Chesapeake, VA Homes for Sale under $400,000

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  /39

  $325,000

  $21K PRICE DROP

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

  4111 Williamson St, Chesapeake, VA 23324

  Stunning renovation in Chesapeake! This 3BR 2BA gem features a brand new roof, new HVAC, and top-to-bottom updates designed for modern living. Gorgeous LVP flooring flows throughout an open, light-filled floor plan perfect for entertaining or working from home. The fully updated kitchen boasts new stainless steel appliances and sleek finishes that will impress any home chef. Retreat to a spacious

  Erika Miller NextHome Beyond Keys

  4111 Williamson St, Chesapeake, VA 23324
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  /30

  $350,000

  • 2 Beds
  • 1.5 Baths
  • 1,293 Sq Ft

  2112 Paramont Ave, Chesapeake, VA 23320

  Beautifully updated home in the desirable Greenbrier area! Features include a renovated kitchen with new appliances, updated baths, bright open living spaces, new flooring and great curb appeal. Enjoy a private backyard perfect for relaxing or entertaining. Conveniently located near Greenbrier Mall, shopping, dining, parks, and major highways. Move-in ready and in a sought-after school zone —

  Amanda Martinez Gallery Realty LLC

  2112 Paramont Ave, Chesapeake, VA 23320
• 

  

  /2

  $240,000

  • Land
  • 5.33 Acres
  • $45,054 per Acre

  B Taft Rd, Chesapeake, VA 23322

  Vacant cleared lot, road access via access easement via lot 1 adjacent to Taft road

  Tom Thrasher Greenbrier Real Estate & Appr.

  B Taft Rd, Chesapeake, VA 23322
• 

  

  /2

  $215,000

  • 3 Beds
  • 1.5 Baths
  • 1,436 Sq Ft

  1014 Castle Ct, Chesapeake, VA 23323

  Welcome to 1014 Castle Court! This three-bedroom, one-and-a-half-bath townhouse offers approximately 1,436 square feet of living space. The two-story layout provides a comfortable main living area and three upstairs bedrooms. Located in Chesapeake’s Camelot community, the property offers convenient access to shopping, restaurants, parks and major roadways serving Chesapeake and the surrounding

  Jim Callahan CoastalVA Realty Inc.

  1014 Castle Ct, Chesapeake, VA 23323
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  /41

  $235,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,306 Sq Ft

  3609 Parr Ln, Chesapeake, VA 23323

  Selling AS-IS. Needs Work/Rehab. Cash Or Hard Money Financing. Clear T&M Reports From Priority Pest

  Roman McClung Integrity Realty LLC

  3609 Parr Ln, Chesapeake, VA 23323
• 

  /2

  $230,000

  • Land
  • 1.38 Acres
  • $166,667 per Acre

  2701 Seven Eleven Rd, Chesapeake, VA 23322

  This is a wooded 1.38 acre lot along a lightly traveled road that's being gradually redeveloped. Survey in hand as well as a wetlands delineation report done in 2025 showing about 0.88 Acre of wetlands and about 0.50 Acre of non-wetlands towards the back of the lot. Seller has already done soil test and the property can accommodate a single-family home. Soil analysis and location of septic field

  Craig Brinn Wainwright Real Estate

  2701 Seven Eleven Rd, Chesapeake, VA 23322
• 

  

  /5

  $320,000

  • 3 Beds
  • 2.5 Baths
  • 1,610 Sq Ft

  709 Montrose Ct, Chesapeake, VA 23320

  Welcome to 709 Montrose Ct., Chesapeake, VA! This well- maintained two-story townhome offers 1,610 +/- sq. ft. of comfortable living space in a convenient location. Built in 1991, the home features 3 bedrooms, 2.5 baths, and a functional floor plan designed for everyday living. The spacious layout provides ample room for relaxing, entertaining, and working from home. Conveniently located near

