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$349,800
5 Beds ⋅ 2 Baths ⋅ 10642460 MLS
Discover one of the best values in Chesapeake! This spacious 5-bedroom, 2-bath home offers over 2,100 square feet of versatile living space with room for everyone. Recent updates include a newer roof, updated HVAC, replacement windows, luxury vinyl plank flooring, fresh paint, and updated lighting, providing peace of mind and modern appeal. The bright kitchen features ample cabinet and counter space, while the open living and dining areas are perfect for everyday living or entertaining. The flexible floor plan includes generously sized bedrooms, making it ideal for a growing family, multi-generational living, or those needing dedicated home office space. Outside, enjoy a large fenced backyard with plenty of room for pets, gardening, play, or future outdoor entertaining. Conveniently located near shopping, dining, military bases, major interstates, parks, and schools, this home offers an easy commute throughout Hampton Roads. With five true bedrooms, substantial square footage, and numerous updates, this home delivers exceptional value compared to other homes in its price range. Whether you're a first-time buyer looking for extra space or an investor seeking a strong opportunity, this property is ready for its next owner. Don't miss your chance to own one of Chesapeake's best buys—schedule your private showing today!

4205 Nautilus Avenue, Central Chesapeake
$452,900
3 Beds ⋅ 3.1 Baths ⋅ 10642448 MLS
Unbelievable Incentives! Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This tri-level Ashbury plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ upgraded quartz countertops & glass subway tile backsplash. Easily maintained & durable LVP flooring & crown molding, as well as 9-foot ceilings on all levels. Lighted tray ceiling in primary suite & double quartz vanity, ceramic tiled floor, & glass-enclosed shower w/ ceramic tile walls in en-suite. WIC. Enjoy exceptional amenities, including a start-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appointment.

4904 Apricot Way, West Chesapeake
$599,000
6 Beds ⋅ 4.1 Baths ⋅ 10642445 MLS
Rare opportunity to own a beautifully updated 6-bedroom, 4.5-bath home featuring a private, fully equipped in-law suite for multigenerational living, extended family, guests, rental income, or a private home office. The main residence offers 5 spacious bedrooms, 3 full baths, and a stunning remodeled kitchen with quartz countertops, sleek high-gloss cabinetry, stainless steel appliances, and space for a large center island. The separate in-law suite lives like its own home, complete with an open loft-style bedroom, 1.5 baths, walk-in closet, full-size laundry, upgraded kitchen with quartz counters and stainless appliances, and generous living space. Recent upgrades include renovated baths, new windows, patio doors, and Nest thermostats. Step outside to your backyard oasis featuring an 8-foot in-ground pool with newer liner, filter, and pump, plus a built-in deck bar ideal for entertaining. Conveniently located near shopping, dining, schools, military bases, beaches, and major commuter routes.

501 Thornloe Ln Lane, South Chesapeake
$550,000
5 Beds ⋅ 3 Baths ⋅ 10642122 MLS
Rare find in sought after neighborhood. Spacious and flexible floor plan features 5 bedrooms and 3 full baths, 4 closets in primary bedroom, huge family room and a flex room with fireplace that would be perfect for an office, library or study. Large back bedroom has its own entrance with easy, close access to full bath. Workshop has electricity. Well maintained by original owners. Make an appointment today to view this treasure and update to make it your own.

1213 Lakeford Place, South Chesapeake
$372,000
3 Beds ⋅ 2.1 Baths ⋅ 10642308 MLS
Well cared for 3 bedroom 2.5 bathroom hoe in sought after neighborhood of Knells Ridge/Oak Lake Estates Freshly painted, new deck, new LVP flooring in hall bathroom, LG smart washer 2024, ADT touchscreen smart alarm system 2024, google nest protect smart smoke & carbon monoxide detector 2024, LG smart dishwasher 2023, LG smart dryer 2021, LG smart refrigerator 2021, hot water heater 2021, ring pro door bell 2018, ecobee smart thermostat 2017, 2013 new roof, new patio door 2013 Condo/HOA fees include mowing of front yard and trimming of bushes, trash pick up and pool

208 Oak Grove Run, South Chesapeake
$358,000
3 Beds ⋅ 2 Baths ⋅ 10641627 MLS
Welcome home to this beautifully maintained property featuring a spacious, well appointed kitchen complete with granite countertops, stainless steel appliances, abundant cabinet storage, and generous counter space-perfect for everyday living and entertaining. The inviting living area boast soaring vaulted ceilings and an expansive open feel, creating the perfect space to relax or gather with family and friends. Outside you will find a large detached shed offering exceptional storage for tools, hobbies, or seasonal items. Conveniently located near shopping, dining, casino, parks and major roadways, this home combines comfort, functionality, and accessibility in an ideal location.

