Chesapeake, VA Homes for Sale under $500,000

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  /33

  $320,000

  • 3 Beds
  • 2 Baths
  • 1,668 Sq Ft

  7 Harbor Watch Dr Unit 221, Chesapeake, VA 23320

  Waterfront living takes center stage in this inviting, third-floor condo in the heart of Great Bridge. Enjoy lovely views of the Intracoastal Waterway from your private balcony where you can relax and watch the boats pass by. Even better, the property includes a deep-water access boat slip - an exceptional feature for boating enthusiasts! Inside, this 3-bedroom home offers an open layout

  Jamie Potts Focus Realty LLC

  7 Harbor Watch Dr Unit 221, Chesapeake, VA 23320
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  /34

  $289,900

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,355 Sq Ft

  The Addison Plan at Grayson Commons - Condominiums, Chesapeake, VA 23320

  Our interior model features an open-concept floorplan & high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with breakfast bar, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms & 2 baths. Owners suite includes a private bath & walk-in closet with custom wood shelving.

  Dragas Companies Builder

  1516 Elbow Rd Unit 36469973, Chesapeake, VA 23320
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  /36

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,786 Sq Ft

  5 Harbor Watch Dr Unit 413, Chesapeake, VA 23320

  PARK YOUR BOAT HERE! Enjoy waterfront living in the heart of Great Bridge. This beautifully maintained 3BR/2BA condo offers an open floor plan and a private balcony with harbor views. The spacious primary suite includes a walk-in closet, double vanity, soaking tub, and separate shower. Sale includes a boat slip in the protected private harbor, two reserved parking spaces, and assigned storage.

  Cosette Lambourne Real Broker LLC

  5 Harbor Watch Dr Unit 413, Chesapeake, VA 23320
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  /2

  $275,000

  $45K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 905 Sq Ft

  843 Quail Ave, Chesapeake, VA 23324

  **Excellent investment opportunity! This tenant-occupied home is situated on a quiet street and offers cozy living with a large rear yard, great for children, pets, gardening, or outdoor entertaining. A property with great potential for investors or future homeowners alike.**

  Paula Moore Keffer Realty

  843 Quail Ave, Chesapeake, VA 23324
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  /32

  $500,000

  $50K PRICE INCREASE

  • 5 Beds
  • 3 Baths
  • 3,166 Sq Ft

  700 Canoe St, Chesapeake, VA 23323

  Situated on a corner lot in sought after Culpepper Landing, this spacious home is ready for new owners to make it their own. A formal living and dining room, both with hardwood floors greet you as you enter. A large living room with gas fireplace opens to the spacious kitchen that includes tons of cabinet space and granite counters. The eat-in kitchen provides access to the large fenced-in

  Julia Shea Keller Williams Coastal VA Norfolk

  700 Canoe St, Chesapeake, VA 23323
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  /28

  $499,900

  • 4 Beds
  • 2 Baths
  • 1,650 Sq Ft

  403 Caravelle Ct N, Chesapeake, VA 23322

  Charming ranch with large backyard and pool! Enjoy the welcoming front porch before heading inside to the thoughtfully updated interior, where fresh paint and beautiful new LVP flooring create a bright, inviting atmosphere. New carpet in the room above the garage adds comfort and versatility to the home's flexible living space. Designed for both everyday living and effortless entertaining, the

  Brooke Titus Own Real Estate LLC

  403 Caravelle Ct N, Chesapeake, VA 23322
• 

  

  /22

  $380,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  716 Hillwell Rd Unit B, Chesapeake, VA 23322

  You know that feeling when a house just makes sense? This one has it. Three bedrooms, two baths, and 1,356 square feet give you real room without a lot of upkeep. The LVP flooring is fresh, the windows are newer, and the kitchen has the space to actually cook and gather in. The cabinets were refinished and paired with butcher-block counters, and the lighting, trim, and fixtures have all been

  Jeremy Johnson Long & Foster Real Estate Inc.

