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$599,999
3 Beds 2.1 Baths 10643390 MLS
Move right into this beautifully upgraded, detached single-family home that perfectly pairs charm with an inviting, modern design. Built in 2014, this roughly 2,389 sq ft masterpiece is fully optimized for comfortable daily living and effortless entertaining. Main Level Highlights: Step through the welcoming entry foyer into a bright, open-concept floor plan radiating with natural light, custom blinds, and beautiful wood and laminate flooring. The expansive living space features a cozy electric fireplace. The updated kitchen boasts stainless steel appliances, a modern tile backsplash, crisp cabinetry, a large pantry, and a sunlit breakfast and dining area. Upper Level Retreats: Find ultimate comfort upstairs with a versatile second-floor loft that could be a home office, play area or convert into 4th Bedroom. The spacious primary bedroom suite serves as your personal oasis, offering a private retreat complete with an en suite bath and a large walk-in closet. Outdoor Living & Efficiency: Relax on the rear deck overlooking a sprawling, fully fenced backyard that directly overlooks a peaceful local farm. Large Modern Play-set conveying to buyer is negotiable. High-value capital updates include a new HVAC system in 2025, a tankless water heater, smart house features, and energy-efficient window tinting. Features an attached 2-car garage used for parking, storage, or a home gym. Centrally located near shopping, interstates, and area military bases. Bonus: Seller's preferred lender is offering closing cost assistance if utilized by buyer ask LA for more information!

712 Appalachian Court, South Chesapeake

$320,000
3 Beds 2.1 Baths 10643459 MLS
Welcome to 709 Montrose Ct., Chesapeake, VA! This well- maintained two-story townhome offers 1,610 +/- sq. ft. of comfortable living space in a convenient location. Built in 1991, the home features 3 bedrooms, 2.5 baths, and a functional floor plan designed for everyday living. The spacious layout provides ample room for relaxing, entertaining, and working from home. Conveniently located near shopping, dining, schools, medical facilities, and major highways, this property offers easy access to everything Chesapeake has to offer. Whether you're a first-time homebuyer, downsizing, or seeking an investment opportunity, this townhome presents n excellent opportunity. Quarterly HOA fees help mINTin the community, providing added convenience nd peace of mind. Don't miss your chance to make this Chesapeake property your next home!

709 Montrose Court, South Chesapeake

$1,104,938
4 Beds 3.1 Baths 10643126 MLS
Warning: You may never want to leave home! Welcome to the Buena Vista by Kirbor Homes, where every room is designed to make everyday life feel a little more extraordinary. Whether you're hosting the holidays, cheering on your favorite team, or simply enjoying a quiet evening in, this home is ready for it all. The show-stopping kitchen is sure to become everyone's favorite gathering spot, featuring our upgraded Chef's Appliance Package, an oversized island, and plenty of room for everything from charcuterie boards to cookie decorating marathons. The open-concept layout keeps the conversation flowing from the kitchen to the dining area and great room, so no one ever misses out on the fun. When it's time to recharge, the luxurious first-floor primary suite offers the perfect escape, while the additional bedrooms and flexible living spaces provide endless possibilities for guests, hobbies, a home office, or that home gym you've been promising yourself. Step outside to the covered rear porch and imagine slow mornings with coffee, backyard cookouts, or winding down with a glass of wine as the sun sets. Located in the desirable Sanderson Estates, the Buena Vista pairs spacious homesites with the quality craftsmanship and thoughtful details Kirbor Homes is known for. This isn't just another new construction home—it's the kind of place where memories are made, traditions begin, and you'll happily volunteer to host every family gathering. Schedule your tour or Design Center appointment today and see why the Buena Vista might just ruin every other floor plan for you. Builder contract. Ask about available lender incentives!

2801 Raccoon Trail, South Chesapeake

$570,000
4 Beds 2.1 Baths 10642996 MLS
Welcome to luxury, low-maintenance living in the highly sought-after Westfield at Hickory Manor! This beautifully upgraded Galloway Model, built in 2018, offers 2,059 sq ft of stylish, thoughtfully designed living space with quality finishes throughout. The open-concept layout is superb for everyday living and entertaining, featuring spacious, light-filled rooms, an upgraded kitchen, a private primary suite, and flexible additional bedrooms. Enjoy resort-style amenities including a pool, 24-hr fitness center, clubhouse/community center, and playgrounds. Located in the sought-after Hickory School District with easy access to shopping, dining, military bases, major interstates, and more, this move-in ready home offers comfort, convenience, and lifestyle. Schedule your private showing today!

