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5 Harbor Watch Drive Unit 405, South Chesapeake
$310,000
3 Beds ⋅ 2 Baths ⋅ 10651901 MLS
Adventure awaits right outside your door! Imagine starting your morning fishing from the dock, spending the afternoon kayaking or boating along the waterways, and ending the day with a waterfront picnic as the sun goes down. With deep-water access, every day offers a new opportunity to explore, unwind, and enjoy life on the water! Gather with friends at the community picnic area, cool off in the pool, or relax at the clubhouse. When the adventures are over, retreat to your spacious, well-maintained 3-bedroom, 2-bath condo offering 1,762 sq. ft. (per MLS) of comfortable, single-level living. Enjoy peaceful water views from your bedroom, abundant natural light, an updated kitchen with stainless steel appliances and wine fridge, and a generous primary suite. Association services include dock maintenance, water, sewer, and trash. Less maintenance, more adventure! Whether you're casting a line, paddling the waterways, or simply soaking up the scenery, this is waterfront living at its best!

5 Harbor Watch Drive Unit 405, South Chesapeake

620 Estates Way Unit 120, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10652230 MLS
FINANCING FLEXIBILITY AVAILABLE! Ask about available seller concessions toward a 2-1 interest rate buydown or other financing options. Surrounded by trees, this 2006 townhome-style condo offers a quieter setting with shopping, dining, parks & interstate access close by. The open main level features flexible living spaces anchored by a gas fireplace. The adjoining kitchen offers granite counters, stainless appliances, & an efficient layout open to the living areas. Upstairs are comfortably sized bedrooms, including a spacious primary suite w/ ensuite bath, double sinks, tiled shower & generous storage. Enjoy a shaded rear deck overlooking the wooded setting plus an oversized attached garage. Major updates include a high-efficiency York heat pump/HVAC installed 12/2025 (includes 10 yr parts/3 yr labor warranty) & architectural-shingle roof estimated at 2–5 years old. Pre-list inspection completed 9/2026; report available.

620 Estates Way Unit 120, South Chesapeake

661 Allery Road, South Chesapeake
$429,900
3 Beds ⋅ 2.1 Baths ⋅ 10652385 MLS
Now preselling by appointment. The Marlow plan offers three 3rd floor bedrooms with the option to add an additional 4th bedroom & full bath on 1st floor. 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. 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.

661 Allery Road, South Chesapeake

649 Allery Road, South Chesapeake
$452,900
4 Beds ⋅ 3.1 Baths ⋅ 10652383 MLS
Now preselling by appointment. This Marlow plan includes our 4th bedroom & full bath on 1st floor already spec'd and included in price. 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. 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.

649 Allery Road, South Chesapeake

1509 Waitsel Drive Unit 206, South Chesapeake
$320,000
2 Beds ⋅ 2 Baths ⋅ 10650907 MLS
Welcome home to this beautiful, like-new condo in the heart of Chesapeake! Built just 2 years ago, this home offers modern finishes, an open layout, and low-maintenance living.The open-concept floor plan connects the kitchen, dining, and living areas, creating a great space for everyday living or entertaining. The kitchen features quartz countertops, stainless steel appliances, upgraded cabinetry, and a large island with plenty of room for seating. LVP flooring, updated lighting, and plenty of natural light give the home a bright, welcoming feel throughout.The spacious primary suite offers a private retreat with a beautifully finished ensuite bath and generous closet space. Conveniently located near shopping, dining, and major interstates, you’ll have easy access to everything Chesapeake and Hampton Roads have to offer.Move-in ready, only 2 years old, and beautifully maintained—this is one you’ll want to see!