  Christy Cole United Country - A B Cole&Asc

  709 Montrose Ct, Chesapeake, VA 23320
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  /41

  $360,000

  • 3 Beds
  • 2 Baths
  • 1,441 Sq Ft

  405 Villanova Ave, Chesapeake, VA 23324

  Welcome home to this beautifully updated brick rancher! This one is truly move-in ready, with LVP flooring throughout and a fresh, updated kitchen featuring soft close cabinets, granite countertops and new appliances. Major updates are already taken care of, too, with a new roof and HVAC in 2026. Outside, you’ll love the fenced-in backyard and the spacious deck, complete with a retractable awning

  Marianna Nice Swell Real Estate Co

  405 Villanova Ave, Chesapeake, VA 23324
• 

  

  /25

  $269,900

  • 3 Beds
  • 2 Baths
  • 1,213 Sq Ft

  1405 Perry St, Chesapeake, VA 23324

  AMAZING CENTRAL LOCATION FOR THIS RENOVATED BEAUTY! JUST A FEW BLOCKS AWAY FROM THE FREEWAY ENTRANCE! FRESH PAINT, LANDSCAPING, CARPETS, AND SO MUCH MORE! NEWER KITCHEN, BATHROOMS, LIGHT FIXTURES, AND PRIVACY FENCE! ADT SECURITY SYSTEM CONVEYS! ENJOY ALL THE BENEFITS OF A LOW ELECTRICITY BILL WITH SOLAR (NO MONEY OWED ON THE SYSTEM!)! BASEBALL FIELD AND LARGE ALL ABILITIES PLAYGROUND WITH A

  Pamela Ibanez LPT Realty LLC

  1405 Perry St, Chesapeake, VA 23324
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  /42

  $290,000

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft

  3010 Menands Dr, Chesapeake, VA 23325

  Welcome to 3010 Menands Drive, a beautifully renovated gem in the heart of Chesapeake. This charming 3-bedroom, 1-bathroom home offers 950 square feet of thoughtfully updated living space—all at a price point that makes homeownership refreshingly attainable.Inside, discover a residence that feels brand new. The kitchen shines with new Harbour Town slow close cabinets and beautiful quartz

  Christian Iturbe LPT Network Realty LLC

  3010 Menands Dr, Chesapeake, VA 23325
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  /14

  $275,000

  • Land
  • 4.87 Acres
  • $56,468 per Acre

  3725 Cornland Rd, Chesapeake, VA 23322

  Centrally located. QUIET, SECLUDED LIVING on 4.87 ACRES IN THE COUNTRY PART OF CHESAPEAKE. Located off RT 17 near the North Carolina line in a growing area. Less than 10 minutes to GREAT BRIDGE and minutes from I-64 for access to all S Hampton Roads and the Peninsula. PRIVACY, SECLUDED LOCATION. THE CITY OF CHESAPEAKE TAX RECORDS DOCUMENT LAND USE AS RESIDENTIAL ACREAGE. THIS IS A GOOD TIME TO

  Ronda Galko Howard Hanna Real Estate Svcs.

  3725 Cornland Rd, Chesapeake, VA 23322
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  /28

  $269,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,372 Sq Ft

  1331 Hull St, Chesapeake, VA 23324

  This home offers a well-maintained and move-in-ready home offering comfort, functionality, and modern updates. It strikes a balance between style, space, and convenience, offering a bright, inviting floor plan with spacious living areas. Outside, you'll find a private yard that's perfect for relaxing or entertaining. Additionally, Lakeside Park is perfect for a walk, just one block away, offering

  Christina Sherrill Creed Realty

  1331 Hull St, Chesapeake, VA 23324
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  /26

  $208,000

  • 3 Beds
  • 1 Bath
  • 975 Sq Ft

  1140 Woodland Terrace Dr, Chesapeake, VA 23323

  Brick ranch home with 3 bedrooms, 1 bath. Living room and dining room adjacent to kitchen. Convenient to interstates, shopping, entertainment and schools. Rooms are nicely sized and you have great sunlight throughout. 1 car attached garage, large yard.

  Charlene Howard Long & Foster Real Estate Inc.

  1140 Woodland Terrace Dr, Chesapeake, VA 23323
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  /4

  $256,000

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2566 Campostella Rd, Chesapeake, VA 23324

  This is a two bedroom home with two full bathrooms and a detached garage.

  Michael Bond Michael J. Bond Realty Inc.

