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$435,000
3 Beds ⋅ 2 Baths ⋅ 10655721 MLS
"Welcome home to the desirable Great Bridge section of Chesapeake! In this beautifully updated 3-bed, 2-bath gem (1,700 sqft per seller), the heavy lifting is already done. Inside, enjoy an inviting layout with a remodeled kitchen, refreshed baths, a new dishwasher, and recent HVAC (2019 AC, new evap coil). Outside, spend your weekends relaxing by the inground pool instead of tackling projects! A detached workshop provides the ultimate space for entertaining. Breathe easy knowing big-ticket items are handled, like a 2014 roof on both structures. The fully fenced yard was professionally graded for optimal drainage and the lowest flood risk. With close trees removed, 6-inch commercial gutters, and a 2019 crawlspace vapor barrier/dehumidifier, this home is expertly protected. Reflecting years of loving care, it offers a wonderfully maintained lifestyle. Just unpack and enjoy! Schedule a tour today."

220 Marion Drive, South Chesapeake
$679,990
5 Beds ⋅ 3 Baths ⋅ 10655662 MLS
The Lehigh single-family home combines smart design with light-filled spaces. Enter the inviting foyer, where versatile flex space can be used as a playroom, living room or office. The gourmet kitchen boasts a large island and pantry and connects to the dining and family room. Off the 2-car garage, a family entry controls clutter and leads to a quiet study/bedroom. Upstairs, a loft is an ideal entertaining spot outside 3 spacious bedrooms and a double vanity bath. The luxurious owner's suite offers a cozy getaway with large closets and private bathroom. You'll love The Lehigh.

205 Gertrude Street, South Chesapeake
$289,900
2 Beds ⋅ 1.1 Baths ⋅ 10655553 MLS
Welcome to this beautifully refreshed 2-bedroom, 1.5-bath townhome tucked away on a quiet cul-de-sac in sought-after Las Gaviotas. Head inside to a spacious living area featuring a cozy brick fireplace and an inviting floor plan perfect for relaxing or entertaining. Recent updates include fresh paint, new flooring and carpet, updated full bath, new rear deck, front porch railing, sliding glass doors, gutters, and water heater. Energy-efficient windows and kitchen appliances were replaced in 2020. Upstairs offers two generously sized bedrooms, a dual-entry full bath, and large hall closet for extra storage. Enjoy a private fenced backyard and new deck, perfect for morning coffee, grilling, or unwinding. Conveniently located near shopping, dining, parks, interstates, Chesapeake City Hall, and Grassfield schools. Move-in ready and waiting for its new owner!

300 San Roman Drive, South Chesapeake
$610,000
5 Beds ⋅ 3.1 Baths ⋅ 10655526 MLS
Beautifully maintained 5-bedroom, 3½-bath home situated on nearly half an acre, featuring generously sized rooms, beautifully landscaped grounds, and tasteful brick garden beds filled with year-round evergreens. The inviting interior offers a sunroom, spacious eat-in kitchen, formal dining room, and formal living room, providing plenty of room for everyday living as well as entertaining family and friends. Step outside to the huge backyard, where you'll find plenty of space to gather and enjoy the outdoors. A charming pergola

3240 Joplin Lane, South Chesapeake
$465,900
4 Beds ⋅ 2.1 Baths ⋅ 10655312 MLS
Welcome home to this beautifully maintained condominium in the highly sought-after Cedar Crossing community. This spacious open concept residence offers over 2,000 square feet of comfortable living space. Four bedrooms featuring a large primary bedroom suite on first level, with double vanity and large walk-in closet. Beautiful hardwood floors, and crown molding throughout. Tile in kitchen, bathrooms and mudroom. Enjoy the privacy of a fenced backyard with storage shed for additional equipment. Two car garage and driveway space. Neighborhood has a well-equipped playground, swimming pool, tennis court and clubhouse. Enjoy low-maintenance living in a vibrant community conveniently located near shopping, dining, schools, and major commuter routes.

