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

$575,000

4 Beds ⋅ 3 Baths ⋅ 10656145 MLS

WESTERN BRANCH HOME WITH A DETACHED 2-CAR GARAGE, SPACIOUS FENCED YARD, AND FLEXIBLE LIVING SPACE! Welcome to 2044 Columbo Avenue, set on a generous .34-acre lot in Chesapeake’s Western Branch area. This well-maintained home is an excellent fit for buyers who need room for vehicles, tools, hobbies, storage, a home business setup, or recreational equipment. In addition to the attached 1-car garage, the property offers an oversized detached 2-car garage with a finished second floor. Built approximately 2009, it includes insulation, drywall, electrical, and a Wi-Fi-controlled mini-split HVAC system—ideal for a workshop, office, studio, recreation room, hobby space, or conditioned storage. Inside, the kitchen features granite countertops, black stainless appliances, a breakfast bar, and an open connection to the great room for easy everyday living and entertaining. A formal dining room, first-floor flex room, full bath, and enlarged laundry room add valuable versatility. Upstairs, the spacious FROG serves as the fourth bedroom with a full bath nearby, while the primary suite includes a refreshed bath. Recent improvements include a Trane dual-zone Wi-Fi HVAC system approximately four months old, vinyl siding, metal exterior wrap, newer front and sliding rear doors, screened porch, LVP/laminate flooring, rear windows, and gutters. Natural gas serves the heat and hot water. Enjoy the large fenced backyard with a deck, screened porch/patio, and hot tub—plenty of room to relax, entertain, play, garden, or let pets roam. Seller is replacing carpet before closing.Convenient to I-664, military installations, tunnels, shopping, dining, and destinations throughout Hampton Roads.

2044 Columbo Avenue, Chesapeake

$611,214

4 Beds ⋅ 2.1 Baths ⋅ 10655732 MLS

The Persimmon is a stunning two story floor plan featuring a first floor bedroom and optional full bath, great for guests or multi-generational living. A welcoming foyer opens into an open-concept design showcasing a well-appointed kitchen with eat-in are and a large center island for gatherings and everyday living. The kitchen flows seamlessly into the family room creating an inviting space for connection & comfort just steps away from your patio expanding your outdoor living & entertaining space. Upstairs you will find a spacious loft providing a setting for family entertaining or relaxation. This level also features a luxurious owner's suite with spa-like bath with dual sinks. A conveniently located laundry room and two additional bedrooms offer comfort and functionality for the entire household. Call to schedule your personal your.

1885 Paw Paw Place, Chesapeake

$489,000

4 Beds ⋅ 2.1 Baths ⋅ 10655779 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

$524,900

4 Beds ⋅ 2.1 Baths ⋅ 10655004 MLS

Welcome home to a spacious & versatile property offering room to live, entertain, and grow! Come inside to a dramatic 2-story foyer & great room designed for living & entertaining. The kitchen opens to the great room and features granite countertops, while hardwood flooring adds warmth and character to the foyer, great room & dining room. A gas fireplace creates a cozy focal point in the great room, and the first-floor primary suite offers the convenience of main-level living. Upstairs, the finished room over the garage provides flexible space that can serve as a fourth bedroom, bonus room, home office, playroom, or whatever best fits your needs. Outside, enjoy a larger lot with a fenced backyard and newer deck—perfect for relaxing, entertaining, pets, or play. One of the standout features of this property is the detached two-car garage with an apartment above! Offering additional living space separate from the main home, the apartment provides incredible flexibility for guests!

5408 Willow Lake Road, Chesapeake

$200,000

10654314 MLS

BUILD YOUR HOME IN WESTERN BRANCH ON THIS QUIET CUL-DE-SAC IN DOCKLANDING AREA. CITY WATER AND SEWER ARE AVAILABLE. DONT MISS OUT ON THIS RARE FIND. BUILDER LIST PROVIDED IF REQUESTED.

.45AC Maple Drive, Chesapeake

$395,000

5 Beds ⋅ 2 Baths ⋅ 10653613 MLS

Beautifully updated 3,333 sq ft. home featuring 5 spacious bedrooms and 2 modern bathrooms. The kitchen offers granite countertops, white cabinetry, and updated appliances, making it both stylish and functional. Enjoy outdoor living on the private deck, perfect for relaxing or entertaining. This move-in-ready home features elegant upgrades throughout and plenty of space for comfortable living. Don’t miss this opportunity—schedule your showing today!