  716 Hillwell Rd Unit B, Chesapeake, VA 23322
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  /4

  $414,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,654 Sq Ft

  MM Railroad (Pullman), Chesapeake, VA 23324

  Full appliance package (including washer/dryer & refrigerator) on all existing inventory! Stunning New Construction Home! Welcome to this beautiful 3 Bedroom, 2.5 Bath home offering 1654 square feet of modern living space. Designed with a spacious open floor plan, It's perfect for entertaining & everyday living. Interior the kitchen shines with soft-close cabinets, granite countertops, bathrooms

  Laura Rowe BHHS RW Towne Realty

  MM Railroad (Pullman), Chesapeake, VA 23324
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  /24

  $329,900

  • 2 Beds
  • 2.5 Baths
  • 1,870 Sq Ft

  514 Trellis Trail, Chesapeake, VA 23320

  Back on the market because a BRAND NEW A/C was installed!! Spacious 1,870-square-foot, 2-bedroom condo tucked away at the rear of a four-unit building, offering added privacy and a peaceful setting. The versatile first-floor office can easily serve as a third bedroom, guest room, or flex space. The oversized kitchen features a generous pantry, breakfast area, and plenty of cabinet space. Sliding

  Kim Kirane RE/MAX Allegiance

  514 Trellis Trail, Chesapeake, VA 23320
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  /39

  $325,000

  • 2 Beds
  • 2.5 Baths
  • 1,582 Sq Ft

  1213 Killington Square, Chesapeake, VA 23320

  MOVE-IN READY end-unit townhome in highly desirable Greenbrier! Fresh paint and brand-new carpet throughout give this home a clean, modern feel. The bright eat-in kitchen features stainless steel appliances and granite countertops, perfect for everyday living and entertaining. The spacious great room includes a dining area, cozy fireplace, and direct access to a large fenced backyard with storage

  Maribeth Dunlap Long & Foster Real Estate Inc.

  1213 Killington Square, Chesapeake, VA 23320
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  /34

  $324,800

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft

  1800 Spar St, Chesapeake, VA 23321

  Charming three bedroom ranch with thoughtful updates throughout. New windows bring an abundance of natural light into the home, while fresh paint, new laminate and carpet flooring and new lighting create a bright, refreshed feel. The welcoming floor plan includes a sizable living room and dining area. The updated kitchen is sure to impress with all new granite countertops, stainless steel

  Michael Daugherty Own Real Estate LLC

  1800 Spar St, Chesapeake, VA 23321
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  /14

  $239,995

  • 2 Beds
  • 2 Baths
  • 1,015 Sq Ft

  516 Rue Marseille, Chesapeake, VA 23320

  Spacious 2 bedroom/2 bath condo featuring an open floor plan and soaring cathedral ceilings. Bright end unit with abundant natural sunlight throughout. Well-designed layout for entertaining. Prime location with easy access to interstate, shopping, and restaurants. Property has been renovated with all new flooring, paint, kitchen cabinets and countertops, and bathroom vanities.

  Deanna Crook Signature Properties

  516 Rue Marseille, Chesapeake, VA 23320
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  /44

  $335,000

  • 3 Beds
  • 2.5 Baths
  • 1,472 Sq Ft

  1016 Winged Foot Ct Unit B, Chesapeake, VA 23320

  One owner condo - shows like a model - professionally decorated - updates include flooring - kitchen - baths - systems - so well cared for - maintained - Cul-de-sac that borders the golf course - no thru traffic - duplex style condo with a garage and driveway parking - In the heart of Greenbrier on the 11th green of the Greenbrier Golf Course - wooded view out the back of the fenced in yard.

  Jessica Downes RE/MAX Allegiance

  1016 Winged Foot Ct Unit B, Chesapeake, VA 23320
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  /33

  $439,900

  New Construction $10K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 1,862 Sq Ft

  1813A Hoover Ave, Chesapeake, VA 23324

  Seller will pay up to $12,000 for closing cost assistance or to be used at buyer's discretion using our preferred lender and our attorney; Stunning New Construction! Welcome to this beautiful 4-bedroom, 2.5-bath home offering 1,762 square feet of modern living space. Designed with a spacious open floor plan, it's perfect for entertaining and everyday family living. Inside, the kitchen shines with

  Laura Rowe BHHS RW Towne Realty

  1813A Hoover Ave, Chesapeake, VA 23324
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  /17

  $235,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 989 Sq Ft

  701 Rapidan River Ct Unit A, Chesapeake, VA 23320

  Welcome home to this beautifully updated 2 bedroom, 2 bath condo in the desirable Riverwalk community! Featuring fresh paint throughout, newer luxury vinyl plank flooring, stylish new cabinetry, and updated countertops, this home is move-in ready. The kitchen is complete with stainless steel appliances, offering both modern style and functionality. Enjoy low-maintenance living with condo fees

