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609 Dupree Lane, Central Chesapeake
$350,000
3 Beds ⋅ 2.1 Baths ⋅ 10654902 MLS
Welcome to 609 Dupree Lane, a spacious 3-story end-unit townhome offering 3 bedrooms, 2.5 baths, and a thoughtfully designed layout. The first floor features a versatile flex room, ideal for a home office, den, fitness space, or additional living area. The main living level showcases new flooring, recessed lighting, and a generously sized kitchen featuring a large center island, pantry, and plenty of space for gathering and entertaining. Step outside to the second-floor balcony for additional outdoor living space. The spacious primary suite offers a walk-in closet and private bath with double bowl sinks. Additional highlights include new ceiling fans and an attached 2-car garage. Enjoy low-maintenance living with grounds upkeep included, along with community amenities featuring a clubhouse, pool, and playgrounds. A wonderful combination of space, style, and convenience in Chesapeake!

609 Dupree Lane, Central Chesapeake

2156 Edwin Drive, South Chesapeake
$577,740
3 Beds ⋅ 3 Baths ⋅ 10655240 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more -all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Estimated Completion December 2026. Photos are to be used as an example and do not represent exact listings selections.

2156 Edwin Drive, South Chesapeake

2180 Edwin Drive, South Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10655238 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2180 Edwin Drive, South Chesapeake

2184 Edwin Drive, South Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10655236 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2184 Edwin Drive, South Chesapeake

2182 Edwin Drive, South Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10655235 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2182 Edwin Drive, South Chesapeake

911 Bainbridge Boulevard, Central Chesapeake
$529,000
4 Beds ⋅ 3 Baths ⋅ 10655168 MLS
NEW CONSTRUCTION Welcome home to this beautifully designed 4-bedroom, 3-bath residence offering modern style and exceptional comfort. The open-concept floor plan features 9-foot ceilings, a spacious family room with a cozy gas fireplace, and a stunning kitchen with granite countertops, stainless steel appliances, and abundant cabinet space. A first-floor bedroom with a full bath is ideal for guests or multi-generational living. The luxurious primary suite offers an oversized tiled shower, double vanity, and a large walk-in closet. Generous secondary bedrooms, ample storage, pull-down attic access to a full attic, Energy Star double-pane windows, and extensive insulation provide year-round efficiency and comfort. Completing this exceptional home is a detached 2-car garage with electricity and plenty of additional storage. Also has a rear alley entrance and a huge fenced backyard. Ready in less than 45 Days.

911 Bainbridge Boulevard, Central Chesapeake

708 Pebble Quay, South Chesapeake
$705,000
4 Beds ⋅ 3 Baths ⋅ 10655182 MLS
Unique custom built home on cul-de-sac with rare 3 car attached garage and extended driveway. This house was made for entertaining - 23' x 14' screened porch off family room for extended living space, along with a 22' x 20' pavilion - both with trek decking, finished wood ceilings, recessed lights and fans. Beautiful extensive landscaping with a stamped concrete walkway winding around house. Impressive 2 story entry has gorgeous chandelier. Dual staircases. Large kitchen includes granite counters, stainless steel appliances with gas stove, tons of cabinets and counterspace as well as deep pantry and eat-in nook. Formal living room and dining room with door leading to large front porch. First floor office in addition to 4 bedrooms upstairs. Full bathroom downstairs. Hardwood floors run through entire 1st floor. Primary bedroom includes corner gas fireplace, 13'x12.5' walk-in closet, and large bathroom with dual sinks and jetted tub . Laundry room has entire wall of cabinets with counter space and fold down ironing board. Lots of built in storage throughout, including a walk in climate controlled attic closet. The rare 3 car garage (owner actually has 4 cars in there!) is decked out for a car aficionado with LED lighting covering the ceiling and rubberized flooring. Additional outside shed. 16 hardwired cameras around exterior convey. Generator hook up in garage. Top of the line outside Charbroil kitchen conveys with acceptable full price offer. Neighborhood dock with boat ramp nearby. Very active River Walk Community Association centers around the beautiful clubhouse (which can be rented) and has a tennis/pickleball court w/pickleball league, garden club, swimming pool w/swim team, concerts in fall, food trucks and more, as well as parks and playgrounds. Tree lined walking paths wind through neighborhood along lakes with gazebos and fountains. Easy to hop on nearby Rt. 168 Chesapeake Expressway to easily get to any area of Hampton Roads.

