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$324,900
4 Beds 1 Baths 10645441 MLS
This beautifully updated property situated on a spacious corner lot of over a quarter acre in Chesapeake! Recent improvements completed in June 2026 include: a brand-new GAF architectural shingle roof, new gutters, new flooring throughout, and fresh interior paint, giving this home a clean, modern feel and added peace of mind. The versatile FLEX room offers endless possibilities and can easily serve as a 4th bedroom, home office, playroom, or home workout space to fit your lifestyle. Step outside to your fully fenced backyard retreat, designed for both relaxation and entertaining. Enjoy summer days in the above-ground pool and unwind or host gatherings under the pergola on the patio while appreciating the privacy this backyard provides. Conveniently located near shopping, dining, schools, and major interstates, this move-in-ready home combines thoughtful updates, flexible living space, and exceptional outdoor setting you won't want to miss.

2801 Southport Ave., Chesapeake

$579,000
4 Beds 2.1 Baths 10645167 MLS
Beautifully updated and impeccably maintained, this exceptional 4BR/2.5BA home offers thoughtfully designed living space in the highly sought-after Kemp Woods neighborhood of Chesapeake. Nestled on a quiet, tree-lined street, this move-in ready home perfectly blends timeless elegance, quality craftsmanship, & modern updates. Step inside to an inviting floor plan filled with natural light, with rich hardwood flooring, elegant plantation shutters, and spacious living areas. Gourmet kitchen is designed to impress, featuring tall cabinetry, built-in appliances, abundant counter space, & oversized breakfast area surrounded by windows that fill the space with natural light. Spacious primary suite is a true private retreat, complete with large walk-in closet & stunning, spa-inspired ensuite featuring beautifully tiled, oversized frameless glass walk-in shower, dual vanity, designer lighting, & luxurious finishes that create a resort-like experience at home. 3 additional generously sized bedrooms. Seamlessly extending the living space outdoors, both the family room and breakfast area open to an expansive multi-level deck overlooking the private backyard. Designed for entertaining and everyday enjoyment, this outdoor retreat offers oversized deck and a hot tub—perfect for summer gatherings, peaceful evenings, or relaxing under the stars. Major improvements provide exceptional peace of mind, including a roof, two-zone HVAC system, & numerous updates completed within the last 5 years, allowing the next owner to simply move in and enjoy. Conveniently located just minutes from Greenbrier’s premier shopping, dining, entertainment, parks, hospitals, and major commuter routes including I-64, this home offers the perfect balance of convenience and the quiet charm of one of Chesapeake’s most established and desirable neighborhoods. Some photos were virtually staged or digitally enhanced for marketing purposes to help buyers visualize the property’s potential. Schedule your showing today to make this house YOUR HOME!!

1045 Winchester Way, Chesapeake

$765,000
5 Beds 2.1 Baths 10645076 MLS
Why wait on new construction when this one's already done? This home was taken all the way down to the foundation and completely rebuilt and expanded — outside of one corner of the home everything here is new. Home inspection is complete, every item addressed, so you can move in with genuine peace of mind. Tucked away on a quiet country road in Chesapeake and surrounded by 3 peaceful acres of mature trees, this modern farmhouse ranch offers the privacy and charm buyers dream about. Huge wraparound-feel porches front and back give you outdoor living space to spare, and the wide-open yard makes this property feel like a true retreat. Inside, gorgeous LVP flooring flows throughout, while the spacious living area with a stunning brick fireplace creates a warm gathering space. The farmhouse-inspired kitchen features white cabinetry, an oversized island with bar seating, and ample storage. Bedrooms are thoughtfully spaced for added privacy, while the hall bath offers a double vanity, step-in shower, and beautiful natural light. The primary suite feels like its own getaway, with private porch access, dual closets, and a spa-style bath featuring a floor-to-ceiling marble-tiled shower. A detached storage shed conveys, and the sprawling backyard offers endless possibilities — gardening, entertaining, or future additions. All the character of country living, with the peace of mind of a brand new home. Welcome home.

