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$665,000
5 Beds 2.1 Baths 10644518 MLS
Beautifully maintained 5-bedroom, 3,383-square-foot home offering peaceful golf course views in sought-after Wedgewood Estates. The thoughtfully designed floor plan features spacious living areas, an updated kitchen with a large center island, abundant cabinetry, and an open flow into the family room, creating a welcoming space for everyday living and entertaining. Large rear windows fill the home with natural light while overlooking the golf course and a beautiful wooded backdrop. Step outside to enjoy the screened porch and expansive patio, creating a private outdoor retreat. Thoughtfully maintained and exceptionally cared for, this home combines timeless character, quality updates, and outstanding curb appeal. Conveniently located in the heart of Greenbrier, just minutes from shopping, dining, parks, major highways, military installations, and healthcare, while offering the privacy and charm of one of Chesapeake's most desirable established neighborhoods.

1118 Fairway Drive, South Chesapeake

$599,000
5 Beds 3 Baths 10644309 MLS
Tired of expensive water and sewer bills, HOA restrictions, or dealing with the stress and cost of a fixer upper? Then this brand new home is exactly what you have been waiting for. Welcome to this stunning 2,600 sq. ft. open concept residence built by local award winning builder. Featuring 5 spacious bedrooms, including a first floor bedroom great for guests or multi generational living, and 3 full baths with upscale designer finishes throughout. Enjoy luxury features including granite countertops, ceramic tile, luxury vinyl plank flooring, a cozy fireplace, and a beautiful standalone soaking tub. With NO HOA, this property is superb for boat owners, campers, trailers, or anyone wanting freedom and flexibility without extra fees or restrictions. Located in a highly sought school district with flexible spaces wonderful for entertaining and everyday living. Everything is brand new, offering peace of mind and low maintenance living.

785 Caddie Street, South Chesapeake

$252,000
2 Beds 1 Baths 10644283 MLS
Affordable Great Bridge lake-view living! Enjoy low-maintenance condo living just off Cedar Road, a short drive from shopping, restaurants, entertainment and everything Great Bridge has to offer. Inside, vaulted ceilings, arched windows and abundant natural light give the home an open, inviting feel. The living room features a cozy fireplace and opens to a private balcony overlooking the lake and mature trees—an ideal spot for morning coffee or winding down at the end of the day. The kitchen offers plenty of cabinet and counter space with a bright dining area highlighted by a dramatic arched window. Two comfortable bedrooms and a full bath complete the home. Residents also enjoy community amenities including the pool, while the location puts you just minutes from the area’s dining, shopping and entertainment. The city’s annual parade route is also just a few blocks away, adding to the convenience and community feel of this Great Bridge location. Whether you’re a first-time buyer, downsizing, or simply looking for an affordable, low-maintenance home in a great location, this lake-view condo offers a lot of value without giving up convenience.

449 E Lake Circle, South Chesapeake

$795,000
6 Beds 3.1 Baths 10643149 MLS
Well-maintained, spacious home on a prime lot in the beautiful Riverwalk community. New Roof, all new Windows, new paint interior and exterior, and new carpet in 2026! Beautiful wood floors in living and dining areas. Six bedrooms, 3 full and 1 half baths. Designed for those who love to entertain, the expansive floor plan offers elegant gathering spaces, abundant natural light, a formal butler station off the dining room. and exceptional flow throughout. The spacious eat-in kitchen and bar-top seating area open to the inviting family room with a cozy fireplace. Three additional bedrooms are located on the second level, including a versatile FROG that can serve as the 6th bedroom, home office, or recreation room. Current cooktop and built-in microwave to be replaced; buyer can choose. Large back deck with gas hookup. Residents of Riverwalk enjoy exceptional neighborhood amenities, including walking trails, a community pool, boat ramp and dock, playground, and a popular summer swim team. This is a wonderful opportunity to own a meticulously cared-for home in one of Chesapeake’s most desirable communities.

804 River Strand, South Chesapeake

$820,000
5 Beds 3 Baths 10643909 MLS
Spacious 5 Bedroom, 3 Bath home on a beautiful 3-acre lot in the Grassfield High School district! On the main level you'll find LVP flooring, elevated lighting, updated Eat-in Kitchen w/huge island, stainless steel appliances including a Viking gas range, pantry and reverse osmosis drinking water, Family room with gas fireplace, Living and Dining Rooms and full bath. Primary Bedroom with walk-in closet and luxury ensuite bath, 4 secondary bedrooms, laundry (combo W/D unit) and full hall bath complete the 2nd floor. 2-car garage and abundant storage. Outside is made for fun and entertaining with an in-ground pool, stamped concrete patio, and an outdoor kitchen with grill, smoker, and pizza oven. A wonderful space to make memories with family and friends! Major updates include a brand-new dual-zone HVAC (2026), water heater (2025), water softener, garage doors and openers, repaved driveway, new soffits, fascia, gutters, window wrap, and front railing. No HOA! Enjoy the best of both worlds with a peaceful private setting while just minutes from shopping, restaurants, highways and everyday conveniences. Move-in ready!