  Eddie Gerardo-Ferrer RE/MAX Allegiance

  701 Rapidan River Ct Unit A, Chesapeake, VA 23320
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  /5

  $450,000

  • Land
  • 24,306 Sq Ft
  • $806,452 per Acre

  2610 Elkhart St, Chesapeake, VA 23323

  Build-ready townhome development opportunity in Chesapeake! This 0.558-acre parcel is approved for 5 townhome units and offers a rare chance to step into an already entitled project. Zoned R-TH-1 with plans and approvals in place, saving valuable time and development costs. Appraisal, site plans, and renderings available. Great location with strong resale potential and easy access to major

  Alex Sanchez Real Broker LLC

  2610 Elkhart St, Chesapeake, VA 23323
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  /32

  $459,900

  $15K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,013 Sq Ft

  2813 Meadow Wood Dr E, Chesapeake, VA 23321

  Welcome home to this 4-bedroom home in a sought-after neighborhood! This property offers plenty of space and versatility, including a detached suite with an additional bedroom and full bathroom, ideal for guests, a home office, or multigenerational living. Additional highlights include a sunroom, plantation shutters, fully finished FROG, and spacious 2.5-car garage. Recent updates include new

  Allison Avila Iron Valley Real Estate HR

  2813 Meadow Wood Dr E, Chesapeake, VA 23321
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  /26

  $235,000

  $25K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,168 Sq Ft

  1002 Willow Green Ct, Chesapeake, VA 23320

  Located in the Riverwalk section of Chesapeake, this corner unit offers added privacy and a great position tucked toward the backside of the building. Enjoy a quiet serene lifestyle. The functional floor plan provides comfortable everyday living. 2 Bedrooms on the 2nd floor along with 2 Full-Baths with a convenient powder room on the 1st floor. Generous closet space and plenty of storage

  Pamela Boone-Skeeter BHHS RW Towne Realty

  1002 Willow Green Ct, Chesapeake, VA 23320
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  /22

  $385,000

  • 4 Beds
  • 2 Baths
  • 1,405 Sq Ft

  2317 Southern Pines Dr, Chesapeake, VA 23323

  Come check out this amazing ranch on Oak Manor before its gone! 4 bedroom 2 bath including FROG. Located in the heart of Chesapeake & sits on .5 acres. Enjoy the cozy wood burning f/p in living room. Updated open kitchen with breakfast area and pantry cabinet. Newly renovated hall bath. Wonderful primary suite with double closets & renovated primary bath. Freshly painted throughout. Fully fenced

  Brianna Seeds Atlantic Sothebys Int'l Realty

  2317 Southern Pines Dr, Chesapeake, VA 23323
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  /20

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,039 Sq Ft

  1302 Portlock Rd, Chesapeake, VA 23324

  Welcome to 1302 Portlock Road, where thoughtful updates and modern style come together to create a home that is truly ready to enjoy! From the moment you arrive, you’ll appreciate the fresh exterior paint, newer windows, and desirable corner-lot setting.Inside, the beautifully upgraded kitchen is sure to impress, featuring granite countertops, new cabinetry, and stainless-steel appliances,

  Kim Stanley Green Tree Real Estate Inc

  1302 Portlock Rd, Chesapeake, VA 23324
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  /3

  $225,000

  • 2 Beds
  • 2 Baths
  • 962 Sq Ft

  401 Bracknell Arch Unit F, Chesapeake, VA 23320

  Tranquil and serene condo living, welcome to this desirably located greenbriar community close to local dinning and shopping. This property also offers quick access to major interstate Hwy and just a few blocks over from Chesapeake General Hospital

  Malcolm Jenkins Swell Realty Co

  401 Bracknell Arch Unit F, Chesapeake, VA 23320
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  /36

  $440,000

  • 4 Beds
  • 3 Baths
  • 1,996 Sq Ft

  1332 Hazel Ave, Chesapeake, VA 23325

  Welcome home to this beautiful property ideally situated on corner lot. 4 spacious bdrms. One downstairs bedroom w/ large walk-in closet and full bath access perfect for in-law or guest suite. Primary suite offers walk-in closet, jetted tub and double vanity. Upstairs laundry with cabinetry and laundry workspace. Kitchen with breakfast bar, pantry, double oven, and newer refrigerator, microwave

  Connie Tanedo Wainwright Real Estate

  1332 Hazel Ave, Chesapeake, VA 23325
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  /7

  $249,000

  • 3 Beds
  • 2 Baths
  • 1,322 Sq Ft

  608 Edinburg Ave, Chesapeake, VA 23324

  Great opportunity to own a brick ranch in Chesapeake! This home features hardwood floors, a spacious front yard, and a fenced-in backyard. Includes a new refrigerator and new cabinets. This freshly painted property has some updates plus it has tons of potential—great for a first-time homebuyer or investor. Being sold as-is. Don’t miss your chance to make it your own!

