Chesapeake County VA Homes under $500,000

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  /50

  $479,000

  • 3 Beds
  • 2 Baths
  • 1,676 Sq Ft

  4817 Charlton Dr, Chesapeake, VA 23321

  Welcome to this beautifully reimagined 3-bedroom, 2-bath home, fully renovated from top to bottom in 2026. Designed for both style and comfort, the home features brand-new HVAC, electrical, plumbing, roof, siding, energy-efficient windows, hot water heater, and appliances—offering true move-in-ready peace of mind. The updated kitchen is the heart of the home, featuring stylish finishes, bar

  Tera Zapata Thrive Realty

  4817 Charlton Dr, Chesapeake, VA 23321
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• 

  

  

  /47

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  1530 Bainbridge Blvd, Chesapeake, VA 23324

  Waterfront home along the Elizabeth River offering both lifestyle & investment potential. This 3 bed, 2.5 bath + Bonus room features a 1st floor primary en-suite, new LVP flooring downstairs, fireplace, & versatile living spaces. Newer upgrades: new HVAC system, new roof, granite countertops, & updated appliances. The second-floor landing offers additional flexible space, including a cozy dormer

  Karen Davis RE/MAX Allegiance

  1530 Bainbridge Blvd, Chesapeake, VA 23324
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  /42

  $475,000

  • 4 Beds
  • 3.5 Baths
  • 2,177 Sq Ft

  1803 Honey Milk Rd, Chesapeake, VA 23323

  This home is still like NEW and move-in ready! Located in young convenient location - Great school district. Close to school bus stops. Main level features an open-concept layout filled with natural light, spacious living, dining area. Stunning kitchen with large center island, tile backsplash, stainless-steel appliances and spacious pantry, flows with gas fireplace and private rear-facing

  Miya Jang The Real Estate Group

  1803 Honey Milk Rd, Chesapeake, VA 23323
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  /50

  $483,000 Open House 4/11

  • 4 Beds
  • 3 Baths
  • 2,842 Sq Ft

  4620 Longleaf Place, Chesapeake, VA 23321

  Prepare to fall in love with this Beauty in the 55+ community of Retreat at Western Branch. You will be impressed as you move through the Entry Way and into the spacious and flowing Lafayette Floorplan that boasts a vaulted Great Room with gas fireplace that opens to the Dining Room and quartz Kitchen with large center island and upgraded appliances including gas range. You will find a 1st flr

  Rachael Kraft Turner GreenTree Realty Inc

  4620 Longleaf Place, Chesapeake, VA 23321
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  /31

  $404,900

  • 3 Beds
  • 2.5 Baths
  • 1,924 Sq Ft

  421 Blue Beech Way, Chesapeake, VA 23320

  Enjoy the carefree lifestyle of this community! Condo amenities include ground maintenance, clubhouse, in-ground swimming pool, sewer, water and trash pickup. This is a one-owner home which displays great pride in meticulous upkeep and cleanliness. LVP flooring was installed two years ago, microwave and water heater were installed in the past year. Neighborhood has a convenient layout for outdoor

  Juanita Harris Waterway Realty

  421 Blue Beech Way, Chesapeake, VA 23320
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  /46

  $437,500

  • 3 Beds
  • 2 Baths
  • 1,871 Sq Ft

  4165 Stonebridge Landing, Chesapeake, VA 23321

  Western Branch move in ready home. Home features nice manicured lot with inground sprinkler system and well. Brick exterior withcontemporary/mid century flair. Spacious back deck with connecting door to dining area or living space. Primary bedroom on level onewith full size double vanity bath, and connects to outdoor deck. Home is under a termite contract. Enjoy the open feel living

  LeAnn Amory BHHS RW Towne Realty

  4165 Stonebridge Landing, Chesapeake, VA 23321
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  /47

  $469,000

  • 4 Beds
  • 2.5 Baths
  • 2,465 Sq Ft

  828 Shadowberry Crest, Chesapeake, VA 23320

  Beautiful 4 Bedroom 2.5 Bath Home! This gorgeous property backs up to a pond with a small dock and an incredible view. A spacious kitchen, large master bedroom with a huge walk in closet. Master bath has dual sinks and a large garden tub.