518 Whisper Walk, South Chesapeake
$699,990
4 Beds ⋅ 3 Baths ⋅ 10655470 MLS
The Savannah offers a well-designed floor plan with a spacious great room centrally located, creating a natural flow into the kitchen and dining area—great for everyday living and gatherings. The home features four generously sized bedrooms, including an owner’s suite positioned at the rear of the home for added privacy. The owner’s suite includes direct access to the covered porch and two large closets. A flexible space just off the foyer provides versatility for use as a home office, additional living area, or formal dining space, depending on your needs. The second floor includes an additional bedroom, a full bath, and a loft area, offering extra living options for guests or multi-functional use. Thoughtful layout and functional spaces make the Savannah a comfortable and adaptable home.

204 Henry Jefferson Way, South Chesapeake
$399,900
4 Beds ⋅ 2 Baths ⋅ 10655390 MLS
Beautiful 4-bedroom, 2-bath home tucked away on a quiet dead-end street in Chesapeake! Situated on an exceptionally large lot surrounded by mature trees, this home offers space, privacy, and plenty of possibilities. Inside you'll find spacious bedrooms, fresh paint, new flooring, updated ceiling fans and fixtures, along with newer siding and windows. One of the standout features is the impressive detached two-story garage/workshop—perfect for a workshop, home gym, office, recreational equipment, or additional storage, with incredible potential for future use. Enjoy a large backyard with plenty of room for entertaining, pets, gardening, or simply relaxing outdoors. Conveniently located near shopping, dining, parks, and everyday necessities. A unique property with tons of potential and room to make it your own!

3605 Mostiler Place, South Chesapeake
$399,000
3 Beds ⋅ 2.1 Baths ⋅ 10654966 MLS
Welcome home to 1710 Defiance Drive! This spacious townhouse-style condo offers 3 bedrooms, 2.5 baths, and 1,577 square feet of comfortable living space. The layout gives you plenty of room to spread out while still offering the easy, low-maintenance lifestyle condo living is known for. Whether you’re enjoying a quiet night at home or taking advantage of the neighborhood amenities, there’s plenty to love here. The community offers a clubhouse, exercise room, playground, pool, and ground maintenance—giving you more time to enjoy your home and less time worrying about exterior upkeep. A great option for anyone looking for space, convenience, and community amenities all wrapped into one!

1710 Defiance Drive, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10655291 MLS
Beautifully maintained, thoughtfully updated, and a backyard you'll want to spend all of your time in! Step inside to a welcoming foyer filled with natural light and discover this inviting 4 bedroom, 2.5 bathroom home in a sought-after neighborhood within the Hickory School District. Updates include Brazilian hardwood, upgraded pet protect carpet padding, PEX plumbing, electrical, solar power, and an electric fireplace with a gas hookup for conversion. With solar, the electric bill averages approximately $70/month. Outside, enjoy a private backyard oasis with manicured gardens, stonework, raised vegetable beds, blueberry bushes, apple trees and even an underground invisible fence! A fully insulated detached workshop with electricity and A/C offers flexible spaces for hobbies, projects, a studio, or workspace. Have instant hot water with top of the line Rinnai tankless water heater! HUGE corner lot! Meticulously maintained inside and out, this charming home is ready to be called home!

841 Woodstream Way, South Chesapeake
$399,900
4 Beds ⋅ 2.1 Baths ⋅ 10652642 MLS
Opportunity knocks in Chesapeake! This property offers a chance to create something truly special in a desirable location. Bring your vision and your renovation plans to unlock the full potential of this home. The expansive lot is a standout feature, providing an abundance of space and endless possibilities for outdoor living, entertaining, gardening, recreation, or future improvements. Whether you're an investor searching for your next project or a buyer looking to build equity and make a home your own, this property is ready for its next chapter. Conveniently located near shopping, dining, schools, parks, major roadways, and everything Chesapeake has to offer. Properties with this much potential and land don't come around every day. Come see the possibilities for yourself! Schedule your showing today!

