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436 Fairfield Drive, South Chesapeake
$465,000
3 Beds ⋅ 2 Baths ⋅ 10636002 MLS
Beautifully maintained all-brick ranch in the highly desirable Hickory school district! This move-in ready home offers incredible indoor and outdoor living space, including an attached garage and a 672 sq. ft. detached garage/workshop complete with parking area, cabinets, counters, and overhead storage. The oversized family room features a cozy fireplace, custom wainscoting, built-in shelving, and abundant natural light. Updated kitchen includes newer cabinetry, countertops, stainless steel appliances, recessed lighting, and a spacious pantry. Both full bathrooms have been tastefully updated with tile finishes. Step outside to a large deck with built-in seating and swing overlooking the beautifully landscaped backyard. Additional features include architectural roof, replacement Low-E vinyl windows, HVAC replaced in 2020, extensive crown/chair-rail molding, irrigation system, and convenient access to shopping, dining, and the Great Bridge Bypass.

436 Fairfield Drive, South Chesapeake
1119 Fenton Quay, South Chesapeake
$465,000
4 Beds ⋅ 2.1 Baths ⋅ 10628395 MLS
Welcome to cul-de-sac living in the heart of Greenbrier. This updated 4 bedroom, 2.5 bath home offers the perfect blend of comfort and style with vaulted ceilings, hardwood floors, and a bright kitchen featuring stainless steel appliances that flows into a second living space with a wood burning fireplace. The main level also includes a beautifully updated half bath. Upstairs, LVP flooring leads to a spacious primary suite with a trey ceiling and private deck, plus an en suite with double vanity, jetted tub, separate shower, and walk in closet. Three additional bedrooms share an updated full bath. Enjoy a fenced backyard with a deck and storage shed, all backing by the 15th hole of Greenbrier Country Club. Complete with a 2 car garage, whole house surge protector, and extra storage. Don’t miss this opportunity.

1119 Fenton Quay, South Chesapeake
1432 Birch Leaf Road, South Chesapeake
$465,000
4 Beds ⋅ 2 Baths ⋅ 10627932 MLS
Excellent opportunity to make this one your own. Wonderful , convenient location. SOLD AS IS WHERE IS with the SELLER TO MAKE NO REPAIRS AND WARRANTS NOTHING. Seller will provide a clear termite and moisture letter. $5000 closing cost assistance on a full price offer using the Seller's attorney for closing.

1432 Birch Leaf Road, South Chesapeake
205 Frank Drive, South Chesapeake
$465,000
4 Beds ⋅ 2 Baths ⋅ 10627499 MLS
Welcome to the heart of Great Bridge! This 4-bedroom, 2-bath home sits on a large lot and includes a 2-car detached garage, offering plenty of space inside and out. Recent updates include new carpet in the primary suite and fresh paint throughout. Conveniently located near shopping, dining, and local amenities.

205 Frank Drive, South Chesapeake
518 Dunning Lane, South Chesapeake
$465,000
3 Beds ⋅ 2 Baths ⋅ 10627314 MLS
Welcome home! Don’t miss this rare opportunity to own a beautifully updated, move-in ready, one-level Berwick plan with a stunning water view in Eagle Pointe, Chesapeake’s Premier 55+ Adult Community. This newer home features a gorgeous granite kitchen with breakfast bar, stainless steel appliances, and a unique custom mural. Enjoy peaceful mornings overlooking the water, along with a spacious formal dining area perfect for entertaining. The first-floor primary suite offers a large walk-in closet, ceramic tile shower, and dual vanities for added comfort and convenience. Recent updates include new flooring, refrigerator, and hot water heater, making this home truly move-in ready. At the heart of the community is The Bay Club, offering resort-style amenities including a heated indoor pool and hot tub, outdoor pool, large fitness center, billiards room, game rooms, ballroom, library, on-site management, and so much more. Call today schedule your private tour.

