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1217 Club House Drive, South Chesapeake
$600,000
4 Beds ⋅ 2.1 Baths ⋅ 10658962 MLS
Las Gaviotas has the name recognition. This Colonial has the character to back it up. Set in one of Chesapeake’s most iconic, sought-after neighborhoods, the traditional exterior opens to an interior that feels bright, fresh, and full of personality. Natural light pours through large windows, playing across light-toned LVP flooring and freshly painted rooms. Updated lighting gives the spaces a current feel while the classic Colonial details retain their charm. The kitchen makes an impression with tall white cabinetry, granite countertops, and newer appliances, while the eat-in area and separate dining room give each occasion its own space. There’s a dedicated office, too, with plantation shutters that add a tailored finish. The living room has a character all its own, centered around a wood-burning fireplace and framed by more plantation shutters. Just beyond, the screened porch provides a natural transition to the deck, where an outdoor sauna adds a feature you don’t find every day. The smaller details are worth noticing, too: a surprise nook tucked beneath the stairs, generously sized bedrooms, and double doors that make the entrance to the primary bedroom feel a little more special. Throughout the home, traditional character meets a refreshed interior without losing the details that give this Colonial its charm. Recent window replacements, an updated water heater, and refreshed paint and lighting bring substance to the improvements. A two-car garage and extended driveway add the practical space to go with it. The neighborhood may be what first draws your attention, but the way this Colonial unfolds from sun-filled rooms to that unexpected outdoor retreat is what makes it memorable.

1217 Club House Drive, South Chesapeake

3422 Anita Circle, West Chesapeake
$595,000
5 Beds ⋅ 3 Baths ⋅ 10658855 MLS
Welcome to this amazing all-brick home in sought after Western Branch! This home offers timeless charm and modern luxury. The heart of the home is a beautifully updated kitchen(new 2024) boasting Fantasy Brown granite countertops, white shaker cabinets, ceramic tile backsplash, a large center island, under cabinet lighting and more. Unwind in the inviting family room by the gorgeous brick fireplace, flanked by built-in glass-door lighted cabinets. Enjoy dual staircases, updated bathrooms, and whole-house water filtration and softening systems, a Texas sized primary bedroom, and the 5th bedroom could be media/game room. Head outside to your private oasis complete with an oversized Trex deck w/a retractable awning, hot tub, a charming trellis-covered patio, firepit area and a detached storage shed with electricity. New roof(2022), tankless water heater(2023), vapor barrier(2026) and so much more! Don't miss this incredible find! Some rooms virtually staged.

3422 Anita Circle, West Chesapeake

707 River Gate Court, South Chesapeake
$674,900
5 Beds ⋅ 2.1 Baths ⋅ 10658800 MLS
Convenient location. 20 min to Downtown Norfolk. 35 min to NAS Oceana, Dam Neck & beaches. 20 min to Norfolk Int Airport. Over 10 grocery stores in a 5 mile radius. 5 min to Hickory H.S., 1 of the BEST in Hampton Roads. Easy access to Chesapeake Bypass, I-64, I-264, & I-464. This property is a gardener's dream sequenced for near year round color. Back yard oasis includes a hot tub, goldfish pond and six foot privacy fence. Two patios are connected by a master-crafted paver walk-way. Oversized garden shed helps keep garage clutter free. In ground sprinkler system fed by well water to keep watering cost low. Two outdoor water taps fed by the well & two additional taps fed by city water. Tank-less water heater provides endless hot water. The oversized Primary Bedroom includes two walk in closets. One large walk-in closet features two side cubby units for storage. The other walk-in closet is medium sized with plenty of storage space. Washer & dryer are on the second floor for convenience to bedrooms. Some photos are AI-virtually staged.

707 River Gate Court, South Chesapeake

3536 Calverton Way, West Chesapeake
$489,900
4 Beds ⋅ 3 Baths ⋅ 10658503 MLS
Welcome to the sought-after Wellington neighborhood in Western Branch, Chesapeake! This charming brick rancher features laminate flooring, an updated kitchen with stainless steel appliances, and a finished room over the garage (FROG) with a mini-split added in 2024 perfect for an office, playroom, or guest retreat. The primary suite offers a tray ceiling, spacious walk-in closet, and walk-in shower. Relax on the screened porch overlooking the private, fenced backyard. Shenandoah plantation shutters and a southern sky-blue porch ceiling add Southern charm. Enjoy a two-car garage and NO HOA! Updates include leaf gutters (2023), HVAC (approx. 7 years old), water heater (2025), dishwasher (2026), sump pump, Aprilaire dehumidifier, and encapsulated crawlspace. Roof and garage door replaced in 2017. Comfort, flexibility, and a desirable location make this home a must see!

