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1916 Orangewood Road, South Chesapeake
$549,900
4 Beds ⋅ 2.1 Baths ⋅ 10649467 MLS
Located in the highly sought-after Grassfield School District, this spacious home offers over 2,400 square feet of comfortable living space with 4 bedrooms, a dedicated study, and 2.5 bathrooms. The thoughtfully designed floor plan features a bright and inviting sunroom sitting area just off the kitchen. Continue outside to enjoy the large backyard, offering plenty of room for gardening, pets, or future entertaining. Recent updates provide added value and peace of mind, including a new hot water heater (2026), new air conditioner condenser (2025), new living room carpet (2026), updated downstairs toilet (2026), and new primary bathroom faucets (2026). Outdoor improvements include a back patio (2020), new back porch (2023), and new front porch/deck stairs (2024), creating welcoming spaces to enjoy both the front and backyard.

1916 Orangewood Road, South Chesapeake

5132 Charlotte Street, West Chesapeake
$479,500
4 Beds ⋅ 2.1 Baths ⋅ 10649469 MLS
Built in 2018, NO HOA, Convenient access to major interstates, shopping, dining & more. Beautifully maintained 4bed/2.5 bath home offering modern comfort, thoughtful upgrades, an open layout designed for everyday living and entertaining. Spacious kitchen features granite countertops, stainless steel appliances, generous cabinetry & large center island overlooking the main living area. Newly added wood flooring and fresh paint provide a polished, updated feel. Upstairs you'll find a generous primary suite with an ensuite bath and ample closet space. Three additional bedrooms provide flexibility for family, guests, a home office or hobbies. Energy conscious features include solar panels with a straight forward lease transfer process and no transfer fee along with an EV charger in the 2 car garage - great for today's modern living.

5132 Charlotte Street, West Chesapeake

609 Howelsen Court, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10649294 MLS
Tucked away on a cul-de-sac in desirable Elbow Estates, this beautifully maintained home offers the perfect combination of modern style, exceptional space and a floor plan made for everyday living and entertaining. Built in 2017, the home features a bright, open-concept main living area with fresh neutral paint, sleek contemporary fixtures and an effortless flow between the kitchen, dining and living spaces. Upstairs, generously sized bedrooms offer plenty of room, but the true showstopper is the oversized primary suite. A striking tray ceiling adds architectural interest, while two closets provide exceptional storage. The expansive primary bath feels like a private retreat with a large tiled jetted tub and separate tiled shower. Outside, the spacious backyard offers plenty of room for entertaining, play or relaxing, all surrounded by a high-quality vinyl privacy fence added in 2022. A two-car garage provides additional parking and storage. With modern finishes, oversized rooms and a fantastic cul-de-sac setting, this Elbow Estates home is one you don’t want to miss.

609 Howelsen Court, South Chesapeake

1601 Lilac Avenue, Central Chesapeake
$418,000
4 Beds ⋅ 2 Baths ⋅ 10648578 MLS
Charming Cape Cod situated on a desirable corner lot in Norfolk Highlands! This 4-bedroom, 2 full bath home offers a fresh, move-in-ready feel with newly painted interiors and new carpet throughout. The renovated kitchen provides an updated and inviting space for everyday living and entertaining. The spacious bedroom count offers flexibility for guests, a home office, or additional living needs. Outside, enjoy the low maintenance, (fiberglass, no liner) salt water in-ground pool and backyard, great to relax and entertain during the warmer months. A nice storage shed provides convenient space for tools, lawn equipment, pool supplies, and more. It is located 20 minutes from the naval base & less than 10 minutes from the shipyard. With its combination of updates, comfortable living space, corner-lot location, and great outdoor amenities, this home is ready for its next owner!

