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817 Doe Run Drive, Chesapeake
$524,900
4 Beds ⋅ 2.1 Baths ⋅ 10649243 MLS
Welcome to this beautifully maintained 4 bedroom, 2 and a half bath, all-brick ranch in the Grassfield School District of Chesapeake. This home features updated eat-in kitchen to include granite counter tops, stainless steel appliances (KitchenAid Refrigerator), gas range, shaker cabinets, and fresh paint. Enjoy an open layout with a very spacious great room, vaulted ceilings and a gas fireplace. French doors offer privacy to the formal dining, living room/office. Stunning bamboo floors throughout the kitchen and living areas. The large finished bedroom over the garage offers new LVP flooring, lighting, shelving, built in reading nook or can be used as a bed. Major system upgrades include TRANE HVAC system installed in 2021 with duct work replaced and system zoned in 2025. RainSoft reverse osmosis, enclosed crawl space with dehumidifier, insulated garage doors, updated vents and a newer gas water heater. Half bath located next to the mudroom/laundry room, washer & dryer to convey. New carpet in all main floor bedrooms. Enjoy outdoor living on your covered front porch or in your private fenced in backyard and deck. Expansive attic space for storage and extended driveway for additional parking. A truly move-in-ready Chesapeake home, minutes to shopping, dining, and interstate access. Please ask for the detailed upgrade list of extensive repairs and improvements. The home has been meticulously maintained with major system updates throughout.

817 Doe Run Drive, Chesapeake

633 Ambrose Street, Chesapeake
$769,900
5 Beds ⋅ 3 Baths ⋅ 10648928 MLS
2.85% ASSUMABLE VA LOAN! $75K+ IN UPGRADES, NO HOA & NO MONTHLY WATER BILL! Located in a welcoming, highly desirable community, this meticulously maintained home offers the feel of new construction with thoughtful upgrades throughout. The customized gourmet kitchen features double ovens, a built-in microwave drawer, designer finishes, and a dry bar with beverage refrigerator—perfect for gathering and entertaining. Pottery Barn lighting and designer accents, custom window treatments, custom glass showers, smart-home features, and a reverse-osmosis water system elevate everyday living. A first-floor bedroom and full bath offer flexibility for guests or multigenerational living. Relax on the inviting front porch or enjoy the screened-in porch, expansive patio, fully fenced yard, and peaceful wooded backdrop. Close to shopping, dining, and everyday conveniences, this move-in-ready home pairs a strong sense of community with privacy in your own backyard. Luxury country living at its finest!

633 Ambrose Street, Chesapeake

1908 Benefit Road, Chesapeake
$935,000
5 Beds ⋅ 3 Baths ⋅ 10648261 MLS
Welcome to your private 3.25-acre country oasis, where luxury finishes, heavy-duty infrastructure, and absolute peace of mind converge. This beautifully updated single-story home offers an open-concept layout and highly functional spaces, making it a rare market find. INTERIOR HIGHLIGHTS Step inside to a bright, airy open floor plan where the living and dining areas flow seamlessly into the chef-inspired kitchen. The kitchen is outfitted with premium Cambria countertops for unmatched durability and sleek modern style. The primary suite serves as a spa-like retreat, boasting natural quartzite surfaces, a deep jetted soaking tub, and a massive 4x4 walk-in shower. Upstairs, a versatile finished room over the garage (FROG) and a charming attic dormer offer excellent bonus spaces for a home office, media room, gym, or guest quarters. OUTDOOR LIVING & ENTERTAINING Embrace the scenic acreage from your choice of outdoor living areas. Relax on the welcoming covered front porch, or host unforgettable gatherings on the expansive rear covered patio. The outdoor living experience is anchored by a fully equipped outdoor kitchen, great for weekend barbecues and dining al fresco while overlooking your sprawling, private acreage. THE ULTIMATE DETACHED WORKSHOP A true standout feature is the massive 2,200 sq. ft. detached workshop. This incredible building is fully powered and completely climate-controlled with heating and cooling, making it an ideal setup for a home business, car enthusiast, hobbyist, or extensive machinery storage. PREMIUM SYSTEMS & INFRASTRUCTURE No expense was spared on the home's mechanics and structural integrity: * Power Security: Whole-home generator supported by a recently added 500-gallon propane tank. * Efficiency: All-new energy-efficient windows and updated insulation throughout. * Roof & Plumbing: Roof is approx. 4 years young. All plumbing has been fully updated with zero cast iron. * Utilities: Tankless water heater for endless hot water; septic system recently serviced. Welcome Home.

1908 Benefit Road, Chesapeake

420 Dundee Lane, Chesapeake
$532,500
3 Beds ⋅ 2.1 Baths ⋅ 10647647 MLS
Welcome home to easy, low-maintenance, luxury living in Eagle Pointe, Chesapeake’s premier 55+ community! This move-in-ready Hamilton plan features brand-new flooring, a new water heater, and TWO spacious primary suites - one on each level - perfect for guests or multi-generational living. The eat-in granite kitchen offers an island and stainless steel appliances and opens to a bright, sunny morning room. A formal dining room features a box-bay window and tray ceiling. The 1st-floor primary includes two closets, a ceramic shower, and a double vanity. Enjoy generous finished walk-in storage, too! At the heart of Eagle Pointe is the Bay Club with indoor & outdoor pools, hot tub, fitness center, billiards, library, game rooms, grand celebration room, catering kitchen, and so much more. Come experience the Eagle Pointe lifestyle! Call today to schedule your personal tour. Some pics digitally staged.

