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3521 Sugar Run, West Chesapeake
$220,000
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
700 Sarasota Arch, South Chesapeake
$595,000
4 Beds ⋅ 2.1 Baths ⋅ 10651170 MLS
Welcome to 700 Sarasota Arch, offering nearly 2,900 sq. ft. of versatile living space on a .36-acre cul-de-sac lot in Chesapeake's Etheridge Lakes community. This 4-bedroom, 2.5-bath home features a spacious floor plan designed for everyday living and entertaining. The family room is anchored by a gas fireplace with custom built-in bookcases, while the bright breakfast nook provides views of the backyard. A formal dining room adds additional space for gatherings and special occasions. The generous FROG serves as the fourth bedroom and offers flexibility for an office, media room, hobby space, or guest accommodations. Located within the Hickory School zone, this home combines space and flexibility. Bring your vision and make this home your own!

700 Sarasota Arch, South Chesapeake
924 Whisper Hollow Drive, South Chesapeake
$585,000
4 Beds ⋅ 2.1 Baths ⋅ 10651144 MLS
This is a charming 4 bedroom, 2,150 square foot home located in one of the most sought after areas of Chesapeake, Great Bridge in the Hickory school district. Located in a quiet cul-de-sac, it features an updated kitchen and updated bathrooms (2 1/2 baths total). A new roof in 2011, a new high efficiency furnace and air conditioning installed in 2015, a 20' x 40' in ground swimming pool, a 12' x 18' sunroom (with it's own mini split for AC and heat) and a 12' x 24' shed are among the many features of this home. New carpet and LVP (luxury vinyl plank) flooring installed in 2021 and new windows by Pella installed in 2016. Located minutes from Greenbrier and downtown Norfolk.

924 Whisper Hollow Drive, South Chesapeake
3201 Letcher Court Court, South Chesapeake
$590,000
5 Beds ⋅ 2.1 Baths ⋅ 10651123 MLS
JUST THE HOME YOU'VE BEEN LOOKING FOR! WELCOME HOME TO THIS BEAUTIFUL 5BR 2.5 BTH 2 CAR GAR HOME OFFERING THE PERFECT BLEND OF SPACE, COMFORT, AND STYLE. DESIGNED WITH BOTH EVERYDAY LIVING AND ENTERTAINING IN MIND. FEATURES GENEROUSLY SIZED BEDROOMS/CLOSET SPACE, INVITING GATHERING SPACES TO INCLUDE A SUNROOM/FLEXROOM, PLUS A ROOM OVER GAR, 4 LINEN CLOSETS, EXTRA STORAGE SPACE AND A WELL-PLANNED LAYOUT SUITED FOR A VARIETY OF LIFESTYLES. TASTEFULLY DESIGNED 2 STORY FOYER WITH ARCHS/COLUMNS AND AN OPEN STAIRCASE AS YOU ENTER HAS A WOW EFFECT. THE KITCHEN HAS A CENTER ISLAND PENDANT LIGHTS, GLASS MOSAIC BACKSPLASH, NEW LIGHT FIXTURES, SAMSUNG MICROWAVE, NEW FAUCET AND MORE. LIKE NEW SS GAS RANGE AND DISHWASHER ARE HIGH END APPLIANCES BY LG. KITCHEN TRANSITIONS INTO THE MAIN LIVING AREA CREATING A WARM AND WELCOMING ENVIRONMENT FOR HOSTING FAMILY AND FRIENDS. PRIMARY SUITE IS A PRIVATE RETREAT WITH A JETTED TUB, SEPARATE SHOWER, HIS/HERS VANITIES, WATER CLOSET, AND A LARGE WALK IN CLOSET. NEW FENCE JUST INSTALLED. SHOWS PRIDE OF OWNERSHIP! MUST SEE TODAY BEFORE IT'S GONE!