1601 Lilac Avenue, Central Chesapeake

1415 Willow Avenue, Central Chesapeake
$382,500
4 Beds ⋅ 3 Baths ⋅ 10649375 MLS
Welcome to this fantastic opportunity in the desirable Norfolk Highlands neighborhood! This versatile property features a spacious 3-bedroom, 2-bath main home plus a detached studio-style in-law suite complete with its own kitchen, full bath, and a new mini split system (2024)for heating and cooling great for multigenerational living, guests, or a private office. Enjoy a fully fenced backyard great for entertaining, pets, or relaxing outdoors. Two powered storage sheds provide ample space for storage, hobbies, or a workshop. Updates include a new HVAC system (2016) and new roofs on both the main home and detached suite (2016), offering added peace of mind. Conveniently located near shopping, dining, schools, and major commuter routes, this unique property offers flexibility, comfort, and value. Schedule your private showing today!

1415 Willow Avenue, Central Chesapeake

613 Corapeake Drive, South Chesapeake
$599,500
4 Beds ⋅ 2.1 Baths ⋅ 10649324 MLS
Beautifully maintained 4 bedroom, 2.5 bathroom colonial home located in the desirable Albemarle West neighborhood and the sought-after Hickory school district. This home is great for both everyday living and entertaining, with a formal living and dining room, spacious eat-in kitchen, and a large family room with a wood burning fireplace and built-in shelving. There are dual staircases with one in the kitchen leading up to the versatile, finished room over the garage which can be used as a 4th bedroom, playroom, guest space or an additional entertaining area. There is even extra room for an office or study area. All the bedrooms are spacious and there is ample storage throughout the home, including 2 pantries in the kitchen and 2 walk-in bedroom closets. The expansive screened porch adds extra usable space to the home and would be great for dining in the warmer months or just relaxing with a cup of morning coffee. The deck leads to a gorgeous, landscaped yard and is a peaceful retreat. Major updates already done in 2026 to include all new: HVAC and air handler, deck, quartz countertops in the kitchen, and garage door opener. The kitchen and bathrooms have all been freshly painted. Convenient to shopping, restaurants and the 168 bypass. Make this one your first stop!

613 Corapeake Drive, South Chesapeake

5101 James Street, West Chesapeake
$520,000
4 Beds ⋅ 3 Baths ⋅ 10649093 MLS
Fully Renovated 2750 Sq Ft Home on 3 Lots. Welcome to a truly exceptional home that has been fully renovated & offers space, flexibility, & value that are hard to find! Situated on an impressive 3 lots, this 2750 SQFT home provides an abundance of outdoor space & endless possibilities. Inside, you’ll find two primary bedrooms en suite & a family room on each level, plus two more bedrooms, offering incredible flexibility for multi-generational living, guests, entertaining, or simply spreading out & enjoying your own space. The renovations include a completely renovated kitchen with beautiful quartz countertops, two new HVAC units, all-new windows, brand-new LVP flooring on the first level, new carpet on the second level, fresh interior paint, all-new light fixtures & ceiling fans throughout, new vanities & a new deck for outdoor enjoyment. With major updates already completed, this home is truly move-in ready. Three lots, two primary bedrooms, two family rooms, & extensive renovations—this is a rare opportunity you won’t want to miss! Some photos are AI enhanced.

5101 James Street, West Chesapeake

2808 Willows Arch, South Chesapeake
$469,900
4 Beds ⋅ 2.1 Baths ⋅ 10648837 MLS
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home on a desirable corner lot in a sought-after, sold-out Chesapeake neighborhood. Tucked away on a quiet cul-de-sac, this home offers a spacious contemporary floor plan perfect for everyday living & entertaining. The main level features a formal living room, dining room, den, & open kitchen with stainless steel appliances and a bright sunroom. The spacious primary suite offers beautiful skylights, abundant natural light, & a private en-suite bath with a relaxing soaking tub. Enjoy outdoor living on the large deck overlooking the expansive backyard, perfect for gatherings, grilling, or relaxing. With generous living spaces, a functional layout, & a prime location, this home is a wonderful opportunity to own in an established neighborhood with No POA & minutes from everything!

