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Lot 22 Trinkle Street, South Chesapeake
$7,500
10632376 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 22 Trinkle Street, South Chesapeake

Lot 21 Caddie Street, South Chesapeake
$7,500
10632306 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 21 Caddie Street, South Chesapeake

203 Hodges Rd, South Chesapeake
$639,155
3 Beds ⋅ 3.1 Baths ⋅ 10614562 MLS
Dreamy Augusta Cottage built by coveted local builder, with unmatched architectural details. Custom arches to soaring 10’ ceilings and stunning hardwood floors. The open-concept first floor effortlessly blends the Dining and Great Room, with French doors leading to your own private courtyard and patio, your personal oasis for outdoor living. Chef’s kitchen is a showstopper w/oversized island, sleek Quartz counters, and custom Kitchen Hood. The generous First-floor BR w/en-suite bath, versatile mudroom with pantry, and powder room of 2-car garage make for easy living. Upstairs, a sun-filled BR3 boasts a walk-in closet and BR4 (or loft) flexible to your needs, with shared dual bath and HUGE laundry room finish off. The private Primary retreat offers spa bath w/dual sinks, garden tub, large tiled shower, and a super-sized closet with two storage areas. Professional management of the of the grounds and a low-maintenance living. Your dream home awaits, come make it yours!

203 Hodges Rd, South Chesapeake

1131 Madison Lynn Way, South Chesapeake
$707,000
5 Beds ⋅ 3 Baths ⋅ 10644005 MLS
Don’t miss this large open-concept home with 5 spacious bedrooms, 3.5 bathrooms, and approximately 2,976 sq ft in the heart of Chesapeake. In addition to this well-appointed home, it features a fully paid-off solar package, offering long-term energy savings. A standout feature is the first-floor flex room, currently staged as a home office with an adjacent full bath—making it an ideal space for multigenerational living, guests, or a private home office. In addition the downstairs open concept floor plan offers room to gather, work from home, or simply relax, while upstairs the primary bedroom and full bathroom, large laundry room and 4 other bedrooms provide comfort and privacy for everyone. The primary suite serves as a peaceful retreat with an en-suite bath, dual closets and views of the water from the back of the home, creating the great place to unwind at the end of the day. This exceptional location combines the charm of a quiet neighborhood with the convenience of everything Hampton Roads has to offer. Don't miss the opportunity to make this wonderful Chesapeake home your own—schedule your private showing today!

1131 Madison Lynn Way, South Chesapeake

503 Nesbit Drive, South Chesapeake
$275,000
2 Beds ⋅ 2.1 Baths ⋅ 10643199 MLS
Back on market as of 7/22 at no fault to the seller. Move-in ready in the Villas at Culpepper Landing! This 1,454 sq ft condo packs 2 bedrooms, 2.5 baths, and a dedicated office into a bright, open floor plan with high ceilings and natural light throughout — great for entertaining or just everyday living. The kitchen is the heart of the home: granite countertops, stainless steel appliances, and plenty of cabinet space, flowing right into the open living and dining area. The office/flex space downstairs works as a home office, guest room, or hobby room — whatever you need it to be. Upstairs, both bedrooms come with their own private en-suite bath, so nobody's fighting over the mirror. Low-maintenance living comes standard here, with community amenities including a clubhouse, pool, fitness center, dog park, playgrounds, and walking trails. Easy access to I64 makes commuting anywhere in Cheasepeake, Norfolk or Virginia Beach possible Style, function, and location — this one's ready for its next owner.

503 Nesbit Drive, South Chesapeake

700 New River Court Unit C, South Chesapeake
$240,000
2 Beds ⋅ 2 Baths ⋅ 10642730 MLS
Welcome to 700 New River Court #C, a refreshed Chesapeake condo offering comfort, style, and low-maintenance living in a convenient Greenbrier-area location. Step inside to bright neutral finishes, updated wood-look flooring, and an inviting layout.The spacious living room features natural light, a cozy fireplace with a bold black mantle, and room to relax or entertain. The dining area offers glass doors leading to a private fenced patio, perfect for morning coffee or quiet outdoor enjoyment. A breakfast bar connects to the kitchen, featuring white cabinetry, black hardware, subway tile backsplash, generous counter space, and a galley layout.Upstairs, the bedrooms feel bright and peaceful with soft neutral colors and great natural light. The primary bedroom offers direct access to the vanity area, while the additional bedroom is ideal for guests, an office, nursery, or hobby space. Convenient to Greenbrier shopping, dining, parks, medical facilities, and major commuter routes!