1629 Shillelagh Road, Chesapeake

$599,999
4 Beds 2 Baths 10644979 MLS
Welcome to this beautifully remodeled all-brick ranch tucked into the peaceful Hickory area of Chesapeake, where country charm meets modern comfort on approximately 3 sprawling acres. This 4-bedroom, 2-bath gem has been thoughtfully updated from top to bottom, featuring luxury vinyl plank flooring, tiled showers, granite countertops, and stainless steel appliances throughout a bright, open layout made for both everyday living and easy entertaining. Step outside and fall in love with the lifestyle this property offers: relax on the covered front porch, host gatherings on the expansive rear deck, or unwind on your own private deck just off the primary suite. Dreaming of homegrown eggs? The property includes chicken coops, ready for you to raise your own flock and enjoy farm-fresh living right in your backyard. A newly poured driveway and a 50-AMP power pole with RV hookup round out the practical upgrades, making this move-in-ready retreat as functional as it is charming. With updated finishes, room to roam, and space to grow your own little homestead, this Chesapeake beauty is ready to welcome you home.

913 Long Ridge Road, Chesapeake

$305,000
2 Beds 1 Baths 10644942 MLS
Welcome home to this charming all brick ranch nestled in Brentwood Estates neighborhood. This well-maintained home offers the perfect combination of classic charm and thoughtful updates making it truly move-in ready. Inside you will find a beautifully updated bathroom. The kitchen provides abundant cabinetry, and the dining room has been enhanced with new windows, elegant chandelier creating a nice setting for family dinners. All appliances convey. Enjoy peace of mind with updated roof, windows (2017), along with a brand-new sidewalk, garage floor and driveway offering exceptional curb appeal. Step outside to a large, fully fenced backyard complete with a covered deck, an ideal space for relaxing, grilling and entertaining family & friends.

2209 Wildwood Road, Chesapeake

$499,895
4 Beds 2.1 Baths 10644750 MLS
Beautifully renovated and move-in ready, this spacious 4-bedroom, 2.5-bath home offers approximately 2,621 square feet, including an addition that provides extra living space. The open and inviting main level features fresh luxury vinyl plank flooring, updated lighting, and a bright sunroom. The updated kitchen offers granite countertops, stainless steel appliances, and attractive cabinetry. Upstairs, you’ll find four comfortably sized bedrooms with new carpeting and updated bathrooms featuring modern ceramic tile. The home is equipped with gas heat and central air conditioning on the first floor and a heat pump serving the second floor. Additional features include an attached garage, a generous lot, and a roof replaced approximately in 2021. Conveniently located in Western Branch near shopping, dining, schools, and major roadways with access throughout Hampton Roads. Schedule your showing and see all this home has to offer.

4257 Meadow Wood Drive, Chesapeake

$499,900
4 Beds 2 Baths 10644453 MLS
Charming ranch with large backyard and pool! Enjoy the welcoming front porch before heading inside to the thoughtfully updated interior, where fresh paint and beautiful new LVP flooring create a bright, inviting atmosphere. New carpet in the room above the garage adds comfort and versatility to the home's flexible living space. Designed for both everyday living and effortless entertaining, the home features a living room, dining room, and a cozy family room accented by wood beams and a fireplace. At the heart of the home, the eat-in kitchen offers all new sleek cabinetry, granite countertops, and stainless steel appliances. Four spacious bedrooms provide comfortable accommodations, while both full bathrooms have been refreshed with stylish new vanities. Outside, you're sure to enjoy the fully fenced backyard featuring a spacious deck overlooking the swimming pool creating an inviting setting for relaxing, entertaining, or enjoying warm summer days. Two storage sheds provide additional room for lawn equipment, tools, or hobbies, while the attached garage adds everyday convenience and extra storage.

403 Caravelle Court N, Chesapeake

$1,269,997
4 Beds 2.1 Baths 10644328 MLS
Custom 4,300+ sq ft estate on 3 private, wooded acres on historic Taft Rd., located in the Hickory/Grassfield school districts. Perfect blend of country living & city access. Inside features exceptional build quality, ornate plasterwork, dentil moulding, & dual staircases. The main level hosts a home office, living room with a wood fireplace, half bath, & a sunroom. The spacious kitchen boasts a center island & matte white cafe; appliances, leading to a laundry room & 2-car heated garage. Upstairs features 4 large bedrooms, including a primary suite with 2 walk-in closets & 3rd-floor access. 2 full baths feature luxury defogging mirrors. The 3rd floor is ideal for a 2nd living room/studio. Outside boasts a wrap-around porch, 32k-gal saltwater pool (new liner 2025; new pump/filter/salt cell 2026), Trex deck, heated 3-car detached garage with mini-split, carport, shed (new roof 2026), & pole barn. Features 400A service (200A panel), generator tie, & grill propane line. Move-in ready!

