Refine Search
Sort by
1329 Penrose Lane, South Chesapeake
$680,000
4 Beds ⋅ 3 Baths ⋅ 10633884 MLS
Custom-built and thoughtfully upgraded, this 4-bedroom, 3-bath ranch offers over 2,300 square feet of refined single-level living in Chesapeake. The open layout features updated finishes throughout, including a well-designed kitchen with granite countertops, stainless steel appliances, custom cabinetry, and generous prep space. The primary suite includes a private office or flex space for remote work, fitness, or a quiet retreat. A rare standout in this market, the property offers SIX total garage spaces with both an attached 2-car garage and an insulated detached garage/workshop complete with mini-split HVAC, loft storage, multiple 30-amp and 240V receptacles, and new deck just completed in 2025. Additional upgrades include a tankless water heater with recirculation system, generator hookup with lockout switch, LED lighting, surround sound wiring, alarm system, and oversized gutters. Centrally located near shopping, dining, and major roads. Parking space for your boat/RV and no HOA!

1329 Penrose Lane, South Chesapeake

1620 Great Bridge Boulevard, South Chesapeake
$370,000
5 Beds ⋅ 3 Baths ⋅ 10642924 MLS
Step Inside This 5 Bedroom 3 Bath Home! It Features A Desirable First-Floor Bedroom With En Suite, Great For An Office Or In-Law. The Spacious Family Room, Highlighted By A Cozy Fireplace, Opens To The Kitchen, Creating An Easy, Open Flow That's Perfect For Everyday Living And Gathering With Family And Friends. The Thoughtfully Designed Floor Plan Includes A Well-Appointed Kitchen, Generously Sized Bedrooms, And Inviting Indoor And Large Outdoor Spaces For Relaxing Or Entertaining. A Convenient Utility Room With A Large Pantry Provides Plenty Of Storage And Helps Keep Daily Routines Organized. Ideally Situated Near Shopping, Dining, Parks, Sought After Great Bridge High School District, And Major Interstates, This Home Offers The Perfect Combination Of Comfort, Functionality, And A Convenient Location.

1620 Great Bridge Boulevard, South Chesapeake

1025 Calloway Avenue, South Chesapeake
$145,000
2 Beds ⋅ 1 Baths ⋅ 10642815 MLS
Investor Special! Selling completely “as is”. Seller to do NO repairs. All contents of house, attic and yard convey to buyer at closing. HVAC is approximately 10 years old. Roof is approximately 8 years old. Gas Water heater new in 2025. Floored attic space. Cash or Renovation Loans only. Buy it, renovate it (cost to renovate estimate approximately $50k) and live there! Or fix it and flip it and make some moola! Probable value after renovations $200k or more. Nice sized fenced yard. Many newer homes on the street. Buy it, renovate it and rent it out! Great income producing potential. Or, knock it down and build a whole new house! You decide! Priced well below city assessed value. Hurry! This one won’t last.

1025 Calloway Avenue, South Chesapeake

912 Oklahoma Drive, South Chesapeake
$349,900
3 Beds ⋅ 2 Baths ⋅ 10641097 MLS
Exceptionally rare oversized lot offering space and flexibility rarely found with typical 3-bedroom homes. Ideal for business owners, contractors, or hobbyists needing room for equipment, additional vehicles, or future expansion. The property offers excellent potential to build a two-story detached garage or create a customized workspace. A powered workshop is already in place, adding immediate function and convenience. The home was thoughtfully renovated prior to the current owner, providing a solid foundation for comfortable living with room to personalize. Enjoy an expansive circular driveway, allowing easy access for multiple vehicles, trailers, or equipment. Conveniently located minutes from the interstate, shopping, and daily essentials, while still situated in a charming community known for its character and appeal. This is not just a home—it’s an opportunity to secure space with lots of options.

912 Oklahoma Drive, South Chesapeake

2261 Shipyard Road, South Chesapeake
$260,000
3 Beds ⋅ 1 Baths ⋅ 10640981 MLS
INVESTOR ALERT! Rare opportunity to own 2.5 acres in the heart of Chesapeake with city water and city sewer already in place. Opportunities like this are becoming increasingly difficult to find, especially in one of Chesapeake’s fastest growing corridors. This 3 bedroom, 1 bathroom home with a screened front porch is ready for its next chapter. Whether you’re looking to renovate, expand, hold as a long term investment, or capitalize on the land itself, the possibilities are endless. Location is everything, and this property delivers. Conveniently located near Deep Creek and Grassfield, you’ll enjoy quick access to major interstates, Route 17, Route 168, shopping, restaurants, shipyards, military installations, and major employment centers throughout Hampton Roads. The property is also zoned for the highly sought after Grassfield High School, Hugo A. Owens Middle School, and Deep Creek Central Elementary School, adding long term appeal for future homeowners and tenants alike. Surrounded by continued residential growth and new development, this is the type of opportunity investors have been waiting for. Large acreage properties with public utilities in Chesapeake are few and far between. Bring your vision, your contractor, and your plans because the potential here is undeniable. Cash or rehab loan only. Property is being sold as is.