3536 Calverton Way, West Chesapeake

1325 Debbs Lane, South Chesapeake
$420,000
4 Beds ⋅ 2.1 Baths ⋅ 10658609 MLS
Welcome to this beautifully updated 4-bedroom, 2.5-bath home in the heart of Chesapeake's Greenbrier area. Enjoy fresh paint, new LVP flooring, and new carpet throughout. The spacious, open floor plain is great for entertaining, hosting gatherings, and everyday living. The generous kitchen features granite countertops and stainless-steel appliances, making meal preparation a pleasure. Head outdoors to your large paver patio and enjoy the privacy of a fenced backyard, desirable for relaxing or entertaining outdoors. The attached garage offers added convenience with a new garage door opener. Centrally located near military bases, beaches, medical facilities, shopping, restaurants, and major interstates, this home combines modern updates, comfortable living, and a convenient location! Don't miss the opportunity to make this wonderful home yours!

1325 Debbs Lane, South Chesapeake

1431 Oliver Avenue, Central Chesapeake
$375,000
4 Beds ⋅ 3 Baths ⋅ 10657417 MLS
Fall in love with this beautifully updated 4-bedroom, 3-full-bathroom home! New luxury vinyl plank flooring throughout the entire downstairs creates a fresh, stylish, low-maintenance space. The open kitchen features a breakfast bar and flows into the spacious living room, making everyday living and entertaining easy. Upstairs, new plush carpeting leads to four generously sized bedrooms, including an expansive primary ensuite with a large bedroom, spacious adjoining bathroom, and large walk-in closet. Three full bathrooms offer added comfort and convenience, and a newly installed HVAC system is another valuable update. Buyers may have the opportunity to assume the existing loan at an attractive 3.5% interest rate, subject to lender approval, eligibility, and assumption terms. With modern updates, spacious gathering areas, and a flexible floor plan, this home offers comfort, practicality, and room to grow. Schedule your showing and discover all this home has to offer!

1431 Oliver Avenue, Central Chesapeake

514 Trellis Trail, South Chesapeake
$329,000
2 Beds ⋅ 2.1 Baths ⋅ 10658445 MLS
Come check out this Spacious 1,870-square-foot, 2-bedroom +1 bonus room townhome in a four-unit building. Peacefully set among trees, the home offers a feeling of privacy. The Grove at the Arboretum neighborhood (situated around Green Tree Road) sits directly adjacent to the arboretum grounds, making it a close distance of less than a half-mile away. A public nature site featuring shaded hardwood forest trails, demo gardens, an 18th-century farmhouse, and Camellia Cove. BRAND NEW air conditioning unit will keep you cool on hot summer days. The versatile first-floor office can easily serve as a third bedroom, guest room, or flex space. Beautiful wood floors throughout the lower level offer aesthetic appeal and simplify cleaning and maintenance. An oversized kitchen features a generous pantry, breakfast area, and plenty of cabinet space & counter seating. Sliding glass doors open to a private, fenced in patio, wonderful for relaxing or entertaining. Upstairs, you'll find two generously sized primary suites, each with its own private full bathroom, providing comfort and privacy for residents and guests alike. A spacious second floor laundry room includes washer and dryer hookups and a utility sink for added convenience. Community amenities include a sparkling swimming pool, grounds maintenance, trash pickup, and sewer, all included with the HOA. Ideally located in the sought-after Greenbrier area, with easy access to interstates 64/264/664/17, shopping centers/mall, and fantastic local dining. Quick move-in available, come see this beauty today! Also for rent $2500/Month, available now.