3916 Port Road, West Chesapeake
$450,000
10642036 MLS
Build-ready townhome development opportunity in Chesapeake! This 0.558-acre parcel is approved for 5 townhome units and offers a rare chance to step into an already entitled project. Zoned R-TH-1 with plans and approvals in place, saving valuable time and development costs. Appraisal, site plans, and renderings available. Great location with strong resale potential and easy access to major commuter routes.

2610 Elkhart Street, South Chesapeake
$457,195
4 Beds ⋅ 2.1 Baths ⋅ 10642211 MLS
Hurry! Under construction and ready for you to personalize interior selections! Located in The Retreat at Western Branch, a 55+ low-maintenance community. This light-filled Shenandoah is designed for everyday living and entertaining, featuring a kitchen that flows seamlessly into the great room. The first-floor includes a spacious primary suite, office, laundry room, and a two-car garage. The great room opens to a covered porch for additional outdoor living space. The 2nd floor offers a loft and three guest bedrooms. Live here and enjoy a clubhouse with billiards and a fitness center, pool, dog park, community garden, and beautifully landscaped grounds, all conveniently located near dining, shopping, and the interstate. Final price determined by buyer selected options.

4609 Longleaf Place, West Chesapeake
$524,900
3 Beds ⋅ 2 Baths ⋅ 10642197 MLS
Recently appraised at $600k, opportunities for instant equity like this are rare. Situated on 5 acres in Chesapeake's Grassfield High School district, this move-in-ready 3-bed, 2-bath home features a 720 sq. ft. detached, fully powered workshop—great for a contractor or hobbyist. Located near Deep Creek Park and the Dismal Swamp Canal Trail, enjoy peaceful surroundings, deer sightings, and views of sailboats on the Intracoastal Waterway. A 2012 renovation opened the layout, updated the kitchen and baths, and added central duct HVAC. Recent improvements include a new 3-ton heat pump (2023), whole-house paint (2024), new carpet (2025), and new utility room vinyl flooring, plus upgraded electrical, plumbing, and replacement windows. Outdoors features a fenced yard with mature fruit and fig trees throughout the property. Motivated seller facing an unexpected military relocation (PCS). Contact agent for more information!

317 George Washington Highway S, South Chesapeake
$430,000
4 Beds ⋅ 2.1 Baths ⋅ 10641959 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
$543,740
2 Beds ⋅ 3 Baths ⋅ 10641942 MLS
The Asheville, one of our quad-style homes, features two bedrooms, a large bonus room and 3 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. Incentives with use of preferred lender! Photos and renderings are from builder's library, actual finishes and features may vary. Photos and renderings are from builder's library, actual finishes and features may vary.

2162 Edwin Drive, South Chesapeake
$349,900
4 Beds ⋅ 2.1 Baths ⋅ 10641818 MLS
Welcome to this spacious two-story home offering a fantastic layout and incredible potential! The first floor features a formal living room, separate dining room, a cozy den, and a convenient half bath. Upstairs, you will find three comfortably sized bedrooms alongside a primary suite complete with its own private en suite bath. Excellent storage and parking are provided by the attached two-car garage. Situated in a prime location just minutes from shopping, local dining, entertainment, major interstates, and area bases. This property is a wonderful opportunity to bring a little elbow grease, add your personal touches, and truly make it your own. Call today to schedule your private showing! Some virtual staging utilized in pictures.