3201 Letcher Court Court, South Chesapeake
1313 Duchess Of York Quay, South Chesapeake
$412,500
3 Beds ⋅ 2.1 Baths ⋅ 10650785 MLS
Well-maintained 3-bedroom (Loft could easily be converted to a 4th bedroom), 2.5-bath home featuring new flooring in the kitchen and bathrooms. Major updates completed in 2018 include the roof, HVAC system, range, microwave, and dishwasher. The functional floor plan offers comfortable living spaces, while the attached 2-car garage and driveway provide ample parking and storage. With key improvements already completed, this home is ready for its next owner to enjoy. Schedule your showing today! This is an AnnieMac Rate Relief Eligible Property! Rate Relief makes this home more accessible and budget-friendly for you. What is a Rate Relief Eligible Property? Rate Relief is a program offered by AnnieMac Home Mortgage where the mortgage interest rate is reduced for the life of the loan. This reduction is achieved through an upfront payment made during the purchase process, and here's the best part — the seller and/or seller's agent have committed to covering this cost for you! The reduced interest rate is available through 11/16/2026. See the full details and disclosure available through the listing agent.

1313 Duchess Of York Quay, South Chesapeake
1435 Seaboard Avenue, Central Chesapeake
$379,900
3 Beds ⋅ 2.1 Baths ⋅ 10650855 MLS
Custom-built in 2025 and completely move-in ready! This beautifully designed home offers great value plus stylish, low-maintenance living with modern conveniences, a bright, open floor plan and attached garage. The modern kitchen features soft-close cabinetry, stainless steel appliances, and a farmhouse sink overlooking the generously sized family room, where a built-in fireplace creates an inviting setting for relaxing or entertaining. A separate dining room provides additional space for gatherings. Three spacious bedrooms include a primary suite with an ensuite bath, dual-sink vanity, and generous walk-in closet. A rear-loading one-car garage and driveway provide convenient off-street parking. Nearly new and ready to enjoy. Call today for your private tour!

1435 Seaboard Avenue, Central Chesapeake
1974 Woodgate Arch, South Chesapeake
$267,500
2 Beds ⋅ 1.1 Baths ⋅ 10650836 MLS
Remodeled townhome around the corner from all your daily necessities including restaurants, shopping, interstate access and parks. New paint, new carpet, new LVP flooring, updated kitchen with new appliances, new light fixtures and hardware throughout, new bathrooms.

1974 Woodgate Arch, South Chesapeake
1010 Cuervo Court, South Chesapeake
$599,900
5 Beds ⋅ 3 Baths ⋅ 10650705 MLS
PRICED TO SELL! Welcome to 1010 Cuervo Court, a spacious 5-bedroom, 3-bath home offering approximately 3,000 sq ft in sought-after Las Gaviotas! Flexible floor plan includes a first-floor bedroom and full bath, formal living room and a separate dining room. The large family room features cathedral ceilings, a stunning floor-to-ceiling brick fireplace, abundant natural light, and golf course views. Spacious primary suite offers a private balcony, large walk-in closet, and spa-like bath with dual vanities, jetted tub, and separate shower. Generously sized bedrooms, excellent closet space throughout, and a finished room over the garage provide plenty of space and flexibility. Additional features include a second level laundry room, side-loading 2-car garage, brand new dehumidifier recently installed in the crawlspace, newer carpet, and fresh paint in select rooms. Enjoy the charm of this established Chesapeake community with beautiful streets, golf course surroundings, cul dec sac living, walking trails, and highly regarded schools.

1010 Cuervo Court, South Chesapeake
1109 Santeetlah Avenue, Central Chesapeake
$369,000
4 Beds ⋅ 2 Baths ⋅ 10650746 MLS
Welcome home to this fully remodeled 4-bedroom, 2-bath residence, thoughtfully updated with modern finishes. The spacious floor plan offers abundant living space for both everyday living and entertaining. The gourmet kitchen is a chef's dream, featuring stylish finishes and ample workspace. Relax in the private primary suite, complete with large walk in his-and-hers closets and a luxurious feel. Outside, enjoy a generously sized backyard with plenty of room for gatherings, play, or future outdoor enhancements. This move-in-ready home combines comfort, style, and lasting value.