2609 Mossgate Court, South Chesapeake
$975,000
6 Beds ⋅ 3.1 Baths ⋅ 10655175 MLS
Discover a private country retreat in the heart of Grassfield, where approximately 5 tree-lined acres create a peaceful setting rarely found with this much space and convenience. Over 4,000 sqft of living space with 6 beds, 3.5 baths, first floor primary ensuite. Spend summer days by the pool, unwind beneath the stars in the hot tub, or enjoy the freedom of acreage with a barn and zoning that permits horses. Mature trees frame the property and provide a sense of privacy while still placing you in the heart of Chesapeake, convenient to shopping, dining, schools and major routes.

2536 Seven Eleven Road, South Chesapeake
$445,000
4 Beds ⋅ 2.1 Baths ⋅ 10655111 MLS
THE WRAP AROUND PORCH WELCOMES YOU TO THIS BEAUTIFUL HOME THAT TRULY HAS IT ALL. THE SPACIOUS FAMILY ROOM OPENS IMMEDIATELY TO THE RIGHT OF THE FRONT DOOR AND WITH ITS NEWER LAMINATE FLOORING LEADS YOU INTO THE SEPARATE DINING ROOM. LARGE GREAT ROOM WITH CATHEDRAL CEILINGS AND SKYLIGHTS ADD SPACE AND LOTS OF NATURAL LIGHT. SPACIOUS KITCHEN WITH BREAKFAST NOOK AND FRENCH DOORS TO THE GENEROUS DECK, GREAT FOR ENTERTAINING AND OUTDOOR LIVING. LARGE MASTER BEDROOM WITH WALK IN CLOSET AND ATTACHED BATHROOM. LARGE FROG WITH PLENTY OF STORAGE. THE LARGE FENCED IN BACK YARD OFFERS ROOM FOR A GARDEN, PLAYGROUND AND EVEN A POOL!! ATTACHED 2 CAR GARAGE!! COME SEE TODAY!

3404 Winterhawk Court, South Chesapeake
$565,000
4 Beds ⋅ 2.1 Baths ⋅ 10655103 MLS
Welcome Home! This 4 bedroom 2.5 bath home located in Beautiful Culpepper Landing is waiting for you to move right in. This well maintained home has an open floor plan that allows tons of natural light. Gourmet kitchen w/island, granite countertops , newer appliances and plenty of cabinet storage. Snuggle up to cozy fireplace in the large family room. Upstairs primary suite with walk in closet, double vanity and 3 more bedrooms, a utility room and a full bath. And don't forget to checkout the garage! Pool, Clubhouse, Playgrounds. Minutes to shopping, restaurants.

737 Big Bear Lane, South Chesapeake
$475,000
3 Beds ⋅ 2.1 Baths ⋅ 10654644 MLS
This Great Bridge home simply makes everyday life more enjoyable. Imagine summer days spent by the in-ground pool, entertaining with friends and family, or hanging out in the detached garage with its wood stove, working on projects in a workshop that gives you room to spread out. This 3-bedroom home offers formal living room, dining room, family room and a primary bedroom with an updated ensuite. The updated kitchen and bathrooms are complimented by hardwood floors and fresh paint. Recent improvements including the roof, heat pump, pool liner and garage door all make this home ready for its next chapter. Come see why the pool, garage and location make this one worth stopping for.

349 Bartell Drive, South Chesapeake
$325,000
2 Beds ⋅ 2 Baths ⋅ 10654731 MLS
Beautiful end-unit condo features an open first-floor layout with tall ceilings and abundant natural light, creating a bright and airy feel. The kitchen is equipped with modern appliances and a well-designed layout for both everyday living and entertaining. The spacious primary suite offers both comfort and style, with an updated attached bath. Additional bedroom provides versatile space for guests, a home office, or hobbies, and are served by a second full bath. All appliances including washer and and dryer convey. Centrally located in the heart of Greenbrier, with easy access to shopping, dining, and major highways.