3861 Ahoy Drive Unit Dr, Chesapeake

$435,000

4 Beds ⋅ 3 Baths ⋅ 10653648 MLS

Beautiful 4-bedroom, 3-bath ranch on a half-acre lot in the sought-after Chadswyck Terrace neighborhood of Western Branch! Tucked into a quieter part of the neighborhood with minimal through traffic, this move-in-ready home offers plenty of space to spread out. The private backyard features a newer privacy fence and sits along a tidal finger of the Western Branch of the Elizabeth River. Inside, you’ll find stainless-steel kitchen appliances replaced in 2021 and a water heater replaced in 2026. $7500 in CCA offered to to be used at buyers discretion. The sellers plan to have the home and carpets professionally cleaned before closing, so it’s ready to welcome its new owners!

1901 Lisbon Road, Chesapeake

$399,000

4 Beds ⋅ 2 Baths ⋅ 10653672 MLS

Well-maintained home, on over half an acre lot in desirable Chadswyck Terrace. Inviting layout is ideal for everyday living & entertaining, with a spacious living room flowing into the dining area & kitchen. Wood-burning fireplace adds warmth & character. The kitchen boasts stainless steel appliances, abundant counter space, & an adjoining utility room that can also serve as a convenient mudroom. Private primary suite features an ensuite bath, creating a comfortable retreat. Above the garage, a versatile bonus room can serve as a bedroom, office, playroom, or guest space. Enjoy the expansive backyard & generously sized deck, perfect for relaxing, grilling, or entertaining. Property extends beyond the fenced area, offering room to expand the enclosure. Updates include a new roof in 2020 & HVAC system in 2018. Close to shopping, dining, the mall, & interstate access. Solar panels will be paid off at closing; the electric bill is $9/mo & VA Assumable loan option with a 2.5% interest rate!

4207 Coffman Boulevard, Chesapeake

$599,900

4 Beds ⋅ 2.1 Baths ⋅ 10653544 MLS

Ready Soon! Your New Home in Western Branch! Exceptional new construction on a spacious half-acre lot, thoughtfully designed for modern living and outdoor enjoyment. This open-concept floor plan features a desirable first-floor guest suite with a private bath and walk-in closet. The chef-inspired kitchen showcases granite countertops, custom cabinetry, stainless steel appliances, and designer lighting. Luxury vinyl plank flooring flows throughout the first floor and all bathrooms. Enjoy a covered front porch, two-car garage, and rear patio overlooking your private backyard, with plenty of space to add a pool and create your own outdoor oasis. Quality craftsmanship and thoughtful design come together in this highly desirable Western Branch location. Completion in Fall 2026. Don't miss the opportunity to make this exceptional new home yours!

1530 Jolliff Road, Chesapeake

$365,000

4 Beds ⋅ 3 Baths ⋅ 10653190 MLS

Welcome to 1308 Sunnybrook Terrace! This well-maintained 4-bedroom, 3-full-bath home offers a spacious and functional layout designed for comfortable everyday living. With generous living areas, four nicely sized bedrooms, and the convenience of three full bathrooms, there’s plenty of room to spread out and make this home your own. Whether you’re a first-time homebuyer, growing household, or investor, this property offers flexibility and plenty of possibilities. Conveniently located in Chesapeake near shopping, dining, schools, and major roadways. Don’t miss the opportunity to call 1308 Sunnybrook Terrace home!

1308 Sunnybrook Terrace, Chesapeake

$245,000

2 Beds ⋅ 2 Baths ⋅ 10653328 MLS

Waterfront brick ranch a tidal canal that leads to the Elizabeth River. The kitchen opens to a spacious family room, with two large bedrooms and two full bathrooms. Oversized attached garage with carport, plus a detached single- ar garage. Flood insurance is not required. Property needs repairs and is being sold strictly AS-IS. Great opportunity for an investor or buyer looking to renovate and make it their own

2112 Christopher Drive, Chesapeake

$509,900

4 Beds ⋅ 2.1 Baths ⋅ 10653139 MLS

Welcome to 508 Schaefer Avenue, a beautifully maintained 2018-built home in Chesapeake’s Deep Creek area! With 4 bedrooms, 2.5 baths, and 2,398 square feet, this home offers the space today’s buyers are looking for. The main level features an open flow between the kitchen, dining, and living areas, along with a separate front flex room ideal for a home office, playroom, or sitting room. The bright kitchen includes white cabinetry, granite countertops, a large island with seating, and stainless steel appliances. Upstairs, the spacious primary suite includes a separate sitting area and an ensuite bath with dual vanities, a soaking tub, and a separate glass shower. Three additional bedrooms and an upstairs laundry room add everyday convenience. Outside, enjoy a level backyard, concrete patio, wooded backdrop, and attached two-car garage. Potential 5.75% assumable loan opportunity for qualified buyers, subject to lender/servicer approval, underwriting, applicable terms, and buyer qualification. Schedule your private showing today!! THIS ONE IS A STEAL!!!

508 Schaefer Avenue, 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.