700 New River Court Unit C, South Chesapeake

1009 Seagull Court, South Chesapeake
$635,000
4 Beds ⋅ 2.1 Baths ⋅ 10642235 MLS
Brand-New 50-Year Roof! Brand-New Deck! Competitively Priced! Beautifully maintained 4-bedroom, 2.5-bath home, where a two-story foyer creates an inviting first impression. Thoughtfully designed, this home offers a formal dining room, spacious living room, and a welcoming family room with a cozy fireplace—ideal for gathering with family and friends. The well-appointed eat-in kitchen is the heart of the home, featuring granite countertops, a large center island with breakfast bar seating, ample cabinetry, and plenty of space for casual dining. Upstairs, you'll find four generously sized bedrooms, including an expansive primary suite with a relaxing sitting area, oversized walk-in closet, and a spa-like ensuite bath. Outside enjoy the fully fenced backyard and brand-new deck, creating the perfect setting for cookouts or simply unwinding in your own private retreat. With major updates already completed, including a brand-new roof with transferable warranty, this home is move in ready!

1009 Seagull Court, South Chesapeake

1713 Orchard Way, South Chesapeake
$283,000
2 Beds ⋅ 2 Baths ⋅ 10641020 MLS
Welcome to 1713 Orchard Way—an inviting home offering comfort, style and versatility. Enjoy 2 dedicated parking spaces + ample guest parking & a charming covered front porch. 1st floor features incl BR with attached bath, soaring vaulted ceilings, new LVP flooring, fresh paint and cozy gas log FP, creating a bright, welcoming living space. Updated kitchen with new counters & SS appliances. Spacious primary BR offers large walk-in closet (easy attic access) & bath with relaxing Jacuzzi tub. Upstairs, HUGE loft/flex area ideal for office, gym or 3rd BR. Add’l highlights: new carpet, generous interior storage, ext storage & screened porch for seamless indoor/outdoor living. Community amenities incl pool. Conveniently located just minutes to bases, interstates, dining, shopping & all of Hampton Roads.

1713 Orchard Way, South Chesapeake

705 Aspen Forest Court, South Chesapeake
$710,000
4 Beds ⋅ 4 Baths ⋅ 10638628 MLS
NEW PHOTOS! This meticulously maintained 4-bedroom, 4-bath home in sought-after Forest Lakes is offering 3,458 sq ft on a .34-acre lot. A versatile FROG serves as a 4th bedroom, second living area, office, or media room. Need storage? There is plenty with attic space, a 2-car attached garage, and a rare 2+ car detached garage with extensive storage and workshop potential. The spacious kitchen features abundant cabinet storage and ample workspace, great for everyday living and entertaining. Step outside to your private backyard oasis featuring beautiful landscaping, a spacious deck, and hot tub—ideal for relaxing or entertaining. Numerous updates include the roof, HVAC, water heater, fence, deck, and front and backyard landscape lighting. Conveniently located near neighborhood amenities, shopping, and dining, this exceptional home offers the perfect blend of space, comfort, and functionality. Don't miss this opportunity! Seller will provide a clear termite/moisture letter.

705 Aspen Forest Court, South Chesapeake

712 Jubilee Court, South Chesapeake
$695,000
5 Beds ⋅ 3 Baths ⋅ 10635747 MLS
Built by respected local builder Ryan Styron of Styron Building Co., this beautifully crafted Hickory home offers quality construction, modern style, and thoughtful design throughout. Features include durable LVP flooring, cathedral ceilings, LED lighting, abundant storage, a stunning kitchen with gas cooking, granite and quartz countertops, soft-close cabinetry, and a built-in office. The spacious primary suite includes a relaxing garden tub, while a first-floor bedroom and full bath provide flexible living options. Enjoy added conveniences like a walk-in attic, laundry room cabinetry, outdoor shed, and a covered screened patio overlooking a large private backyard. Nestled on a quiet cul-de-sac with wooded surroundings, this home offers exceptional privacy in a highly desirable, family-oriented neighborhood with top-rated Hickory schools.