1932 Foxwood Drive, South Chesapeake

$630,000
4 Beds 2.1 Baths 10644442 MLS
Experience the lifestyle you've been searching for in one of Chesapeake's most desirable communities, just minutes from top-rated Grassfield High School. This beautifully maintained home welcomes you with a charming front porch and gleaming hardwood floors throughout the main level. A versatile flex room that can be used for a home office, playroom, or sitting area, while the formal dining room flows into the updated chef's kitchen featuring granite countertops, refreshed cabinetry, and new stainless steel appliances. The kitchen opens to a spacious family room centered around a cozy fireplace and an inviting sunroom filled with natural light. Upstairs, the expansive primary suite offers a spa-inspired bath with dual vanities, a jetted tub, and a glass-enclosed shower, along with three additional bedrooms, a full bath, and a convenient second-floor laundry room. Step outside to your own private backyard retreat complete with a stamped concrete patio, sparkling in-ground pool, and fully fenced yard—ready for relaxing or entertaining all summer long. Additional upgrades include a tankless water heater, solar panels that significantly reduce electric costs, updated main-level lighting, and a VA assumable loan with an incredible 3% interest rate for qualified buyers. Tesla EV charger.

2101 Beeblossom Lane, South Chesapeake

$190,000
2 Beds 2.1 Baths 10644380 MLS
Unlock incredible potential with this two-bedroom, two-bathroom condo, offering a fantastic blank canvas for investors, flippers, or homeowners looking to customize their own space. The main living area features a bright, open-concept layout with wood floors, a cozy fireplace, and sliding glass doors that open to a private patio. The adjacent kitchen features white cabinetry and a convenient breakfast bar that overlooks the dining and living spaces, creating a great flow for daily living and entertaining. Upstairs, the home offers two bedrooms, including a spacious primary suite complete with a walk-in closet and an en-suite vanity area. While the property requires cosmetic updates and repairs throughout—including new flooring, fresh paint, and bathroom updates—it presents the perfect opportunity to build immediate equity. Bring your vision and design ideas to transform this property into a modern personal retreat or a highly profitable addition to your portfolio! Residents will enjoy low-maintenance living with HOA dues that cover community pool and clubhouse access, ground maintenance, and trash pickup.

747 Ridge Circle, South Chesapeake

$500,000
5 Beds 3 Baths 10644216 MLS
Situated on a corner lot in sought after Culpepper Landing, this spacious home is ready for new owners to make it their own. A formal living and dining room, both with hardwood floors greet you as you enter. A large living room with gas fireplace opens to the spacious kitchen that includes tons of cabinet space and granite counters. The eat-in kitchen provides access to the large fenced-in backyard, great for entertaining. A bedroom and full bath are also located on the first floor. Upstairs, the primary bedroom includes an attached bath with double vanity, soaking tub and walk-in shower. Three more bedrooms and an impressive laundry room complete the second level. The attached 2-car garage provides excellent additional storage space. Neighborhood amenities include a clubhouse, exercise room, playgrounds, pool and more!

700 Canoe Street, South Chesapeake

$577,740
3 Beds 3 Baths 10644251 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.

2164 Edwin Drive, South Chesapeake

$506,990
2 Beds 2 Baths 10644247 MLS
The Asheville, one of our quad-style homes, features two bedrooms and two full baths. Refreshing and cottage-like, The Asheville is single level living at its finest. A welcoming covered front porch leads you to a spacious living room with fireplace. At the heart of the home, the Kitchen is within reach of the dining room, pantry, laundry room, and access to the two-car garage. The Kitchen is accented with Shaker style cabinets, quartz countertops, tile backsplash, and stainless-steel appliances. The primary bedroom with ensuite offers a spacious walk-in closet, tiled shower with glass enclosure, counter-height vanity with double sinks and a separate water closet. For guests or an office, you’ll find a secondary bedroom with an adjacent full bath. $10,000 closing cost incentive with use of preferred lender! Photos and renderings are from builder's library, actual finishes and features may vary.