2261 Shipyard Road, South Chesapeake

2204 Battery Park Road, South Chesapeake
$275,000
2 Beds ⋅ 1 Baths ⋅ 10640829 MLS
Come see this charming and well-maintained brick ranch on a large lot in the idyllic neighborhood of Brentwood, where the homes are quaint and yards are well-established and inviting. Original hard wood floors throughout the living area and bedrooms, and tile in the kitchen and bath. This home has been thoughtfully updated to promote a clean living environment and protect the home: HVAC with UV light air purifier, tankless natural gas water heater, and whole house water filtration system are all approximately 4 years old. Roof is 7 years old. Kitchen was updated about 5 years ago with granite countertops and stainless-steel appliances (range is new). New walk-in shower installed about 3 years ago for ease, safety and an updated look. The interior of the home has also been freshly painted. The large back yard offers plenty of space for pets, entertaining, games and time around the fire pit. Large, detached garage with room for 1 car, storage for toys or for use as a workshop.

2204 Battery Park Road, South Chesapeake

2839 Lambert Trail, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10640055 MLS
Welcome home to this charming ranch tucked away on a quiet street, offering comfort, functionality & an incredible backyard retreat. Designed for relaxing & entertaining, the backyard features lush banana trees, tranquil koi pond w/ waterfall, hot tub, paver patio ideal for grilling, fire pit area w/ pavers & space for seating - all surrounded by a full privacy fence. Impressive 2 story detached garage complete w/power, workbenches & upstairs storage. Featuring 3 bedrooms & 2 full baths the layout provides spacious living. Oversized kitchen w/ abundant counter space, large eat-in area w/backyard views. Converted garage creates second den, flex space, laundry, attic storage access. Expanded driveway offers plenty of parking. Relax on the welcoming front porch, unwind in the backyard, enjoy the comforts throughout the property.

2839 Lambert Trail, South Chesapeake

504 Bonsack Court, South Chesapeake
$580,000
4 Beds ⋅ 2 Baths ⋅ 10638636 MLS
Check out this cream puff! Beautifully maintained and thoughtfully updated, this standout home in sought-after Pines of Warrick is ready to impress. Situated on an oversized lot, the backyard is an entertainer's dream with a sparkling in-ground pool and plenty of space to relax and unwind. Gorgeous hardwood floors flow throughout the first floor. The expanded primary suite features two closets and a beautifully updated bath with dual vanities, a walk-in shower, and oversized soaking tub. Updated kitchen and baths offer timeless appeal. The FROG provides a flexible fourth bedroom, office, or media room, while abundant storage includes a floored attic. Meticulously maintained and move-in ready, this is the one you've been waiting for in Great Bridge!

504 Bonsack Court, South Chesapeake

964 Saint Andrews Reach Unit B, South Chesapeake
$212,500
1 Beds ⋅ 1 Baths ⋅ 10638379 MLS
Tucked away in the sought-after Saint Andrews Condos of Greenbrier, this inviting 1-bedroom, 2-story home with a loft blends comfort, style, and convenience. Set back from the street for added privacy and just moments from the golf course and everyday amenities, it’s an easy fit for low-maintenance living.Step inside to a bright, airy first floor with a vaulted ceiling opening to the loft, creating a spacious, contemporary feel. The refreshed kitchen makes meal prep a pleasure, while the upstairs primary suite offers a true retreat with its own full bath, a separate vanity area, and an in-unit laundry nook for effortless routines.Fresh paint throughout gives the home a crisp, move-in-ready finish. Condo fees cover water, sewer, and trash—so you can spend more time enjoying the neighborhood and less time on chores. A smart, stylish choice in a prime Greenbrier location.

