Refine Search
Sort by
$554,718
4 Beds 2 Baths 10645495 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 3% CCA (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.

2207 Hampton Roads Parkway, West Chesapeake

$574,900
4 Beds 2.1 Baths 10645491 MLS
Located in the Hickory school district, the home is less than one mile from the interstate and just minutes from the shopping, dining, and everyday conveniences of Edinburgh. With its bright interior, flexible layout, generous outdoor space, and convenient location, this home is ready to welcome its next owners. Tucked along a quiet, tree-lined street, this beautifully updated home offers a light, welcoming atmosphere and plenty of space to enjoy. Natural light fills the thoughtfully refreshed interior, creating bright and comfortable living spaces throughout. At the heart of the home is an inviting kitchen featuring stone countertops, newer cabinetry, stainless steel appliances, and durable LVT flooring—perfect for everyday living and entertaining. The spacious fourth bedroom above the garage offers wonderful flexibility as a home office, gym, playroom, guest suite, or private retreat. Outside, the expansive backyard provides plenty of room for gatherings, gardening, play, or simply relaxing beneath the open sky. The home also features a long list of valuable improvements, including PEX plumbing in place of the original polybutylene, an upgraded electrical panel, replacement of most windows, updated lighting and flooring, select exterior doors, siding, and trim. A private well serves the irrigation system, and the roof was replaced in 2014.

712 Woodcott Drive, South Chesapeake

$575,000
4 Beds 2.1 Baths 10645393 MLS
Premium location in one of Western Branch’s most sought-after neighborhoods & schools. Beautiful, manicured homes w/large lots & no homeowner’s association. Just minutes to 664 & ALL of Hampton Roads Military bases, shopping & entertainment and medical facilities. Step inside to a welcoming foyer that leads to a formal dining room, living room and a custom kitchen with an Island. The sunken den features a gas fireplace which exits to a multi-level deck for cookouts and entertaining. The upstairs features a primary suite for a private retreat with an en-suite bath, a large walk-in closet for keeping all your items organized, while two additional bedrooms (all with walk-in closets) provide versatility for guests or even a game (flex) room. In addition, a 4th bedroom is located over the 576 SQFT. Attached garage. New interior paint and carpet, move in ready. Some rooms virtually staged.

1416 Pine Grove Lane, West Chesapeake

$584,900
5 Beds 2.1 Baths 10645337 MLS
A versatile floor plan with ample space for entertaining! Tha Palm offers 5 Bedrooms , 2.5 Baths, a large Family room, open to the kitchen, all BR's on 2nd floor, large patio space for outdoor living. A desirable Primary Suite bath & walk-in closet.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.

2202 Wilmington Avenue, West Chesapeake

$315,000
3 Beds 1 Baths 10645059 MLS
This lovely 3 bedroom/1 bath abode is fresh, charming and a perfect fit for the whole family! Enjoy the benefits of solar panels that keep energy costs low. The spacious backyard is ideal for curious kids to explore, energetic pups to play fetch or a small-scale gardener’s dreams to come true. Gorgeous warm wooden cabinets , coffee bar, custom island , pantry and gas stove create a luxurious feel in this gourmet kitchen. Enjoy time in the open family room complete with striking wood flooring, a cozy and comfortable space for family movie nights and memory making, find a bonus room that offers endless possibilities creates a cozy playroom, a productive home office or transform it into an extra bedroom. Take comfort in the attractive brick exterior of the home as it’s sure to stay tidy and effortless to maintain for years to come. Check out this wonderful opportunity to live the good life in Chesapeake!

3944 Port Road Road, Central Chesapeake

$645,000
4 Beds 2.1 Baths 10645288 MLS
To Be Built - Financing 5.75 rate, NO PMI! Joseph’s Meadow MODEL GPS 369 Scotland Ln. Chesapeake. Nestled in Greenbrier come visit the newest community by renowned local builder. Lily Cottage welcomes you w/ a full front porch, soaring 10-foot ceilings, & beautiful hardwood floors throughout the first floor. Designed for entertaining, the open-concept layout seamlessly connects the living room, dining area, & stunning chef’s kitchen featuring a 9-foot quartz island, custom hood, & oversized walk-in pantry. Mudroom & powder room are conveniently tucked away by 2-car garage. Upstairs, a sun-filled loft, two spacious bedrooms, loft (opt 4th), & a large laundry room provide exceptional functionality. The private primary suite offers a custom walk-in closet & spa-inspired bath w/ quartz countertops, dual vanities, freestanding tub, tiled shower, & private water closet. Easy living with professionally managed grounds ensures low-maintenance living, making your dream truly a peaceful haven.

365 Scotland Lane, South Chesapeake

$285,000
2 Beds 2.1 Baths 10645264 MLS
This beautifully updated 2 bedroom, 2.5 baths, 2 story condo features 2 full primary ensuite bedrooms w/updated bathrooms including new sinks, counter, vanities, lighting, & toilets. In addition, brank new LPV flooring, new upgraded carpet 2nd floor, fresh paint throughout, new kitchen cabinets, new granite counters and new stainless-steel appliances create a clean and modern feel. There is a reserved parking spot plus plenty of visitor parking. Enjoy maintenance free living with condo fees, that include access to clubhouse, community pool maintenance & trash pickup. Convenient Greenbrier location near shopping, dining, easy I-64 access. This move-in ready home offers comfort and convenience and makes this home a must see!