2150 Edwin Drive, South Chesapeake

$468,900
3 Beds 2.1 Baths 10643511 MLS
Make this your first stop! Beautiful maintained townhome located in the highly sought-after Hickory School District. This move-in ready home features a spacious first-floor primary suite with a large walk-in closet, 9-foot ceilings, quartz countertops, stainless steel appliances, and upgraded luxury vinyl plank flooring throughout. Upstairs, you'll find two generously sized bedrooms, each with its own walk-in closet, plus a walk-in attic offering abundant storage. Additional highlights include a one-car garage, a private patio, and low-maintenance living. Conveniently located near Route 168, shopping, dining and the Coast Guard Chesapeake Annex. Don't miss the opportunity to make this beautiful home yours! Newly painted throughout home, electric fireplace to convey. ***Seller needs rent back ~ Nov 1st for new build completion.

1915 Canning Place, South Chesapeake

$916,000
3 Beds 2.1 Baths 10643968 MLS
HURRY; THIS HOME WON’T LAST!!! If you are looking for privacy this single family home situated on a spacious 1-acre lot with “no” HOA fee & convenient interstate access is for you!!! The attention to detail & custom upgrades are simply “impeccable”! Home features double door front entrance, 3 bedrooms including that much sought after “first floor primary” with a luxurious spa inspired bath, custom closet, 2 & 1/2 baths, family room with gas fireplace, gourmet kitchen with upgraded “GE Cafe” appliances, loads of custom cabinetry, huge kitchen island, custom trim work though-out, upgraded flooring, enhanced lighting & plumbing fixtures, mudroom with customized storage, large loft with window nook, extra large rear “screened” in covered porch & 2 car side load garage! This amazing home on this incredible lot is a true must see!!!

109 Ballahack Road, South Chesapeake

$397,490
3 Beds 2 Baths 10643999 MLS
Welcome to this charming 3-bedroom, 2-bath Cape Cod nestled on 1.4 private acres in the Deep Creek area of Chesapeake! This property offers the perfect blend of peaceful outdoor living and everyday convenience. Enjoy gardening in the fenced garden, unwind in the wooded backyard, or take advantage of easy access to the nearby Portsmouth Ditch Trail for walking, biking, and outdoor recreation. Inside, you’ll find a warm and inviting layout with classic Cape Cod character and plenty of space to make your own. Whether you’re looking for room to spread out, enjoy nature, or simply escape the hustle while staying close to shopping, dining, and major commuting routes, this home checks all the boxes. Don’t miss this unique opportunity to own your own slice of Deep Creek!

3433 Martin Johnson Road, South Chesapeake

$277,000
3 Beds 2.1 Baths 10644053 MLS
Well maintained, tenant occupied 1,275 sf, 3-bedroom, 2.5 bath Townhouse in Chesapeake's Woodgate Commons community. Ideally located near restaurants, shopping, interstate access, military bases, and a nearby golf course, this home offers both convenience and value. Recent updates include new first-floor flooring, remodeled bathrooms, fresh interior and exterior paint, updated kitchen appliances and floor coverings, an upgraded HVAC system, a smart thermostat & deck. The attached storage provides extra space for tools, seasonal items, or outdoor gear. The total community features 78 acres of common grounds w/ sidewalks throughout connecting neighborhoods, 7 playgrounds, a fishing pier, and a kayak ramp, offering plenty of outdoor recreation. Full of potential! Present tenant pays $2,200 per month on a 60-day notice lease.

1806 Beckwood Common, South Chesapeake

$1,069,417
5 Beds 4 Baths 10643118 MLS
The Rivermont is where everyday living feels just a little more special. Designed with comfort, style, and connection in mind, this thoughtfully crafted home offers the perfect spaces to gather, relax, and make lasting memories. At the heart of the home, the chef-inspired kitchen flows effortlessly into the spacious dining area and inviting great room, creating the ideal setting for everything from Sunday brunches to holiday celebrations. Just beyond, step onto the covered rear porch—your new favorite spot for morning coffee, evening cocktails, or cheering on a summer thunderstorm from the comfort of home. The vaulted first-floor primary suite provides a peaceful retreat, while generously sized secondary bedrooms and flexible living spaces offer room for family, guests, hobbies, or a home office. Every detail reflects the quality craftsmanship and thoughtful design Kirbor Homes is known for. Located in the desirable Sanderson Estates, you'll enjoy spacious homesites and the perfect blend of peaceful surroundings with convenient access to shopping, dining, recreation, and major commuting routes. Whether you're hosting family dinners, relaxing on the porch, or simply enjoying the comfort of a brand-new home, the Rivermont is designed for the moments that matter most. Come see why this could be the perfect place to call home! Contact LA to schedule an appointment at our design center today! Builder Contract. Ask about our current incentives!