420 Dundee Lane, Chesapeake

1758 Barkadeer Cove, Chesapeake
$430,000
3 Beds ⋅ 2.1 Baths ⋅ 10647905 MLS
Built in 2021, this beautifully designed townhouse-style condo offers 2,234 square feet of thoughtfully designed living space, featuring an open floor plan and a desirable first-floor primary suite. The spacious great room with soaring ceilings flows seamlessly into the kitchen, complete with granite countertops, stainless steel appliances, a pantry, peninsula seating, and an adjoining dining area. The primary suite features a generous walk-in closet and an en-suite bath with a double vanity and oversized shower. Upstairs, you'll find two spacious bedrooms, a full bath, a loft overlooking the great room, and an unfinished storage room for abundant storage. Additional highlights include a two-car attached garage, large laundry room, and tankless water heater. A private rear patio provides the perfect spot to relax and unwind. Enjoy low-maintenance living with resort-style amenities including a clubhouse, pool, dock, playgrounds, private beach, and ground maintenance, all within the highly sought-after Grassfield school district.

1758 Barkadeer Cove, Chesapeake

1928 Rockwood Drive, Chesapeake
$645,000
4 Beds ⋅ 2.1 Baths ⋅ 10647705 MLS
Experience the perfect blend of quality, comfort, and outdoor living at 1928 Rockwood Drive in the highly sought-after Grassfield School District! Originally built by Stephen Alexander Homes, this beautifully maintained home is tucked away in a quiet neighborhood and features a dedicated office/study, second-floor laundry, and a spacious primary suite with soaring cathedral ceilings. The inviting living room showcases a gas fireplace flanked by custom built-ins. Outside, enjoy a private backyard oasis with an in-ground pool and TREX decking, installed in 2020. Additional updates include new windows and doors, installed in 2021. Complete with a two-car attached garage and driveway parking for four vehicles, this home truly has it all!

1928 Rockwood Drive, Chesapeake

1837 Benefit Road, Chesapeake
$825,000
4 Beds ⋅ 4 Baths ⋅ 10647485 MLS
Welcome to this custom-built retreat situated on 5 acres in a highly desirable Grassfield school district. Thoughtfully designed this exceptional property offers generous indoor and outdoor space with features ideal for multigenerational living, entertaining, hobbies, and storage. The private in-law suite includes a kitchenette and its own screened porch, creating a welcoming space for guests or extended family. Upstairs, you’ll find two ensuite bedrooms, along with an additional bedroom that offers excellent potential as a theater room, home office, or flexible living space. Car enthusiasts, hobbyists, and those seeking extra workspace will appreciate the two-car attached garage, one-car detached garage with work area, and two storage sheds. From the inviting front porch—perfect for quiet mornings and scenic views—to the rear deck designed for gathering with family and friends, this one-of-a-kind property offers the space, privacy, and versatility today’s buyers are looking for.

1837 Benefit Road, Chesapeake

1732 Defiance Drive, Chesapeake
$419,900
3 Beds ⋅ 2.2 Baths ⋅ 10646321 MLS
Built in 2022, this move-in-ready end-unit townhome in the sought-after Bryan's Cove community offers the perfect blend of modern design, comfort, and convenience. This three-story home features a flexible first-floor bonus room ideal for a home office, gym, or guest suite, plus an attached two-car garage. The open-concept main level is filled with natural light and showcases a gourmet kitchen with granite countertops, stainless steel appliances, a large center island, and an adjoining dining area with access to a private balcony—perfect for relaxing or entertaining. Upstairs, the spacious primary suite features a tray ceiling, walk-in closet, dual vanities, a soaking tub, and separate shower. Enjoy resort-style amenities including a clubhouse, fitness center, swimming pool, dog parks, playgrounds, pier, and docks. Conveniently located near shopping, dining, military bases, and major interstates, this low-maintenance townhome offers exceptional value and an unbeatable lifestyle.

1732 Defiance Drive, Chesapeake

891 Bells Mill Road, Chesapeake
$519,998
4 Beds ⋅ 3.1 Baths ⋅ 10646463 MLS
BACK ON MARKET DUE TO NO FAULT OF THE SELLER! If you’ve been searching for true peace and privacy without sacrificing convenience, this Grassfield gem is an absolute must-see. Set back from the street on a private driveway, the property opens up to nearly an acre of total solitude, completely enveloped by woods and lush mature greenery. Inside, fresh paint brings a bright, inviting energy to a floor plan built for real life. The layout is a rare find for multi-generational living, featuring two distinct main-level suites. The in-law wing includes its own living room, making it easy to use as a private apartment, a 5th bedroom, or a home office. The primary suite feels like a custom getaway with live-edge wood countertops, dual shower heads, and a custom walk-in closet system. Out back, the property turns into a full outdoor retreat featuring a storage shed, a chicken coop, separate hookups ready for a pool and hot tub, and a massive detached two-car workshop/garage complete with a carport and RV hookup. Welcome home!

