Chesapeake, VA Homes for Sale under $500,000

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  /32

  $320,000

  • 3 Beds
  • 2.5 Baths
  • 1,416 Sq Ft

  4128 Williamson St, Chesapeake, VA 23324

  Charming 3-bedroom, 2.5-bath home built in 2005. New outdoor wood grill/stove and recently replaced the oven/stove (February). Enjoy a functional layout with comfortable living spaces, all in a convenient location close to the highway for easy commuting. Move-in ready and waiting for its new owners!

  Helen Anderson World Class Realty

  4128 Williamson St, Chesapeake, VA 23324
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  /43

  $289,900

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  2917 Berkley Ave, Chesapeake, VA 23325

  Charming 3-bedroom, 1-bath home offering comfortable living space on a nice sized lot. Fully RENOVATED...NEW GUTTERS, NEWER ROOF, NEW HVAC, NEW GAS WATER HEATER, NEW DRIVEWAY, Vinyl Windows. The floors are equipped with Water Proof Luxury Vinyl Plank Flooring and Plush Carpeting in the ample sized bedrooms. The Kitchen is stacked with QUARTZ COUNTERTOPS, BRAND NEW SOFT-CLOSE CABINETS & DRAWERS,

  Joseph Igana Iron Valley Real Est Norfolk

  2917 Berkley Ave, Chesapeake, VA 23325
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  /32

  $449,000

  New Construction

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

  903 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 orto 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

  Laura Rowe BHHS RW Towne Realty

  903 Railroad Ave, Chesapeake, VA 23324
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  /20

  $267,500

  • 2 Beds
  • 2.5 Baths
  • 1,026 Sq Ft

  1974 Woodgate Arch, Chesapeake, VA 23320

  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.

  Kathryn Sharpe Howard Hanna Real Estate Svcs.

  1974 Woodgate Arch, Chesapeake, VA 23320
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  /43

  $425,000

  • 3 Beds
  • 1.5 Baths
  • 1,439 Sq Ft

  604 Winscott Ct, Chesapeake, VA 23322

  Welcome to this charming 3-bedroom, 2-bath Colonial style home tucked away on a quiet cul-de-sac in Etheridge Manor! Full of character and warmth, this inviting home features exposed wood beams in the living room, a cozy fireplace, a sunny breakfast area, and new carpet throughout. Step outside onto the new deck, for morning coffee, weekend gatherings, or relaxing evenings. With its classic

  Morgan Carter Water Street Real Estate Group

  604 Winscott Ct, Chesapeake, VA 23322
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  /47

  $430,000

  • 5 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  320 Oak Lake Terrace, Chesapeake, VA 23320

  Welcome to 320 Oak Lake Terrace. This beautifully updated 5-bedroom, 2.5-bathroom home offers approximately 2,300 square feet of living space. The move-in-ready interior features an open-concept layout, a custom upgraded kitchen, modern finishes, barn doors, and updated flooring throughout generous living areas. Upstairs includes a large primary suite with a walk-in closet and private en-suite

  JT Ramsey Own Real Estate LLC

  320 Oak Lake Terrace, Chesapeake, VA 23320
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  /22

  $315,000

  • 2 Beds
  • 2.5 Baths
  • 1,352 Sq Ft

  316 Esplanade Place, Chesapeake, VA 23320

  INVESTMENT LOAN OR CASH - TENANTS IN THE PROPERTY UNTIL 31 JAN 2027. TWO PRIMARY SUITES EACH WITH A FULL BATH, EAT-IN KITCHEN WITH REFRIGERATOR, ELECTRIC RANGE, DISHWASHER, BUILT-IN MICROWAVE, AND PANTRY. LARGE FAMILY ROOM WITH GAS FIREPLACE, PEDESTAL SINK IN HALF BATH, TRAY CEILINGS, WASHER/DRYER HOOKUP, WOOD FLOORS, CEILING FANS, NEWER CARPET AND PAINT, FRENCH DOORS, PULL DOWN ATTIC STEPS,

  Walter Sims North Star Real Estate Inc.