708 Pebble Quay, South Chesapeake

911 Intracoastal Way, South Chesapeake
$797,640
5 Beds ⋅ 3.1 Baths ⋅ 10655214 MLS
The Tillman offers 3,226 sq. ft. of stylish and flexible living - great for multigenerational living! This spacious home includes 5 bedrooms, 3.5 baths, and a 2-car garage. The first-floor primary suite provides the perfect retreat with a massive walk-in closet, dual vanities, and a private water closet. Upstairs, you’ll find a second primary-style bedroom with direct access to a full bath, offering comfort and privacy. Three additional bedrooms (each with walk-in closets), a large loft, and a convenient laundry room complete the second floor. The open-concept main level features a welcoming dining room, expansive kitchen with an oversized island and two pantries, including a Costco pantry, and a bright family room. Photos and renderings are from builder's library, actual finishes and features may vary.

911 Intracoastal Way, South Chesapeake

2609 Mossgate Court, 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

2107 Stalham Road, Central Chesapeake
$369,900
5 Beds ⋅ 2.1 Baths ⋅ 10654947 MLS
Hard-to-find first-floor bedroom! This well-maintained 5-bedroom, 2.5-bath Chesapeake home delivers the space, flexibility and convenience buyers are looking for. The spacious downstairs bedroom is ideal for guests, a home office, workout room or versatile flex space, while four additional bedrooms upstairs provide plenty of room to spread out. The kitchen features granite countertops and stainless-steel appliances and opens to the den, creating an easy flow for everyday living and entertaining. Step outside to the backyard for even more room to enjoy. Built in 2000 with a comfortable two-story layout and generous living areas, this home is ready for its next owner. Conveniently located near shopping, restaurants, military bases and major commuting routes with easy access throughout Hampton Roads. Five bedrooms, flexible living space and a great Chesapeake location—this one checks a lot of boxes!

2107 Stalham Road, Central Chesapeake

4332 Hillingdon Bend Unit 206, West Chesapeake
$227,000
2 Beds ⋅ 2 Baths ⋅ 10653350 MLS
Welcome home! This beautiful residence features an open floor plan and soaring nine-foot ceilings. The layout includes two bedrooms and two full bathrooms, highlighted by a primary suite with dual closets. The kitchen is equipped with stainless steel appliances and ample cabinetry, flowing seamlessly 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, this property offers one assigned parking space and access to shared amenities, including a swimming pool, grounds maintenance, and trash removal. Conveniently located near major highways, military bases, local shipyards, and the retail options surrounding Chesapeake Square, this home is perfectly positioned. Call today to schedule your private showing!

4332 Hillingdon Bend Unit 206, West Chesapeake

1511 Hazel Avenue, Central Chesapeake
$335,000
3 Beds ⋅ 1.1 Baths ⋅ 10654700 MLS
This charming 3-bedroom, 1.5-bath ranch offers comfortable one-level living with a fresh, updated feel. Upgrades include: New electrical panel (2026), paint (2026), carpet (2026), flooring (2026) and moisture barrier (2026). Creating a clean, inviting interior that is move-in ready and waiting for someone to make it their own. The functional floor plan provides plenty of space for everyday living and entertaining as well as a bonus area that can be used as a second living room, play area or office space. Enjoy the spacious backyard, ideal for relaxing or gathering with friends, plus a shed offering additional storage or workshop space. Located in an established neighborhood convenient to shopping, dining, bases and major roadways. Schedule your private showing today!