  Cassie Parker Renters Warehouse

  828 Shadowberry Crest, Chesapeake, VA 23320
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  /30

  $450,000

  • 6 Beds
  • 4.5 Baths
  • 3,534 Sq Ft

  2224 Lloyd Dr, Chesapeake, VA 23325

  Come see this home in the heart of Georgetown Colony. This property is a prime addition to your portfolio. Don't miss out on this opportunity to maximize your income and create a steady return on investment.

  Travis Bouldin KW Coastal Virginia Chesapeake

  2224 Lloyd Dr, Chesapeake, VA 23325
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  /27

  $489,000

  • 4 Beds
  • 2.5 Baths
  • 2,410 Sq Ft

  1127 Norcova Ct, Chesapeake, VA 23320

  Beautiful single family detached home in convenient Greenbrier area of Chesapeake, with plenty of space for entertaining. This solid home offers a spacious living area with gas fireplace, which opens to a large kitchen w/ granite countertops and two separate sinks (one in the kitchen island) and breakfast nook. This home also features a separate formal dining room and 2nd living room that could

  Michael Reilly The Bryant Group

  1127 Norcova Ct, Chesapeake, VA 23320
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  /48

  $412,000

  • 4 Beds
  • 2.5 Baths
  • 2,036 Sq Ft

  1808 Aft Way, Chesapeake, VA 23323

  This beautiful tri-level 2-car garage condo in the sought-after Grassfield district offers luxurious and maintenance-free living! The first floor features a huge flex room that leads out to the backyard with a wooded view- ideal for a 4th bedroom, in-law suite, den, or office. The second floor features an open floor plan with a spacious living room, dining area, and the kitchen with an island,

  Amanda Ackiss Triumph Realty

  1808 Aft Way, Chesapeake, VA 23323
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  /25

  $475,000

  • 4 Beds
  • 2.5 Baths
  • 2,825 Sq Ft

  2804 Meadow Wood Dr W, Chesapeake, VA 23321

  Embrace timeless charm and modern comfort in this beautiful Colonial on a spacious .75-acre corner lot. Inside, a warm family room with a cozy fireplace flows into a sunlit eat-in kitchen with granite counters and a bay window. Host with ease in the formal dining room, then unwind on the screened porch or deck surrounded by nature. The spacious primary suite offers two walk-in closets and a

  Debbie Reynolds Keller Williams Richmond West

  2804 Meadow Wood Dr W, Chesapeake, VA 23321
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  /36

  $499,000

  • 5 Beds
  • 3.5 Baths
  • 3,338 Sq Ft

  2252 Dunbarton Dr, Chesapeake, VA 23325

  Discover this beautifully maintained 3338 square foot, six-bedroom, three-and-a-half-bath ranch home featuring an inground pool and versatile living spaces throughout. The main level offers a spacious primary suite, along with three additional bedrooms and a full bath. Upstairs, you’ll find two more generously sized bedrooms and another full bathroom. A flexible bonus room provides the perfect

  Jaime King Signature Homes

  2252 Dunbarton Dr, Chesapeake, VA 23325
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  /4

  $439,900

  • Land
  • 27.23 Acres
  • $16,154 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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  /34

  $460,000

  • 3 Beds
  • 3.5 Baths
  • 2,141 Sq Ft

  427 Life Tree Trail, Chesapeake, VA 23323

  STUNNING end-unit townhouse-design condominium in Grassfield. First floor living area is perfect flex space and includes full bath and drop zone next to the garage. Sleek gourmet kitchen with huge island opens to spacious family room with beautiful built-ins. Primary bedroom has custom accent wall and two walk-in closets. Spa-like primary bath has custom tile and double vanity. So many custom

  Kimberly Dykes Aweigh Real Estate

  427 Life Tree Trail, Chesapeake, VA 23323
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  /41

  $424,500

  • 3 Beds
  • 2.5 Baths
  • 1,791 Sq Ft

  557 Bright Red Run, Chesapeake, VA 23323

  Like New Construction! This stunning end-unit townhome-style condo, is only 4 years young. Nestled in the highly sought-after Grassfield area of Chesapeake. This beautifully maintained property offers the perfect blend of comfort and convenience. As you step inside, you’ll be greeted by an abundance of natural light that flows through the open layout. The kitchen is a true highlight, featuring

  Diara Roberson RHOAD & CO.