  2566 Campostella Rd, Chesapeake, VA 23324
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  /28

  $282,400

  $3K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,315 Sq Ft

  1927 Candlelight Dr, Chesapeake, VA 23325

  Welcome to this immaculately maintained townhome with no HOA or condo fees! Offering two spacious bedrooms, each with it's own private en-suite full bathroom. Major updates including roof and HVAC system are both about 3 years old. This home features a spacious first floor with a kitchen and eat in area, a living room with a wood burning fireplace, a convenient half bath, and laundry. Sliding

  Mellissa Hecker Iron Valley Real Estate Prestige

  1927 Candlelight Dr, Chesapeake, VA 23325
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  /19

  $319,000

  $16K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,500 Sq Ft

  2801 Southport Ave, Chesapeake, VA 23324

  This beautifully updated property situated on a spacious corner lot of over a quarter acre in Chesapeake! Recent improvements completed in June 2026 include: a brand-new GAF architectural shingle roof, new gutters, new flooring throughout, and fresh interior paint, giving this home a clean, modern feel and added peace of mind. The versatile FLEX room offers endless possibilities and can easily

  Ryan Kilmon A Better Way Realty Inc.

  2801 Southport Ave, Chesapeake, VA 23324
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  /33

  $308,900

  • 2 Beds
  • 2.5 Baths
  • 1,456 Sq Ft

  3106 Barred Owl Ln, Chesapeake, VA 23323

  Welcome to this beautiful, meticulously maintained end-unit condo in the highly sought-after Culpepper Landing community! Updated lighting and fresh paint throughout. Offering privacy, abundant natural light, and a spacious feel. Enjoy an open layout with generously sized living spaces and low maintenance living. Enjoy the resort style amenities of the pool and fitness center! Conveniently

  Dawn Boyer The Bryant Group

  3106 Barred Owl Ln, Chesapeake, VA 23323
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  /43

  $379,999

  • 4 Beds
  • 2 Baths
  • 1,762 Sq Ft

  832 Parapet Rd, Chesapeake, VA 23323

  Nestled in Chesapeake’s established Camelot neighborhood, this beautifully updated vinyl and brick ranch offers 4 bedrooms, 2 full baths, and 1,762 square feet of comfortable single-level living. Luxury vinyl plank flooring flows throughout the main living areas, while the freestanding wood-burning stove creates a warm focal point for gathering. The kitchen features an oversized island, abundant

  Cristian Juarez ONYX Realty Professionals LLC

  832 Parapet Rd, Chesapeake, VA 23323
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  /32

  $399,999

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,903 Sq Ft

  2604 Elkhart St, Chesapeake, VA 23323

  R. Anne Ahluwalia 1st Class Real Estate Integrity

  2604 Elkhart St, Chesapeake, VA 23323
• 

  

  /18

  $349,900

  New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,495 Sq Ft

  2044 Mango St, Chesapeake, VA 23321

  1st LEVEL PRIMARY BDRM EN-SUITE featuring upgraded granite vanity & shower. This 2-level plan beautifully showcases an open floor plan w/ luxurious upgrades. The kitchen stuns guests w/ upgraded granite countertops, tile backsplash, & soft-close drawers. Easily maintained & durable LVP flooring throughout, crown molding 1st level main areas. 12' ceilings on 1st level & 9' ceilings on 2nd level.

  Leslie Lambert Corinth Realty LLC

  2044 Mango St, Chesapeake, VA 23321
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  /45

  $314,999

  Open Sun 10AM - 1PM $5K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,740 Sq Ft

  340 Gracie Rd, Chesapeake, VA 23325

  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

  Ron Sawyer RE/MAX Prime

  340 Gracie Rd, Chesapeake, VA 23325
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  /39

  $349,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,186 Sq Ft

  4201 Nautilus Ave, Chesapeake, VA 23325

  Charming cape cod home situated on a corner lot with 3 bedrooms and 2 bathrooms, including a brand-new primary bedroom suite. This home has been completely renovated and is move-in ready. The kitchen has new cabinets, granite countertops, stainless steel appliances and a pantry. There is a utility room with a new washer/dryer and additional storage space. Additional improvements in the home