712 Jubilee Court, South Chesapeake

2504 Calabria Dr Drive, South Chesapeake
$810,000
5 Beds ⋅ 4 Baths ⋅ 10644739 MLS
This home has it all! Tall ceilings,recessed lighting throughout,custom built ins, ship lap walls, a high end kitchen with a built in area with electrical for a wine or beer fridge, frosted glass barn doors, a mud room, a primary suite like no other with a cool room off it that could be turned into a secret room for fun or games. The open floor plan and large lot invites entertaining or relaxation while spending time with friends or loved ones. The property line goes back into the woods beyond the large fenced in area. There is an extended drive way for plenty of parking, a large professionally built and installed shed that replicates a small home. Plush grass with installed drainage.There is so much more to tell but seeing is believing don't wait to take a tour of this magnificent home located on a small culdesac.

2504 Calabria Dr Drive, South Chesapeake

1740 Land Of Promise Rd Road, South Chesapeake
$729,000
4 Beds ⋅ 2.1 Baths ⋅ 10643077 MLS
Sitting on just under 1 ACRE escape to your own private retreat in the heart of Hickory! Nestled on a peaceful wooded setting, this beautifully maintained home offers the perfect blend of space, comfort and modern updates. Inside, you'll find souring ceilings, abundant natural light, and inviting living spaces designed for both relaxing and entertaining. Enjoy the tranquility of country style living while still being conveniently located near shopping, dining, and sought after schools. Major system updates provide peace of mind including updated heat pump, septic improvements, well and water filtration updates, gutter systems enhancements, oversized shed, extended driveway offering ample space for boat or RV storage, and a generator hookup. This property combines rural charm with everyday practicality. Whether you're hosting guests, enjoying quiet mornings outdoors, or simply looking for more privacy and space, this property offers a rare opportunity to enjoy the best of Chesapeake.

1740 Land Of Promise Rd Road, South Chesapeake

804 Greenspring Court, South Chesapeake
$480,000
4 Beds ⋅ 2 Baths ⋅ 10642873 MLS
Tucked away on a quiet wooded cul-de-sac in Brandermill, this quality-built 4-bedroom, 2-bath home blends timeless charm with modern updates. New Architectural roof, new beautifully renovated bathrooms, new kitchen countertops, newer LVP flooring. Centrally located dining area creates the warm, functional heart of the home. A spacious sun-filled addition with cathedral ceiling opens to the perfect patio gathering area for cookouts and a large backyard made for entertaining, yard games and having fun with family and friends. Unwind on the spacious shaded front porch and soak in the peaceful surroundings. This home has been thoughtfully maintained, a genuine gem offering comfort, character and is convenient to schools, shopping, dining and everyday essentials. Sparkling with style and ready to welcome you home!

804 Greenspring Court, South Chesapeake

208 Robinhood Road, South Chesapeake
$553,000
4 Beds ⋅ 2.1 Baths ⋅ 10641154 MLS
Welcome to Sherwood Forest, located in the desirable Great Bridge area. This beautiful home features 4 bedrooms and 2.5 baths, offering a bright and welcoming atmosphere that truly feels like home. Huge primary bedroom with room that can be use as a flex room. The updated, classic style kitchen flows seamlessly into the family room, creating an ideal space for everyday living and entertaining.The first floor features hardwood floors and has been meticulously maintained. A 2 car garage and a huge backyard provide plenty of space for family gatherings, outdoor entertaining, or simply relaxing with your morning coffee or evening cocktail.The property is located in an X-500 flood zone, with no mandatory flood insurance required. Best of all, there is no HOA! Schedule your tour today!

208 Robinhood Road, South Chesapeake

1525 Scoonie Pointe Drive, South Chesapeake
$429,900
3 Beds ⋅ 2.1 Baths ⋅ 10635265 MLS
Welcome to easy, low-maintenance living in this beautifully appointed 3-bedroom, 2.5-bath condo located in a desirable 55+ community. Designed with comfort and convenience in mind, this home features an open, light-filled floor plan with an abundance of natural light throughout. The spacious main-level primary suite offers the ease of first-floor living, while engineered hardwood flooring adds warmth and elegance to the main living areas. The kitchen is equipped with stainless steel appliances, hard-surface countertops, and ample cabinetry, making it both stylish and functional for everyday living and entertaining. Additional highlights include a two-car garage with a durable epoxy-coated floor, generous secondary bedrooms, and thoughtfully designed living spaces that provide flexibility for guests, hobbies, or a home office. Enjoy the relaxed lifestyle and amenities of this welcoming 55+ community, where comfort, quality, and convenience come together.