  316 Esplanade Place, Chesapeake, VA 23320
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  /30

  $460,000

  • 4 Beds
  • 2.5 Baths
  • 2,723 Sq Ft

  1316 Hawthorne Dr, Chesapeake, VA 23325

  This beautiful spacious 4 bedroom home has soaring ceilings and a very open and inviting layout. The large private backyard and deck create the perfect setting for entertaining, relaxing, or enjoying outdoor living. The garage retains its original concrete floor and has not been converted to living space, easy to restore to a traditional garage door if desired. Conveniently located with quick

  Brent Montella Sea Shore Realty & Prop. Mgmt.

  1316 Hawthorne Dr, Chesapeake, VA 23325
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  /43

  $450,000

  • 4 Beds
  • 2.5 Baths
  • 1,759 Sq Ft

  3632 Davis Ave, Chesapeake, VA 23325

  Welcome to 3632 Davis Avenue, where comfortable living meets a backyard made for enjoying! This four bedroom, two and a half bath home has so much to offer. Come inside to a welcoming living room with a fireplace that adds warmth and character to the space. LVP flooring provides a fresh, updated feel, while the kitchen features an island and eat in area, great for everything from morning coffee

  Brittany Hendrickson Keller Williams Coastal Virginia Chesapeake

  3632 Davis Ave, Chesapeake, VA 23325
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  /50

  $444,000

  $5K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,513 Sq Ft

  3106 Lantern Place, Chesapeake, VA 23321

  Enjoy low-maintenance living in this beautifully maintained end-unit townhome in a sought-after 55+ community. This home features a first-floor primary suite, an open-concept living area with a gas fireplace, a spacious kitchen with upgraded cabinetry, a dining room, private office, and a convenient first-floor laundry room. Step outside to the screened-in porch, where you can enjoy views of the

  Devin Lundy Realty Source

  3106 Lantern Place, Chesapeake, VA 23321
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  /26

  $269,500

  $7K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,212 Sq Ft

  63 Colonial Way, Chesapeake, VA 23325

  Welcome home to this charming 3BR, 1.5BA townhome nestled in the highly sought after Georgetown area of Chesapeake! The exterior features brick, while the interior offers many updates including new LVP and carpet flooring, fresh paint, and updated kitchen with stainless-steel appliances. Enjoy the covered, screened-in back porch for relaxing summer days and nights or entertaining family and

  Anthony Horner Paragon Real Estate Group

  63 Colonial Way, Chesapeake, VA 23325
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  /27

  $450,000

  $15K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,129 Sq Ft

  4005 Terry Dr, Chesapeake, VA 23321

  Beautiful brick ranch in Western Branch with gorgeous updates! Remodels/refreshes include a new roof (2020), dining and living rooms (2019), and kitchen/den/bathrooms (2016). Three bedrooms are on the first floor, and a finished room over the garage can be your home office or even a home gym. Enjoy a quiet evening on the screened-in back porch while dinner cooks on the grill on the adjacent

  Lee Cross Cross Realty

  4005 Terry Dr, Chesapeake, VA 23321
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  /22

  $399,000

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,051 Sq Ft

  844 Jo Anne Cir, Chesapeake, VA 23322

  Calling all investors! Opportunity awaits at 844 Joanne Circle. Situated on approximately 0.74 acres in the Hickory School District, this 2,051-square-foot home offers three bedrooms, two full bathrooms, and a cozy fireplace. The large, treed, fenced-in backyard provides plenty of space and potential. Built in 1980, the home is ready for someone to bring their vision and personal touches.

  Patience MacCartney Iron Valley Real Est Norfolk

  844 Jo Anne Cir, Chesapeake, VA 23322
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  /14

  $287,000

  • 2 Beds
  • 2.5 Baths
  • 1,353 Sq Ft

  322 Holyoke Ln, Chesapeake, VA 23320

  Come fall in love with this beautiful move-in ready corner unit in sought-after Greenbrier. You will be impressed by this spacious & bright open-concept layout connecting the living & dining areas, the updated kitchen with granite countertops & SS appliances. Kitchen & half bath grouted tile. New flooring downstairs in 2025. Home features 2 large bedrooms with 2 full en-suite baths & 2 large

  Elaine Schoening Wainwright Real Estate

  322 Holyoke Ln, Chesapeake, VA 23320
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  /50

  $497,000

  $53K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 3,789 Sq Ft

  4000 Wyant Ct, Chesapeake, VA 23321

  Looking for space? This is the home for you. Entertaining? This home is for you. Tranquility? This home is for you. This home has has 2 primary bedrooms and an in-law suite. The main bedroom is 24X30. Huge backyard and near bases, shopping and restaurants. Pool table, riding lawn mower, and horseshoe convey with the home. Brand new HVAC and furnace.