844 Parapet Road, South Chesapeake
$525,000
5 Beds ⋅ 3.1 Baths ⋅ 10641817 MLS
Tucked away on a quiet end street shared by only three other homes, this brand new construction offers a rare sense of privacy while still being close to everything Western Branch has to offer. With minimal traffic and a park-like setting, it’s the kind of place where evenings are quiet, kids can play outside, and home truly feels like a retreat. Inside, this thoughtfully designed 5 bed, 3.5 bath home is built for both comfort and flexibility. The open concept living area flows effortlessly into a spacious, modern kitchen. A 1st floor primary bedroom provides the ease of main level living, while a 2nd floor owner’s suite creates the ideal private escape or multi-generational option. Additional highlights include a two car attached garage, generous bedroom sizes, and beautifully planned finishes throughout all while located within the sought after Western Branch school district. You’re not just purchasing new construction - you’re securing space, privacy, flexibility, and a lifestyle.

5041 Queen Street, West Chesapeake
$525,000
5 Beds ⋅ 3.1 Baths ⋅ 10641815 MLS
Tucked away on a quiet end street shared by only three other homes, this brand new construction offers a rare sense of privacy while still being close to everything Western Branch has to offer. With minimal traffic and a park-like setting, it’s the kind of place where evenings are quiet, kids can play outside, and home truly feels like a retreat. Inside, this thoughtfully designed 5 bed, 3.5 bath home is built for both comfort and flexibility. The open concept living area flows effortlessly into a spacious, modern kitchen. A 1st floor primary bedroom provides the ease of main level living, while a 2nd floor owner’s suite creates the ideal private escape or multi-generational option. Additional highlights include a two car attached garage, generous bedroom sizes, and beautifully planned finishes throughout all while located within the sought after Western Branch school district. You’re not just purchasing new construction - you’re securing space, privacy, flexibility, and a lifestyle.

5036 Queen Street, West Chesapeake
$310,500
3 Beds ⋅ 2.1 Baths ⋅ 10641664 MLS
Welcome home to this beautifully maintained 2-bedroom condo featuring an open and functional floor plan. The spacious primary suite offers a private sitting area and an ensuite bath with a separate soaking tub and shower. A versatile first-floor media room or office provides the perfect space for working from home, entertaining, or relaxing. The gourmet kitchen boasts ample cabinetry, generous counter space, and a walk-in pantry. Enjoy low-maintenance living with HOA amenities that include a clubhouse, pool, water, and grounds maintenance. Schedule your private showing today!

2409 Leytonstone Drive, West Chesapeake
$569,900
4 Beds ⋅ 3 Baths ⋅ 10641728 MLS
Welcome to The Dogwood in Jolliff Landing, one of the community’s most sought after floor plans offering the perfect blend of luxury, flexibility, and everyday comfort. This beautifully designed ranch features 4 bedrooms, 3 full baths, and 2 true primary suites including a spacious upstairs FROG suite with its own private full bath ideal for multigenerational living, guests, a private retreat, office, or media space.Why wait on new construction when this move in ready home already offers the upgrades, space, and versatility buyers are searching for? The open concept design is perfect for entertaining while the resort style community amenities including a clubhouse, pool, playgrounds, sports field, and scenic sidewalks create a lifestyle buyers fall in love with.In a neighborhood full of inventory, this layout stands apart. Schedule your private tour today before this opportunity is gone.

5103 Annapolis Drive, West Chesapeake
$404,900
3 Beds ⋅ 3.1 Baths ⋅ 10641733 MLS
Now preselling by appointment. Estimated early 2027delivery. The Caldwell plan offers a first-floor bedroom suite with flex space and one-car garage. 2 spacious owner suites are on the 3rd floor with convenient 3rd floor laundry. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. Community will feature pool, playground, dog park and grilling stations, all surrounded by a protected forested area and conveniently located just 2 miles from Virginia Beach. Seller to pay up to $8,000 in closing cost assistance when using preferred lender, see agent for details. Special presale incentive: Receive a $15,000 anyway allowance to use at buyer's discretion when using seller's preferred lender, listed price reflects allowance taken off base price, see agent for details. Photos & video are of previous model, for illustrative purposes, finishes and upgrades vary in actual home to be built.

657 Allery Road, South Chesapeake
$399,900
2 Beds ⋅ 2.1 Baths ⋅ 10641732 MLS
Now preselling by appointment. The Bristol plan offers 2 spacious owner suites on 3rd floor with convenient 3rd floor laundry. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. First floor flex space with 2-car rear-loading garage. Community will feature pool, playground, dog park and grilling stations, all surrounded by a protected forested area and conveniently located just 2 miles from Virginia Beach. Seller to pay up to $8,000 in closing cost assistance when using preferred lender, see agent for details. Special presale incentive: Receive a $15,000 anyway allowance to use at buyer's discretion when using seller's preferred lender, listed price reflects allowance taken off base price, see agent for details. Photos & video are of previous model, for illustrative purposes, finishes and upgrades vary in actual home to be built.