514 Trellis Trail, South Chesapeake

905 Camp Street, South Chesapeake
$599,000
4 Beds ⋅ 3.1 Baths ⋅ 10658354 MLS
A Community with year-round events, clubhouse, pool, playgrounds and a brand NEW school scheduled to open in 2027, that would be Culpepper Landing in Chesapeake! The BEST part is this like new home, built in 2021 & meticulously maintained! It offers 4 Bedrms, 3 1/2 Bath, almost 2,500 sqft of open, bright natural light, living space. A FROG that is private off of the kitchen w/its own full bath & walk-in closet, could be used as multi-generational liv'g as an In-law Suite, or flex space. A Large eat-in kitchen w/custom cabinets, an abundance of storage, granite counters, SS appliances, & an XL island perfect for a family & entertaining. Upstairs you'll find a large laundry room, primary bedroom w/tray ceiling, ensuite bath, & walk-in closet it truly is your own peaceful retreat. A 3rd full bath & 2 large bedrooms upstairs give you a very versatile layout. Relax in fenced in backyard, this home was designed for everyday living w/plenty of room to spread out! Min from shopping/interstates

905 Camp Street, South Chesapeake

2220 Capri Circle, West Chesapeake
$425,000
4 Beds ⋅ 3 Baths ⋅ 10658268 MLS
Welcome home to this spacious brick ranch in a desirable Chesapeake neighborhood! Set on a corner lot with great curb appeal, this 4-bedroom, 3-bath home offers approximately 2,100 sq ft of living space-larger than most homes in the neighborhood. Enjoy a spacious living room with high ceilings, newer LVP flooring, and a gas fireplace framed by a beautiful exposed brick wall. Need extra space for hobbies, projects, or storage? The oversized 672 sq ft detached 2-car garage, carport, and storage shed deliver! A large covered porch is perfect for relaxing and entertaining. Many updates, including a newer roof with LeafGuard gutters, replacement windows, and HVAC replaced in 2019. Seller to provide a clear termite letter. Convenient to Chesapeake Square Mall, shopping, and interstate access, this home offers space, character, and convenience all in one! Make your appointment for a private tour today!

2220 Capri Circle, West Chesapeake

518 Silk Tree Lane, South Chesapeake
$449,900
3 Beds ⋅ 2.1 Baths ⋅ 10658185 MLS
See into unparalleled luxury at 518 Silk Tree Lane, nestled in the quaint, village-like community of North Trail in the highly sought-after Greenbrier area. This 2,366 square-foot masterpiece is completely turn-key. Absolutely no upgrades are needed here. Every high-end detail has already been meticulously curated for you. The stunning gourmet kitchen is a true showstopper, featuring custom cabinetry and countertops, stainless steel appliances from the Frigidaire Professional Series - double wall ovens, a gas range, microwave, wine refrigerator, and built-in ice maker. Porcelain flooring flows throughout the living room, dining area, and kitchen, while well-maintained carpeting adds warmth and comfort to the upstairs and bedrooms. The commitment to high-end living extends into the bathrooms, which have been transformed into private, spa-like retreats featuring breathtaking custom walk-in showers with artisan tile work and built-in bench seating. A cleverly crafted bonus office space is perfectly situated just at the top right of the staircase, offering an ideal, quiet sanctuary for remote work. Storage abounds with custom built-ins and a walk-in attic. Enjoy the spacious custom paver patio with views of the serene community pond and fountains. Additional highlights include three-zone HVAC, Rinnai tankless water heater, custom trim and moldings, Bose surround sound, Cox security wiring, and an EV charging station. Embrace the ultimate low-maintenance lifestyle. The comprehensive condo fee covers all exterior grounds maintenance and trash pickup. Conveniently located in the heart of Chesapeake. Truly a must-see!

518 Silk Tree Lane, South Chesapeake

4640 Ballahack Road, South Chesapeake
$589,900
3 Beds ⋅ 2.1 Baths ⋅ 10657850 MLS
Welcome home to this well-built, lovingly maintained brick ranch framed by mature trees, dogwoods, boxwoods and elephant ear plants that offer beautiful summer shade on 1.67+ acre lot. A charming front porch with newer brick flooring and stately columns sets the tone. Inside, enjoy updated flooring throughout, an updated primary bath and a stunning French country kitchen, remodeled floor to ceiling, expanded into the den with extra cabinetry (wine, & dish cabinet and bench) and a breakfast area. The bright FROG offers flexible space for a home theater, hobby room, playroom or 4th guest bedroom with access to a huge floored and lighted attic. Relax on the screened porch with its "pet and kid friendly" brick base, gather on the paver patio or unwind by the fire pit. Custom Shutters offer evening privacy. A garden for homegrown produce, detached lighted garage with large workshop. French drain system, multiple parking spots and freshly painted trim complete this inviting home!