1741 Taft Road, Chesapeake

$224,000
2 Beds 1.1 Baths 10644391 MLS
Welcome home to this well-maintained 2-bedroom, 1.5-bath townhome nestled in the highly desirable Western Branch area of Chesapeake! Offering a low-maintenance lifestyle with no HOA fees, this home is an excellent opportunity for first-time homebuyers, those looking to downsize, or savvy investors seeking to add a solid rental property to their portfolio. Inside, you'll find a galley style kitchen with stainless steel appliances, LVP flooring, ceramic tile, and updated bathrooms. The fenced backyard provides space to relax, entertain, or enjoy your morning coffee, plus a storage shed for added convenience. Conveniently located near shopping, dining, top-rated schools, military bases, and major highways, this move-in ready home offers comfort, value, and an unbeatable location. Don't miss your chance to make it yours!

3204 Clover Road E, Chesapeake

$685,000
5 Beds 3 Baths 10643877 MLS
A Gem! Pristine condition all brick transitional on 1/3 acre cul de sac lot in Great Bridge. 5 bedrooms plus 1st floor 6th bedroom or office with ensuite. Open floor plan with huge updated kitchen (quartz counters), breakfast room and family room overlooking impeccably landscaped and treed backyard. Remodeled primary & hall bathrooms. 2 zone HVAC. Wood burning fireplace also plumbed for gas. Spacious family room, living and dining rooms, bedrooms and FROG. Screened porch with concrete floor. 2 car side loading garage with long driveway. Updates include windows, roof, 1st floor gas pack HVAC, garage door and leaf filter gutters. Award winning Cheshire Forest community. Amenities include clubhouse, pool, tennis/pickleball court, parks and playground. In-ground sprinkler system, appliances, and window treatments convey "as is". Home warranty.

810 Hedgerow Court, 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, Chesapeake

$700,000
4 Beds 3.1 Baths 10643713 MLS
Welcome home to this classic brick home tucked in a cul-de-sac, with comfortable living spaces, thoughtful updates, and a backyard made for enjoying Virginia summers. The main level offers inviting living and dining areas, a large bright kitchen with island seating, and an easy flow into the vaulted family room with skylights, a brick fireplace, and access to the deck and pool area. Upstairs, the spacious bedrooms offer flexibility for guests, hobbies, work, or everyday living. The primary suite features vaulted ceilings, generous closet space, and a large bath with a soaking tub set beneath a window-filled nook. Outside, enjoy an in-ground pool, deck space for relaxing or entertaining, mature landscaping, and a peaceful setting. Recent updates include new flooring, upstairs, HVAC, a new pool liner, an updated front door, refreshed lighting and fixtures, and new fencing. Come see all this home has to offer!

701 Aspen Forest Court, Chesapeake

$560,000
5 Beds 3.1 Baths 10642155 MLS
This beautiful home is perfect for multi-generational living, featuring 2 spacious primary suites—one located on the main level and another upstairs. The entertainer's kitchen is a standout, offering abundant granite countertop space, gas cooking, large pantry, and ample cabinetry for all your storage needs. Overlooks the family room and the expansive backyard. An additional flex room on the first floor provides endless possibilities such as a home office, fitness room, playroom, or hobby space. One of the largest lots in the neighborhood - more than one-third of an acre with a fully fenced backyard. The outdoor space is designed for everyday enjoyment, with patio pavers and room for a pool, garden, or play area. Other conveniences: Second floor laundry room. Two-car garage. Need to move before the new school year begins? We can make that happen!

2851 Crossings Drive, Chesapeake

$440,000
6 Beds 3 Baths 10643653 MLS
15K INSTANT EQUITY!!!!!!! A peaceful neighborhood in the Deep Creek area of Chesapeake with close water views and wooded scenery. This home is one of the largest homes, in the neighborhood, spacious bedrooms 6 & 3 full bathrooms. This home features a modern open layout with generous living areas and a well-appointed kitchen open for entertaining. 3 first-floor bedrooms and 1 full bath provide ideal flexibility for guests or multi-generational living while the other 3 to include the Primary bedroom on the second floor. The home has a new LVP life proof floors, New paint, New carpet, New two car driveway with a wrap around sidewalk and a generous size yard for gathering a outdoor activities. Flood Insurance of 880 yearly (Never floods) SOME CLOSING COST ASSISTANCE AVAILABLE.