1109 Santeetlah Avenue, Central Chesapeake
1605 Laurel Avenue, Central Chesapeake
$299,500
3 Beds ⋅ 1.1 Baths ⋅ 10650769 MLS
Single family two-story detached home located in the Norfolk Highlands section of Chesapeake. 3 bedrooms, 1.5 bathrooms. Spacious layout with a bedroom and half bathroom on the second floor. Many updates completed in 2021. First floor laundry. Large lot with huge fenced in backyard with an oversized shed. Seller has clear termite and moisture letter in hand.

1605 Laurel Avenue, Central Chesapeake
1209 Holly Avenue, Central Chesapeake
$465,000
4 Beds ⋅ 4 Baths ⋅ 10650575 MLS
Welcome to 1209 Holly Avenue—where timeless historic charm meets modern luxury. Nestled in the heart of Chesapeake's desirable South Norfolk Historic District, this beautifully renovated 4-bedroom, 4-bath home offers over 2,100 square feet of thoughtfully designed living space. Every detail has been carefully updated, creating a home that truly feels better than new. Step inside to an inviting open-concept floor plan featuring a stunning gourmet kitchen with granite countertops, custom cabinetry, stainless steel appliances, and generous space for entertaining family and friends. The sought-after first-floor primary suite provides comfort and convenience, while the flexible office space and expansive upstairs loft offer endless possibilities for working from home, a media room, or additional living space. Upstairs, spacious secondary bedrooms include a private en-suite, making the layout great for guests or multigenerational living.

1209 Holly Avenue, Central 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
705 Creekwood Drive, South Chesapeake
$595,000
5 Beds ⋅ 4 Baths ⋅ 10650611 MLS
This meticulously maintained home in the sought-after Grassfield area of Chesapeake is waiting for you! Featuring 5 bedrooms and 4 full bathrooms, this spacious home offers plenty of room for everyday living and entertaining. The upstairs primary suite provides a relaxing retreat with two closets, a double vanity, stand-up shower, and garden tub. Three additional bedrooms and two full bathrooms complete the upstairs living space. The downstairs bedroom with an en-suite bathroom offers flexibility for guests, an in-law suite, or home office. The well-appointed kitchen features granite countertops, a breakfast bar, and updated appliances. The spacious living room is warmed by a gas fireplace, creating a cozy gathering space. A bright sunroom offers peaceful views of the wooded backyard, where mature trees create a private and tranquil setting. Don't miss the opportunity to make this home in the desirable Grassfield area your next home! Come see today!

705 Creekwood Drive, South 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
4126 Scotfield Drive, West Chesapeake
$469,000
4 Beds ⋅ 2.1 Baths ⋅ 10650475 MLS
In a quiet cul-de-sac, this brick-front home features high ceilings in the entryway, a formal living room, and family room. It also offers a two-car garage, a spacious yard, and a large storage shed with electricity. New HVAC installed in 2021. Flooring allowance with acceptable offer.

4126 Scotfield Drive, West Chesapeake
504 Plummer Drive, South Chesapeake
$315,000
3 Beds ⋅ 1 Baths ⋅ 10650561 MLS
Investor Special! Brick ranch in Chesapeake featuring 3 bedrooms, 1 bathroom, a detached garage/workshop, and a spacious yard. This fixer-upper is being sold as-is and offers plenty of potential for renovation and customization. Bring your vision and transform this property into a great investment or personal home!

504 Plummer Drive, South Chesapeake
714 Edinburg Avenue, Central Chesapeake
$309,000
3 Beds ⋅ 2 Baths ⋅ 10650522 MLS
Brick ranch has hardwood floors and new carpet. Updated windows. Deck off kitchen. Updated baths. Primary has jetted tub. Fireplace and shed convey as is. Washer/dryer hookups in garage. Spacious 2 car garage.