4640 Ballahack Road, South Chesapeake

1505 Waitsel Drive Unit 306, South Chesapeake
$310,000
2 Beds ⋅ 2 Baths ⋅ 10658216 MLS
Enjoy the perfect blend of comfort, style, and low-maintenance living in this inviting third-floor Chesapeake condo with no neighbors above! Soaring ceilings, abundant natural light, and an open layout with LVP flooring in the living area create a bright and airy atmosphere. The spacious kitchen features quartz countertops, stainless steel appliances, and a breakfast bar that flows effortlessly into the main living area, great for everyday living or entertaining. The primary suite offers a relaxing retreat with a private bath and generous walk-in closet featuring custom wood shelving. Beyond your front door, enjoy a peaceful community pond with a walking loop and dedicated dog park. With water, sewer, trash pickup, and grounds maintenance included in the condo fees, there's more time to enjoy the things you love! Conveniently located near shopping, dining, and major commuter routes, this home offers an easygoing Chesapeake lifestyle!

1505 Waitsel Drive Unit 306, South Chesapeake

844 Greenfield Lane, South Chesapeake
$950,000
6 Beds ⋅ 5.1 Baths ⋅ 10658157 MLS
All-brick home offering over 5,000 sq. ft. of versatile living space and exceptional indoor–outdoor amenities. With 6 bedrooms, 5.5 bathrooms, and an additional first-floor flex room perfect as a 7th bedroom, home office, or formal living area, this home adapts beautifully to your lifestyle. Five of the bedrooms include private en-suite bathrooms, giving everyone their own comfortable retreat. A bright, oversized sunroom—equipped with heating and cooling but not included in the home’s total square footage—adds even more year-round living space. Step outside to your own backyard oasis. Brick pool house with heating/cooling + full bathroom. In-ground saltwater pool with a new liner ( installed 2025). Hot tub for 6. Expansive patio area for entertaining and relaxing. The property also features a three-car garage plus a half-circle driveway providing abundant parking for guests. freshly painted, new carpets, refinished wood floors. Interior pics virtually staged.

844 Greenfield Lane, South Chesapeake

614 Middleton Way, South Chesapeake
$589,000
4 Beds ⋅ 2.1 Baths ⋅ 10657970 MLS
Welcome home to Hickory Manor! This crisp, and move-in ready 4-bedroom, 2.5 bath, 2456 sqft property sits in the highly desirable Hickory school district delivering space, comfort, and community amenities buyers love. The inviting foyer entry leads into an open, light-filled main level featuring an inviting living room, spacious dining area, modern kitchen with pantry, and mudroom ideal for entertaining. Upstairs offers all four bedrooms, including a generous primary suite with a custom walk-in closet system and convenient second floor laundry. The fenced backyard provides a ideal outdoor retreat. Located in the amenity-rich Hickory Manor community with access to the clubhouse, pool, fitness center, and playground. With paid off Solar Panels and a transferable warranty, your dream home awaits offering long-term energy savings and peace of mind. Seller is offering closing cost assistance, making this an exceptional value you won't want to miss!

614 Middleton Way, South Chesapeake

821 Redleafe Circle, South Chesapeake
$980,000
6 Beds ⋅ 4 Baths ⋅ 10657839 MLS
An exceptional opportunity to own a Stephen Alexander custom home in Greystone, one of Chesapeake's premier luxury communities where homes are rarely available. This expansive executive residence blends timeless craftsmanship with the space, flexibility, and resort-style amenities today's luxury buyers seek. A first-floor bedroom with an adjacent full bath offers versatility for guests, a home office, or multi-generational living. The primary suite is a true retreat with a fireplace, sitting area, and four closets. Enjoy a private backyard oasis featuring an in-ground pool, hot tub, screened porch, gazebo, fire pit, privacy fence, irrigation well, and expanded parking for a boat or RV. Scenic walking paths enhance this sought-after community. Significant recent investments include a new roof (2026), three HVAC systems, an encapsulated crawl space, new hardwood flooring, updated bath vanities, freshly painted kitchen cabinetry, and a new oven. Schedule your private showing today!