964 Saint Andrews Reach Unit B, South Chesapeake

2241 Tennessee Drive, South Chesapeake
$349,000
3 Beds ⋅ 2 Baths ⋅ 10637273 MLS
Welcome to this beautifully updated, move-in-ready ranch home blending modern style with exceptional functionality. Step inside to find stunning new flooring, fresh paint, a brand-new water heater, and beautifully updated bathrooms with custom tile work. The gourmet kitchen is a chef’s dream, featuring white shaker cabinets, sleek stone countertops, and stainless steel appliances.Outside, the property sits on a spacious double lot featuring a unique detached screened patio, perfect for seasonal outdoor enjoyment. Car enthusiasts and mechanics will love the impressive 625-square-foot detached garage, complete with two brand-new doors. One door is oversized, and the reinforced concrete flooring is designed to handle heavy or oversized vehicles easily. An attached rear garden shed provides excellent extra storage. Parking is effortless with dual driveways, a circular drive, and a large carport. Schedule your showing today!

2241 Tennessee Drive, South Chesapeake

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

861 George Washington Highway S, South Chesapeake
$469,500
3 Beds ⋅ 2.1 Baths ⋅ 10634825 MLS
Meticulous and inviting inside and out! Immaculate, comprehensively maintained home that sits in a serene nature lover's fully fenced green space oasis. Top rated Grassfield school district. Backyard ideal for entertaining or your own retreat. Lovely open layout still has private spaces. Family room has Built in Propane Fireplace and opens to kitchen and out to what feels like your own park and gardens!. Modern LVP throughout downstairs. Intracoastal Waterway directly across which adds to privacy. Home located very close to Deep Creek City Park, biking trails, playground, fishing access. Sellers have grown bushels of fresh fruits and vegetables on this nature lover's paradise. Ample parking. Property line goes all the way to the picket fence. 3 bedrooms plus finished room over garage with its own mini split makes great bonus room for office, playroom or anything you want. Appliances convey! Attached garage too. A lovely home you will. be proud to call your own. Come see!

861 George Washington Highway S, South Chesapeake

415 Prince Michael Court, South Chesapeake
$430,000
4 Beds ⋅ 2.1 Baths ⋅ 10632343 MLS
Located in the highly desirable Battlefield Commons neighborhood of Chesapeake, this well-maintained home offers beautiful LVP flooring, upgraded cabinetry, recessed lighting, a flat cooktop, double wall oven, coffee bar, pantry, and a custom movable island that adds both function and charm to the kitchen. There is plenty of storage throughout the home, and the oversized primary bedroom offers plenty of room for a sitting area, office space, or whatever fits your lifestyle. The backyard features a full privacy fence maintained by the association and a pergola that conveys, creating a great space for relaxing or entertaining. The association handles lawn maintenance, including mulch and tree trimming, and the community also offers a dog park. Just minutes from Oak Grove Lake Park, shopping, some of the best restaurants in Chesapeake, Lowe's, The Home Depot, and quick interstate access. Ask about the opportunity to assume the current VA loan for a better interest rate!

415 Prince Michael Court, South Chesapeake

2412 Benefit Road, South Chesapeake
$899,999
5 Beds ⋅ 2.2 Baths ⋅ 10631352 MLS
Welcome home! 3,766 sq ft SOLID BRICK home on 5 acres in sought-after Grassfield schools. This spacious home in the country is made for gatherings! 325+ ft of driveway, 3 acres (cleared), 650 sq ft FROG & large living areas. New windows, roof, exterior doors, new and refinished hardwood floors. Renovated primary & 1/2 baths. Custom finishes throughout add elegance including custom stairwell, crown molding, board and batten, contemporary paneling, pencil framing, solid wood doors, ceiling textures, limewash brick, lighting, hardware & fresh paint. Office w/ new cabinetry & 2 work stations. Spacious kitchen w/ refreshed solid wood cabinets, new granite tops, coffered ceiling, 2 pantries, double oven, new stove top, microwave & dishwasher. Other features include 2 fireplaces, XL closets, oversized 2 car garage, new FROG mini-split, attic insulation, first floor ducting, hot water tank, encapsulated crawl with continuous contract w/ pre-home inspection. This quality home is ready for you.