1509 Waitsel Drive Unit 206, South Chesapeake

2454 Whitman Street, West Chesapeake
$292,000
3 Beds ⋅ 3 Baths ⋅ 10651528 MLS
This like-new beauty is a rare find, featuring THREE en-suite bedrooms (one on the first floor, and two on the second floor) each with their own bathrooms and walk-in closets. There is an additional bonus/flex room upstairs as well- perfect for an office, media room, workout space, or just extra storage space. Downstairs boasts an open kitchen with a breakfast bar, recessed & pendant lighting and stainless steel appliances. The sliding doors lead to a fully fenced backyard with a patio and storage shed. With no water bill, lawns to mow, or exterior building maintenance, this is truly maintenance-free living. Just come home and relax, or sit by the pool. This home is located on a dead-end street, and convenient to interstates, library, Western Branch Park, shopping, restaurants, and more. Welcome home! Back on market due to no fault of the seller.

2454 Whitman Street, West Chesapeake

1505 Waitsel Drive Unit 304, South Chesapeake
$317,000
2 Beds ⋅ 2 Baths ⋅ 10651771 MLS
Welcome home to easy, low-maintenance living in this beautifully appointed 3rd-floor condo! Featuring an open-concept floor plan, soaring ceilings, and large windows that fill the space with natural light, this home offers comfortable one-level living with stylish interior finishes throughout. The spacious kitchen is designed for both everyday living and entertaining, with quartz countertops, stainless steel appliances, and a convenient breakfast bar. The owner's suite provides a relaxing retreat with an attached bath and walk-in closet featuring custom wood shelving. Outside, enjoy a peaceful pond with a short trail loop, plus a dedicated dog park in this pet-friendly community. Condo amenities include ground maintenance, sewer, trash pickup, and water for added convenience. Located just minutes from shopping and dining at Sam's Circle and offering an easy Battlefield commute, this home truly has everything you need for comfortable Chesapeake living!

1505 Waitsel Drive Unit 304, South Chesapeake

1440 Rollesby Way, South Chesapeake
$320,000
3 Beds ⋅ 2.1 Baths ⋅ 10651374 MLS
Beautiful 3-bedroom, 2.5-bath condo offering 1,870 sq ft of spacious, low-maintenance living! This condo has been UPDATED with new flooring, lighting, and fixtures throughout, along with a newly upgraded kitchen and bathrooms featuring beautiful cherrywood cabinets. The condo also features a pantry, two walk-in closets, a private primary bath, and a convenient half bath on the main level. Enjoy the private patio and community pool. Great location just 5 MINUTES from Greenbrier Mall and next to Greenbrier Golf Course. Move-in ready and waiting for its new owner! GREAT OPPORTUNITY FOR BUYERS! Seller is offering assistance toward mortgage interest-rate buydown points or buyer closing costs with an acceptable offer! Take advantage of this opportunity to make your new home more affordable! MAKE YOUR NEW HOME MOVE-IN READY! Seller is also offering a credit of up to $1,500 toward a washer and dryer package of the buyer’s choice with an acceptable offer! Choose the set that best fits your style and enjoy an added bonus with your new home!

1440 Rollesby Way, South Chesapeake

1561 Rollesby Way, South Chesapeake
$335,000
3 Beds ⋅ 2.1 Baths ⋅ 10651317 MLS
Welcome to 1561 Rollesby Way! This well-appointed 3-bedroom, 2.5-bathroom home offers a spacious and functional layout in the desirable Greenbrier area of Chesapeake. The first-floor primary suite features a large walk-in closet & private bathroom for added convenience. The kitchen offers stainless steel appliances, ample cabinetry, & a convenient bar overlooking the dining area. The living room provides a comfortable gathering space with a sliding glass door leading to the fenced-in backyard & patio, great for relaxing or entertaining. A first-floor half bath is conveniently located for guests. Upstairs, you’ll find two additional bedrooms, both featuring walk-in closets, along with a full bathroom & a versatile bonus room that would make an ideal home office, reading room, or flex space. Condo dues include access to the community pool, ground maintenance, trash pickup, & water service. Conveniently located in Greenbrier with easy access to shopping, dining, & entertainment.