670 Allery Road, South Chesapeake
$394,900
2 Beds ⋅ 2.1 Baths ⋅ 10641729 MLS
Now preselling by appointment. The Bristol plan offers 2 spacious owner suites on 3rd floor with convenient 3rd floor laundry. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. First floor flex space with 2-car rear-loading garage. Community will feature pool, playground, dog park and grilling stations, all surrounded by a protected forested area and conveniently located just 2 miles from Virginia Beach. Seller to pay up to $8,000 in closing cost assistance when using preferred lender, see agent for details. Special presale incentive: Receive a $15,000 anyway allowance to use at buyer's discretion when using seller's preferred lender, listed price reflects allowance taken off base price, see agent for details. Photos & video are of previous model, for illustrative purposes, finishes and upgrades vary in actual home to be built.

674 Allery Road, South Chesapeake
$498,000
4 Beds ⋅ 2.1 Baths ⋅ 10641660 MLS
Come check out this amazing well kept two story home in the heart of Greenbrier. Conveniently located to shopping, restaurants, parks, military bases and major interstates. Roof was replaced in 2015, HVAC in 016, gutter and vinyl wrap in 2017, master shower replaced in 2022. Home features a huge master bedroom sitting area as a bonus complete with an additional fireplace! Outside folks will love the proximity to the Chesapeake City Park!Romantic gas fireplace in primary suite and more!

527 Windward Drive, South Chesapeake
$439,900
3 Beds ⋅ 3.1 Baths ⋅ 10641594 MLS
Unbelievable Incentives! Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This tri-level Ashbury plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ upgraded quartz countertops & subway tile backsplash. Easily maintained & durable LVP flooring & crown molding throughout 1st level. Lighted tray ceiling in primary suite & double quartz vanity, & glass-enclosed shower in en-suite. WIC. Enjoy exceptional amenities, including a start-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appointment.

4906 Apricot Way, West Chesapeake
$494,900
4 Beds ⋅ 2.1 Baths ⋅ 10641167 MLS
Welcome home to Wellington! This spacious 4-bedroom, 2.5-bath traditional home offers over 2,300 square feet of comfortable living space with room to spread out. The inviting family room features a gas fireplace, while the kitchen boasts newer appliances, abundant cabinet space, an open pantry, and a separate pantry closet for exceptional storage. Upstairs, the large primary suite includes two walk-in closets. Flooring throughout includes luxury vinyl plank, ceramic tile, and carpet.Enjoy outdoor living on the large deck overlooking the fully privacy-fenced backyard. An oversized 2-car garage and generous driveway provide plenty of parking and storage. Major updates have already been completed for added peace of mind, including a roof with covered gutters installed in 2020 and several recently replaced windows. Conveniently located in the desirable Wellington neighborhood of Chesapeake, this home is ready for its next owner.

3614 Elkton Drive, West Chesapeake
$559,000
4 Beds ⋅ 2.1 Baths ⋅ 10641342 MLS
Spacious Riverwalk home offering over 3,372 sq. ft. with 4 bedrooms, 2.5 baths, a two-car garage, 2 decks with private views of the lake. Recent improvements include gas HVAC in 2022, roof approximate 6 years old, Anderson windows with warranty, and new kitchen appliances. Large family room and kitchen - great for everyday life and easy hosting. Enjoy Riverwalk amenities including clubhouse, pool, playgrounds, and tennis courts. A wonderful opportunity to personalize a spacious home in a sought-after Chesapeake community. Close to the Hospital, Dining, Shopping and Interstates. Home needs TLC. Buyer can make it their own.

220 Marsh Island Drive, South Chesapeake
$420,000
4 Beds ⋅ 2.1 Baths ⋅ 10640779 MLS
Welcome home to Knells Ridge! This 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and convenience. Inside, you’ll find a functional layout designed for everyday living, while outside, the spacious backyard provides endless possibilities for entertaining, family gatherings, or simply relaxing after a long day. Conveniently located near shopping, dining, parks, schools, and major commuter routes, this property offers a wonderful opportunity to make it your own and create the home you’ve been dreaming of.