1525 Scoonie Pointe Drive, South Chesapeake

334 Scone Castle Loop, South Chesapeake
$1,800,000
5 Beds ⋅ 5.3 Baths ⋅ 10630815 MLS
Location is Key! Enjoy peaceful country living In the city. This centrally located Hampton Roads neighborhood is close to shopping, restaurants, and entertainment. A meticulously maintained stately brick home nestled in the heart of Edinburgh Meadows. You'll be proud to make this the home of your dreams! Upgrades throughout this 5650SF, 5BR. 5BA, 3 half baths turnkey home that is situated on .75 acre lot with a pond behind the back yard and an In-ground saltwater pool. The first floor primary suite includes a gorgeous and multi functional bathroom. The open floor concept, a generous yard with a pool house an extra large back porch with 5 ceiling fans, a half bath. and a gas fireplace combine to make this a perfect home for entertaining and family gatherings. This home has all the bells and whistles!

334 Scone Castle Loop, South Chesapeake

837 Greenfield Lane, South Chesapeake
$720,000
4 Beds ⋅ 4 Baths ⋅ 10645397 MLS
Welcome home to Rollingwood Estates in the highly sought after Great Bridge school district. This one owner brick transitional home offers 4 bedrooms and 4 full baths with an open, bright floor plan designed for comfortable living and effortless entertaining. The spacious FROG serves as the fourth bedroom and features its own private full bath, making it ideal for guests or multigenerational living. The kitchen offers Corian countertops, generous workspace and opens to the main living areas. Step outside to your own backyard retreat with a sparkling inground pool, dedicated pool bath, stamped concrete patio, outdoor bar/kitchen area, screened porch, and professionally landscaped yard. A two car attached garage, irrigation well, and thoughtful layout add to the appeal. Offering exceptional value in an established neighborhood, this home is priced to sell and ready for its next owner to make it their own.

837 Greenfield Lane, South Chesapeake

656 Parker Road, South Chesapeake
$695,000
4 Beds ⋅ 2.1 Baths ⋅ 10644240 MLS
Vacation at home! Beautifully updated 4-bedroom, 2.5-bath home in sought-after Cheshire Forest and the desirable Great Bridge school district. The backyard is the star, transformed in 2024 with a saltwater in-ground pool with built-in hot tub, expansive patio, refreshed deck, fire pit, and hardtop gazebo with Blackstone grill, Traeger smoker, and two mini refrigerators. Fully fenced yard backs to the neighborhood lake with access for fishing or a lakeside stroll. Powered shed with well, plus deck furniture and pool accessories convey. Inside offers LVP flooring throughout, a spacious great room with gas fireplace, formal dining room with pocket doors, and a sunroom with mini-split (2024). Recent updates include HVAC (2025), water heater (2026), electrical panel (2024), windows (approx. 2021), new gutters, bath tile, plantation shutters, shiplap, roof (2014) and more. 2-car garage. Community amenities complete the package!

656 Parker Road, South Chesapeake

1615 Thomason Trail, South Chesapeake
$380,000
3 Beds ⋅ 2.1 Baths ⋅ 10643889 MLS
Easy living in South-Central Chesapeake ! Just moments from everything you need! This beautifully maintained condo offers the perfect blend of comfort, style, and convenience. Thoughtfully designed with open spaces throughout along with the soaring ceilings helps to create the perfect blend of peaceful, pressure-free, serenity. The gracious floor plan invites unencumbered joy that is down-right pleasant! This is where you will look forward to coming home to every day! The first floor serves as the heart of the home, featuring an open concept kitchen, spacious living room, dining area, and private patio enclosed by the maintenence-free privacy fence...ideal for morning coffee or evening cocktails. On your way up to the second floor you are greeted by a spacious flex space for multiple uses before reaching your primary suite that offers an over-sized walk-in closet along with your private deep soaking tub and generously sized shower. Two additional bedrooms, full bath, and conveniently located laundry area complete this upper level. One can actually feel the pride in ownership simply by approaching the front door and of course, especially once you cross the threshold! The seller has thouroughly enjoyed this home but is relocating for a new opportunity, creating a rare chance for the next owner to enjoy as well! Ready for a stress-free transition into your next opportunity??? Your search is over!