2808 Willows Arch, South Chesapeake

1320 Bainbridge Boulevard, Central Chesapeake
$479,900
4 Beds ⋅ 3 Baths ⋅ 10647982 MLS
READY NOW, NEW CONSTRUCTION Welcome home to this beautifully designed 4-bedroom, 3-bath residence offering modern style and exceptional comfort. The open-concept floor plan features 9-foot ceilings, a spacious family room with a cozy gas fireplace, and a stunning kitchen with granite countertops, stainless steel appliances, and abundant cabinet space. A first-floor bedroom with a full bath is ideal for guests or multi-generational living. The luxurious primary suite offers an oversized tiled shower, double vanity, and a large walk-in closet. Generous secondary bedrooms, ample storage, pull-down attic access to a full attic, Energy Star double-pane windows, and extensive insulation provide year-round efficiency and comfort. Completing this exceptional home is a detached 2-car garage with electricity and plenty of additional storage.

1320 Bainbridge Boulevard, Central Chesapeake

1044 Olmstead Street, South Chesapeake
$544,900
4 Beds ⋅ 3.1 Baths ⋅ 10648745 MLS
Welcome to 1044 Olmstead St in Chesapeake! This almost new home was built in 2022 & still feels like new! Featuring 4 bedrooms, 3.5 bathrooms spread out over 2337sq ft. Entering into the home from your covered front porch you will be greeted by natural sunlight beaming into the foyer. A home office/flex space is on the left & a half bath & laundry room on the right. Proceeding to the rear of the home you will walk into the open floor plan style kitchen w/a large island w/ seating for 4, stainless appliances & granite tops. With no walls separating the kitchen, living room, & formal dining room spending quality time w/ friends & family is easy in this space. Upstairs you will find all 4 bedrooms to be good sized with the primary bedroom being oversized w/a large walk-in closet, an en-suite bathroom w/ soaking tub, a separate shower area, & double sinks. The room over the garage is the 4th bedroom & has its own separate entrance w/a dedicated full bathroom. Call to schedule your showing!

1044 Olmstead Street, South Chesapeake

2021 Guava Lane, West Chesapeake
$449,900
3 Beds ⋅ 3.1 Baths ⋅ 10649023 MLS
Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This tri-level END UNIT 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, crown molding & soft-close drawers. Easily maintained & durable LVP flooring throughout 1st level & baths. Crown molding throughout 1st level. Lighted tray ceiling in primary suite & WIC. Double upgraded quartz vanity & 5' glass-enclosed shower in en-suite. 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.

2021 Guava Lane, West Chesapeake

5025 Duxbury Road, West Chesapeake
$529,900
4 Beds ⋅ 2.1 Baths ⋅ 10648991 MLS
The beautiful 4 bdrm Buxton model is MOVE-IN READY & features a 1st level primary bedroom! Throughout this charming, tree-lined neighborhood are an assortment of exceptional amenities including a resort-style pool, community trails, pocket parks & plazas w/ outdoor seating, a playground, natural preservation areas & state-of-the-art clubhouse w/ kitchen, conference room, & fitness center. This homes gourmet kitchen features an upgraded appliance package, including gas range, upgraded granite countertop, & glass subway tile backsplash. 9 foot ceilings on both 1st & 2nd levels & durable LVP flooring in select areas of 1st level. The primary bdrm, w/ lighted tray ceiling, has an en-suite that includes double vanity w/ granite tops, a soaking tub, & 5' glass-enclosed shower. Gas heat & tankless hot water heater.

5025 Duxbury Road, West Chesapeake

3820 Mcneal Avenue, Central Chesapeake
$382,000
3 Beds ⋅ 2 Baths ⋅ 10648733 MLS
Discover the perfect blend of comfort, convenience in this charming brick ranch situated on a spacious lot. Updates for peace of mind, this home features a new roof and gutters (2021), an upgraded Bosch HVAC system (2020), and a new water heater (2024). Enjoy added efficiency with a professionally encapsulated crawl space complete with a dehumidifier (2020), while beautiful hardwood floors enhance the bedrooms and hallway. The cozy wood-burning fireplace is equipped with an electric heat insert, providing warmth and ambiance year-round. Relax in the inviting four-season room, where you'll enjoy picturesque views of the expansive backyard and tranquil Indian River setting. Additional features include generator hook up for added security & convenience. Easy access to the interstate, beaches, shopping, dining, and more, this well-maintained home offers the perfect combination of updates w/ timeless charm.