2861 Raccoon Trail, South Chesapeake

$682,500
5 Beds 3 Baths 10643877 MLS
This well maintained all brick home with 2-car side loading garage with long driveway and 1/3 acre beautifully landscaped lot is situated on a cul-de-sac in Great Bridge. Open floor plan features Huge kitchen with quartz counter tops and overlooks Fam. Rm. 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 bath on first floor. Recent updates include replacement windows, roof, water heater, garage door and leaf filter gutters. New 3 ton upstairs HVAC installed in Sept. 2026. Award winning Cheshire Forest community amenities include clubhouse, pool, tennis/ pickleball court , parks, and playgrounds. Seller to provide 1 year home warranty. The screened porch with concrete floor overlooks the beautiful backyard.

810 Hedgerow Court, South Chesapeake

$549,000
4 Beds 2.1 Baths 10642714 MLS
Impeccably maintained brick ranch with 4 bedrooms, 2.5 baths, an attached one-car garage, wood-burning fireplace and a spacious backyard. The remodeled kitchen features quartz countertops, soft-close cabinetry, stainless steel appliances, under-cabinet lighting, and a movable island. Updated bathrooms, custom wood trim, and closet organization systems add thoughtful touches throughout. Enjoy the 15x40 deck, fenced yard, storage shed, and newly expanded driveway with RV pad, 50-amp hookup, and generator connection. Major improvements over the years include windows, HVAC, 200-amp electrical panel, flooring, garage door, water heater, sprinkler/well system, and more. Convenient to bases, shopping & highways for easy access in Hampton Roads and to NC. Hickory HS district. This home has been diligently cared for inside and out and is truly move-in ready!

1025 Ramsgate Lane, South Chesapeake

$247,500
2 Beds 1 Baths 10643751 MLS
Move-in ready and beautifully updated, this home offers the perfect blend of modern style and everyday functionality. Step inside to a bright, inviting interior featuring a beautifully renovated kitchen with soft-close shaker cabinetry, granite countertops, and brand-new stainless steel appliances—perfect for cooking, gathering, and entertaining. Outside, the spacious backyard provides plenty of room for pets, gardening, play, or weekend cookouts. An oversized detached garage/workshop offers exceptional space for storage, hobbies, or DIY projects. Major updates have already been done for you, including a new roof, HVAC, upgraded panel and windows. Situated in an established neighborhood, this home is conveniently located just minutes from shopping, dining, major highways, the shipyard, and military bases, making daily commuting a breeze. Combining comfort, convenience, and thoughtful updates, this is a home you won't want to miss!

2317 Wildwood Road, South Chesapeake

$647,499
5 Beds 3 Baths 10643675 MLS
Rare find on Cedar Road! This multi-generational 5-bed, 3-bath home features two primary bedrooms one downstairs and a larger one upstairs deal for multigenerational, extended family or flexible living. The Open Living Format seamlessly connects the kitchen, dining, and great room for effortless entertaining. Enjoy LVP flooring, quartz counters, tile backsplash, pendant lighting, and a first-floor bedroom with full bath. Set on 2.5 acres with a wooded backyard, it offers a true mini wilderness escape while still near to everything. The upstairs primary suite includes a garden tub, tile shower, and generous closet space. Modern finishes, private acreage, and a two-car garage make this a standout home that will not last!

2116 Cedar Road, South Chesapeake

$894,595
5 Beds 3 Baths 10643669 MLS
Fair warning: Your guests may start inviting themselves over. Welcome to the Whitehurst by Kirbor Homes—a home that's equal parts stylish, spacious, and dangerously comfortable. Once you move in, don't be surprised if everyone suddenly volunteers your house for every birthday, football Sunday, and holiday gathering. The heart of the home is the incredible chef-inspired kitchen, complete with our upgraded Chef's Appliance Package, an oversized island, and enough counter space to pretend you're on a cooking show (or just unpack takeout in style). The open-concept layout keeps everyone connected, whether you're entertaining a crowd or trying to keep an eye on whoever keeps sneaking cookies before dinner. Designed with convenient first-floor living, the private primary suite is your personal escape after a long day, featuring a spa-like bathroom and a spacious walk-in closet that's ready for everything from everyday essentials to those online shopping "must-haves." Two additional bedrooms offer space for family and friends, while the upstairs bonus room can transform into whatever life calls for—a movie lounge, game room, home office, fitness studio, or the ultimate hideaway when you need a little peace and quiet. Out back, the covered porch is practically begging for morning coffee, summer cookouts, and evenings where you swear you'll only sit outside for five minutes...until it's dark. Every inch of the Whitehurst showcases the quality craftsmanship and thoughtful details Kirbor Homes is known for, blending comfort, flexibility, and timeless design into a home you'll love coming back to every day. So go ahead, schedule your private tour or Design Center appointment today. Just don't blame us when your friends start referring to your house as "the gathering place." Builder contract required. Ask about available lender incentives!

2857 Raccoon Trail, 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.