  557 Bright Red Run, Chesapeake, VA 23323
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  /44

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 2,315 Sq Ft

  816 Great Marsh Ave, Chesapeake, VA 23320

  Here's your chance to move into a well sought after community w/serene tree-lined views, private patio area & covered front porch. This beautiful huge corner lot townhome is move-in ready! It's all brick, 3 bed, 2.5 bath w/1 car attached garage, open-concept layout w/9' ceilings, crown molding, granite countertops, stainless appliances, primary bedroom features a tray ceiling, walk-in closet,

  Kimberly Bedsole BHHS RW Towne Realty

  816 Great Marsh Ave, Chesapeake, VA 23320
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  /49

  $494,500

  • 3 Beds
  • 2.5 Baths
  • 1,982 Sq Ft

  2011 Canning Place, Chesapeake, VA 23322

  Gorgeous pristine end unit on the water offers contemporary luxury and low maintenance lifestyle.The first floor features an open layout that combines the living and dining spaces with direct access to a private patio overlooking the pond. Windows have custom blinds with cornices that allow natural light to flow throughout. Gorgeous kitchen with cathedral ceiling, quartz countertops, stainless

  Robin Brinn Swell Real Estate Co

  2011 Canning Place, Chesapeake, VA 23322
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  /36

  $439,900

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft

  937 Mount Pleasant Rd, Chesapeake, VA 23322

  Welcome home to this move in ready, updated brick ranch situated on a spacious 2/3-acre lot in the heart of Chesapeake. Offering classic curb appeal and room to breathe, this home also boasts new paint & flooring throughout, all new kitchen cabinets, granite & appliances with breakfast bar. Large family room w loads of natural sunlight add to the functional, single-level layout designed for

  Denise Cowan Iron Valley Real Est Norfolk

  937 Mount Pleasant Rd, Chesapeake, VA 23322
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  /43

  $449,990

  • 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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  /13

  $450,000

  • Land
  • 0.54 Acre
  • $841,121 per Acre

  341 Scone Castle Loop, Chesapeake, VA 23322

  This is a rare chance to own a vacant lakefront lot in a prestine, established community of luxury custom homes valued between $1,300,000 and $2,000,000, a former HOMEARAMA neighborhood. Enjoy serene water views, mature landscaping, with proximity to top schools and convenient shopping. A soil report is available for your builder's review, and the seller is willing to provide custom house plans

  Jennifer Cool BHHS RW Towne Realty

  341 Scone Castle Loop, Chesapeake, VA 23322
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  /28

  $429,900

  • 3 Beds
  • 2 Baths
  • 1,771 Sq Ft

  2309 Drum Creek Rd, Chesapeake, VA 23321

  Beautiful Renovated Brick Ranch on a quiet street! Shows like a model, this 3 bedroom 2 bath home nestled on over a half acre lot (.69)! Open floor plan with huge great room that features a traditional wood burning fireplace! Chef's Kitchen with replaced shaker cabinets, upgraded stainless steel appliances and granite counters! Converted garage could be used as a 4th bedroom - spacious bedrooms,

  Michael Miller RE/MAX Allegiance

  2309 Drum Creek Rd, Chesapeake, VA 23321
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  /46

  $490,000

  • 4 Beds
  • 3 Baths
  • 2,842 Sq Ft

  4646 Longleaf Place, Chesapeake, VA 23321

  Welcome to easy living in this beautifully upgraded, better than new condo in a vibrant 55+ community! This home is packed with upgrades and thoughtful touches throughout featuring custom Closet Factory closets, built in bookcases, high end appliances, and decorative molding. Bright open concept layout with a gourmet kitchen, oversized island, upgraded cabinetry and upgraded lighting. Spacious

  Danielle Brinson KW Coastal Virginia Chesapeake

  4646 Longleaf Place, Chesapeake, VA 23321
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  /38

  $440,000

  • 3 Beds
  • 4 Baths
  • 2,089 Sq Ft

  914 Avast Way, Chesapeake, VA 23323

  Immaculate move in ready condition, 1 owner condo! This unit is the The Strauss model which offers the space of single-family living with the convenience of being maintenance-free. Espresso cabinetry throughout with granite in the kitchen & lvp flooring in the foyer, powder rooms, living room & kitchen. The lower level features a study with french doors and convenient powder room plus 2-car rear