1615 Thomason Trail, South Chesapeake

700 Turnbuckle Court, South Chesapeake
$590,000
4 Beds ⋅ 2.1 Baths ⋅ 10643821 MLS
Lovely 4 bedroom, 2.5 bath home located in desirable Great Bridge area. This beautiful home has been well maintained by original owners and boasts custom features throughout including cathedral ceilings, custom crown molding and chair rail. New LVP flooring in primary bathroom and hall bathroom. New stainless steel appliances and granite counter tops in bright open kitchen that flows into the family room with a cozy gas fireplace for relaxing. Large bedrooms that are bright and inviting. Huge primary suite with cathedral ceiling, walk in closet, jetted tub & double sinks. Located in a cul de sac with wrap around front porch that overlooks the lush front yard & deck in the "secret garden" back yard with mature trees and shrubbery for privacy. Partially encapsulated crawl space & dehumidifier. Updates include HVAC (2022), windows (2016), Roof (2014), new rear sliding door & LVP flooring. 2 car garage with new side entry door. Freshly painted exterior. This truly feels like HOME!

700 Turnbuckle Court, South Chesapeake

2025 Hallmark Way, South Chesapeake
$885,000
4 Beds ⋅ 3.1 Baths ⋅ 10643488 MLS
Set on just over three private wooded acres in sought after Shillelagh Farms and located in the Grassfield School District, this custom-built home offers a rare combination of privacy, space, and freedom with no HOA restrictions. A dramatic two story foyer, soaring vaulted ceilings, and front and rear staircases add character and functionality while the inviting floor plan is designed for both everyday living and entertaining. Featuring four bedrooms, 3.5 baths, a dedicated office, spacious FROG with full bath, and a primary suite with oversized walk-in closet. Enjoy the expansive multi-level deck overlooking the private wooded backyard. The detached 1,092 square foot garage/workshop with full attic storage offers endless possibilities for car enthusiasts, crafts people, or those needing exceptional storage and workspace for RVs, boats, and recreational vehicles. Rarely does a property offer this combination of acreage, privacy, detached workshop, no HOA and prime Grassfield location.

2025 Hallmark Way, South Chesapeake

224 Essex Drive, South Chesapeake
$430,000
4 Beds ⋅ 2 Baths ⋅ 10643538 MLS
Welcome home to this charming brick ranch near Summit Pointe in Chesapeake, Virginia.Brick ranch near Summit Pointe! The heart of the home is the inviting country kitchen, equipped with stainless steel appliances and plenty of space for gathering with family and friends. The standout feature is the oversized primary suite, providing a private retreat with room for a sitting area, home office, or workout space! The huge backyard features a 2-year-old above-ground saltwater pool surrounded by a wraparound deck with recess lighting, creating the ideal setting for cookouts, entertaining, and relaxing weekends at home. Spacious floor plan featuring a welcoming living room and cozy den, both complete with fireplaces, perfect for relaxing on cool winter evenings. Upgrades for peace of mind include newer paint, newer windows, newer stainless steel appliances, newer vapor barrier, newer drain line, newer roof, newer ceiling fans and 200 amp electric panel. Call today to view!

224 Essex Drive, South Chesapeake

1089 Saint Julian Drive, South Chesapeake
$375,000
4 Beds ⋅ 2 Baths ⋅ 10643138 MLS
Wonderfully updated and absolutely meticulously maintained and spotless ranch style home with 4 bedrooms 2 baths a 2 car DETACHED GARAGE in this lovely Chesapeake waterfront neighborhood! Modest sized home that comes to life with an open concept lover's dream!! This is the perfect house for entertaining! Sprawl out on the kitchen island and enjoy hosting- make sure to invite all your friends; the driveway and backyard can hold just about anyone and anything! Exclusive access to a public boat ramp—perfect for weekend adventures on the water!! Enjoy the convenience of a dedicated laundry room, and take full advantage of the expansive, fully fenced backyard—perfect for pets, play, and outdoor gatherings. Everything in the home has been updated in the last few years. Roof, hvac, water heater, flooring, kitchen, bathrooms and all new appliances. It’s all virtually new. All that’s missing is YOU!

1089 Saint Julian Drive, 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.

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