508 Cavendish Way, South Chesapeake

$329,900
3 Beds 2.1 Baths 10643331 MLS
Seller is offering $5,000 toward the buyer’s closing costs with an acceptable offer! Welcome to this beautifully maintained 3-bed, 2.5-bath townhome built in 2020, offering the perfect blend of style, comfort, and low-maintenance living. The open-concept floor plan features a spacious kitchen with granite countertops, a walk-in pantry, and plenty of cabinet space, flowing seamlessly into the living and dining areas—can be used for everyday living and entertaining. Upstairs, you’ll find a generous primary suite with a private bath, along with two additional bedrooms and a full bath. Come outside to enjoy the private rear deck, designed for relaxing after a long day. Condo fees include water, sewer, trash, grounds maintenance, and playground access, making homeownership even more convenient. Ideally located near military bases, shopping, dining, and major highways, this move-in ready home offers exceptional value in the heart of Chesapeake. Take advantage of the $5,000 seller concession and schedule your private showing today!

2833 Estella Way, Central Chesapeake

$239,900
2 Beds 2 Baths 10643303 MLS
Located in the Western Branch North area of Chesapeake, Virginia, 4332 Hillingdon Bend, Unit 206, is a second-floor condominium built in 2014. The residence offers approximately 1,367 square feet of single-level living space with an open floor plan and nine-foot ceilings. It features two bedrooms and two full bathrooms, including a primary suite equipped with dual closets. The kitchen includes stainless steel appliances and ample cabinetry, opening directly into the main living and dining areas. Additional interior features include central air conditioning, forced air heating, and dedicated washer and dryer hookups. As part of a common-interest community, the property provides one assigned parking space and access to shared amenities, such as a swimming pool, ground maintenance, and trash removal. Positioned near major highways, military bases, local shipyards, and retail options surrounding Chesapeake Square.

4332 Hillingdon Bend Unit 206, West Chesapeake

$284,000
2 Beds 2.1 Baths 10643295 MLS
Located in one of the most private settings in The Woodlands, this condo offers a spacious, modern layout with wooded views and no buildings directly behind. The open first floor features a bright living area, dining space, and a well-equipped kitchen with abundant counter space, breakfast bar, stainless steel appliances, and a large pantry. Sliding doors open to a fenced patio with a storage shed, creating a private outdoor retreat. Upstairs, the flexible bonus room is ideal for a home office, media room, workout space, or guest area. Both primary suites include large closets. Condo fees cover the community pool, exterior maintenance, sewer, and trash pickup. Conveniently located just 0.3 miles from Russell Memorial Library.

2806 Baldwin Drive, West Chesapeake

$524,900
3 Beds 2.1 Baths 10643243 MLS
Beautifully maintained 55+ condominium in the desirable Greenbrier area. Built by Stephen Alexander Homes, this elegant residence blends historically inspired architecture with timeless craftsmanship, featuring 10-foot ceilings, transom windows, custom crown moulding and trim work, and hardwood floors. Offering 3 bedrooms plus a spacious room over the garage, this home provides exceptional flexibility for guests, hobbies, or a home office. The gourmet kitchen with double ovens is designed for everyday living and entertaining. An interior private elevator provides effortless access to both levels. Additional features include an attached two car garage with overhead storage and utility sink, brand-new dual-zone HVAC, a Rinnai tankless water heater, and a freshly painted exterior. Relax on the spacious front porch or entertain on the private tiled patio with a SunSetter retractable awning. Whole-house audio and family room surround sound add comfort and ambiance throughout. Move in ready!

1016 Briars Landing, South Chesapeake

$684,900
5 Beds 2.1 Baths 10642890 MLS
This property is a gardener's dream. It has a variety of flowering plants that provide blossoms throughout the growing season. Blooms are sequenced for near year round color. There are 10 field-stone edged garden beds add stunning features to the landscape. One garden bed in the back has a goldfish pond. One in the front features an unique natural stone bench. Back yard includes vegetable garden plot that faces the sun for garden fresh produce. Back yard oasis includes a hot tub and six foot privacy fence. Two patios are connected by a master-crafted pave walk-way. Oversized garden shed helps keep garage clutter free. Two lockable gates one on each side of the property. In ground sprinkler system fed by well water to keep watering cost low. Two outdoor water taps fed by the well and 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 and dryer are on the second floor for convenience to bedrooms.