714 Edinburg Avenue, Central Chesapeake
336 Spice Bush Court, South Chesapeake
$584,900
4 Beds ⋅ 3 Baths ⋅ 10650501 MLS
Welcome to 336 Spice Bush in Chesapeake, VA! This stately two-story brick home offers classic curb appeal, a two-car garage, beautiful landscaping, and a spacious yard in a desirable location near Greenbrier. Inside, you’ll find bright living spaces with hardwood flooring, detailed trim, and comfortable flow for everyday living and entertaining. The family room features a cozy brick fireplace and opens to the screened porch, creating a relaxing indoor-outdoor retreat. The updated kitchen is a standout with white cabinetry, granite countertops, stainless steel appliances, subway tile backsplash, recessed lighting, and an island with prep space. A formal dining room and flexible living/office area provide room for gatherings, work, or hobbies. Upstairs, spacious bedrooms include a primary suite with updated bath featuring a soaking tub, separate shower, and stylish vanity. Enjoy the screened porch overlooking the large backyard, great for relaxing, play, pets, gardening, or entertaining. ASK ME ABOUT CLOSING COST ASSISTANCE!

336 Spice Bush Court, South Chesapeake
2502 Livesay Road, South Chesapeake
$290,000
3 Beds ⋅ 2 Baths ⋅ 10650500 MLS
Welcome home to this charming 1,224-square-foot home with a comfortable layout and plenty to offer. Inside, you'll find an updated kitchen and bathrooms, inviting living spaces, and a home that's been freshly cleaned and is ready for its next chapter. A little fresh paint gives the new owner an easy opportunity to add their own style. Outside, enjoy a manageable yard and convenient driveway parking. Whether you're buying your first home, downsizing, or looking for an investment, this one is worth a look!

2502 Livesay Road, South Chesapeake
3116 Dunworken Drive, West Chesapeake
$374,900
4 Beds ⋅ 2 Baths ⋅ 10650484 MLS
Move-in ready and beautifully refreshed! This vacant 4-bedroom Chesapeake home has been thoughtfully updated from top to bottom, featuring a new roof (2025), HVAC (2026), water heater (2021), new LVP flooring, new carpet in all four bedrooms, renovated bathrooms, new kitchen appliances and custom cabinetry, new interior and exterior doors, updated GFCI outlets in the kitchen and bathrooms, and new light fixtures throughout. Enjoy the added curb appeal of a freshly repaved driveway and new framing around the left front window. Inside, a newly installed decorative TV wall with backlighting creates a stylish focal point for entertaining and relaxing. Located in the convenient Western Branch area, you're close to shopping, dining, recreation, schools, and major Hampton Roads routes. With major updates already completed and easy showings available, this home is ready for you to move in and make it yours! Schedule your showing today?this one is ready to impress

3116 Dunworken Drive, West Chesapeake
423 Seahorse Run, South Chesapeake
$262,500
2 Beds ⋅ 2.1 Baths ⋅ 10650478 MLS
PRICE REDUCED-WOW-Come see this beautiful 2 bedroom 2.5 bath condo in Mariner's Quay with 3rd floor loft and ready for you to move in-located in Riverwalk and near shopping and major routes. The eat-in kitchen is open with electric range, dishwasher and refrigerator. The primary bedroom is well proportioned with carpeting-the remaining bedroom is also good sized-bathrooms feature tub/shower combinations-the outdoor shed is there for extra storage. SOLD AS-IS, with no repairs by Seller. This property may qualify for Seller Financing (Vendee). If Property was built prior to 1978, Lead Based Paint Potentially Exists.

423 Seahorse Run, South Chesapeake
4908 Portsmouth Boulevard, West Chesapeake
$400,000
3 Beds ⋅ 1.1 Baths ⋅ 10650403 MLS
Prime Commercial Potential! Located in the Fast-Growing Southwest Corner of Portsmouth Blvd. & Jolliff Rd. Corridor of Chesapeake across from The Grove At Western Branch & Amazon Processing Center. This Property has been Designated for Commercial Development, Additional Adjoining Acres Available Boarding Hotels, across from Lowes Home Improvement, Cracker Barrel, 7-11, Navy Federal, etc. Just Block from I-664 Interstate & Chesapeake Sq. Mall. Property is being Sold in "AS IS" Condition, Info is as per City Records; Value is in the Land