518 Dunning Lane, South Chesapeake
804 Erik Paul Drive, South Chesapeake
$465,000
4 Beds ⋅ 2 Baths ⋅ 10627082 MLS
Beautiful Brick ranch in sought-after school district! Well maintain 4 bedrooms and 2 full bathroomsthat host SS appliances, LVP flooring, fireplace and huge loft/bonus room. Ready to move in! A truly unique home in a highly desirable community—don’t miss this rare find.

804 Erik Paul Drive, South Chesapeake
911 Mount Pleasant Road, South Chesapeake
$465,000
4 Beds ⋅ 2.1 Baths ⋅ 10603007 MLS
Bright open floor plan with cathedral ceilings in the family room which opens to the kitchen and breakfast area. Formal living room and dining room. Finish room over the garage. Lots of upgrades to include granite counters, new light fixtures. Finished room over the garage. Floored attic for additional storage. Shed conveys as is.

911 Mount Pleasant Road, South Chesapeake
444 Fleming Circle, South Chesapeake
$464,000
4 Beds ⋅ 3 Baths ⋅ 10639032 MLS
Welcome to this well-maintained Chesapeake home tucked away on a cul-de-sac! Offering approximately 2,100 square feet of living space, this versatile property features 4 bedrooms, 3 full bathrooms, and plenty of room to fit your lifestyle. Inside, you’ll find fresh paint, abundant storage, and a flexible floor plan that includes a flex room, formal dining room, and a family room. The spacious eat-in kitchen offers ample cabinetry and storage, making meal prep and entertaining a breeze. One of the home’s standout features is the converted garage, creating a large additional living area complete with a full bathroom. This versatile space could serve as a second primary suite, guest quarters, media room, playroom, or whatever best suits your needs. Situated on a generous 0.4-acre lot, the expansive backyard provides endless opportunities for outdoor entertaining, gardening, or simply relaxing. Conveniently located near shopping, dining, schools, and major commuting routes.

444 Fleming Circle, South Chesapeake
404 Rhema Road, South Chesapeake
$461,500
4 Beds ⋅ 3.1 Baths ⋅ 10634289 MLS
Discover this stunning 2021-built 3-story 2177 square foot home in Chesapeake’s coveted school district (Grassfield/Great Bridge). Featuring 4 bedrooms and 3.5 baths, this home boasts a rare top-floor private suite for ultimate privacy, home office, or multi generational living. The upgraded interior includes a large bumped-out Chef style kitchen, stylish glass backsplash, premium cabinets, and luxury LVP flooring. Say goodbye to yard work with your own antibacterial pet-grade turf backyard! Additional perks: Fully finished garage with a side-mount opener preserving valuable ceiling storage space. Enjoy maximum convenience with a tankless water heater. Easy commute to Naval Stations & beaches. This is the perfect blend of luxury, comfort, and low-maintenance living.

404 Rhema Road, South Chesapeake
300 Sikeston Lane, South Chesapeake
$460,000
4 Beds ⋅ 3 Baths ⋅ 10647060 MLS
Welcome home to this beautifully maintained luxury end unit townhome in the highly sought after Great Bridge School District! Less than seven years old, this move in ready home offers stylish, low-maintenance living with thoughtful upgrades throughout. Enjoy luxury laminate plank flooring throughout the entire home, smart switches compatible with Alexa, and an upgraded custom walk in closet in the spacious primary suite. The gourmet kitchen features granite countertops, a large island, upgraded cabinetry, refrigerator only 6 months old and a flat top stove. Soaring 9-foot ceilings, multiple walk-in closets, a spacious laundry room, garage, driveway, and covered front porch add to the home's appeal. The HOA handles yard maintenance, giving you more time to enjoy nearby shopping, dining, entertainment, and quick highway access. Schedule your private showing today!