3820 Mcneal Avenue, Central Chesapeake

934 Ferryman Quay, South Chesapeake
$495,900
4 Beds ⋅ 2 Baths ⋅ 10648870 MLS
Tucked away in the established Deep Creek Landing community, this custom built Cape Cod offers wooded water views and the privacy so many buyers are seeking. The original owner took great care in crafting this home, with great attention to detail. A first floor primary bedroom adds convenience, while two generous upstairs bedrooms each feature large walk-in closets plus ample storage in the eaves. A finished room over the garage provides flexible space for a fourth bedroom, home office, or rec room. The attached one car garage adds ease of access. Generator, sprinkler system, and a whole house fan add peace of mind and comfort year round. This home carries all of its original character, making it a wonderful opportunity for a buyer ready to refresh and personalize. Enjoy the wooded backdrop and the quiet of this beloved neighborhood while being minutes from I-64, shopping, schools, and military bases.

934 Ferryman Quay, South Chesapeake

2208 Wilmington Avenue, West Chesapeake
$599,900
5 Beds ⋅ 2.1 Baths ⋅ 10648848 MLS
A versatile floor plan with ample space for entertaining! The Palm offers 5 Bedrooms, 2.5 Baths, a large Family room, open to the kitchen, all BRs on the 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! The 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.

2208 Wilmington Avenue, West Chesapeake

1 Sandy Point Lane Unit 216, South Chesapeake
$295,000
3 Beds ⋅ 2 Baths ⋅ 10648784 MLS
Welcome to easy, low maintenance living at 1 Sandy Point Lane #216! This beautifully refreshed condo offers an open layout, fresh paint, and a 2025 kitchen remodel that brings a modern feel to the heart of the home. Major systems are already in place with a 2019 HVAC and 2021 water heater, giving you added peace of mind. The main living space has been freshly painted in a neutral color, ready for your personal touch! The HOA takes care of the details that make condo living truly convenient, including building and grounds maintenance, roof, master insurance, water, sewage, biweekly trash pickup, and 2 assigned parking spaces. Residents also enjoy an impressive array of community amenities, including a pool, picnic area, gazebo, and 1,700 square foot clubhouse available for both private gatherings and community events. With thoughtful updates, a desirable open-concept design, and amenities that simplify everyday living, this is a home that lets you spend less time on maintenance and more time enjoying the lifestyle.

1 Sandy Point Lane Unit 216, South Chesapeake

3010 Menands Drive, Central Chesapeake
$285,000
3 Beds ⋅ 1 Baths ⋅ 10648672 MLS
Fully renovated 3-bedroom ranch — move-in ready, zero renovation timeline needed. Every major system and finish has been updated: a brand-new 30-year roof (July 2025), a completely reimagined kitchen with Harbour Town slow-close cabinetry, quartz countertops, and new stainless appliances (refrigerator, electric range, dishwasher), plus an all-new bathroom, fresh paint throughout, and modern lighting in every room. This 950-square-foot Plymouth Park home lives larger than its footprint thanks to a thoughtful, brand-new layout feel — nothing left to update, nothing left to guess about. Step outside to a fenced backyard and a storage shed that conveys as-is, ideal for tools, hobbies, or extra storage. Location seals the deal: minutes to Indian River High School, easy bus access, and just a couple of miles to the Ballentine/Broad Creek light rail station for an easy Norfolk commute. Grocery, shopping, and Poplar Hall Park are all close by. Whether you're a first-time buyer or an investor, this is a rare turnkey opportunity in one of Chesapeake's most accessible neighborhoods — roof, kitchen, bath, paint, and lighting are done. Schedule your showing today!

3010 Menands Drive, Central 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.

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