  Rene Bagne Creed Realty

  4201 Nautilus Ave, Chesapeake, VA 23325
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  /34

  $325,000

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

  650 Lacy Oak Dr, Chesapeake, VA 23320

  Welcome to this spacious two-bedroom, two-and-a-half-bath condo in the desirable Greenbrier/Kempsville area. The versatile bonus room on the main level is ideal for a home office, playroom, or guest space. The kitchen features stainless steel appliances and opens to the dining area, with a walk-in pantry and convenient half bath nearby. Laminate flooring flows throughout the first floor, while

  Stephanie Hynes Redefy Real Estate

  650 Lacy Oak Dr, Chesapeake, VA 23320
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  /27

  $250,000

  • 2 Beds
  • 2.5 Baths
  • 1,254 Sq Ft

  206 Attwick Ct, Chesapeake, VA 23320

  Nicely updated 2bed, 2.5 bath condo in Knell's Ridge ready for you to move-in today! Both bedrooms with private, updated baths and walk-in closets. Fenced courtyard. Storage Shed. Convenient location. Community amenities include Pool, Clubhouse, Grounds Maintenance and Trash Collection.

  Karen Darden Aweigh Real Estate

  206 Attwick Ct, Chesapeake, VA 23320
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  /38

  $259,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,215 Sq Ft

  500 Judah Way Unit 123, Chesapeake, VA 23320

  Gated Community! Elevator! Move in ready for serene living. Bright and modern condo with elevator access to the 2nd floor. Open floor plan, family room with fireplace, kitchen with granite counter tops and upgraded cabinetry, stainless steel appliances, pantry and utility room. Two primaries with en-suites and balcony. Hardwood floors. Upgraded custom built-ins throughout. Private storage room on

  Paul Bauer The Bauer Group-RE Solutions

  500 Judah Way Unit 123, Chesapeake, VA 23320
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  /18

  $219,900

  $8K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  2041 Lockard Ave, Chesapeake, VA 23320

  Great starter home! This charming 3-bedroom, 1-bath ranch offers comfortable single-level living with plenty of potential. Enjoy the bright front sunroom, perfect for relaxing or creating additional living space, plus a screened-in side porch that provides a cozy, private retreat. The fenced backyard and storage shed offer room for hobbies, pets, gardening or future improvements. Conveniently

  Andreia Worst Wainwright Real Estate

  2041 Lockard Ave, Chesapeake, VA 23320
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  /44

  $354,900

  • 3 Beds
  • 1.5 Baths
  • 1,340 Sq Ft

  2001 Athens Ct, Chesapeake, VA 23323

  Water access, generous outdoor space, and exceptional garage possibilities make this ranch in the sought after Geneva Shores one to see! Situated on a cul-de-sac, this well maintained 3-bedroom, 1.5-bath home features beautiful hardwood floors, an updated kitchen with granite countertops, stainless-steel appliances, and beautiful soft close cabinetry and updated bathrooms. The fenced backyard

  Wendy Carbaugh Better Homes & Gdns Ntv Am Grp

  2001 Athens Ct, Chesapeake, VA 23323
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  /8

  $234,900

  $15K PRICE DROP

  • Land

  2716 Seven Eleven Rd, Chesapeake, VA 23322

  Excellent building opportunity. Great location. Surrounded by several custom built homes. Very private and priced below market.

  Fred Helm BHHS RW Towne Realty

  2716 Seven Eleven Rd, Chesapeake, VA 23322
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  /48

  $369,000

  $1K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 1,916 Sq Ft

  4122 Riverside Dr, Chesapeake, VA 23321

  Welcome to this well-maintained, like-new townhome in the desirable Fairview Towns community! Enjoy low-maintenance living in this newer gated community, conveniently located in Western Branch. This spacious tri-level townhome features 3 bedrooms, 2 full bathrooms, and 2 half bathrooms, along with two family rooms providing plenty of space for entertaining, relaxing, or creating a home office or

  Melissa Gibbs Howard Hanna Real Estate Svcs.