  Glenda Battle BHHS RW Towne Realty

  4000 Wyant Ct, Chesapeake, VA 23321
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  /38

  $440,000

  • 4 Beds
  • 2 Baths
  • 2,188 Sq Ft

  2213 Wildwood Rd, Chesapeake, VA 23323

  Welcome home to this classic 4 bedroom, 2 bath brick home offering timeless character and plenty of space to enjoy inside and out. A charming side porch adds to the home’s inviting appeal, while the spacious backyard is made for warm-weather living with a large in-ground pool and plenty of room to relax or entertain. An additional detached brick building, formerly used as a garage, offers

  Ann Crusenberry The Real Estate Group

  2213 Wildwood Rd, Chesapeake, VA 23323
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  /26

  $310,000

  • 3 Beds
  • 1.5 Baths
  • 1,620 Sq Ft

  1535 Lyons Ave, Chesapeake, VA 23324

  POND VIEWS + ONE-LEVEL LIVING! This 3-bedroom, 1.5-bath brick ranch offers 1,620 square feet, freshly painted, new LVP flooring and a wood-burning fireplace. Step outside to a fenced backyard overlooking the pond—a setting that’s hard to find at this price point. No HOA and convenient to shopping, dining, military installations and major commuting routes. Come see what makes 1535 Lyons Ave stand

  Joshua Britt Prodigy Realty

  1535 Lyons Ave, Chesapeake, VA 23324
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  /24

  $360,000

  • 2 Beds
  • 1 Bath
  • 1,128 Sq Ft

  3124 Old Mill Rd, Chesapeake, VA 23323

  Opportunity awaits in desirable Deep Creek! Charming one-level home AND 1,440 sq ft detached garage. Located on over 1.3 acres, this charming bungalow is ready for you to call it home. Charming original wood flooring throughout the spacious living area. Eat-in kitchen with solid wood cabinetry, offering plenty of storage space. Granite counters & stone backsplash. The two bedrooms offer solid

  Conner Walters World Class Realty & Prop Mgmt

  3124 Old Mill Rd, Chesapeake, VA 23323
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  /32

  $285,000

  • 3 Beds
  • 1.5 Baths
  • 1,240 Sq Ft

  1204 Cedar Mill Square, Chesapeake, VA 23320

  Ideally located in the heart of Greenbrier, this move-in-ready three-bedroom townhouse is the perfect find! Recently refreshed with updated flooring and renovated bathrooms, this home is ready for its new owners. Features include a spacious kitchen with plenty of counter space, a convenient laundry area, and roomy, comfortable bedrooms. Complete with a private, fenced-in backyard and patio, this

  Eric Overmyer Own Real Estate LLC

  1204 Cedar Mill Square, Chesapeake, VA 23320
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  /37

  $410,000

  • 4 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  4200 White Cap Crescent, Chesapeake, VA 23321

  Welcome to this inviting 4-bedroom, 2½-bath home offering a thoughtfully designed floor plan with plenty of space for comfortable living. The main level features a formal living room, a spacious kitchen that opens to the family room with a cozy gas fireplace, and convenient access to the 2-car garage, while upstairs you’ll find four generously sized bedrooms, two full baths, and the added

  Karen Bradley Coldwell Banker Premier

  4200 White Cap Crescent, Chesapeake, VA 23321
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  /4

  $269,000

  $6K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,218 Sq Ft

  1250 Corkwood Cir, Chesapeake, VA 23320

  Move in condition Freshly painted. New carpets, flooring and kitchen cabinets. Close to interstate Close to Oak Grove Park