300 Sikeston Lane, South Chesapeake
812 Gloss Street, South Chesapeake
$460,000
4 Beds ⋅ 2 Baths ⋅ 10637927 MLS
This well maintained 4 bedroom (FROG is 4th), 2 bath home will not disappoint. With a custom gourmet kitchen featuring granite counters, soft close cabinets, GE matte gray appliances, updated light fixtures, and a large eat in area. LVP flooring throughout, updated hall bath, newer replacement vinyl windows, Furnace replaced in 2023. The deck has been updated with pergola, for great outdoor space. Brand new fence, and updated shed with new siding and roof. The seller is offering a 1 year home warranty with AHS. Will need to rent back after closing.

812 Gloss Street, South Chesapeake
1616 Whittamore Road, South Chesapeake
$460,000
4 Beds ⋅ 2.1 Baths ⋅ 10633922 MLS
Enjoy the peaceful feel of country living without sacrificing city convenience. Tucked away in a quiet setting yet minutes from shopping, dining, and major routes, this home offers the space and lifestyle you’ve been looking for. Located in the highly desired Hickory School district near Battlefield Golf Club and Fentress Airfield. The open layout features spacious living and dining areas flowing into a large kitchen with granite countertops and stainless steel appliances. The primary suite offers a large bedroom, walk-in closet, and bath with double sinks, jetted tub, and separate shower. Secondary bedrooms are generously sized with walk-in closets. Enjoy the large fenced backyard complete with a playset that conveys and spacious shed, perfect for entertaining, relaxing evenings, pets, and play.

1616 Whittamore Road, South Chesapeake
305 Plummer Drive, South Chesapeake
$460,000
4 Beds ⋅ 3 Baths ⋅ 10632717 MLS
Welcome to this beautifully maintained all-brick ranch nestled on a quiet cul-de-sac in desirable Deep Creek community. This spacious home offers 4 bedrooms and 3 full bathrooms, providing plenty of room for comfortable living. It features an updated kitchen, modern appliances and ample space for cooking and gathering. Enjoy the stunning heated and cooled sunroom—the perfect year-round space. Outdoor living shines with a large deck ideal with retractable awning for entertaining, a generously sized shed for additional storage, and direct access to a peaceful creek, creating a serene backyard retreat. The property is beautifully landscaped and equipped with in-ground sprinklers to keep everything lush and green. Located in a quiet, established neighborhood, this home is a must-see!

305 Plummer Drive, South Chesapeake
409 Heartfield Drive, South Chesapeake
$460,000
3 Beds ⋅ 2.1 Baths ⋅ 10629659 MLS
Welcome to this beautifully updated end-unit condo offering comfort, space, and convenience! Freshly painted throughout, this home features a desirable first-floor primary suite with dual vanities, a walk-in shower, and an oversized walk-in closet. The kitchen offers abundant cabinetry, stainless steel appliances, a large island, and pantry storage. Enjoy the private, fenced-in back patio—perfect for relaxing or entertaining. The home also features great storage, including a walk-in attic. Upstairs includes two additional bedrooms and a full bath, ideal for guests or flex space. Community amenities include a pool, playground, beautiful landscaping upkeep and more! Conveniently located near shopping, dining, and easy access to NC and the OBX!

409 Heartfield Drive, South Chesapeake
427 Life Tree Trail, South Chesapeake
$460,000
3 Beds ⋅ 3.1 Baths ⋅ 10619830 MLS
STUNNING end-unit townhouse-design condominium in Grassfield. First floor living area is perfect flex space and includes full bath and drop zone next to the garage. Sleek gourmet kitchen with huge island opens to spacious family room with beautiful built-ins. Primary bedroom has custom accent wall and two walk-in closets. Spa-like primary bath has custom tile and double vanity. So many custom features, including quartz counters, tankless water heater, custom woodwork and trim, custom blinds throughout, paver landscaping, garage door opener, under cabinet lighting and epoxy garage flooring. Community offers dog park, playground, pavilion, pond and many community activities.