948 Shoal Creek Trail Unit A, South Chesapeake
$300,000
3 Beds ⋅ 2.1 Baths ⋅ 10654893 MLS
Largest floor plan in the neighborhood! Lovingly maintained and thoughtfully updated, this spacious brick townhome is tucked away on a quiet cul-de-sac in the heart of Chesapeake. Enjoy a private, fully fenced backyard with no homes directly behind you and no HOA. Inside, you’ll find fresh paint, new carpet and flooring, updated bathrooms, new fixtures and hardware, and gleaming hardwood floors. The brand-new kitchen features granite countertops, stainless-steel appliances, a gas range, and full-size refrigerator. A wood-burning fireplace adds warmth and character, while abundant natural light fills the home. Plenty of indoor and outdoor storage provides added convenience. With a low-maintenance brick exterior, spacious floor plan, thoughtful updates, and a private backyard, this home is truly move-in ready. Pride of ownership is evident throughout—come see it today!

302 Fairfax Terrace, South Chesapeake
$549,900
4 Beds ⋅ 2 Baths ⋅ 10654828 MLS
Remarkable brick ranch situated on a corner lot overlooking the community pond! Meticulously maintained and beautifully updated, this home offers exceptional style and comfort throughout. Recent improvements include gorgeous flooring, fresh paint, and updated fixtures that create a warm, inviting atmosphere. The spacious room over the garage serves as a fourth bedroom and offers additional space perfect for a home office, hobby room, or flex area. The well-appointed kitchen features gas appliances, while the cozy gas fireplace adds charm to the living space. Step outside to your private backyard retreat featuring a sparkling in-ground pool, captivating landscaping, and multiple deck areas designed for relaxing and entertaining. Every detail has been thoughtfully maintained, making this home truly move-in ready. A rare opportunity, don't sit on this one

1300 Oregon Crossing, South Chesapeake
$715,000
6 Beds ⋅ 3 Baths ⋅ 10654725 MLS
Your weekends just got an upgrade at 728 Angel Wing Drive! Located in the sought-after Grassfield school district, this meticulously maintained home offers 5 bedrooms, 3 full baths, and a media room that could serve as a 6th bedroom. A first-floor bedroom and full bath are ideal for multigenerational living or guests, while a space for a home office and formal dining room add flexibility. Your private backyard oasis features a heated saltwater pool, spacious patio, and pergola overlooking peaceful woods with no rear neighbors. Perfect for poolside afternoons and football Sundays! The oversized garage includes shelving and a dedicated workspace. Freshly painted inside and out within the past 3 years and cared for by just two owners, this home also features a whole-house water softener, separate drinking water system, and 32 fully paid-off solar panels for potential monthly energy savings. Thoughtful upgrades, exceptional outdoor living, and room for everyone. Your next chapter starts here!

728 Angel Wing Drive, South Chesapeake
$574,900
4 Beds ⋅ 2.1 Baths ⋅ 10654685 MLS
Located in the Hickory school district, the home is less than one mile from the interstate and just minutes from the shopping, dining, and everyday conveniences of Edinburgh. With its bright interior, flexible layout, generous outdoor space, and convenient location, this home is ready to welcome its next owners. Tucked along a quiet, tree-lined street, this beautifully updated home offers a light, welcoming atmosphere and plenty of space to enjoy. Natural light fills the thoughtfully refreshed interior, creating bright and comfortable living spaces throughout. At the heart of the home is an inviting kitchen featuring stone countertops, newer cabinetry, stainless steel appliances, and durable LVT flooring—perfect for everyday living and entertaining. The spacious fourth bedroom above the garage offers wonderful flexibility as a home office, gym, playroom, guest suite, or private retreat. Outside, the expansive backyard provides plenty of room for gatherings, gardening, play, or simply relaxing beneath the open sky. The home also features a long list of valuable improvements, including PEX plumbing in place of the original polybutylene, an upgraded electrical panel, replacement of most windows, updated lighting and flooring, select exterior doors, siding, and trim. A private well serves the irrigation system, and the roof was replaced in 2014.

712 Woodcott Drive, South Chesapeake
$385,000
3 Beds ⋅ 2.1 Baths ⋅ 10654632 MLS
Wonderful end-unit townhome in the sought-after community of Culpepper Landing! Great open concept living area with hardwood flooring and large kitchen for entertaining!!! This property has been well maintained and includes granite counters throughout with high ceilings and all the updates that like-new construction provide!! Includes a huge, 2 car garage with plenty of storage as well as an inviting patio/courtyard area! Enjoy the clubhouse, pool, exercise room and playgrounds!! See this one today before it is SOLD!!!