  Lakilla Puryear KW Coastal Virginia Chesapeake

  914 Avast Way, Chesapeake, VA 23323
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  /11

  $475,000

  • 4 Beds
  • 2.5 Baths
  • 1,858 Sq Ft

  2308 Dunbarton Dr, Chesapeake, VA 23325

  Stop the Car!!! Come check out this beautiful brick rancher tucked away in the highly sought after area of Georgetown! Hard wood floors through the main living areas, plenty of garage & attic space for storage, and perfect sized backyard for hosting your guests! Conveniently located within minutes of schools, shopping, and dining. It's an opportunity you don't want to miss! New Roof (February

  Dolores Knight A Better Way Realty Inc.

  2308 Dunbarton Dr, Chesapeake, VA 23325
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  /49

  $445,000

  • 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 square feet! Kitchen has tons of cabinets. lots of counter space and opens to a large living area. Huge first floor primary bedroom with walk in closet and extra large master bath. Stainless appliances,recessed lighting, lvp flooring, heat 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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  /26

  $500,000

  • 4 Beds
  • 3.5 Baths
  • 1,973 Sq Ft

  627 Luray Terrace, Chesapeake, VA 23322

  Discover storybook charm and modern luxury in this Glenwood home on a picturesque corner lot. An artisan front door welcomes you to an effortless, one-story feel. The inviting family room, with its cozy decorative fireplace, flows into an updated, open-concept kitchen featuring gleaming granite countertops. Your private primary suite is a true escape with two closets, a renovated bath with a

  Melanie Gniewek Better Homes & Gdns Ntv Am Grp

  627 Luray Terrace, Chesapeake, VA 23322
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  /37

  $435,000

  1300 Bainbridge Blvd, Chesapeake, VA 23324

  Hurry to see a LUCRATIVE Mixed Use Property that is FULLY RENTED and generating exceptional income right now! The very attentive owner of 50 YEARS has skillfully maintained and improved this premium property that features TWO Commercial Spaces + THREE Residential Apartments. The Gross Monthly Rents total $3,825 and there are 5 SEPARATE METERS for the Electricity. The Owner occupies an additional

  George Trotman BHHS RW Towne Realty

  1300 Bainbridge Blvd, Chesapeake, VA 23324
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  /29

  $465,500

  • 4 Beds
  • 2 Baths
  • 2,079 Sq Ft

  557 Waters Rd, Chesapeake, VA 23322

  Welcome to your new home! This beautifully maintained 4-bedroom, 2-bathroom house offers a perfect blend of comfort and style. This home includes Newly installed Roof and water heater for year-round comfort and efficiency. Kitchen is cozy and Fully equipped with all-new stainless steel appliances, granite counter-tops, stylish fixtures, and ample counter space, great for cooking and entertaining.

  Tyleshia Stanley 1st Class Real Estate Norfolk

  557 Waters Rd, Chesapeake, VA 23322
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  /2

  $481,500

  • 4 Beds
  • 3 Baths
  • 2,108 Sq Ft

  500 Stillwater Dr, Chesapeake, VA 23320

  Bring your vision to this spacious 4 bedroom, 3 full bath split-level home located in the desirable Stillwater Farms neighborhood. Being sold as-is, this property is a rare opportunity for a growing or multi-generational family to move into a premier location and add their own personal touch. This home features formal fining room with hardwood flrs, eat-in kitchen, complete with granite

  Mahama Gonzales BHHS RW Towne Realty

  500 Stillwater Dr, Chesapeake, VA 23320
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  /19

  $438,900 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,044 Sq Ft

  4928 Apricot Way, Chesapeake, VA 23321

  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 granite countertops, subway tile backsplash, & soft-close drawers. Easily maintained &

  Angela McCaskill Corinth Realty LLC

  4928 Apricot Way, Chesapeake, VA 23321
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  /23

  $434,900 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,044 Sq Ft

  4932 Apricot Way, Chesapeake, VA 23321

  Unbelievable Incentives! Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This tri-level 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. Easily maintained & durable

  Angela McCaskill Corinth Realty LLC

  4932 Apricot Way, Chesapeake, VA 23321
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  /23

  $479,500 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,555 Sq Ft

  3511 Elaina Way, Chesapeake, VA 23321

  Move-in ready end-unit Nansemond in the 55+ community of The Retreat at Western Branch. This home presents a great value opportunity with an open layout designed for easy living. The kitchen sits at the heart of the home, featuring bar seating, a walk-in pantry, and convenient access to the living and dining areas. The first floor features a spacious primary suite, while the second floor includes