  Dorie D'Imperio Keffer Realty

  1250 Corkwood Cir, Chesapeake, VA 23320
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  /29

  $335,000

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

  1440 Rollesby Way, Chesapeake, VA 23320

  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. Washer

  Marie Banks Swell Real Estate Co

  1440 Rollesby Way, Chesapeake, VA 23320
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  /30

  $309,900

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,386 Sq Ft

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

  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. Owners suite includes a private bath and walk-in closet with custom wood shelving. Enjoy a private patio

  Dragas Companies Builder

  1516 Elbow Rd Unit 36501719, Chesapeake, VA 23320
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  /9

  $292,000

  • 4 Beds
  • 2 Baths
  • 1,275 Sq Ft

  3931 Port Rd, Chesapeake, VA 23321

  4 bedroom ranch offering an open layout. This home features a converted garage that provides additional living space. Come check this home out, it wont last long!

  Kevin Pall Brooke Madison & Associates

  3931 Port Rd, Chesapeake, VA 23321
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  /45

  $495,900

  • 4 Beds
  • 2 Baths
  • 2,075 Sq Ft

  934 Ferryman Quay, Chesapeake, VA 23323

  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

  Kelly Hollowell BHHS RW Towne Realty

  934 Ferryman Quay, Chesapeake, VA 23323
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  /12

  $419,900

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,076 Sq Ft

  The Caldwell Plan at Grayson Commons - Townhomes, Chesapeake, VA 23320

  The Caldwell brings together flexible living, elevated design, and thoughtful privacy across three beautifully appointed floors. Whether you're hosting friends or settling in for a quiet evening, every level has a purpose and a personality to match. The first floor welcomes you to your own retreat from the moment you arrive. A private bedroom suite on the entry level offers the ultimate in

  Dragas Companies Builder

  1516 Elbow Rd Unit 40352099, Chesapeake, VA 23320
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  /43

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1726 English Ave, Chesapeake, VA 23320

  Welcome home to this beautifully maintained 3-bedroom, 2-bath brick ranch, where classic character meets thoughtful modern updates! The remodeled eat-in kitchen features quartz countertops, brand-new stainless steel appliances, and soft-close cabinetry, creating a stylish and functional space for everyday living and entertaining. Cozy living room with a wood-burning fireplace and LVP flooring,

  Brian Wurst A Better Way Realty Inc.

  1726 English Ave, Chesapeake, VA 23320
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  /32

  $344,900

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,386 Sq Ft

  1540 Eldwick Dr Unit 101, 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 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

  Dragas Companies Builder

  1540 Eldwick Dr Unit 101, Chesapeake, VA 23320
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  /39

  $305,000

  • 3 Beds
  • 2.5 Baths
  • 1,360 Sq Ft

  839 Sommerville Crescent, Chesapeake, VA 23320

  Beautiful waterfront view townhouse located near Greenbrier. New HVAC and water heater in 2023. New in 2022 kitchen cabinets, granite countertops, stainless steel appliances. Beautiful townhome in highly sought-after community near Greenbrier Mall, Chesapeake hospital, outstanding restaurants, parks, interstate, and more. Backyard feels like a beautiful oasis overlooking the pond. Great backyard

  Valerie Williams BHHS RW Towne Realty

  839 Sommerville Crescent, Chesapeake, VA 23320
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  /25

  $399,000

  • 4 Beds
  • 2.5 Baths
  • 2,576 Sq Ft

  2217 Georgetown Blvd, Chesapeake, VA 23325

  Welcome home to this beautiful brick home in the desirable Georgetown Colony neighborhood of Chesapeake. Propertybeing SOLD-AS-IS. This spacious home offers 2,576 square feet of living space with a functional layout perfect forcomfortable living and entertaining. This property provides two generous living areas, spacious bedrooms, and plenty ofnatural light throughout the home. The

  Taisha Reid EXIT Realty Central

  2217 Georgetown Blvd, Chesapeake, VA 23325
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  /42

  $329,700

  $10K PRICE DROP

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

  2833 Candlewood Cir, Chesapeake, VA 23324

  Four bedroom ranch with thoughtful updates throughout. The home features a freshly painted interior, new lighting, new interior doors, and updated laminate and carpet flooring. A spacious living room welcomes you inside, while a cozy den with a fireplace offers a great place to unwind. The kitchen has been refreshed with new granite countertops and stainless steel appliances. Each bedroom is