707 River Gate Court, South Chesapeake

$949,608
4 Beds 3.1 Baths 10643106 MLS
Welcome to the Kentland by Kirbor Homes; where your Pinterest board finally gets to come to life! Designed for the way you really live, this home offers the perfect blend of style, comfort, and flexibility. With a luxurious first-floor primary suite, spacious open-concept living, and room to spread out upstairs, there's a place for everyone (and everything). The chef-inspired kitchen is ready for everything from holiday feasts to takeout nights, featuring our upgraded Chef's Appliance Package, a large center island, and plenty of space to gather. The great room is designed for game nights, movie marathons, or simply relaxing after a long day. Located in the sought-after Sanderson Estates, you'll enjoy spacious homesites, beautiful surroundings, and the quality craftsmanship Kirbor Homes is known for. Whether you're entertaining friends, hosting family, or just enjoying a quiet morning coffee on the porch, the Kentland is ready to fit your lifestyle. Come see why your next chapter deserves a home this fun to live in! Contact Listing Agent to schedule a tour or appointmnet at our design center today! Builder contract. Ask about Lender incentives!

1516 Cedarville Court, South Chesapeake

$580,000
4 Beds 3 Baths 10642916 MLS
Retreat to the expansive second-level primary suite, featuring a private sunroom, spacious loft, luxurious garden tub, separate tiled shower, and beautiful cherry hardwood flooring. The main level offers three additional bedrooms, two full bathrooms, and a generous sunroom complete with a built-in bar—perfect for entertaining or relaxing. Enjoy 3.16 acres of peaceful outdoor living, featuring a barn, chicken coop, and storage shed, offering endless possibilities for hobbies, animals, or gardening. Major updates provide peace of mind, including a new roof (2017), two-zone HVAC system (2020), and water heater (2023). Fresh interior paint throughout and brand-new downstairs carpet make this home truly move-in ready. Welcome Home!

2600 Saint Brides Road W, South Chesapeake

$710,000
5 Beds 3.2 Baths 10642808 MLS
A Full Acre of Land in the Heart of Southern Chesapeake.... Two Primary Suites. Room for Everyone! Over 3,600 sf. Renovated 5-bedroom home on a beautiful piece of land in Chesapeake — brand new carpet, all freshly painted. The space, privacy, and flexibility that rarely come together at this price point. Two primary suites, one up and one down, give you real options: multigenerational living, long-term guests, or a main-level owner's retreat. The downstairs in-law suite/owners suite has its own private entrance — space for older parents, adult kids, or a home business with client access that never touches your living space. The renovated kitchen features stainless steel appliances and opens to living areas built for gathering. The upstairs primary offers double sinks and a large walk-in closet. A mudroom with half bath handles the daily traffic so the rest of the house stays put together. Outside is where this property separates itself. A wrap-around deck surrounds the above-ground pool — your built-in venue for summer weekends. The roundabout driveway and attached 2-car garage mean parking is never a problem, whether it's a cookout for twenty or just everyday life. And the full acre gives you room to add, expand, or simply breathe — no neighbors ten feet from your window. Homes with this much land, this much flexibility, don't sit long in Chesapeake. Schedule your showing today. Sellers are motivated. Some images are digitally staged.

1833 Benefit Road, South Chesapeake

$1,750,000
4 Beds 4 Baths 10642797 MLS
Set at the end of a quiet Hunters Ridge cul-de-sac, this custom brick estate rests on three private, gated acres, held by a single owner since its 2006 build. Beyond its 5,707 square feet of main finished living space, the home offers approximately 1,800 additional square feet of year-round conditioned space. A two-story foyer with a curved staircase opens to formal rooms and a two-story great room with a see-through gas fireplace. The island kitchen features granite, stainless, and a wet bar. The primary suite is a private retreat with a tray ceiling and a spa bath with a soaking tub. A temperature-controlled pool room, a rarity in Hunters Ridge, holds a heated pool beneath vaulted, skylit ceilings for year-round swimming and entertaining. A detached guest suite of about 715 finished square feet adds a kitchenette and full bath, ideal for extended family or long-term guests. A three-car garage, brick-pillar drive, pergola with hot tub, and patios complete the grounds.