  Monique McClellan BHHS RW Towne Realty

  3511 Elaina Way, Chesapeake, VA 23321
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  /40

  $449,900 New Construction

  • 4 Beds
  • 3 Baths
  • 2,880 Sq Ft

  3509 Elaina Way, Chesapeake, VA 23321

  An incredible value opportunity in The Retreat at Western Branch. This move-in ready Lafayette floorplan backs to the wooded area, is priced to move, and offers space, flexibility, and comfort in a 55+ active adult community with low-maintenance living. The home features a first-floor primary bedroom, a huge island kitchen open to the living room, and a first-floor office or guest bedroom with a

  Monique McClellan BHHS RW Towne Realty

  3509 Elaina Way, Chesapeake, VA 23321
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  /31

  $449,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,557 Sq Ft

  4725 Mahogany Run, Chesapeake, VA 23321

  Move-in ready end-unit Nansemond floorplan with first-floor primary suite and 2-car garage in The Retreat at Western Branch, a 55+ community. Priced to sell. Open-concept kitchen with bar seating overlooking the living area with built-in shelves flanking the gas fireplace. Roomy walk-in pantry to keep everything organized and within reach. Enjoy outdoor living on the covered rear porch with

  Monique McClellan BHHS RW Towne Realty

  4725 Mahogany Run, Chesapeake, VA 23321
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  /38

  $449,900 New Construction

  • 4 Beds
  • 3 Baths
  • 2,880 Sq Ft

  3503 Elaina Way, Chesapeake, VA 23321

  Move-in ready Lafayette floor plan in the 55+ active adult community of The Retreat at Western Branch, backs to the wooded area and offers exceptional value. The open-concept layout features a spacious kitchen with a large island and two pantries for storage and organization. The first floor includes a primary suite and a flexible office or guest bedroom with a full bath. Upstairs offers a loft

  Monique McClellan BHHS RW Towne Realty

  3503 Elaina Way, Chesapeake, VA 23321
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  /29

  $467,843 Open Fri 12PM - 5PM

  • 3 Beds
  • 2.5 Baths
  • 1,740 Sq Ft

  711 Flatrock Ln, Chesapeake, VA 23320

  Under construction 2 story townhome condo w/ front load 1-car garage. Amenities include covered entry with built in mudroom hall tree w/ cubbies,1/2 bath, Luxury LVP, Kitchen breakfast bar, Ge Cafe Black Matt appliances w/refrigerator, pantry,Living area w/linear fireplace w/shiplap surround. Quartz tops all baths,Wood shelving all closets, 2nd floor:Primary,Tile Shower w/2-shower heads,

  Donna Melzer The Real Estate Group

  711 Flatrock Ln, Chesapeake, VA 23320
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  /41

  $498,575 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,614 Sq Ft

  4719 Mahogany Run, Chesapeake, VA 23321

  Ready Now! Don't miss your chance to own an end-unit Shenandoah at The Retreat at Western Branch, a 55+ low-maintenance community. This light-filled townhome is ideal for daily living and entertaining, featuring a kitchen that flows seamlessly into the great room with granite countertops and stainless-steel appliances. Luxuriate in the ease of first-floor living with your primary suite, office

  Monique McClellan BHHS RW Towne Realty

  4719 Mahogany Run, Chesapeake, VA 23321
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  /30

  $480,392 Open Fri 12PM - 5PM

  • 4 Beds
  • 3.5 Baths
  • 2,011 Sq Ft

  1062 Mesa Loop, Chesapeake, VA 23320

  Under Construction:LuxuryTownhome w/2-car garage, covered entry,fenced front yard w/gate to multi trail,covered entry.LVP floors select areas. 2nd floor:Kitchen center island w/shiplap, GE Cafe Stainless appliances w/ refrigerator,pantry,living area w/linear fireplace and shiplap surround w/ built ins,dining area access to covered front deck.3rd flr: Primary:tile shower 2-shower heads, dual

  Donna Melzer The Real Estate Group

  1062 Mesa Loop, Chesapeake, VA 23320

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