2351 Old Greenbrier Road, Central Chesapeake

$9,900
10645258 MLS
Lot 100 Farmington Acres, approximately 0.36ac. Lot is located at 3509 Sigmon Dr. which is a paper street. 150' in from where Newport Dr. currently stops then turn right onto Sigmon Dr. heading back North approximately 300'. A gorgeous lot, will require improvements including but not limited to: wetlands delineation, and improvement of Newport Dr. and Sigmon Dr. to city standards before construction, lot is priced accordingly.Fantastic opportunity for sweat equity, or buy and hold as part of diversifying your investments or long term retirement. The property is minutes away from the booming North Suffolk area. Neighborhood also borders the north side of the gorgeous Retreat at Western Branch Subdivision as well as the Dunedin neighborhood.Don't miss the chance to scoop up your piece of Western Branch now at a discount!Please be mindful of neighbors when parking on Newport Dr. to view. Call listing agent with any questions!

3509 Sigmon Drive, West Chesapeake

$577,740
3 Beds 3 Baths 10645211 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2166 Edwin Drive, South Chesapeake

$629,900
4 Beds 2.1 Baths 10645157 MLS
BUY THIS AWESOME HOME, WE'LL BUY YOURS!* Welcome to your low-maintenance luxury retreat in the sought-after 23322 zip code! This beautifully designed 4-bedroom, 2.5-bath home offers 2,598 sq ft of stylish, comfortable living with minimal upkeep. The highlight is the exceptional outdoor living space—a 529 sq ft covered, screened patio with premium epoxy flooring for entertaining, outdoor dining, or relaxing in privacy. An additional patio and custom walkway are surrounded by professionally landscaped, easy-care grounds. Enjoy a true lock-and-leave lifestyle with an HOA that maintains the front yard, giving you more time to enjoy life instead of yard work. Resort-style community amenities while shopping, dining, parks, and major commuter routes are all nearby. This home offers the perfect blend of luxury, convenience, and carefree living.

1910 Briton Lane, South Chesapeake

$568,000
4 Beds 2.1 Baths 10645016 MLS
*Seller to contribute an amount of $7K toward the Buyer's allowable closing costs and prepaid expenses subject to lender guidelines with an acceptable offer.* Welcome to this beautifully maintained 4-bedroom, 2.5-bath home offering an open-concept floor plan designed for comfortable everyday living and effortless entertaining. Conveniently located near shopping, dining, and with easy interstate access, this home combines comfort with convenience. Relax and unwind on the spacious deck while enjoying peaceful views of the pond and the surrounding wildlife. The generous primary suite features a large walk-in closet, providing plenty of storage space. The well-appointed kitchen includes a gas range, a large pantry, and ample workspace for cooking and gathering. Located in the highly sought-after Chesapeake School District, this home also offers numerous valuable upgrades, including a new roof (2024), HVAC system (2024), and water heater (2021). Additional features include solar panels for energy efficiency, an irrigation system with a dedicated well, a security system, and the washer and dryer, all of which convey with the home.

1311 Piedmont Arch, South Chesapeake

$735,000
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, South Chesapeake

$16,500
10645088 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 9 Tuck Street, South Chesapeake

$16,500
10645087 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 8 Tuck Street, South Chesapeake

$16,500
10645086 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 7 Tuck Street, South Chesapeake

$16,500
10645083 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 6 Tuck Street, South Chesapeake

$16,500
10645082 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 5 Tuck Street, South Chesapeake

$16,500
10645001 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 4 Tuck Street, South 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, South Chesapeake

$524,500
4 Beds 3 Baths 10644867 MLS
Welcome home to this beautiful Craftsman-style ranch in highly desirable Culpepper Landing! This spacious 4-bedroom, 3-bath home offers approximately 2,380 square feet of thoughtfully designed living space with an open floor plan, soaring 10-foot ceilings, hardwood floors, upgraded trim, and surround sound in the living room. The gourmet kitchen features granite countertops, custom cabinetry, a large center island with bar seating, and ample storage—perfect for large families or entertaining. The first-floor primary suite offers a tray ceiling, walk-in closet, and an ensuite bath with double vanities, a garden tub, and a tiled walk-in shower. A finished room over the garage with a full bath and walk-in closet provides the perfect guest suite, home office, or flex space. Enjoy relaxing on the inviting front and side porches or entertaining on the rear deck. Additional features include a two-car attached garage, sprinkler system, and garage door opener with a transferable warranty and MyQ smart access for convenient remote operation and secure package delivery. Inground Sprinkler System has recently been inspected, a new back flow preventer was added and sprinkler heads relocated to accommodate a future fence. Interior professionally painted, new easy open window blinds installed thoughout w/4 yr warranty (2025). Located across from the neighborhood dog park, Culpepper Landing offers outstanding amenities including a clubhouse, community pool, fitness center, playgrounds, and walking trails, all with convenient access to shopping, dining, military bases, and major interstates.

3209 Dodd Drive, South Chesapeake

$325,000
3 Beds 1.1 Baths 10644798 MLS
Own A Piece Of "Country Living" In "The City!" Original Farmhouse Type Home Situated On Approx. 2 Acres - Very Unusual Lot! Really Private Setting! Home Needs Renovating...Has Lots Of Potential! Located Off Shell Rd. (Firman St) With Flag Driveway To Back Of Properties. HVAC System 2 Years Old, Roof Approx 16 Years Old, 3 Bedrooms, 1 Bathroom Upstairs, Half Bath Downstairs. Good Sized Kitchen With Real Knotty Pine Cedar Cabinets! Laundry Room Off Kitchen. French Doors Into Living Room And Columns Into Dining Room. Original Hardwood Floors Downstairs. Just A Charming House...Needs Renovation! Huge "Pie Shape" Additional Lot...All On One Deed. Interested In Building Another Dwelling? Look Up The New Senate Bill 531 Which Requires All Localities To Allow Assessory Dwelling Units (ADVs) "By Right" In Single Family Residential Zones...It Might Apply! Buyer Would Do Their Own Due Diligence On This Property.

772 Shell 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.