facilities. Step inside to a welcoming foyer that leads to a formal dining room, living room and a custom kitchen with an Island. The sunken den features a gas fireplace which exits to a multi-level deck for cookouts and entertaining. The upstairs features a primary suite for a private retreat with an en-suite bath, a large walk-in closet for keeping all your items organized, while two additional bedrooms (all with walk-in closets) provide versatility for guests or even a game (flex) room. In addition, a 4th bedroom is located over the 576 SQFT. Attached garage. New interior paint and carpet, move in ready

1416 Pine Grove Lane, Chesapeake

$315,000

3 Beds ⋅ 1 Baths ⋅ 10645059 MLS

This lovely 3 bedroom/1 bath abode is fresh, charming and a perfect fit for the whole family! Enjoy the benefits of solar panels that keep energy costs low. The spacious backyard is ideal for curious kids to explore, energetic pups to play fetch or a small-scale gardener’s dreams to come true. Gorgeous warm wooden cabinets , coffee bar, custom island , pantry and gas stove create a luxurious feel in this gourmet kitchen. Enjoy time in the open family room complete with striking wood flooring, a cozy and comfortable space for family movie nights and memory making, find a bonus room that offers endless possibilities creates a cozy playroom, a productive home office or transform it into an extra bedroom. Take comfort in the attractive brick exterior of the home as it’s sure to stay tidy and effortless to maintain for years to come. Check out this wonderful opportunity to live the good life in Chesapeake!

3944 Port Road Road, 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.