609 Veery Street, South Chesapeake
$239,900
2 Beds ⋅ 1.1 Baths ⋅ 10642707 MLS
Located in the heart of Great Bridge, this townhome combines comfort with easy, low-maintenance living. Great for first-time buyers, downsizers, or anyone looking to settle in one of Chesapeake’s top school districts. Enjoy the convenience of nearby shopping, dining, parks, and military bases. Property is sold as-is, where-is, with no repairs by the seller. Call today to schedule a private showing.

815 Mill Landing Road, South Chesapeake
$799,900
6 Beds ⋅ 4 Baths ⋅ 10654449 MLS
Welcome to this beautiful home in the highly sought-after community of Culpepper Landing! Offering an impressive 3,656 square feet of living space, 6 bedrooms, 4 full bathrooms, and a dedicated office that provides the flexibility of a 7th room, this beautifully designed home delivers the perfect blend of space, comfort, and functionality. Step inside to discover an inviting open-concept floor plan, designed for everyday living and effortless entertaining. The kitchen is the heart of the home, showcasing custom cabinetry and a large center island creating a welcoming space for gatherings with family and friends. A convenient first-floor bedroom provides added flexibility for guests or multigenerational living. With generous living areas, a versatile layout, and plenty of room to spread out, this home is designed to accommodate a variety of lifestyles. Whether you're hosting memorable gatherings or enjoying a quiet evening at home, this spacious Chesapeake property has room for it all.

732 Colonel Byrd Street, South Chesapeake
$305,000
2 Beds ⋅ 2 Baths ⋅ 10654480 MLS
Welcome to 816 Shenandoah River Road! Spacious 2 bedroom 2 bathroom condo tucked away in established Riverwalk! This move in ready home offers a cool modern feel with many updates throughout. Main living area welcomes you with fresh paint and LVP flooring. Kitchen has been updated to include custom cabinetry, quartz countertops and tile backsplash. One bedroom / bath occupy first floor and One bedroom / bathroom occupy second floor. Association is responsible for all exterior maintenance to include grounds and roof. Skylights were replaced in 2026. Enjoy all the riverwalk community has to offer, including Clubhouse, Pool, Tennis Courts, Boat Ramp, Playgrounds, Walking Trails and trash pickup.

816 Shenandoah River Road, South Chesapeake
$550,000
5 Beds ⋅ 3.1 Baths ⋅ 10654324 MLS
Welcome to this spacious 5-bedroom 3.5 bath home tucked away on a quiet cul-de-sac in the highly desirable Greenbrier area of Chesapeake. Offering over 3500 square feet, this home features a functional layout for everyday living and entertaining with generous living spaces with a enclosed sunroom, large kitchen, and a comfortable primary suite with fireplace. Enjoy a spacious yard with a large inground pool, shed, deck and gazebo and no HOA/Condo association dues. This home presents a fantastic opportunity for buyers looking to personalize and update their own style. A desirable location minutes away from golf, near shopping, dining, and major highways, and plenty of space to make it your own.

1340 Danielle Court, South Chesapeake
$425,000
4 Beds ⋅ 2.1 Baths ⋅ 10654335 MLS
Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

744 Helmsdale Way, South Chesapeake
$425,000
3 Beds ⋅ 2.1 Baths ⋅ 10654218 MLS
Welcome to this beautifully maintained 3 bedroom, 2.5 bath home. Step inside to a bright, open floor plan featuring rich dark wood floors that flow throughout the main living areas. The stunning kitchen is designed to impress with custom cabinetry, upgraded appliances, and plenty of space for cooking and entertaining. The inviting great room is the heart of the home, complete with gas fireplace and custom built-in shelving, creating the perfect space to relax or gather with family and friends. Upstairs, you'll find spacious bedrooms, including a comfortable primary suite, offering room for everyone to spread out. Outside, enjoy your own private patio, ideal for morning coffee or simply unwinding after a long day. Residents enjoy fantastic community amenities, including a pool, clubhouse, and exterior grounds maintenance, allowing you to spend more time enjoying your home and less time on upkeep. BRAND NEW ROOF (July 2026). Don’t miss your opportunity to make this your next home!