2505 Sylvia Court, South Chesapeake

$775,000
5 Beds 2.1 Baths 10642786 MLS
One of a kind property in Hickory area of Chesapeake with 2 (YES TWO) SFH that are legally deeded, WATERFRONT (ocean access) ~3.5 ac lot, with no neighbors in sight! Main house is over 3,000 sqft 5/2.5. Smaller house about 1200 sqft, 2/. Both have newer systems and New Roofs. Each home has its own Septic/Well system & pumped in 2024-large house/2025-small house. Property backs to 60 ft of riverfront that leads through the sounds and into the ocean. The main farmhouse has modern amenities but the old charm and character with original hardwoods, curved arches and entry ways, Juliet Balcony overlooking estate, 3rd floor finished attic bonus room and solid walk down basement foundation that can be turned into a finished room or used for storage. This home is solid and well maintained, being sold as is, seller to make no repairs. Call today for your private showing!

112 Station Road, South Chesapeake

$400,000
4 Beds 2 Baths 10642623 MLS
Welcome to 700 Cardover Avenue, where timeless character meets modern luxury in this beautifully fully renovated Chesapeake home. Offering 4 spacious bedrooms, 2 full baths, and approximately 1,900 square feet of thoughtfully reimagined living space, this stunning property blends classic charm with today’s most desirable finishes and functionality. Originally built in 1958, this home has been completely transformed to deliver a move-in-ready experience while preserving the quality craftsmanship and character buyers appreciate. From the moment you step inside, you’ll be welcomed by bright, airy living spaces filled with natural light and a warm, inviting atmosphere. The thoughtfully designed floor plan offers exceptional versatility with generous living areas and spacious bedrooms, creating the perfect balance of comfort and function. Whether hosting gatherings, enjoying quiet evenings at home, or creating flexible work-from-home space, this home adapts beautifully to your lifestyle. At the heart of the home, the seamless flow between living spaces creates an effortless environment for everyday living and entertaining. Every detail has been carefully curated to offer elevated style with modern convenience. Step outside to your private outdoor retreat featuring a brand-new backyard deck, suitable for morning coffee, weekend barbecues, evening gatherings, or simply unwinding outdoors. The deck creates an ideal extension of the home, inviting you to enjoy indoor-outdoor living year-round. Adding even more value and versatility, the detached garage offers excellent storage, workshop potential, hobby space, or additional parking—an increasingly desirable feature for today’s buyers. Conveniently located near shopping, dining, parks, schools, major commuter routes, and all that Chesapeake has to offer, this beautifully renovated home combines modern updates, functional living, and timeless appeal. This is more than just a renovation—it’s a fresh new chapter waiting to be written. Don’t miss your opportunity to make it yours.

700 Cardover Avenue, Central Chesapeake

$879,000
3 Beds 2 Baths 10642255 MLS
If these walls could talk, they would tell you 175 years of stories. Rare pre-Civil War farmhouse charm meets modern comfort in this private retreat that feels like a vacation every day. This 2-story home is filled with character, featuring 4 fireplaces, gorgeous original hardwood floors, 10-foot ceilings, hand-sawed original moldings, intricate ceiling details, and antique lighting. The living room offers a cozy wood-burning stove, while the family room showcases coffered ceilings and original hardwood floors. The spacious primary suite stands out with a beautiful fireplace and a wall of built-in cabinetry offering storage rarely found in modern homes. Enjoy two laundry areas, including one in the ADU over the detached tandem 4-car garage, plus a flexible space for an office or mudroom off the back of the main house. Outside, unwind and entertain by the pool oasis, or sit on the 250 sqft covered porch. There is a huge new chicken coop (26), and 2 dog runs for that farm life as well as a shed (as is). The brick walkways are the original bricks from the chimney repurposed. Updates include painted kitchen cabinets/walls (26), sealed and painted metal roof with 20 year paint (26), new pool liner (25), encapsulated crawlspace with dehumidifier/support beams (25), 50-gallon hot water heater (25), HVAC, and ductwork (23), new steps and railing out to the pool (26), breaker upgrade to house (25) 2 solar systems one to the main house and one to the ADU/garage (23). More updates listed in agent remarks. Near Hickory schools, shopping, Bypass, and OBX. Come own a piece of history in Hickory!