821 Redleafe Circle, South Chesapeake

810 Hedgerow Court, South Chesapeake
$675,000
5 Beds ⋅ 3 Baths ⋅ 10657871 MLS
Well maintained all brick home with 2-car side loading garage, long driveway, 1/3 acre beautifully landscaped lot, situated on a cul-de-sac in Great Bridge. Open floor plan features huge kitchen with quartz countertops and overlooks fam room. FR has wood burning FP which is also plumbed for gas. In addition to the 5 bedrooms on 2nd floor, there is a 6th bedroom/office with adjacent full bathroom on 1st floor. Recent updates include 2nd floor 3 ton HVAC (Sept 2026), new carpets (Sept 2026), windows, roof, water heater, garage door, leaf filter gutters, more. Award winning Cheshire Forest community amenities include clubhouse, pool, tennis/pickle ball courts, parks and playgrounds. Screened porch with concrete floor overlooks the beautiful backyard. Seller to provide clear Termite/Moisture letters and 1 year home warranty.

810 Hedgerow Court, South Chesapeake

3301 Settlement Court, West Chesapeake
$269,999
2 Beds ⋅ 2 Baths ⋅ 10657817 MLS
Welcome to highly sought-after, single-story living in the wonderful 55+ community of One Ford Place! This beautifully maintained Western Branch condo offers the ultimate "no-maintenance" lifestyle. The inviting layout features a spacious great room with sliding doors opening to a private patio. The well-appointed kitchen includes a pantry and conveys with all appliances. Enjoy a luxurious primary suite adorned with picture frame molding and a beautiful en-suite bath featuring a granite double vanity, tub, and separate shower. A second bedroom and full bath on the opposite side of the home create the perfect private guest suite! Enjoy the rare convenience of a one-car garage, a two-car driveway, and ample guest parking. Move in with total peace of mind thanks to major recent updates to the HVAC, water heater, and appliances. With TVs conveying and additional furniture negotiable, your transition will be a breeze. Located minutes from the YMCA, I-664, and I-164!

3301 Settlement Court, West Chesapeake

1324 Cambridge Way, South Chesapeake
$615,000
3 Beds ⋅ 2.1 Baths ⋅ 10657862 MLS
Welcome to this truly custom-built home in the highly desirable Hunningdon Woods neighborhood nestled in the heart of Greenbrier! Situated on a beautiful corner lot, this charming home offers a wonderful blend of comfort, character, and thoughtful design. The inviting living area flows into a lovely eat-in kitchen, creating the perfect setting for everyday living and entertaining. The spacious first-floor primary suite offers comfort and convenience, while the generously sized other bedrooms provide plenty of room for family or guests. Enjoy relaxing on the screened porch overlooking a beautifully landscaped yard filled with absolutely stunning array of blooming perennials that provide color and beauty throughout the seasons. Complete with a side-load garage, this special home offers timeless appeal. A wonderful opportunity to make this exceptional property your own.

1324 Cambridge Way, South Chesapeake

628 Gladesdale Drive, South Chesapeake
$499,900
4 Beds ⋅ 2 Baths ⋅ 10657378 MLS
Well maintained all brick ranch on a large .34 acre corner lot in the Hickory School District . Enter the large greatroom through foyer which opens to formal dining room. Greatroom features chairrail, wainscoating, exposed beams, built in bookcase and masonry wood burning fireplace.Kitchen has been updated with new cabinet faces, countertops and laminate floors; all appliances convey. Primary bath updated with new vanity, toilet and has tile floor. Hall bath updated with new toilet. Laundry closet convenietly off eat-in area in kitchen. Large frog has plenty of head space and large closet; partially floored walk in attic. HVAC, hot water heater newer, encapsulated crawl with dehumidifier. Large deck off greatroom. No neighborhood fees.

628 Gladesdale Drive, South Chesapeake

616 Rutherford Drive, South Chesapeake
$549,900
3 Beds ⋅ 1.1 Baths ⋅ 10657745 MLS
Well-maintained, move-in-ready brick ranch in an established neighborhood with wide sidewalks! Features attractive LVP flooring throughout, three bedrooms, and a primary suite with a walk-in closet. Enjoy the gas log fireplace and additional storage with floored attic space. The converted attached garage is currently equipped as a beauty salon with styling station, shampoo sink, built-in cabinetry, and laundry area. A bright 20' x 20' sunroom with three walls of casement windows overlooks the backyard. Outdoor amenities include a 20' x 20' composite deck, fenced yard, and a 20' x 40' in-ground pool with cover. The detached three-bay garage includes power, workbenches, and pull-down access to a large, floored attic. A rare combination of comfort, functionality, and exceptional indoor and outdoor living space.

616 Rutherford 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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