1561 Rollesby Way, South Chesapeake

1519 Rollesby Way, South Chesapeake
$299,900
3 Beds ⋅ 2.1 Baths ⋅ 10651219 MLS
Looking for low-maintenance living without giving up space? This 3-bedroom, 2.5-bath condo in the heart of Greenbrier has plenty to offer! The bright living area features great natural light, while the spacious kitchen provides plenty of cabinet and counter space, a walk-in pantry, and an easy flow into the dining area. A first-floor bedroom gives you options for guests, an office, or additional living space. Go outside to your private fenced patio for morning coffee, grilling, or relaxing. Upstairs are two spacious bedrooms, each with a private bath and walk-in closet. The primary bath includes a soaking tub and separate shower. Even laundry gets an upgrade with a second-floor laundry room and utility sink! Community amenities include a pool, yard maintenance, trash pickup, sewer, and water. Within close proximity to Greenbrier shopping, dining, and interstates.

1519 Rollesby Way, South Chesapeake

2114 Edwin Drive, South Chesapeake
$539,999
4 Beds ⋅ 3 Baths ⋅ 10651115 MLS
Welcome to The Retreat at Edinburgh, a sought-after community. Move in ready NO WAITING. This beautifully upgraded home features high ceilings, and a spacious open-concept layout. The kitchen is stunning with quartz countertops, soft-close shaker cabinetry, stainless steel appliances, and a gas range. This home has two primary suites. The first-floor primary suite boasts a tray ceiling, oversized walk-in closet, dual vanities, quartz counters, and a tiled shower with frameless glass. Upstairs you will find a spacious primary suite with a private full bath. An additional bedroom on the main floor with adjacent full bath. Bonus room great for a home office or hobby room. Amenities include a clubhouse, pool, fitness center. Conveniently located just minutes from Walmart, Target, grocery stores, restaurants, shopping and easy access to interstate.

2114 Edwin Drive, South Chesapeake

3521 Sugar Run, West Chesapeake
$210,000
2 Beds ⋅ 2 Baths ⋅ 10651040 MLS
Welcome to 3521 Sugar Run! Step inside and you’ll immediately notice the high ceilings and open, inviting feel. Offering 2 bedrooms, 2 full baths, and over 1,100 square feet, all living spaces are conveniently located on one level, with exterior stairs providing access to the home. Both bathrooms have been updated, while thoughtful touches like the barn door entrance to the pantry add character and style. The primary bedroom features its own private bath, and the second bedroom offers flexibility for guests, a home office, or additional living space. Conveniently located in Chesapeake’s Western Branch area near shopping, dining, and major roadways. If you’re looking for a move-in ready home that offers comfort, character, and an attractive Chesapeake price point, 3521 Sugar Run is one you’ll want to see. Schedule your private showing today!

3521 Sugar Run, West Chesapeake

4987 Boone Road, West Chesapeake
$334,900
2 Beds ⋅ 2.1 Baths ⋅ 10650732 MLS
Welcome to Piney Grove, an exquisite community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level plan beautifully showcases an open floorplan w/ luxurious upgrades. The kitchen stuns guests w/ upgraded quartz countertops, subway tile backsplash, & soft-close drawers. Easily maintained & durable LVP flooring & crown molding throughout 1st level. Lighted tray ceiling in primary bedroom. WIC's in both bedrooms. Quartz vanity in primary bath w/ glass-enclosed shower. Enjoy exceptional amenities, including stet-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appointment & to take advantage of pre-opening special pricing!

4987 Boone Road, West Chesapeake

1540 Eldwick Drive #303, South Chesapeake
$295,130
2 Beds ⋅ 2 Baths ⋅ 10650606 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Addison model features an open-concept floorplan & high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with center island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms & 2 baths. Owner’s suite includes a private bath & walk-in closet with custom wood shelving. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #303, South Chesapeake

1540 Eldwick Drive #103, South Chesapeake
$325,130
2 Beds ⋅ 2 Baths ⋅ 10650599 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Addison model features an open-concept floorplan & high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with center island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms & 2 baths. Owner’s suite includes a private bath & walk-in closet with custom wood shelving. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #103, South Chesapeake

