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$692,950
4 Beds ⋅ 2.1 Baths ⋅ 10634859 MLS
The Derring isn’t just a house; it’s a high-energy hub designed for the pulse of a busy, modern life. Forget those traditional, boxy layouts—this plan throws the doors open with a massive, light-drenched great room that flows straight into a kitchen built for "main character" energy, complete with a substantial floating island that’s destined to be your morning coffee spot and evening social headquarters. While the main floor offers a versatile flex room designed for a high-productivity home office or a sun-soaked reading nook, the second floor is where everyone gets their own space to recharge. We’re talking four spacious bedrooms, each featuring its own walk-in closet (yes, really!), all centered around a massive loft that’s ready to become anything from a cinema to a dedicated gaming zone. The Derring is all about "Truly Living" without the clutter. Snag those Trusted Lender Incentives and book your design center appointment to see how we can level up your lifestyle!

MM Taft (Derring A-5) Road, South Chesapeake
$914,500
5 Beds ⋅ 4.1 Baths ⋅ 10633056 MLS
Welcome to The Miles at Sanderson Estates! This stunning new construction by Kirbor Homes masterfully balances everyday functionality with refined comfort. Boasting 3,585 square feet, this home features 5 spacious bedrooms, 4.5 bathrooms, and an open-concept layout designed for modern living. The main level greets you with a grand foyer flanked by a home office and a formal dining room. The heart of the home is the expansive great room that flows into a chef-inspired kitchen and breakfast area. A unique first-floor flex room with an adjacent full bath offers the perfect space for a guest suite or playroom. Upstairs, enjoy a versatile loft, a convenient laundry room, and a luxurious primary retreat with a spa-like bath and massive walk-in closet. Experience a home designed to help you "Truly Live" in the heart of Chesapeake! Reach out today to schedule an appointment at our design center! HOA is for common ground maintenance only! You can still live the way you want to live!

2808 Raccoon Trail, South Chesapeake
$849,900
4 Beds ⋅ 3.1 Baths ⋅ 10634643 MLS
The Holden, where every detail is meticulously crafted to elevate your daily routine. Morning light floods the first-floor primary wing, a sanctuary complete with a room-sized walk-in closet and a spa-inspired bath. The heart of this home is a masterclass in modern architecture, featuring a soaring great room that flows into a chef’s kitchen and sun-drenched breakfast area—designed for everything from quiet espresso shots to grand holiday hosting. Beyond the communal spaces, The Holden offers an intelligent layout designed for the modern lifestyle, including a dedicated front-end flex space designed for a quiet home office. Venture upstairs to discover the expansive loft and media room, providing the perfect canvas for a cinema, a library, or a high-tech gaming hub. With 4 to 5 generous bedrooms and the seamless functionality of a mudroom and independent laundry, this home doesn't just provide space; it provides a tailored backdrop for your most cherished memories.

MM Taft (Holden 2-A) Road, South Chesapeake
$2,425,000
10634546 MLS
Escape the ordinary with this expansive 25.84-acre parcel located in the highly sought-after Western Branch area of Chesapeake. This rare offering provides a unique blend of privacy, natural beauty, and strategic location, making it an ideal canvas for a private estate, a boutique residential development, or a long-term land investment. Subject to local zoning, the size and location of this tract present significant opportunities for residential growth in a high-demand corridor. Nestled in the heart of Western Branch, known for its strong community feel, excellent school districts, and convenient access to the Hampton Roads region.

25+AC S Military Highway, Central Chesapeake
$509,900
4 Beds ⋅ 2.1 Baths ⋅ 10634235 MLS
Welcome to this beautifully maintained condo in one of Chesapeake's most desirable 55+ communities where, comfort and convenience come together in a park-like setting. Surrounded by mature landscaping, a scenic pond, and inviting seating area with a fireplace, this neighborhood offers a relaxed lifestyle with thoughtfully designed community spaces. Inside, this spacious home offers four bedrooms and two and a half bathrooms with a layout designed for both everyday living and entertainment. The primary suite provides a comfortable retreat with generous space and privacy. An in-unit elevator adds exceptional convenience and accessibility between levels. Call today for your private tour.