427 Life Tree Trail, South Chesapeake
208 Old Drive, South Chesapeake
$459,999
3 Beds ⋅ 3 Baths ⋅ 10628054 MLS
Beautifully updated ranch home located in the heart of Great Bridge! This 3-bedroom, 3-full-bath home has been completely refreshed with a brand-new roof, new windows, fresh paint, and new LVP flooring and carpet throughout. The updated kitchen features new appliances and modern finishes, making it move-in ready from day one. Situated on a spacious .40-acre lot, the home offers a huge, fully fenced backyard—perfect for entertaining, pets, or enjoying outdoor living. Conveniently located near shopping, dining, and top-rated schools, this home combines quality updates with an unbeatable location. A must-see!

208 Old Drive, South Chesapeake
3600 Martin Johnson Road Unit RD, South Chesapeake
$459,900
3 Beds ⋅ 2 Baths ⋅ 10642749 MLS
Welcome to this lovingly maintained, one-owner ranch-style home nestled on 3 private acres. This well-built residence has been meticulously cared for and is ready for its next chapter — offering the perfect canvas for cosmetic updates to make it entirely your own. The open, manageable layout is ideal for those seeking single-level living with room to breathe. A standout feature is the oversized detached 2-car garage/workshop, perfect for hobbyists, car enthusiasts, or anyone needing serious storage and workspace. The expansive acreage provides privacy and tranquility rarely found at this price point, with mature surroundings that create a true retreat from the everyday. Whether you are looking to personalize a solidly built home or simply enjoy the peace and space this property offers, the opportunity here is undeniable. Priced to reflect its cosmetic potential while honoring the exceptional care this home has received throughout its single ownership.

3600 Martin Johnson Road Unit RD, South Chesapeake
929 Thatcher Way, South Chesapeake
$458,000
4 Beds ⋅ 2.1 Baths ⋅ 10631726 MLS
Welcome home! Spacious and well-maintained 4-bedroom, 2.5-bathroom single-family home offering over 2,100 sq ft of living space in the heart of Chesapeake. Situated on a 0.136-acre lot, this property provides a great balance of indoor and outdoor living. Generously sized bedrooms, functional layout, and ample natural light throughout make this home ideal for both everyday living and entertaining. The attached garage allows for additional parking or storage! A wonderful opportunity to own a home with space, versatility, and charm. Conveniently located near dining, shopping, and more! Call today for more information and to schedule your tour!

929 Thatcher Way, South Chesapeake
513 Eldridge Lane, South Chesapeake
$456,000
3 Beds ⋅ 2.1 Baths ⋅ 10638615 MLS
Enjoy low-maintenance living in this spacious 3-bedroom, 2.5-bath townhouse with over 2,000 square feet of living space. Located in the desirable Grassfield School District. Built just 3 years ago and meticulously maintained, this home features a first-floor primary suite with a large walk-in closet, an open floor plan, LVP flooring, granite countertops, two pantries, and a convenient first-floor laundry room. Upstairs offers two spacious bedrooms, each with a walk-in closet, plus a loft and flex/storage room. Backing to a wooded common area, the community also offers walking trails, a dog park, pavilion, splash pad, and playground. Items to convey: Washer, Dryer, Garage Freezer. Conveniently located near shopping, dining, and everyday amenities.

513 Eldridge Lane, South Chesapeake
1009 Priscilla Lane, South Chesapeake
$456,000
4 Beds ⋅ 2 Baths ⋅ 10630833 MLS
Welcome to this charming 4-bedroom, 2-bath home located in one of the area’s most sought-after neighborhood Hickory, known for its top-rated schools and unbeatable community feel. Situated on a spacious corner lot, this property offers both privacy and room to grow. While the home carries a bit of its original character, it has been thoughtfully maintained and updated where it matters most. Major systems provide peace of mind, newer HVAC and water heater, this home also includes a JES-encapsulated crawl space, humidity control, and dehumidifier/maintenance system an incredible added value for long term comfort and protection. Step outside to enjoy a fully fenced yard with garden beds ready for planting, a chicken coop for those seeking a homestead touch, and mature fig, persimmon, and crabapple trees ready for the next owner to enjoy. Now it is your turn to own a well loved home in an amazing neighborhood with space, functionality, and endless potential to settle.