4908 Portsmouth Boulevard, West Chesapeake
320 Esplanade Place, South Chesapeake
$325,000
2 Beds ⋅ 2.1 Baths ⋅ 10650351 MLS
Welcome home to this cozy 2-bedroom, 2.5-bath townhome in the desirable Riverwalk community, offering 1,352 square feet of comfortable, light-filled living space. The open-concept kitchen and living area creates an inviting space for everyday living and entertaining. The kitchen features granite countertops and stainless steel appliances, while the main living area offers durable LVP flooring and a gas fireplace for added warmth and character. Two sets of double French exterior doors fill the space with natural light and open directly onto the refinished back deck. Step outside to enjoy a refinished private deck surrounded by flower beds, creating a relaxing outdoor retreat. Upstairs, both bedrooms feature comfortable carpeting, while the home's bathrooms are fully tiled for a clean, polished finish. Enjoy everything the Riverwalk community has to offer, including a clubhouse, swimming pool, tennis courts, and multiple walking trails throughout the neighborhood.

320 Esplanade Place, South Chesapeake
2218 Vicker Avenue, Central Chesapeake
$399,900
4 Beds ⋅ 2 Baths ⋅ 10650357 MLS
Fully remodeled in 2018. This contemporary open floor plan has 2 large living areas and 2677 sqft! Kitchen has tons of cabinets, lots of cabinet space and opens to a large living area. Huge primary first floor bedroom with walk in closet and extra large primary bath. Stainless appliances, recessed lighting, lvp flooring, hat pump 2018 walk in attic, oversized living area with contemporary fireplace, large pantry with barn doors, circular driveway, lots of curb appeal. Move in ready! Lots of room to unpack and relax.

2218 Vicker Avenue, Central Chesapeake
4700 Harlequin Way, West Chesapeake
$560,000
4 Beds ⋅ 2.1 Baths ⋅ 10649934 MLS
Wonderful home located in the desirable Joliff Woods neighborhood. This 4 bedroom, 2.5 bath offers approx. 2,710 square feet of living space. Situated on a generous size corner lot. Screen Porch and rear yard is completely fenced. Seller took care of all the big ticket items. Downstairs hardwood floors have just been refinished. New Windows & Slider Doors 2020, Brand New Upstairs HVAC systems, All Exterior Composite Trim, Leaf Filter Gutter Guards, & more. Conveniently located with easy access to the Southside & Peninsula, military bases, shipyards, dining, and shopping.

4700 Harlequin Way, West Chesapeake
1152 Crystalwood Circle, South Chesapeake
$519,900
5 Beds ⋅ 2.1 Baths ⋅ 10649924 MLS
Make this your first stop! This spacious home sits in a sought-after area and offers an incredible amount of space for the price. Featuring a large custom kitchen, generous living areas, and a huge deck for entertaining, this home has plenty of room to make it your own. One of the larger homes in the area, it backs directly to a wooded portion of Oak Grove Lake Park, creating a private backyard setting with direct access to running and biking trails. With a fantastic location, tons of square footage, and endless potential, it's hard to find this much home at this price point.

1152 Crystalwood Circle, South Chesapeake
340 Gracie Road, Central Chesapeake
$299,999
4 Beds ⋅ 1.1 Baths ⋅ 10649849 MLS
Welcome home to this well-maintained 4-bedroom, 1.5-bath ranch in the heart of Chesapeake! This move-in ready home offers a updated bathroom, replacement windows, and an inviting layout perfect for everyday living. Major updates include HVAC approximately 5 years old, crawlspace repairs completed within the last 5 years, updated appliances. Enjoy the spacious fenced backyard featuring a deck added in 2021 and a detached 12’ x 24’ garage/workshop, ideal for hobbies, storage, or a home workshop. Conveniently located near shopping, dining, schools, and major interstates, this home is ready for its next owner. Don’t miss this opportunity—schedule your private showing today!

340 Gracie Road, 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.