  Melissa Gibbs Howard Hanna Real Estate Svcs.

  608 Edinburg Ave, Chesapeake, VA 23324
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  /12

  $260,000

  • 2 Beds
  • 2 Baths
  • 1,214 Sq Ft

  1914 Woodgate Arch, Chesapeake, VA 23320

  Open House Saturday 7/18/26, 10 am - 2 pm. Welcome to this beautifully renovated 2-bedroom, 2 bathroom townhome featuring impressive high ceilings that create an open, airy feel throughout. The updated interior boasts modern finishes, refreshed flooring, and a stylish kitchen perfect for both everyday living and entertaining. Spacious bedrooms offer comfort and privacy, while the thoughtfully

  Ashley Faulk Wainwright Real Estate

  1914 Woodgate Arch, Chesapeake, VA 23320
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  /32

  $394,000

  $3K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,605 Sq Ft

  1415 Willow Ave, Chesapeake, VA 23325

  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

  Melissa Gates The Bryant Group

  1415 Willow Ave, Chesapeake, VA 23325
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  /31

  $446,500

  New Construction

  • 5 Beds
  • 2.5 Baths
  • 1,862 Sq Ft

  901 Railroad Ave, Chesapeake, VA 23324

  Full appliance package (including washer/dryer & refrigerator) on all existing inventory! Seller will pay up to $12,000 for closing cost assistance or to be used at buyer's discretion using our preferred lender and our attorney; Stunning New Construction! Welcome to this beautiful 5-bedroom, 2.5-bath home offering 1,862 square feet of modern living space. Designed with a spacious open floor plan,

  Laura Rowe BHHS RW Towne Realty

  901 Railroad Ave, Chesapeake, VA 23324
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  /11

  $394,900

  New Construction $13K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,847 Sq Ft

  676 Allery Rd, Chesapeake, VA 23320

  Estimated early 2027 delivery. The Bristol plan offers 2 spacious owner suites on 3rd floor with convenient 3rd floor laundry. 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. First floor flex space with 2-car rear-loading garage. Community will feature pool, playground, dog park and grilling

  Dragas Companies Builder

  676 Allery Rd, Chesapeake, VA 23320
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  /4

  $434,900

  $5K PRICE DROP

  • Land
  • 27.23 Acres
  • $15,970 per Acre

  Lot D Buskey Rd, Chesapeake, VA 23322

  Your going to want to see this listing! Available acreage in the highly sought after Hickory and Grassfield school districts. This recently platted 27.232 acres of raw farm land is a rare find in southern Chesapeake. The property is not currently leased, but can be an option if desired. This parcel is the largest of four and is Lot D on the plat. Buyer to do their due diligence on well, septic,

  Gilbert Falk III EXP Realty LLC

  Lot D Buskey Rd, Chesapeake, VA 23322
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  /29

  $430,000

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  1112 Sir Gawaine Dr, Chesapeake, VA 23323

  Spacious 4 bedroom, 2.5 bath home built in 2014. Welcoming front porch leads into a bright interior featuring an open flow between the main living spaces and a large eat-in kitchen with ample cabinetry and counter space. Separate dining area provides flexibility for everyday living or entertaining. Upstairs offers well-sized bedrooms, including a comfortable primary suite with private bath.

  Shynara Manley ONYX Realty Professionals LLC

  1112 Sir Gawaine Dr, Chesapeake, VA 23323
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  /5

  $289,900

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,355 Sq Ft

  1540, Chesapeake, VA 23320

  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,

  Clarice Savereux Dragas Companies Realty Inc

  1540, Chesapeake, VA 23320
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  /43

  $449,000

  • 4 Beds
  • 3 Baths
  • 2,206 Sq Ft

  301 Sikeston Ln, Chesapeake, VA 23322

  Welcome home to this luxurious 4-bed, 3 full bath home located in the highly sought-after Great Bridge school district. The open floorplan is enhanced by 9-foot ceilings on both levels, recessed lighting, and plenty of natural light. The kitchen serves as the heart of the home, offering a large island, quartz countertops, and stainless-steel appliances— for both entertaining and everyday living.