  Michael Daugherty Own Real Estate LLC

  2833 Candlewood Cir, Chesapeake, VA 23324
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  /26

  $310,000

  • 2 Beds
  • 2.5 Baths
  • 1,256 Sq Ft

  1904 Woodgate Arch, Chesapeake, VA 23320

  Welcome to this fully remodeled 2-bedroom, 2.5-bathroom condo offering approximately 1,256 square feet of living space. Remodeled in 2026, this home offers updated finishes and a refreshed interior. The community features association-maintained trails and a playground, providing convenient access to outdoor amenities. Located near shopping and the local intermediate school, with everyday

  Autumn Proffitt Own Real Estate LLC

  1904 Woodgate Arch, Chesapeake, VA 23320
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  /43

  $399,900

  • 4 Beds
  • 2 Baths
  • 2,692 Sq Ft

  2218 Vicker Ave, Chesapeake, VA 23324

  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

  Julie Perkins Swell Realty Co

  2218 Vicker Ave, Chesapeake, VA 23324
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  /35

  $429,999

  • 3 Beds
  • 2.5 Baths
  • 2,225 Sq Ft

  808 Monroe Ct, Chesapeake, VA 23320

  Low-maintenance living awaits in this rare detached 3 BR, 2.5 BA Greenbrier condo. Enjoy a 2-car garage, fully fenced backyard, & primary en-suite and laundry on the first-floor. The open kitchen to main living area with gas fireplace. Additional flex room great for a home office, or media room. Recent 2025 updates include a new HVAC, granite counters with subway tile backsplash, LED recessed

  Michelle LeFante BHHS RW Towne Realty

  808 Monroe Ct, Chesapeake, VA 23320
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  /2

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft

  3536 Dunedin Dr, Chesapeake, VA 23321

  Denise Winslow CENTURY 21 Nachman Realty

  3536 Dunedin Dr, Chesapeake, VA 23321
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  /25

  $419,900

  • 3 Beds
  • 1.5 Baths
  • 1,331 Sq Ft

  229 Cedar Rd, Chesapeake, VA 23322

  Welcome to this beautifully renovated Great Bridge classic! This all-brick ranch sits on an expansive half-acre, wood-lined lot and blends timeless charm with thoughtful 2025 updates. The home was completely renovated in 2025, featuring new flooring, appliances, a refreshed kitchen, and updated bathrooms. The spacious living room is filled with natural light from oversized windows and offers a

  Kris Weaver Atlantic Sothebys Int'l Realty

  229 Cedar Rd, Chesapeake, VA 23322
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  /12

  $434,900

  New Construction $33K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  668 Allery Rd, Chesapeake, VA 23320

  Estimated early 2027 delivery. The Marlow plan offers 3 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,

  Dragas Companies Builder

  668 Allery Rd, Chesapeake, VA 23320
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  /22

  $430,000

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,984 Sq Ft

  744 Helmsdale Way, Chesapeake, VA 23320

  Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully

  Angela Kennedy 1st Class Real Estate Integrity

  744 Helmsdale Way, Chesapeake, VA 23320
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  /36

  $294,900

  New Construction

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

  1540 Eldwick Dr Unit 303, 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, quartz

  Dragas Companies Builder

  1540 Eldwick Dr Unit 303, Chesapeake, VA 23320
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  /41

  $399,990

  • 3 Beds
  • 2 Baths
  • 1,607 Sq Ft

  3433 Martin Johnson Rd, Chesapeake, VA 23323

  Welcome to this charming 3-bedroom, 2-bath Cape Cod nestled on 1.4 private acres in the Deep Creek area of Chesapeake! This property offers the perfect blend of peaceful outdoor living and everyday convenience. Enjoy gardening in the fenced garden, unwind in the wooded backyard, or take advantage of easy access to the nearby Portsmouth Ditch Trail for walking, biking, and outdoor recreation.

  Ron Sawyer RE/MAX Prime

  3433 Martin Johnson Rd, Chesapeake, VA 23323

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