1540 Eldwick Drive #101, South Chesapeake
$345,130
2 Beds ⋅ 2 Baths ⋅ 10650588 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Rowen model is a 1st floor corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms and 2 baths. Owner’s suite includes a private bath and walk-in closet with custom wood shelving. Enjoy a patio or balcony space off living room. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #101, South Chesapeake

1540 Eldwick Drive #302, South Chesapeake
$320,130
2 Beds ⋅ 2 Baths ⋅ 10650581 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Rowen model is a corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms and 2 baths. Owner’s suite includes a private bath and walk-in closet with custom wood shelving. Enjoy a patio or balcony space off living room. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #302, South Chesapeake

2048 Mango Street, West Chesapeake
$359,900
2 Beds ⋅ 2.1 Baths ⋅ 10650281 MLS
Welcome to Boone Grove, an exquisite boutique community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level plan beautifully showcases an open floor plan w/ luxurious upgrades. 1st LEVEL PRIMARY BDRM W/ EN-SUITE featuring ceramic tiled floor, glass-enclosed shower & quartz vanity! The kitchen stuns guests w/ upgraded quartz countertops, tile backsplash, & soft-close drawers. Easily maintained & durable LVP flooring throughout, crown molding 1st level & cased windows & openings. 12' ceilings on 1st level & 9' ceilings on 2nd level. WIC's in both bdrms & walk-in attic. Enjoy a partially wooded view & exceptional community amenities, including state-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appt & to take advantage of pre-opening special pricing!

2048 Mango Street, West Chesapeake

4985 Boone Road, West Chesapeake
$330,900
2 Beds ⋅ 2.1 Baths ⋅ 10650280 MLS
Welcome to Piney Grove, an exquisite community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level plan beautifully showcases an open floorplan w/ luxurious upgrades. The kitchen stuns guests w/ upgraded granite countertops, subway tile backsplash, & soft-close drawers. Easily maintained & durable LVP flooring & crown molding throughout 1st level. Lighted tray ceiling in primary bedroom. WIC's in both bedrooms. Quartz vanity in primary bath w/ 5' shower. Enjoy a wooded view & exceptional community amenities, including stet-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appointment & to take advantage of pre-opening special pricing!

4985 Boone Road, West Chesapeake

MM Boone Grove, West Chesapeake
$324,900
2 Beds ⋅ 2.1 Baths ⋅ 10650099 MLS
MASTER MODEL. 1st LEVEL PRIMARY EN-SUITE! Welcome to Boone Grove, an exquisite boutique community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level plan beautifully showcases an open floor plan w/ luxurious upgrades. The kitchen stuns guests w/ shaker-style cabinets, stone countertops, tile backsplash, & soft-close drawers. Easily maintained & durable flooring throughout 1st level & secondary baths. 12' ceilings on 1st level & 9' ceilings on 2nd level! WIC's in both bdrms, & generous walk-in attic. Enjoy exceptional community amenities, including state-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appt & to take advantage of pre-opening special pricing!

MM Boone Grove, West Chesapeake

MM Piney Grove, West Chesapeake
$299,900
2 Beds ⋅ 2.1 Baths ⋅ 10649988 MLS
Master Model. Welcome to Piney Grove, an exquisite community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level plan beautifully showcases an open floorplan w/ luxurious upgrades. The kitchen stuns guests w/ stone countertops, tile backsplash, & soft-close drawers. Easily maintained & durable flooring throughout 1st level & secondary baths. WIC's in both bedrooms & 9' ceilings. Primary en-suite. Downstairs Flex Space great for an office/study. Enjoy exceptional amenities, including stet-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appointment & to take advantage of pre-opening special pricing!

MM Piney Grove, West Chesapeake

2154 Edwin Drive, South Chesapeake
$577,540
3 Beds ⋅ 3 Baths ⋅ 10649722 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 beautiful 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. Incentives available with use of preferred lender. Photos are to be used as an example and do not represent exact listings selections.

2154 Edwin Drive, 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

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

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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