2410 Centerville Turnpike, South Chesapeake

$370,000
4 Beds 2.1 Baths 10642424 MLS
Welcome to this exceptional end-unit luxury townhome, original owner bought as the community's model home. Built in 2014 and thoughtfully upgraded throughout, Thomason Trail offers nearly 1,900 square feet of living space, combining timeless finishes with everyday comfort. You'll appreciate the warmth of rich hardwood flooring, abundant natural light, and the attention to detail that sets this home apart. The kitchen is designed to impress, featuring granite countertops, ample cabinetry, a pantry and an open layout that flows seamlessly into the main living and dining areas. All of the mechanicals have been recently updated to include hot water heater 2026. Ceiling fans in every room plus custom wood blinds provide both style, privacy and comfort. One of the home's most distinctive features is the versatile loft, complete with custom built in shelves. Minutes from Greenbrier for shopping and restaurants you won't want to miss this opportunity.

1601 Thomason Trail, South Chesapeake

$359,800
5 Beds 2 Baths 10642460 MLS
Discover one of the best values in Chesapeake! This spacious 5-bedroom, 2-bath home offers over 2,100 square feet of versatile living space with room for everyone. Recent updates include a newer roof, updated HVAC, replacement windows, luxury vinyl plank flooring, fresh paint, and updated lighting, providing peace of mind and modern appeal. The bright kitchen features ample cabinet and counter space, while the open living and dining areas are perfect for everyday living or entertaining. The flexible floor plan includes generously sized bedrooms, making it ideal for a growing family, multi-generational living, or those needing dedicated home office space. Outside, enjoy a large fenced backyard with plenty of room for pets, gardening, play, or future outdoor entertaining. Conveniently located near shopping, dining, military bases, major interstates, parks, and schools, this home offers an easy commute throughout Hampton Roads. With five true bedrooms, substantial square footage, and numerous updates, this home delivers exceptional value compared to other homes in its price range. Whether you're a first-time buyer looking for extra space or an investor seeking a strong opportunity, this property is ready for its next owner. Don't miss your chance to own one of Chesapeake's best buys—schedule your private showing today!

4205 Nautilus Avenue, Central Chesapeake

$554,500
4 Beds 3.1 Baths 10642380 MLS
Welcome to Miars Farm in sought-after Western Branch! This beautifully maintained 4BR, 3.5BA home offers ~2,500 sq ft of inviting living space on a .25-acre lot with timeless curb appeal and modern farmhouse touches. Enjoy a classic front porch, spacious driveway, and attached garage. Inside, the open layout features a stunning eat-in kitchen with granite countertops, stainless steel appliances, gas cooking, an island seating area, and a sunny breakfast area overlooking the backyard. The family room shines with exposed beams and a cozy fireplace. The vaulted primary suite features a spa-like bath with a soaking tub and a tiled shower. A large FROG/bonus room with a full bath adds flexibility. Step outside to your private fenced yard with a deck, above-ground pool, and storage/workshop shed with electricity. Convenient to schools, shopping, and commuting—this home truly has it all!

3421 Anita Circle, West Chesapeake

$452,900
3 Beds 3.1 Baths 10642448 MLS
Unbelievable Incentives! Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This tri-level Ashbury plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ upgraded quartz countertops & glass subway tile backsplash. Easily maintained & durable LVP flooring & crown molding, as well as 9-foot ceilings on all levels. Lighted tray ceiling in primary suite & double quartz vanity, ceramic tiled floor, & glass-enclosed shower w/ ceramic tile walls in en-suite. WIC. Enjoy exceptional amenities, including a start-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appointment.

4904 Apricot Way, West Chesapeake

$614,900
6 Beds 4.1 Baths 10642445 MLS
Rare opportunity to own a beautifully updated 6-bedroom, 4.5-bath home featuring a private, fully equipped in-law suite for multigenerational living, extended family, guests, rental income, or a private home office. The main residence offers 5 spacious bedrooms, 3 full baths, and a stunning remodeled kitchen with quartz countertops, sleek high-gloss cabinetry, stainless steel appliances, and space for a large center island. The separate in-law suite lives like its own home, complete with an open loft-style bedroom, 1.5 baths, walk-in closet, full-size laundry, upgraded kitchen with quartz counters and stainless appliances, and generous living space. Recent upgrades include renovated baths, new windows, patio doors, and Nest thermostats. Step outside to your backyard oasis featuring an 8-foot in-ground pool with newer liner, filter, and pump, plus a built-in deck bar ideal for entertaining. Conveniently located near shopping, dining, schools, military bases, beaches, and major commuter routes.

501 Thornloe Ln Lane, 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.