515 Sweet Leaf Place, South Chesapeake
$565,000
5 Beds ⋅ 2.1 Baths ⋅ 10654262 MLS
Charming, Spacious and Functional Living throughout this ultimate retreat in the heart of Grassfield! Nestled in a quiet cul-de-sac in the highly sought-after Sawyers Mill community, this expansive 5-bedroom, 2.5-bath home features vaulted ceilings with a bright open floor plan. New light fixtures, New Ceiling Fans, New Vanity, New Flooring & Carpet, Fresh Paint. The Wide open kitchen is equipped w/ granite countertops, SS appliances, kitchen island and new tile backsplash. Step through the relaxing sunroom onto a sprawling backyard deck serving as an outdoor oasis designed for grand-scale entertaining. First Floor Bedroom or Office with Primary bedroom featuring tray ceilings, big walk-in closet, a large & elegantly designed en-suite bathroom. Located near shopping, dining, and major commuter routes. This home offers interior comfort, plenty of outdoor entertaining space, privacy, modern updates, & community. Large Open Floor Plan and Completely Move-In Ready...This is a must see!

402 Undershot Court, South Chesapeake
$267,500
3 Beds ⋅ 2.1 Baths ⋅ 10654163 MLS
Welcome to 1245 Corkwood Circle! This well-maintained 3-bedroom, 2.5-bath home offers approximately 1,340 square feet of comfortable living space in a convenient Chesapeake location. The kitchen features stainless steel appliances, a built-in microwave and dishwasher, while the functional floor plan provides plenty of space for everyday living and entertaining. Step outside to enjoy the fully fenced backyard, offering a private space for relaxing, grilling or outdoor activities. Additional features include central air, washer and dryer hookups, and extra storage. Conveniently located in the Greenbrier area with easy access to shopping, dining, entertainment, interstate access and major employment centers. This is an excellent opportunity to own a 3-bedroom home in Chesapeake. Schedule your private showing today!

1245 Corkwood Circle, South Chesapeake
$625,000
4 Beds ⋅ 2.1 Baths ⋅ 10653790 MLS
Gorgeous and nearly new, this 4 BR 2.5 Bath bath Single-Family Home~(the Becker model) offers the community’s most spacious floor plan and is situated on an exceptionally large corner lot—the largest in the development. An inviting covered front porch welcomes you into a well-designed layout that flows beautifully from room to room, with tasteful color choices and meticulous upkeep creating a polished, move-in-ready feel throughout.The impressive Chef’s kitchen is highlighted by an oversized center island, beautiful countertops, stainless steel appliances, and soft-close cabinetry. The kitchen opens naturally to the main living area, creating a comfortable and inviting space for everyday living and entertaining.Upstairs, the spacious Primary Suite features a Huge Walk-in Closet, an additional closet, Private bath with dual sinks. 3 additional Bedrooms offer plenty of flexibility for family, guests, or a home office.Fully fenced yard & 2-car garage provides plenty of parking & storage!

913 Brenner Road, South Chesapeake
$290,000
2 Beds ⋅ 2 Baths ⋅ 10654011 MLS
Welcome home to easy living in Orchard Grove! This spacious 2-bedroom, 2-bath condo offers a flexible layout designed for both everyday comfort and entertaining. Start your morning at the dedicated coffee bar before settling into the light-filled living room, where soaring ceilings and skylights create an open, airy feel. When the weather cools down, the gas fireplace makes the perfect spot to unwind. The updated kitchen features new cabinets, quartz countertops, stainless steel appliances, and plenty of space for preparing meals and gathering. Upstairs, the loft adds even more flexibility—create a home office, workout space, reading nook, hobby room, or explore modifications for an additional sleeping area. With two bedrooms and two full baths, there’s room to spread out while still enjoying the convenience of condo living. Orchard Grove puts shopping, dining, interstate access, military installations, and everyday conveniences nearby, making it easy to spend less time getting where you need to go and more time enjoying home.

1547 Orchard Grove 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.