925 Cranberry Drive Unit 70, South Chesapeake
$260,000
2 Beds ⋅ 2 Baths ⋅ 10633391 MLS
Open House Saturday 7/18/26, 10 am - 2 pm. Welcome to this beautifully renovated 2-bedroom, 2 bathroom townhome featuring impressive high ceilings that create an open, airy feel throughout. The updated interior boasts modern finishes, refreshed flooring, and a stylish kitchen perfect for both everyday living and entertaining. Spacious bedrooms offer comfort and privacy, while the thoughtfully updated bathrooms add a touch of luxury. Move-in ready and designed for low-maintenance living, this home is a perfect blend of style and convenience.

1914 Woodgate Arch, South Chesapeake
$915,500
4 Beds ⋅ 3.1 Baths ⋅ 10633216 MLS
Experience The Holden at Sanderson Estates, an exquisite Portfolio Collection design perfectly suited for this expansive 1-acre homesite on well and septic. This masterfully designed floorplan features 4–5 spacious bedrooms and 3.5–4 bathrooms. The main level is a showcase of sophistication, anchored by a first-floor primary suite with a spa-inspired standalone shower and a room-sized walk-in closet. A gourmet kitchen with a massive center island and walk-in pantry serves as the heart of the home, flowing seamlessly into the great room and a sun-drenched breakfast area. Upstairs, the versatility continues with a generous loft and a dedicated media room, can be used for a home theater or library. The Holden blends practical design with high-end style. Ask about TRUSTED LENDER INCENTIVES. Prices vary by homesite and selected options; call today to schedule a tour and explore the possibilities of building your dream home in Chesapeake!

2864 Raccoon Trail, 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
$233,500
3 Beds ⋅ 1.1 Baths ⋅ 10633826 MLS
Two-story traditional in Chesapeake's Quincy Place. 3 beds, 1.5 baths, ~1,360 sq ft. The new roof carries a 30-year warranty that transfers to the buyer—peace of mind for years to come. Updated light fixtures throughout, central air with forced hot air heat, and a partially finished attic for bonus living space. Two-space driveway on a low-maintenance ~0.07-acre lot. Single-family home in the Oscar Smith school zone (elementary, middle, high). Public water and sewer, outside the Flood Hazard Area, with easy access to I-464.

1603 Seaboard Avenue, South Chesapeake
$695,351
3 Beds ⋅ 2 Baths ⋅ 10633226 MLS
The Squire offers a living experience centered on ease, elegance, and flexibility. The main-level primary suite provides a peaceful escape, thoughtfully positioned and enhanced by a spa-inspired bathroom and a generously sized walk-in closet. Flowing from room to room, the home’s open layout creates a natural sense of connection. The great room, filled with natural light, opens seamlessly to a well-appointed kitchen designed to handle both everyday meals and special occasions with equal ease. With the option for 3 to 5 bedrooms—including a dedicated study or home office—The Squire adapts effortlessly to your needs, whether you're growing, hosting, or simply enjoying quiet moments at home. Ask about available Trusted Lender Incentives to make this home yours. Call today to make an appointment at our design center.

MM Fields At Taft (Squire A-5) Road, South Chesapeake
$769,900
3 Beds ⋅ 2.1 Baths ⋅ 10633234 MLS
In The Kentland, every day unfolds in a home designed for both comfort and connection. The primary suite offers a retreat, where natural light and generous proportions create a relaxing escape from the pace of daily life. Thoughtful architectural details, including elevated ceilings, add depth and character throughout. The main living area is designed with versatility in mind, bringing together the great room, kitchen, and breakfast space into one cohesive environment. Whether preparing meals, entertaining guests, or enjoying a quiet night in, this central space easily adapts to your needs. On the main level, two secondary bedrooms provide flexibility for guests or family members. Upstairs, a spacious loft expands the home’s possibilities—designed for a home office, creative studio, or entertainment space tailored to your lifestyle. Design center appointments available now! Trusted lender incentives available.

MM Taft (Kentland B-1) Road, South Chesapeake
$729,000
4 Beds ⋅ 3.1 Baths ⋅ 10632479 MLS
Gorgeous custom-built home by award winning builder. Loaded with upgrades and fabulous features. Dramatic foyer with cathedral ceiling, hand crafted circular staircase, and electronic chandelier that lowers for easy cleaning. Gourmet kitchen with custom cabinets, granite counters, stainless steel appliances, and reverse osmosis water filtration. Luxurious master suite with panned ceiling and rope lighting set in crown molding. Huge in-law suite with private bath. Open and flowing floor plan with large rooms throughout. Drive through portico leads to rear loading 2 car garage and additional parking. Assumable loan. Conveniently located to interstate, shopping, and dining. Come see this gorgeous custom house and make it your next home!