421 Plummer Drive, Chesapeake

$299,000
3 Beds 2 Baths 10643657 MLS
Welcome home to this charming all-brick ranch offering the ease of one-level living! Move-in ready and full of warmth, this inviting home features an open-concept floor plan centered around a cozy brick wood-burning fireplace. Enjoy spacious living areas, generously sized bedrooms, and abundant closet space throughout. Recent updates include a newer roof, HVAC, hot water heater, and windows, providing peace of mind for years to come. Fresh paint, stainless steel appliances, and a private laundry room add to the home's appeal. Relax on the welcoming front porch and enjoy the convenience of easy access to the interstate, downtown Norfolk, military bases, shopping, dining, and entertainment. Just right for first-time buyers, downsizers, or anyone seeking low-maintenance living with timeless charm. Don't miss the incredible preferred lender incentives available to qualified buyers, making homeownership even more affordable. Schedule your private tour today!

609 Crystal Avenue, Chesapeake

$379,900
3 Beds 2 Baths 10643565 MLS
Welcome to one of Chesapeake's best opportunities! This well-maintained brick ranch offers 1,976 square feet of comfortable living space with 3 bedrooms, 2 full bathrooms, and an oversized 520-square-foot attached two-car garage. The updated kitchen features quartz countertops and beautifully refreshed cabinetry, while numerous major improvements have already been completed, including a newer roof, inverter heat pump, refurbished concrete driveway and walkway, updated awning, LeafGuard gutters, and professional foundation repair. Situated on a generous 0.30-acre lot with no HOA and no flood insurance required, this home offers exceptional value, thoughtful updates, and pride of ownership throughout. Schedule your private showing today!

420 Oaklette Drive, Chesapeake

$550,000
4 Beds 2.1 Baths 10643196 MLS
Welcome to this one of a kind custom all brick home designed for buyers who appreciate true craftmanship, architectural character, and timeless traditional design. Offering nearly 3000 sqft, 4 bedrooms and 2.5 baths, this home showcases features rarely found in newer construction, including a stunning wood spiral staircase, custom millwork, rich hardwood flooring, and 3 fireplaces that bring warmth and character throughout. This is not a builder grade flip or cookie cutter renovation, but a home built with quality, detail, and lasting charm. Outside, enjoy a private backyard retreat with a saltwater inground pool. Ideally located near local bases, shopping, dining, and major interstates, this is a rare opportunity to own a home with true character and lasting value.

913 Montebello Circle, Chesapeake

$295,000
2 Beds 1.1 Baths 10642955 MLS
Welcome home to this beautifully updated 2-bedroom, 1.5-bath townhome tucked away on a quiet cul-de-sac in desirable Las Gaviotas. Head inside to a spacious living area featuring a cozy brick fireplace, fresh finishes, and an inviting layout perfect for everyday living or entertaining. Recent improvements include fresh paint, new flooring, new carpet, an 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 bath, and a large hall closet for extra storage. Enjoy a private fenced backyard with a new deck, ideal for relaxing or entertaining. Conveniently located near shopping, restaurants, parks, major interstates, Chesapeake City Hall, and award-winning Grassfield schools, this move-in ready home is ready for its new owner.

300 San Roman Drive, Chesapeake

$775,000
4 Beds 3 Baths 10643343 MLS
Live the fresh life! Rarely does something this special come to market. Come see one of Western Branch's loveliest riverfront properties in an established neighborhood with no HOA. Designed for a lifetime of family fun and multigenerational living, this beautifully crafted 2-story on the Elizabeth River combines timeless elegance with all modern comforts. Through the soaring two-story foyer, you'll discover thoughtful details around every corner...signature hardwood floors, spa-like bathrooms, custom kitchen cabinetry, and more. A luxurious primary suite awaits you upstairs with its own balcony overlooking the pool. This lot has deep water access with beautiful views of the water. Relax in the saltwater pool during the hot summer days or relax in the hot tub for those cooler winter evenings. New roof (2025), water heater (2022), pool pump (2024), and salt cell (2026). A truly rare waterfront retreat.

3808 Stonebridge Landing, 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.