1009 Priscilla Lane, South Chesapeake
462 Weeping Cedar Trail, South Chesapeake
$455,000
4 Beds ⋅ 2.1 Baths ⋅ 10650088 MLS
Welcome home to Hillside Landing in South Chesapeake! This inviting two-story home offers a cozy, functional layout with thoughtful updates throughout. Step inside to find new LVP flooring and a bright eat-in kitchen featuring granite countertops, a natural stone stacked marble mosaic backsplash, touchless kitchen faucet, brand-new appliances, and plenty of natural light. The living area offers a warm place to unwind with a gas fireplace and built-in bookshelves adding both character and functionality. Upstairs, you’ll find comfortable carpeted bedrooms, conveniently located laundry, and a spacious primary suite with a private bathroom featuring a step-in shower with attractive tile surround. Additional improvements include updated lighting, HVAC, and a new door. Outside, the large backyard provides plenty of room for entertaining, relaxing, or enjoying the peaceful views of the neighborhood pond. A spacious red storage shed offers additional room for lawn equipment, tools, and more. Complete with a two-car garage and a roof replaced in 2015, this Hillside Landing home combines comfortable living, useful updates, and a beautiful waterfront backdrop in South Chesapeake. Schedule your tour today!

462 Weeping Cedar Trail, South Chesapeake
419 Heartfield Drive, South Chesapeake
$455,000
3 Beds ⋅ 2.1 Baths ⋅ 10648866 MLS
Experience low-maintenance living at its finest in this beautifully appointed home in the heart of Chesapeake. Built in 2019, this 3-bed, 2.5-bath residence offers a modern, open-concept design w/stylish finishes and thoughtful details throughout. The spacious main living area flows seamlessly into a well-designed kitchen. A first-floor primary suite provides comfort and convenience, while additional bedrooms offer flexibility for guests, a home office, or hobbies. Enjoy the ease of a low-maintenance lifestyle with community amenities that elevate everyday living, all in a sought-after location near shopping, dining, and top conveniences. This is the perfect blend of comfort, style, and simplicity, great for those ready to enjoy more and maintain less.

419 Heartfield Drive, South Chesapeake
602 Windward Drive, South Chesapeake
$455,000
4 Beds ⋅ 2.1 Baths ⋅ 10646630 MLS
Beautiful, brick front, 4 bedroom home in sought after Greenbriar Estates. The newly renovated kitchen boasts SS appliances, new cabinets, Quartz counters with a large island that is open to the family room. Other features include an architectural roof, wood floors, HVAC and wood floors all replaced approximately 5 years ago! The large primary suite features a walk-in closet, dual sinks, a separate soaker tub, a skylight and a custom glass shower door. LOCATION-LOCATION! Less than 30 minutes to Naval Station Norfolk & little creek bases, as well as the Virginia Beach Oceanfront . Chesapeake City Park is at the end of the street, and Greenbriar Mall is just minutes away. Schedule your showing soon, this one won't last!

602 Windward Drive, South Chesapeake
903 Adventure Way, South Chesapeake
$455,000
3 Beds ⋅ 2.1 Baths ⋅ 10644927 MLS

903 Adventure Way, South Chesapeake
3205 Holly Ridge Drive, South Chesapeake
$455,000
4 Beds ⋅ 2.1 Baths ⋅ 10640543 MLS
Back on market through no fault of the seller. Welcome home to this fantastic 2-story home tucked away in the back of Mill Creek! Major updates have already been completed, including new LVP flooring, solid surface flooring throughout, custom bathrooms, aluminum-wrapped fascia, a new HVAC coil (2025), and 14 replacement windows with a transferable lifetime warranty from Better View Windows. The spacious floor plan offers a formal dining room, large family room, and an oversized FROG great for a playroom, home office, media room, or guest space. Retreat to the generous primary suite featuring a walk-in closet and beautifully updated bath. Make sure to check behind the mirror in the walk in closet for hidden storage! With plenty of room to grow, stylish updates, and endless possibilities to make it your own, this home is ready for its next chapter!