401 White Egret Cove, South Chesapeake
$639,900
4 Beds ⋅ 2 Baths ⋅ 10633148 MLS
This custom-built ranch has been refreshed and is ready for its next owner. Featuring 4 bedrooms, 2 baths, soaring 12-foot ceilings, and approximately 2,863 square feet of living space, this home offers comfortable one-level living on a private setting. Enjoy kitchen w/ granite countertop, bar seating, stainless steel energy efficient appliances, custom cabinets, w/recessed lights; large breakfast nook overlooking a tranquil country backyard. Stunning great room with gas fireplace; hardwood floors, crown molding; Large formal dining room w/chair rails. Private study/office w/ custom built cabinets and bookshelves, granite counters and full-light doors; tray ceiling, primary bedroom w/large custom design walk-in closet. Finished room over garage serves as 4th bed/bonus room. No HOA; Encapsulated crawlspace; Great Bridge, but relatively near the heart of Chesapeake, minutes from shops, schools, interstate, & hospitals. Some photos are virtually staged.

732 Washington Drive, South Chesapeake
$230,000
2 Beds ⋅ 1 Baths ⋅ 10633141 MLS
Great starter home with huge backyard and easy access to highway, military bases & shopping.

2425 Lofurno Road, South Chesapeake
$680,000
4 Beds ⋅ 3.1 Baths ⋅ 10632952 MLS
Step into a home that truly stands out from the moment you arrive. Eye-catching gray brick, an extended front porch, and custom stamped concrete details create unforgettable curb appeal. Inside, over 3,500 sq ft, of open-concept living offers space and flexibility with 4 oversized bedrooms and 3 ensuite baths. The layout flows effortlessly, great for both daily living and hosting. The kitchen is the centerpiece—featuring an extended island, custom finishes, and stylish storage designed for both function and style. The family room adds warmth with a gas fireplace, while a custom mudroom keeps everything neatly organized. The backyard is designed for enjoyment with a fully fenced yard, deck, gazebo, and app-controlled lighting—great for relaxing or entertaining. This is more than a home—it’s an elevated living experience.

1633 Banff Court, South Chesapeake
$497,000
6 Beds ⋅ 4 Baths ⋅ 10632780 MLS
Looking for space? This is the home for you. Entertaining? This home is for you. Tranquility? This home is for you. This home has has 2 primary bedrooms and an in-law suite. The main bedroom is 24X30. Huge backyard and near bases, shopping and restaurants. Pool table, riding lawn mower, and horseshoe convey with the home. Brand new HVAC and furnace.

4000 Wyant Court, West Chesapeake
$399,000
2 Beds ⋅ 1.1 Baths ⋅ 10632703 MLS
Welcome to this stunning, move-in-ready masterpiece located in the heart of Hickory. This home has been meticulously renovated, boasting new siding for exceptional curb appeal and energy efficiency. Step inside to discover a bright, open interior featuring stylish new flooring throughout and a renovated kitchen complete with modern cabinetry and high-end finishes. Combining the charm of an established Chesapeake neighborhood with the luxury of a brand-new renovation, this home offers a rare opportunity to enjoy high-end living in a premier location.

224 Hickory Road E, South Chesapeake
$638,553
6 Beds ⋅ 3 Baths ⋅ 10632620 MLS
An open concept ranch style floor plan built with space for EVERYONE! Our Myrtle offers 6 BR's & 3 full bathrooms @2812 sq ft ! Kitchen with island & breakfast space opens up to the large family room. This plan offers adequate spacing between guest bedrooms, PBR, FROG & bedrooms on 2nd floor. Custom finishes include: PBTH Granite top vanity, Tile Shower, LVP in Family, Dining, Laundry rooms. Extended kit island, Wainscoting in DR ,Kit sink & faucet upgraded, w/ Quartz counter tops. The Estates at Jolliff Landing offers single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, green space for games, playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style swimming pool. Builder is offering partial CCA & $15,000 buyer incentive (See LA for details. Restrictions may apply) using our preferred lenders. Model home open daily 12-5:00 pm at 5023 Annapolis Drive. Call for delivery updates.