1511 Hazel Avenue, Central Chesapeake

1016 Thoroughgood Way Unit 302, Central Chesapeake
$225,000
2 Beds ⋅ 2 Baths ⋅ 10654835 MLS
Welcome to Village at Gateway in the heart of South Norfolk! This beautifully maintained third-floor condo is easily accessed via elevator and features an open-concept floor plan with oversized rooms and abundant natural light from skylights. The upgraded kitchen provides ample cabinetry, a pantry, and bar seating for four for casual dining or entertaining. Enjoy indoor-outdoor living with a spacious 8x12 covered porch just off the living room. The primary suite includes a glass-enclosed shower and dual closets, while the second bedroom is generously sized for guests or a home office. Additional highlights include in-unit stacked washer and dryer, secured building access, and gated parking with fob entry. Conveniently located near shopping, dining, and major interstates, don’t miss this opportunity for low-maintenance living!

1016 Thoroughgood Way Unit 302, Central Chesapeake

1540 Eldwick Drive #202, South Chesapeake
$300,130
2 Beds ⋅ 2 Baths ⋅ 10655131 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, listed price reflects $10K incentive taken off price of home, see agent for details. Our Rowen model is a corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms and 2 baths. Owner’s suite includes a private bath and walk-in closet with custom wood shelving. Enjoy a patio or balcony space off living room. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #202, South Chesapeake

1644 Chesapeake Drive, Central Chesapeake
$365,000
4 Beds ⋅ 2.1 Baths ⋅ 10655000 MLS
Beautiful 4 Bedroom Home with Modern Updates and Spacious Layout This stunning 4-bedroom, 2.5-bath home features fresh paint, new carpet, and stainless-steel appliances throughout. The open floor plan creates a seamless flow that’s perfect for entertaining and cooking, with large, bright rooms that feel warm and welcoming.Enjoy a formal dining room, a comfortable family room, and a charming breakfast nook. A cozy fireplace adds the perfect touch for relaxing evenings.Step outside and take your entertainment outdoors to your private, fenced-in backyard — ideal for gatherings, play, or quiet mornings.At the end of the day, retreat to the primary suite, complete with a spacious ensuite bathroom, offering comfort and privacy. LOCATED CLOSE TO BASES, MEDICAL, INTERSTATES, ENTERTAINMENT, BEACHES AND RETAIL.

1644 Chesapeake Drive, Central Chesapeake

901 Stewart Street, Central Chesapeake
$215,000
2 Beds ⋅ 1 Baths ⋅ 10655021 MLS
Welcome to 901 Stewart Street! This charming 2-bedroom, 1-bath ranch offers comfortable single-level living in the South Norfolk area of Chesapeake. With approximately 825 square feet, the home features a functional layout with plenty of opportunity to make the space your own. Enjoy a spacious yard with room for outdoor entertaining, gardening, or creating your own outdoor retreat. Conveniently located near shopping, dining, major roadways, and everyday amenities, this property offers easy access throughout Chesapeake and surrounding Hampton Roads. Whether you're looking for your next home or an investment opportunity, 901 Stewart Street is ready for its next chapter. Schedule your private showing today!

