Chesapeake, VA Homes for Sale under $300,000

• 

  

  /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

  $7,000

  • Land
  • 10,018 Sq Ft
  • $30,435 per Acre

  1737 Binford St, Chesapeake, VA 23322

  One of four adjacent parcels offered for sale in the Hillcrest neighborhood. Fantastic opportunity for holding as an investment, camping, urban archery hunting, riding fourwheelers, etc. Not required but you can buy all four and have a full acre for activities just 10 minutes from the heart of Great Bridge or Edinburgh! Roughly 900' from the paved St. of Arthurs Ct.

  Dustin Floyd Howard Hanna Real Estate Svcs.

  1737 Binford St, Chesapeake, VA 23322
• 

  

  /2

  $7,334

  • Land
  • 10,018 Sq Ft
  • $31,887 per Acre

  Lot 33 Trinkle St, Chesapeake, VA 23322

  Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the

  Dustin Floyd Howard Hanna Real Estate Svcs.

  Lot 33 Trinkle St, Chesapeake, VA 23322
• 

  

  /2

  $16,500

  • Land
  • 10,018 Sq Ft
  • $71,739 per Acre

  Lot 7 Tuck St, Chesapeake, VA 23322

  Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on

  Dustin Floyd Howard Hanna Real Estate Svcs.

  Lot 7 Tuck St, Chesapeake, VA 23322
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  /15

  $95,000

  • Land
  • 3,484 Sq Ft
  • $1,187,500 per Acre

  427 Freeman Ave, Chesapeake, VA 23324

  Prime opportunity in Chesapeake’s South Norfolk/Money Point area! This property is zoned M-2 (Heavy Industrial), offering excellent potential for commercial or industrial use. The parcel is approx. 3,572 sq ft and well-situated with convenient access to major thoroughfares, ports, and interstates.Onsite is a 2-bedroom, 1-bath home (approx. 1,016 sq ft) that can provide immediate rental income,

  Robert Rogers Real Broker LLC

  427 Freeman Ave, Chesapeake, VA 23324
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  /3

  $239,900

  $40K PRICE DROP

  • Land
  • 3.77 Acres
  • $63,702 per Acre

  743 Bedford St, Chesapeake, VA 23322

  This is a 3+ acre lot zoned A1 for agriculture use and barns. Build your own barn for your personal equipment or animals. Potential for commercial office/warehouse use with a conditional use variance from the Chesapeake City Council and Navy. Septic and well approvals are available. This lot cannot be used for a residential building site and air rights have been sold off. Owner will consider

  Robert Wadsworth Pungo Realty LLC

  743 Bedford St, Chesapeake, VA 23322
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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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  /40

  $299,900

  • 2 Beds
  • 2.5 Baths
  • 1,334 Sq Ft

  1313 Quail Creek Hollow Unit C, Chesapeake, VA 23320

  Private end-unit in desirable Greenbrier Fairways with a first-floor primary suite and spacious second bedroom. Versatile loft with closet overlooks the great room, great for an office, flex space, or potential third bedroom. Kitchen features ample cabinetry, pantry, and breakfast bar. Enjoy a backyard patio and attached storage shed. HVAC & roof (2019), flooring (2017), paint (2023). FHA/VA

  Cindy Mayberry BHHS RW Towne Realty

  1313 Quail Creek Hollow Unit C, Chesapeake, VA 23320
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  /2

  $9,900

  • Land
  • 15,681 Sq Ft
  • $27,500 per Acre

  3509 Sigmon Dr, Chesapeake, VA 23321

  Lot 100 Farmington Acres, approximately 0.36ac. Lot is located at 3509 Sigmon Dr. which is a paper street. 150' in from where Newport Dr. currently stops then turn right onto Sigmon Dr. heading back North approximately 300'. A gorgeous lot, will require improvements including but not limited to: wetlands delineation, and improvement of Newport Dr. and Sigmon Dr. to city standards before

  Dustin Floyd Howard Hanna Real Estate Svcs.

  3509 Sigmon Dr, Chesapeake, VA 23321
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  /18

  $285,000

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft

  4000 Kilbride Dr, Chesapeake, VA 23325

  All Brick Ranch with a detached garage on a fenced corner lot. The home is almost waterfront, neighbors just a few doors down are waterfront. Established area centrally located to interstates, schools, and shopping. Three bedrooms, one bath and no power bill. This home boasts a Solar system that cuts the power bill to the connection fee. Pavers off the back door offer added area for relaxing. The

  Charles Beeson Wainwright Real Estate

  4000 Kilbride Dr, Chesapeake, VA 23325
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  /2

  $285,000

  • 3 Beds
  • 2.5 Baths
  • 1,703 Sq Ft

  4606 Old Fox Trail, Chesapeake, VA 23321

  Tucked-Away Condo Charm in Western Branch!Located in the back of the community away from the street, this 3-bedroom, 2.5-bath townhomeoffers 1,703 square feet of comfortable living surrounded by peaceful green space and mature trees. Step inside to an open-concept layoutfeaturing a bright and airy eat-in kitchen with abundant storage, generous counter space, and an oversized pantry —

  Katherine Durbin Shaffer Real Estate Inc.