2412 Benefit Road, South Chesapeake

716 River Strand, South Chesapeake
$685,000
5 Beds ⋅ 3 Baths ⋅ 10622954 MLS
Welcome Home! This masterpiece is located in a sought -after neighborhood, this beautifully maintained home offers the perfect blend on comfort , style and functionality. Featuring spacious living areas, abundant natural light, and a thoughtfully designed layout, this property is ideal for both everyday living and entertaining. The Kitchen provides ample cabinetry and workspace, flowing seamlessly into the main living areas. Generous bedrooms offer comfort and privacy, while the primary suite serves as relaxing retreat. Enjoy outdoor living with a backyard perfect for gatherings, quiet evenings, or creating your own private oasis. Conveniently located near shopping, dining, military bases, and major interstates, this home delivers both lifestyle and location. Enjoy top-tier amenities including a clubhouse, pool, tennis court, playground, deck, and private boat slip. Perfect for relaxing, entertaining, and embracing a true waterfront lifestyle. Schedule your showing Today!

716 River Strand, South Chesapeake

1219 Granton Terrace, South Chesapeake
$428,500
3 Beds ⋅ 2.1 Baths ⋅ 10643172 MLS
Start packing...this exceptional Westport is the one you've been waiting for! Beautifully updated & move-in ready, it showcases a stunning, timeless black-&-white open-concept kitchen w/brand-new stainless GE range (plumbed for gas), custom roll-out pantry, built-in cupboard, updated flooring, stairs/railings & custom primary closet. The inviting family room features soaring vaulted ceilings, gas FP & hi-def home theater wiring - perfect for entertaining or relaxing at home. Spacious first-floor primary suite offers tray ceiling, spa-like bath w/walk-in shower, built-in bench, double vanities & large linen closet. Upstairs offers a generous loft, 2 guest BRs, full BA & finished/conditioned walk-in storage (chairlift available). Energy-efficient spray-foam insulation, Rinnai tankless WH, finished 2-car garage & tinted windows. Premium homesite overlooking the park & pavilion. Resort-style living awaits in Chesapeake's premier 55+ community, Eagle Pointe. Some photos virtually staged.

1219 Granton Terrace, South Chesapeake

1028 Pleasant Ridge Drive, South Chesapeake
$765,000
4 Beds ⋅ 3 Baths ⋅ 10641597 MLS
Welcome to 1028 Pleasant Ridge Drive, where space, privacy, and comfort come together on a beautifully wooded three-acre homesite. From the moment you arrive, the setting is peaceful and private with natural light filling spacious living areas. The layout is ideal for both everyday living and entertaining, with generous gathering areas and well-sized bedrooms. This custom ranch-style residence offers approximately 3,700 square feet of thoughtfully designed living space, featuring four bedrooms, three full baths, and flexible areas suited for a growing family and today’s lifestyle. The first-floor primary suite provides a relaxing escape with a large walk-in closet and an ensuite bath featuring a beautiful tiled shower, separate tub and large vanity. This home opens to serene outdoor views of your private backyard retreat, complete with an in-ground saltwater pool, mature trees, and room to enjoy the peaceful setting that makes this one of Chesapeake’s most sought-after addresses. Whether you’re looking for space for family, hobbies, recreational vehicles, or simply a quieter way of life, this property delivers the rare combination of acreage, convenience, and versatility. Located within the highly regarded Hickory area, residents enjoy a rural atmosphere while remaining minutes to shopping and major highways. Also conveniently located to beaches, amazing restaurants and military bases with No HOA making this property truly the perfect blend of tranquility and accessibility.

1028 Pleasant Ridge Drive, South Chesapeake

1307 Old Coach Road, South Chesapeake
$882,000
4 Beds ⋅ 2.1 Baths ⋅ 10641127 MLS
Some homes offer a backyard. This one offers a lifestyle. This exceptional property showcases a resort-inspired outdoor retreat featuring a saltwater pool, Trex decking, multiple gathering spaces, a waterfront firepit, & breathtaking views that set the stage for unforgettable entertaining. From quiet mornings overlooking the water to evenings spent poolside with family & friends, every detail was designed to be enjoyed. Inside is every bit as stunning; a grand foyer welcomes you inside, where soaring ceilings, beautiful hardwood floors & stunning lake views create an unforgettable first impression. The spacious kitchen features brand-new quartz countertops, SS appliances, & overlooks the heart of the home. The luxurious primary suite offers a spa-like bath & an incredible custom closet. The 4th bedroom upstairs? The choice is yours: gym/movie room or extra guest room…and don’t miss the additional attic storage! This one-of-a-kind home won’t last, schedule your showing today!