  J Adam Harris LPT Realty LLC

  301 Sikeston Ln, Chesapeake, VA 23322
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  /9

  $240,000

  $10K PRICE DROP

  • Land
  • 6 Acres
  • $40,000 per Acre

  4809 Sondej Ave, Chesapeake, VA 23321

  Western Branch school zoned 6 acre parcel ready for you to build your dream home. NO Hoa fees or rules. Seller will provide survey just recently done and a copy of perk test for approved offers only. Non conforming septic systems can be used, and you will need to dig a private deep water well. Listing agent can provide some options for septic and local well companies, along with local builders

  LeAnn Amory BHHS RW Towne Realty

  4809 Sondej Ave, Chesapeake, VA 23321
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  /3

  $400,000

  • 3 Beds
  • 1.5 Baths
  • 1,421 Sq Ft

  4908 Portsmouth Blvd, Chesapeake, VA 23321

  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

  Denise Winslow CENTURY 21 Nachman Realty

  4908 Portsmouth Blvd, Chesapeake, VA 23321
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  /15

  $425,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  1436 Atlantic Ave, Chesapeake, VA 23324

  New Construction. Spacious 4 bedroom/2.5 bath home with an open concept floor plan.Granite kitchen counter tops and hard surface bath counter top colors.The kitchen has an island for additional work space and casual meals. Builder purchases and installs stainless appliances. Refrigerator is not included.Laundry is on 2nd level.Can be completed within approx. 45-60 days of a

  Barbara Humphreys Glasser Glasser Real Estate LLC

  1436 Atlantic Ave, Chesapeake, VA 23324
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  /34

  $454,900

  $35K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,484 Sq Ft

  121 Causeway Dr, Chesapeake, VA 23322

  Welcome to 121 Causeway Drive, a classic Great Bridge ranch situated on an oversized lot within convenient walking distance to the shopping center. This property offers a 2-car attached and detached garage. The detached garage is great for someone looking for a workshop. This meticulously maintained and well cared for, one-owner custom-built ranch features 4 bedrooms, 2.5 bathrooms, spacious

  Weeden Blair Keffer Realty

  121 Causeway Dr, Chesapeake, VA 23322
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  /48

  $380,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,716 Sq Ft

  700 Saxon Ct, Chesapeake, VA 23323

  Tucked away on a peaceful cul-de-sac, this charming Chesapeake property welcomes you with exceptional features and inviting style. Inside, the home boasts premium, eco-friendly bamboo flooring across most of the living areas, creating a clean, modern ambiance. A standout highlight is the unique two-section screened porch, carefully crafted for year-round enjoyment, morning coffees, or evening

  Aaron Gutierrez Creed Realty

  700 Saxon Ct, Chesapeake, VA 23323
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  /45

  $225,000

  • 2 Beds
  • 2 Baths
  • 1,362 Sq Ft

  4316 Hillingdon Bend Unit 305, Chesapeake, VA 23321

  Move in ready! Welcome to easy, low-maintenance living in the sought-after King's Pointe at Western Branch! This beautifully maintained 3rd-floor, 2-bedroom, 2-bath condo offers added privacy, abundant natural light, and peaceful treetop views from the large picture window. The open-concept living and dining areas create a comfortable space for everyday living and entertaining, while the kitchen

  Bridgette Hamm The Real Estate Group

  4316 Hillingdon Bend Unit 305, Chesapeake, VA 23321
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  /42

  $285,000

  $13K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 996 Sq Ft

  1225 Jackson Ave, Chesapeake, VA 23324

  Recently renovated and move-in ready, this charming home is the perfect place to call your own! Featuring a bright, refreshed interior, freshly painted and a brand-new HVAC system. This home offers comfort and peace of mind from day one. Whether you're a first-time buyer, looking to downsize, or searching for an investment opportunity, this cute Chesapeake home is one you won't want to miss.

  Ron Sawyer RE/MAX Prime

  1225 Jackson Ave, Chesapeake, VA 23324
• 

  /2

  $285,000

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,402 Sq Ft

  2016 Rokeby Ave, Chesapeake, VA 23320

  Nice brick ranch with wooded views of the park. Great flow in this home with cozy family room with wood burning fireplace. Large lot with detached garage. Great layout. This fixer upper is just waiting for the next owners and updates!

  Renee Perry BHHS RW Towne Realty

  2016 Rokeby Ave, Chesapeake, VA 23320
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  /38

  $299,000

  • 3 Beds
  • 3 Baths
  • 1,329 Sq Ft

  2454 Whitman St, Chesapeake, VA 23321

  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

  Amanda Ackiss Triumph Realty

  2454 Whitman St, Chesapeake, VA 23321

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