  4606 Old Fox Trail, Chesapeake, VA 23321
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  /17

  $265,000

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft

  2317 Wildwood Rd, Chesapeake, VA 23323

  Move-in ready and beautifully updated, this home offers the perfect blend of modern style and everyday functionality. Step inside to a bright, inviting interior featuring a beautifully renovated kitchen with soft-close shaker cabinetry, granite countertops, and brand-new stainless steel appliances—perfect for cooking, gathering, and entertaining. Outside, the spacious backyard provides plenty of

  Brian Wurst A Better Way Realty Inc.

  2317 Wildwood Rd, Chesapeake, VA 23323
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  /38

  $264,900

  $5K 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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  /28

  $239,900

  • 3 Beds
  • 1.5 Baths
  • 1,268 Sq Ft

  824 Huntly Dr, Chesapeake, VA 23320

  Tyler Keffer Keffer Realty

  824 Huntly Dr, Chesapeake, VA 23320
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  /11

  $165,000

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  3301 Clover Meadows Dr, Chesapeake, VA 23321

  Welcome home to this charming first-floor end-unit condo in the desirable Clover Meadows community of Western Branch! Offering 2 bedrooms and 1 full bath, this well-maintained condo features an open and functional layout with abundant natural light and added privacy as an end unit. Enjoy easy one-level living with a spacious living area, cozy dining space, and a bright kitchen with ample cabinet

  Jessica Cecchini RE/MAX Alliance

  3301 Clover Meadows Dr, Chesapeake, VA 23321
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  /14

  $227,900

  • 3 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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  /8

  $250,000

  • 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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  /30

  $237,500

  $8K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,255 Sq Ft

  1016 Thoroughgood Way Unit 307, Chesapeake, VA 23324

  Beautifully maintained, one-owner, 3rd-floor condo with elevator access in a secure-entry building. This open-concept home offers a bright, airy layout with a private balcony—great for relaxing. Gated parking adds convenience and peace of mind. Ideally located near downtown Norfolk, Waterside District, military bases, shipyard, interstates, dining, shopping, and entertainment venues. Adjacent to

  Sherri Bryant The Bryant Group

  1016 Thoroughgood Way Unit 307, Chesapeake, VA 23324
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  /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
• 

  /2

  $7,334

  • Land
  • 10,018 Sq Ft
  • $31,887 per Acre

  Lot 38 Trinkle St, Chesapeake, VA 23322

  Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the

  Dustin Floyd Howard Hanna Real Estate Svcs.

  Lot 38 Trinkle St, Chesapeake, VA 23322
• 

  /2

  $95,000

  $3K PRICE INCREASE

  • 2 Beds
  • 1 Bath
  • 764 Sq Ft

  2053 Iowa St, Chesapeake, VA 23323

  Value is in the land. Property being sold as-is. Home is not in livable condition.

  Dwayne Hart Keller Williams Coastal Virginia Chesapeake

  2053 Iowa St, Chesapeake, VA 23323
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  /39

  $299,000

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft

  746 Sendero Ct, Chesapeake, VA 23322

  Welcome to Sendero Ct! Located with-in a Cul-de-sac. Spacious End unit townhome has 2 bedrooms, Loft and 2 baths. Head inside and notice the bold, beautiful new flooring and freshly paint, updated Kitchen and 2 updated bathrooms. Fenced Backyard Oasis with Hot Tub and Grilling area. Located near Hwy 17 and easy access to Downtown Norfolk, VA Beach, Suffolk, Military Bases, Shopping, Restaurants

  Corinne Zedd The Real Estate Group

  746 Sendero Ct, Chesapeake, VA 23322
• 

  /2

  $7,334

  • Land
  • 10,018 Sq Ft
  • $31,887 per Acre

  39 Trinkle St, Chesapeake, VA 23322

  Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the

  Dustin Floyd Howard Hanna Real Estate Svcs.