  4122 Riverside Dr, Chesapeake, VA 23321
• 

  

  /27

  $239,900

  • 2 Beds
  • 2 Baths
  • 1,098 Sq Ft

  3528 Sugar Run, Chesapeake, VA 23321

  Welcome to this beautifully maintained 2 bedroom, 2 full bathroom, first floor condo. Freshly painted throughout, this home gives a bright, welcoming feel. Seamlessly flowing from the living area into the kitchen, the open floor plan makes daily living and entertaining a delight. Enjoy the convenience of first-floor access with no stairs. Additional highlights include close proximity to highways,

  Stephen Do Iron Valley Real Est Norfolk

  3528 Sugar Run, Chesapeake, VA 23321
• 

  

  /13

  $275,000

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

  1321 Seaboard Ave, Chesapeake, VA 23324

  Beautifully updated 4 bedroom, 2 bath home in Chesapeake! Spacious home that features modern updates throughout and offers easy access to nearby interstates for a quick commute. Don’t miss the amazing blend of style, comfort, and convenience!

  Tavion Baker World Class Realty & Prop Mgmt

  1321 Seaboard Ave, Chesapeake, VA 23324
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  /31

  $369,999

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,970 Sq Ft

  4225 High Tide Way Unit 111, Chesapeake, VA 23321

  Welcome to this corner lot, 3 bedroom, 2.5 bath home located in Western Branch. LARGE primary bedroom with 2 walk- in closets & bath with jetted tub & separate shower. Jack & Jill bath for other 2 bedrooms. This home features a two-car garage with finished floor. Spacious, open floorplan with a family room open to the breakfast area & kitchen. Kitchen has ample granite counter space with an

  Carol Gardner Swell Realty Co

  4225 High Tide Way Unit 111, Chesapeake, VA 23321
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  /9

  $389,990

  New Construction $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,436 Sq Ft

  905 Railroad 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 3-bedroom, 2.5-bath home offering a modern living space. Designed with a spacious open floor plan, it's perfect for entertaining and everyday family living. Inside, the kitchen shines with soft-close

  Laura Rowe BHHS RW Towne Realty

  905 Railroad Ave, Chesapeake, VA 23324
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  /6

  $285,000

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft

  4024 Oak Dr, Chesapeake, VA 23321

  3 bedroom ranch in Western Branch ready to be updated into an amazing home!

  Erin Ward LPT Network Realty LLC

  4024 Oak Dr, Chesapeake, VA 23321
• 

  

  /8

  $324,900

  New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,495 Sq Ft

  MM Boone Grove, Chesapeake, VA 23321

  MASTER MODEL. 1st LEVEL PRIMARY EN-SUITE! Welcome to Boone Grove, an exquisite boutique community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level plan beautifully showcases an open floor plan w/ luxurious upgrades. The kitchen stuns guests w/ shaker-style cabinets, stone countertops, tile backsplash, & soft-close drawers. Easily

  Leslie Lambert Corinth Realty LLC

  MM Boone Grove, Chesapeake, VA 23321
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  /28

  $399,000

  $6K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,409 Sq Ft

  224 Hickory Rd E, Chesapeake, VA 23322

  Welcome to this stunning, move-in-ready masterpiece located in the heart of Hickory. This home has been meticulously renovated, boasting new siding for exceptional curb appeal and energy efficiency. Step inside to discover a bright, open interior featuring stylish new flooring throughout and a renovated kitchen complete with modern cabinetry and high-end finishes. Combining the charm of an

  Brian Mansfield Wainwright Real Estate

  224 Hickory Rd E, Chesapeake, VA 23322
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  /43

  $365,000

  $35K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft

  1073 Scenic Blvd, Chesapeake, VA 23322

  Closing cost assistance! Welcome to 1073 Scenic Boulevard! This beautifully updated ranch-style home offers modern finishes, flexible living space, and a private setting on approximately .4 acres in the desirable Great Bridge area. Step inside to an open and inviting floor plan featuring updated flooring, fresh paint, modern fixtures, and a stunning kitchen w/ white shaker cabinetry, granite

  Chris Jenkins Better Homes & Gdns Ntv Am Grp

  1073 Scenic Blvd, Chesapeake, VA 23322
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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
• 

  

  /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
• 

  

  /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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