891 Bells Mill Road, Chesapeake

1833 Shillelagh Road, Chesapeake
$849,900
5 Beds ⋅ 4.1 Baths ⋅ 10646141 MLS
Under Construction – Luxury New Construction with Timeless Coastal Farmhouse Style! This stunning 3-level home blends classic board-and-batten architecture, clean lines, black-framed windows, and thougthful accents to create exceptional appeal. Inside, an open-concept first floor is designed for modern living, featuring a spacious family room, dining area, and a designer kitchen with a large center island, custom cabinetry, and premium finishes. The second level offers four generously sized bedrooms, including an impressive owner's suite with a spa-inspired bath, plus two full bathrooms to comfortably accommodate family and guests. The third floor provides incredible flexibility with a spacious bonus room or fifth bedroom, a full bath, and convenient walk-in attic storage. With 5 bedrooms, 4.5 baths, thoughtful craftsmanship, and stylish finishes throughout, this exceptional new home offers the perfect blend of luxury, comfort, and functionality for today's lifestyle.

1833 Shillelagh Road, Chesapeake

1536 Tuck Street, Chesapeake
$16,700
10645394 MLS
Three adjoining wooded residential lots available as a package in the established Hillcrest area of South Chesapeake. Includes 1534, 1536 & 1538 Tuck St. These contiguous parcels offer a unique opportunity for builders, investors, or buyers looking to get multiple lots for future development or personal use. Conveniently located near S. Battlefield Blvd and Johnstown Road with access to nearby shopping, dining, and major roadways. No utilities currently installed. No survey available. Buyer to perform all due diligence regarding lot dimensions, boundaries, zoning, buildability, utility availability/access, and development requirements with the City of Chesapeake and appropriate authorities. Rare opportunity to acquire three adjoining parcels in an established Chesapeake neighborhood with future potential.

1536 Tuck Street, Chesapeake

1534 Tuck Street, Chesapeake
$16,700
10645392 MLS
Three adjoining wooded residential lots available as a package in the established Hillcrest area of South Chesapeake. Includes 1534, 1536 & 1538 Tuck St. These contiguous parcels offer a unique opportunity for builders, investors, or buyers looking to get multiple lots for future development or personal use. Conveniently located near S. Battlefield Blvd and Johnstown Road with access to nearby shopping, dining, and major roadways. No utilities currently installed. No survey available. Buyer to perform all due diligence regarding lot dimensions, boundaries, zoning, buildability, utility availability/access, and development requirements with the City of Chesapeake and appropriate authorities. Rare opportunity to acquire three adjoining parcels in an established Chesapeake neighborhood with future potential.

1534 Tuck Street, Chesapeake

1538 Tuck Street, Chesapeake
$16,700
10645395 MLS
Three adjoining wooded residential lots available as a package in the established Hillcrest area of South Chesapeake. Includes 1534, 1536 & 1538 Tuck St. Offered at $16,700 per lot. These contiguous parcels offer a unique opportunity for builders, investors, or buyers looking to get multiple lots for future development or personal use. Conveniently located near S. Battlefield Blvd and Johnstown Road with access to nearby shopping, dining, and major roadways. No utilities currently installed. No survey available. Buyer to perform all due diligence regarding lot dimensions, boundaries, zoning, buildability, utility availability/access, and development requirements with the City of Chesapeake and appropriate authorities. Rare opportunity to acquire three adjoining parcels in an established Chesapeake neighborhood with future potential.

1538 Tuck Street, Chesapeake

Lot 9 Tuck Street, 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, Chesapeake

Lot 8 Tuck Street, 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, Chesapeake

Lot 7 Tuck Street, 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, Chesapeake

Lot 6 Tuck Street, 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, Chesapeake

Lot 5 Tuck Street, 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, Chesapeake

Lot 4 Tuck Street, 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, Chesapeake

1933 Reefwood Road, Chesapeake
$609,900
4 Beds ⋅ 3.1 Baths ⋅ 10644569 MLS
100% move-in ready in the Grassfield school district! This open floor plan offers quality finishes throughout. Hardwood flooring runs throughout the main living areas. The first-floor office/study has direct access to the wraparound front porch. The family room opens to the dining area and spacious kitchen featuring granite countertops, white soft-close cabinets, a large island, stainless steel appliances, and a walk-in pantry. Enjoy the private, fully fenced backyard with a custom paver patio. The room over the garage is a private guest suite with a full bath and separate access from the foyer. Upstairs also offers a loft, 2 spacious bedrooms, and the primary suite with a large walk-in closet, soaking tub, oversized tiled shower with custom glass enclosure, and private water closet. No HOA. Convenient to schools, shopping, dining, and major commuter routes.

1933 Reefwood Road, 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.