1307 Old Coach Road, South Chesapeake

205 Wisdom Path, South Chesapeake
$700,000
5 Beds ⋅ 3.1 Baths ⋅ 10638795 MLS
Located in the beautiful Viridian Reserve neighborhood, surrounded by serene ponds and peaceful natural scenery, this home is also zoned for sought after Great Bridge Schools. Warm tones fill this inviting 5 bed, 3.5 bath home, creating a sense of comfort the moment you enter inside. The main floor features the primary bedroom with ensuite plus two additional bedrooms and a full bath, offering easy, connected living. The kitchen brings everyone together with GE stainless steel appliances and a gas range perfect for home cooked moments. Washer and dryer included. Upstairs offers two more bedrooms, a full bath, and a walk in attic for exceptional storage. A 2 car garage and 10x10 shed add even more convenience. Durable Hardie Plank siding enhances beauty and longevity. This is a home that feels warm, welcoming, and part of a truly special community.

205 Wisdom Path, South Chesapeake

3616 Parr Lane, South Chesapeake
$447,000
3 Beds ⋅ 2 Baths ⋅ 10638544 MLS
Welcome home to this beautiful single-story property in the highly sought-after Deep Creek school district! Situated on a fully fenced half-acre lot, this property offers the space, privacy, and flexibility you’ve been searching for. Inside, you’ll find an open-concept layout featuring two living areas, a dining area, and a beautifully updated kitchen with granite countertops, pantry storage, and all new appliances. This home offers 3 bedrooms, 2 updated full bathrooms, and generous closet space throughout. Enjoy cozy evenings by the wood-burning fireplace and the convenience of one-level living. Step outside to a large deck overlooking the expansive backyard, just in time for your summer BBQs! The detached workshop is a standout feature, complete with electricity and a Mini split AC, it provides the ideal space for hobbies, projects, storage, or a home business. Call Laura Blackwood for a private showing!

3616 Parr Lane, South Chesapeake

2508 S Battlefield Boulevard, South Chesapeake
$725,000
4 Beds ⋅ 3 Baths ⋅ 10632598 MLS
Bayberry Model- READY NOW! Rare opportunity to own new construction on 3 private acres in the sought-after Hickory school district. Set back from the road with a long paved driveway, this home offers a secluded, estate-like setting while remaining conveniently close to top-rated schools, shopping, and everyday amenities. Inside, you'll find a thoughtfully designed layout featuring upgraded finishes, open-office, and a versatile flex room that can function as a guest suite or bonus space. The expansive homesite provides endless possibilities-create your own private oasis with a pool, detached garage, garden, or outdoor retreat. Move-in ready and professionally staged. Builder is offering an incentive that may be used toward a rate buy-down, closing costs, or upgrades. A rare blend of space, privacy, and new construction in Hickory. Don't miss this opportunity!

2508 S Battlefield Boulevard, South Chesapeake

514 Cavendish Way, South Chesapeake
$547,500
3 Beds ⋅ 2.1 Baths ⋅ 10632032 MLS
Discover 514 Cavendish Way, a stunning former Brinsley model home in Westfield at Hickory Manor. This 2,431 sq. ft. residence features 3 bedrooms, 2.5 baths, and a seamless open-concept design. The first floor boasts high-end wood flooring, custom blinds, and designer drapes. A gourmet kitchen awaits with quartz countertops, stainless steel appliances, a large island, and a spacious pantry, all bathed in natural light. Upstairs, the luxurious owner's suite offers a custom-shelved walk-in closet and a private spa-like bath with a separate walk-in shower and soaking tub. Experience all the space and privacy of a single-family home with none of the yard work, allowing you more time to enjoy the vibrant Hickory Manor lifestyle. Community amenities include a resort-style pool, 24/7 fitness center, community center, and playground. Zoned for Hickory schools, this home perfectly combines elegance with unparalleled convenience. Don’t just imagine your dream home—live it!

514 Cavendish Way, 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.

Copyright 2026 NCRMLS. All rights reserved. North Carolina Regional Multiple Listing Service, (NCRMLS), provides content displayed here (“provided content”) on an “as is” basis and makes no representations or warranties regarding the provided content, including, but not limited to those of non-infringement, timeliness, accuracy, or completeness. Individuals and companies using information presented are responsible for verification and validation of information they utilize and present to their customers and clients. NCRMLS will not be liable for any damage or loss resulting from use of the provided content or the products available through Portals, IDX, VOW, and/or Syndication. Recipients of this information shall not resell, redistribute, reproduce, modify, or otherwise copy any portion thereof without the expressed written consent of NCRMLS.

How much is your home worth?

Get instant property value now!