3205 Holly Ridge Drive, South Chesapeake
308 Cotton Mill Court, South Chesapeake
$455,000
4 Beds ⋅ 3 Baths ⋅ 10634973 MLS
Welcome to this beautifully updated 4 Bedroom, 3 Bathroom detached home in the sought after Old Mill Landing community of Deep Creek in Chesapeake. This property offers rare privacy along with a serene water view that sets the perfect backdrop for everyday living. Inside, you’ll find spacious, light-filled living areas, including two fireplaces adding warmth & charm. The updated kitchen with granite countertops & updated bathrooms blend modern convenience with timeless style. A versatile Florida room extends your living space year-round, opening to a large deck ideal for entertaining or simply enjoying the peaceful surroundings. The fenced yard is perfect for pets, gardening, or simply relaxing in your own space. Inside, the home offers generous bedrooms, refreshed bathrooms, & inviting living areas designed for comfort. All appliances convey! Custom plantation shutters throughout! This home blends privacy, charm, & convenience in one beautiful package!

308 Cotton Mill Court, South Chesapeake
417 Saddle Court, South Chesapeake
$455,000
4 Beds ⋅ 2 Baths ⋅ 10633143 MLS
Positioned on half acre cul-de-sac lot in Elmwood Landing! This 4-bedroom, 2-bath ranch offers over 2,000 sq ft with a well-designed layout. Brick fireplace with built-ins anchors the main living space. Renovated primary bathroom with modern finishes. Walk-in attic offers exceptional storage and future potential. Spacious backyard with deck, great for entertaining! Roof replaced in 2022; new gutters in 2025. Schedule your showing today!

417 Saddle Court, South Chesapeake
536 Cristfield Road, South Chesapeake
$454,500
3 Beds ⋅ 2.1 Baths ⋅ 10636127 MLS
If owning a stunning former model home, with all the bells and whistles, is on your radar.. Look no further! This gorgeous condo with a single family feel, is simply unmatched. Designed with all the contemporary touches, this one is ready for its next chapter. This home features a spacious kitchen with an extra-long island, with seating up to five! Charming living and dining room is open and airy, great for cozy movie nights and entertaining. Three spacious bedrooms, primary bedroom offers a spa like bathroom and walk in closest. Additional flex room downstairs with french doors, insure you don't have to sacrifice a bedroom for an office or gym! Mudroom outfitted with custom storage system. This home was also built with a fire suppression system throughout! The generous backyard is wonderful for gatherings or gardening. Tucked away, pristine community just minutes from Chesapeake Towne Center & Summit Point. Condo fee covers roof, ground maintenance, fence and pressure washing!

536 Cristfield Road, South Chesapeake
125 Millwood Avenue, South Chesapeake
$452,555
4 Beds ⋅ 2 Baths ⋅ 10634335 MLS
Beautifully maintained 4 bed, 2 bath home in Chesapeake featuring a spacious backyard, attached garage, detached garage, and greenhouse. Interior improvements include an updated kitchen, fresh paint, updated flooring, and new carpet throughout. Functional layout offers flexible living space with ample storage and outdoor possibilities. Conveniently located near shopping, dining, parks, and major commuter routes. Move in ready with a combination of indoor comfort and outdoor versatility. Some photos are AI generated to properties full potential.

125 Millwood Avenue, South Chesapeake
244 Kalmar Drive, South Chesapeake
$452,000
4 Beds ⋅ 3 Baths ⋅ 10625367 MLS
Welcome to this versatile 3-bedroom, 2-bath ranch in the desirable Greenbrier area! This well-maintained home offers comfortable single-level living with spacious bedrooms, a functional layout, and plenty of natural light throughout.A standout feature is the detached rear unit—complete with its own 1 bedroom, 1 bath, living room, and kitchen—perfect for multi-generational living, guests, or potential rental income.Enjoy a generous yard, ample parking, and a convenient location close to shopping, dining, and major commuter routes. Whether you’re looking for extra space or flexible living options, this property delivers both comfort and opportunity!

244 Kalmar 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.