901 Stewart Street, Central Chesapeake

1713 Sanderson Road, South Chesapeake
$1,300,000
4 Beds ⋅ 2.1 Baths ⋅ 10654856 MLS
Elegant custom details and room to live the life you’ve imagined! Sweeping down a long, paved driveway, this beautiful 4-bedroom home pairs comfortable country living with a thoughtfully arranged estate. Set on over 12 pristine acres in Chesapeake, zoned for Hickory schools, this property is a rare rural sanctuary. A wraparound porch welcomes you inside to 9' ceilings, 8' doors, and reclaimed knotty pine floors. The living room features a stone fireplace, opening to a bright kitchen with soft-close cabinets, Samsung Bespoke appliances, and butler’s pantry. Outside, enjoy a saltwater pool, fire pit, and private porches within a completely fenced in yard. The farm boasts a 6-stall barn with wash station, hot water, and mini-split, plus 5 watered pastures, 3 run-ins, and a 50x42 Morton building. An additional 1.5 acres offers potential for a riding arena or agriculture gardening, while a chicken coop, fruit trees, and berries complete the setting. Enjoy southern Chesapeake's rural character, with conveniences and Route 168 nearby.

1713 Sanderson Road, South Chesapeake

435 Gallbush Road, South Chesapeake
$849,900
4 Beds ⋅ 3 Baths ⋅ 10655045 MLS
Welcome to The Ashford by Wetherington Homes -Move-In Ready! A 5-bedroom, 3-bath new construction home with over 2,700 sqft on approximately 2 acres in Hickory School District with NO HOA! Designed for todays buyer, this open-concept floorplan offers luxury finishes, designer details, outdoor entertaining, & flexible living spaces. The kitchen features quartz countertops, Frigidaire Professional appliances, custom wood hood, shaker cabinetry, & upgraded lighting. The 1st floor Primary Suite includes a tiled spa-style shower, dual vanities, & oversized walk-in closet. Two additional 1st floor bedrooms offer flexibility for guests or office space. Upstairs includes 2 bedrooms, full bath, & loft ideal for media room, playroom, or gym. Enjoy luxury new construction convenient to Edinburgh, Greenbrier, shopping, dining, & commuter routes while still offering privacy & acreage!

435 Gallbush Road, South Chesapeake

3208 Pineridge Drive, West Chesapeake
$525,000
5 Beds ⋅ 3.1 Baths ⋅ 10654949 MLS
Classic character meets seriously usable space. Tucked beneath the trees in the highly desirable Silverwood neighborhood, this 5 bedroom, 3.5 bath Dutch Colonial brings together original character and thoughtful updates without losing its charm. Natural light fills the rooms and plays across the original refinished hardwood floors, bringing warmth throughout the 2,602 square foot home. The brand-new kitchen brings new cabinetry, countertops, appliances and LVP, while the stunningly updated bathrooms add a fresh, polished finish. A gas fireplace adds another touch of original character to the living room, and the finished room over the garage offers flexible space for whatever the home needs. The EZBreeze porch takes outdoor living a step further, with heat and air conditioning that keep the space comfortable throughout all the seasons. Whether enjoying a mild morning or settling in on a cooler evening, this is outdoor space with the comfort to make it genuinely usable year-round. A home with the kind of character you notice right away, paired with a fresh kitchen, beautiful updates, and spaces that make you want to stay awhile. Move in with nothing to do!

3208 Pineridge Drive, West Chesapeake

1514 Myrtle Avenue, Central Chesapeake
$339,900
3 Beds ⋅ 2 Baths ⋅ 10654924 MLS
The possibilities are endless with this spacious ranch-style home! Offering a flexible layout ideal for multi-generational living, the home features two separate living areas and bathrooms with a shared kitchen and laundry. A separate side entrance leads to the rear living space with a large bedroom, walk-in shower and private living area, offering great potential for an in-law suite or extended family. The large kitchen offers a pantry and tons of cabinet space, with neutral colors and updated windows throughout. Major improvements include a new roof, newer HVAC, 2026 furnace, encapsulated crawl space with dehumidifier and new sewer line from the home to the street. Enjoy a fenced backyard, storage shed and fantastic detached garage with plenty of room for vehicles, workshop, hobbies or storage. Convenient to shopping and everyday amenities. Seller will be holding an estate sale; some listing photos have been AI-enhanced to digitally remove personal belongings and estate sale items to better showcase the rooms and space.

1514 Myrtle Avenue, Central 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.