371 Knells Ridge Drive, South Chesapeake
$410,000
4 Beds ⋅ 2.1 Baths ⋅ 10641084 MLS
Welcome home to this beautifully maintained 4-bedroom, 2.5-bath home in Chesapeake! Built in 2018, this two-story residence offers over 2,000 sq ft of modern living space. The open-concept layout features a bright living area that flows into the dining space and kitchen—perfect for entertaining or relaxing at home. Upstairs includes four spacious bedrooms, highlighted by a private primary suite with a spa-like bath and ample closet space. Additional rooms offer flexibility for guests, a home office, or playroom. Situated on a corner lot in an established neighborhood, this home provides both privacy and convenience. Close to shopping, dining, major interstates, and military bases. Move-in ready and full of charm—don’t miss this Chesapeake gem!

4101 2nd Street Unit A, Central Chesapeake
$419,900
3 Beds ⋅ 2.1 Baths ⋅ 10641328 MLS
This end unit townhome has been meticulously cared for by the original owners since purchasing it new in 2023. From the welcoming foyer, LVP flooring throughout the 1st floor leads to a stunning great room, which flows nicely into the dinette and gourmet kitchen that provides abundant counter space for all your kitchen storage needs. Upstairs, 3 spacious bedrooms and 2 full bathrooms provide privacy and comfort. Your luxurious owner’s suite includes tray ceilings, a generous sized walk-in closet, a double vanity sink and large stand up shower. When you live in Cardinal Meadows, you’ll love the easy access to Route 17, Cedar Road, I-64 and I-464, not to mention being located right off Cahoon Parkway puts you just minutes away from all your shopping needs at Cahoon Commons.

1607 Songbird Lane, South Chesapeake
$550,900
4 Beds ⋅ 2.1 Baths ⋅ 10641029 MLS
This traditional floor plan offers 4 Bedrooms, 2.5 Baths, and 2420 sq ft. Enjoy the grand design of the Primary Suite with a spacious Walk-In Closet from the Primary Bath. The dining room, kitchen & family room on the first floor allow for many entertaining evenings at home. The open floor plan provides ample space with room to stretch out. 2nd floor is spacious with 4 bedrooms & utility room. The Estates at Jolliff Landing will be a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and a tree-lined sidewalks. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

2206 Wilmington Avenue, West Chesapeake
$539,900
4 Beds ⋅ 2 Baths ⋅ 10641024 MLS
A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch-style living with 4 bedrooms, including a large finished room over the garage. From the front porch to the Family Room also open to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, a community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your doorstep in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details, as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5 pm at 5023 Annapolis Drive.

2204 Wilmington Avenue, West Chesapeake
$550,900
4 Beds ⋅ 2.1 Baths ⋅ 10641022 MLS
This traditional floor plan that offers 4 Bedrooms, 2.5 Baths, and 2400+ sq ft. Enjoy the grand design of the Primary Suite with a spacious Walk-In Closet from the Primary Bath. The dining room, kitchen & family room on the first floor allow for many entertaining evenings at home. The open floor plan provides ample space with room to stretch out. 2nd floor is spacious with 4 bedrooms & utility room. The Estates at Jolliff Landing will be a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and a tree-lined sidewalks. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

2205 Hampton Road, West Chesapeake
$553,900
3 Beds ⋅ 3 Baths ⋅ 10641052 MLS
Enjoy peaceful country living on 1.77 acres in the highly sought-after Hickory School District! This charming 3-bedroom, 3-full-bath home offers plenty of space both inside and out, making it perfect for those seeking privacy, comfort, and room to roam.Step inside and discover a welcoming open layout designed for everyday living and entertaining. The spacious heated sunroom deck provides the perfect spot to relax year-round. Huge pantry storage room off kitchen to keep those grocerie store runs to a minimum. The expansive 1.77-acre lot includes a chicken coop, large detach garage, fenced area, carport, and open fields making this property ideal for hobby farmers, homesteaders, or anyone looking to embrace a more self-sufficient lifestyle. With plenty of room for gardening, recreation, and outdoor activities, the possibilities are endless. The back half of detached garage needs work, but has lots of potential for a nice workshop, game room, mancave, apartment, etc.

2420 Mount Pleasant Road, 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.