2209 Hampton Roads Parkway, West Chesapeake
$550,900
4 Beds ⋅ 2.1 Baths ⋅ 10632280 MLS
This traditional floor plan offers 4 Bedrooms, 2.5 Baths, and 2420 sq ft. Enjoy the grand design of the Primary Suite with a spacious Walk-In Closet from the Primary Bath. The dining room, kitchen & family room on the first floor allow for many entertaining evenings at home. The open floor plan provides ample space with room to stretch out. 2nd floor is spacious with 4 bedrooms & utility room. The Estates at Jolliff Landing will be a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and a tree-lined sidewalks. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

MM Sycamore, West Chesapeake
$959,900
4 Beds ⋅ 3.1 Baths ⋅ 10632724 MLS
Open House Sunday, August 30th, 1:00 - 3:00!! Private 3+ acre sanctuary, complete with outbuildings and fenced areas in front and back. Fenced areas are an oasis for animals including horses, goats, chickens and rabbits. Includes horse stables and coops. Property offers both seclusion & space, great for families and children. Outbuildings for animal care, workshop, or get away space. Features a paved driveway & expansive stamped-concrete parking area. Charming, custom-built home boasts 10-foot ceilings & an open concept floor plan. Large, eat-in kitchen with center island and breakfast bar. For more formal occasions or a home office, the dining room offers flexibility to fit your needs. Home includes two en-suite bedrooms. Generously sized upstairs bedrooms filled with natural light. Master bedroom includes oversized bathroom and spacious walk-in closet. Lots of storage space. Outdoors, a sprawling deck to relax on and enjoy both wooded and field views. Convenient location - balance country feel with suburban dining/shopping access.

1149 Beaver Dam Road, South Chesapeake
$1,075,000
6 Beds ⋅ 4.1 Baths ⋅ 10632029 MLS
Luxury Redefined at 1301 Simon Drive Experience the pinnacle of Chesapeake living in this custom 5,612 sq. ft. brick estate. Nestled on a spacious corner lot in Greenbrier, this 6-bed, 4.5-bath masterpiece blends timeless elegance with modern high-tech luxury. The Interior Experience: Ultimate Comfort: Enjoy radiant heated floors Chef’s Dream: Gourmet kitchen with high-end appliances and a sleek wet bar. Grand Design: Cathedral ceilings and a dramatic winding staircase. Your Private Oasis: Step outside to a brand-new, gorgeous pool oasis. Whether you're hosting a summer gala or a quiet evening by the water, this backyard is designed for pure relaxation. The Bells & Whistles: Oversized 3-car garage. Lavish primary suite with a champagne bubble spa-tub. Premium finishes and smart-home integration throughout. 1301 Simon Drive | Luxury is in the details.

1301 Simon Drive, South Chesapeake
$579,005
4 Beds ⋅ 2.1 Baths ⋅ 10632324 MLS
This traditional floor plan offers 4 Bedrooms, 2.5 Baths, and 2420 sq ft. Enjoy the grand design of the Primary Suite, which features a spacious Walk-In Closet adjacent to the Primary Bath. The open floor plan provides ample space for entertaining. 2nd floor is spacious with 4 bedrooms & utility room. Upgrades include- Kitchen: Two tone cabinets, Quartz counter top, backsplash, pre-wired pendant lights. PBTH: Granite vanity top, Tile shower. LVP in Dining, Laundry & Family rooms. Recessed LED in PBR & Fam room. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and a tree-lined sidewalks. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Call for construction timeline updates. Model home open daily 12-5:00 pm at 5023 Annapolis Drive.

2211 Hampton Roads Parkway, West Chesapeake
$7,334
10632409 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

19-20 Caddie Street, South Chesapeake
$7,334
10632400 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

Lot 38 Trinkle Street, South Chesapeake
$7,334
10632393 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

39 Trinkle Street, South Chesapeake
$7,334
10632385 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

Lot 37 Trinkle Street, South Chesapeake
$7,334
10632384 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

36 Trinkle Street, South Chesapeake
$7,334
10632383 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

15 Binford Street, South Chesapeake
$7,334
10632374 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

34 Trinkle Street, South Chesapeake
$7,334
10632328 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

Lot 33 Trinkle Street, South Chesapeake

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.