  39 Trinkle St, Chesapeake, VA 23322
• 

  

  /25

  $299,900

  Open Thu 1PM - 3PM $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  508 Mooney Rd, Chesapeake, VA 23325

  Move-in ready Chesapeake ranch with major system updates buyers will appreciate. The roof was replaced in 2025, and the water heater is less than 5 years old. This 3 bedroom, 2 bath brick home offers a comfortable floor plan with a spacious kitchen, family room addition, and flexible living spaces for everyday living and entertaining. The fenced backyard provides outdoor space for relaxation,

  Missy Abrams L'Hoste Keller Williams Realty Twn Ctr

  508 Mooney Rd, Chesapeake, VA 23325
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  /18

  $249,999

  $125K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,170 Sq Ft

  604 Amick Rd, Chesapeake, VA 23325

  Beautiful property offering both investment and owner-occupant potential. Located in a desirable area. Sold As-Is. Seller will not make repairs . 4bedrooms 2full baths.

  Norman Domingo XRealty.NET LLC

  604 Amick Rd, Chesapeake, VA 23325
• 

  /2

  $16,500

  • Land
  • 10,018 Sq Ft
  • $71,739 per Acre

  Lot 9 Tuck St, Chesapeake, VA 23322

  Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on

  Dustin Floyd Howard Hanna Real Estate Svcs.

  Lot 9 Tuck St, Chesapeake, VA 23322
• 

  

  /11

  $255,000

  • 3 Beds
  • 1.5 Baths
  • 1,292 Sq Ft

  74 Colonial Way, Chesapeake, VA 23325

  BEAUTIFUL ALL-BRICK END-UNIT TOWNHOME!Don't miss this exceptional opportunity to own this beautifully maintained all-brick end-unit townhome in a well-established neighborhood that truly reflects pride of ownership.Features include:Beautiful all-brick constructionDesirable end-unit locationNO HOA!Conveniently located near major interstates for an easy commuteMinutes from hospitals, shopping,

  Willie Farmer Weichert Realtors-KBL Company

  74 Colonial Way, Chesapeake, VA 23325
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  /6

  $65,000

  • Land
  • 2,613 Sq Ft
  • $1,083,333 per Acre

  0 Folk St Unit 10640840, Chesapeake, VA 23323

  Corner lot for sale in established neighborhood. Buy individually or in conjunction with 28 Hinton.

  Jamey Fereday World Class Realty

  0 Folk St Unit 10640840, Chesapeake, VA 23323
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  /16

  $255,000

  $5K 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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  /20

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,245 Sq Ft

  4626 Old Fox Trail, Chesapeake, VA 23321

  Welcome home to this well-maintained 3-bedroom, 2-bath end-unit condo in the sought-after Western Branch area. The bright and inviting living room features a tray ceiling, natural light, and a gas fireplace. The spacious primary suite offers a walk-in closet and private en-suite bath. The kitchen includes newer appliances, a convenient bar-height counter, and a breakfast nook for casual dining.

  Jonathan Shepheard House Goals

  4626 Old Fox Trail, Chesapeake, VA 23321
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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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  /7

  $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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  /34

  $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
• 

  

  /17

  $300,000

  • 2 Beds
  • 2 Baths
  • 1,141 Sq Ft

  1311 Eagles Path Trace Path Unit A, Chesapeake, VA 23320

  Single level Condo in Greenbrier Country Club golfing community. Wooded. This 1 level 2 bedroom home is an great option for today's discerning buyer who is looking for simplicity and location. As-is where is. Seller cannot make repairs. Garage is designed for storage. No parking

  sean schroeder Explore Coastal Virginia Homes Inc.

  1311 Eagles Path Trace Path Unit A, Chesapeake, VA 23320
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  /2

  $7,334

  • Land
  • 10,018 Sq Ft
  • $31,887 per Acre

  Lot 18 Binford St, Chesapeake, VA 23322

  Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the

  Dustin Floyd Howard Hanna Real Estate Svcs.

  Lot 18 Binford St, Chesapeake, VA 23322
• 

  

  /3

  $50,000

  • Land
  • 3,049 Sq Ft
  • $714,286 per Acre

  1316 20th St, Chesapeake, VA 23324

  This buildable lot with existing driveway is next door to 1314 20th street in Chesapeake, and can be negotiated together, or sold separately. Seller is a licensed Virginia Realtor.

  Elizabeth DeVault Better Homes & Gdns Ntv Am Grp

  1316 20th St, Chesapeake, VA 23324
• 

  

  /29

  $289,000

  • 3 Beds
  • 1.5 Baths
  • 1,112 Sq Ft

  718 Osborn Ave, Chesapeake, VA 23325

  Don’t miss this charming brick starter home offering 3 bedrooms, 2 full baths, and just under 1,200 sq. ft. The updated kitchen, newer roof, HVAC, and windows (all under 5 years old) provide peace of mind, while the fully fenced backyard offers plenty of space to relax or play. Conveniently located near interstates, military bases, shopping, and restaurants, and zoned for Indian River schools. A

  Jennifer Lamb Triumph Realty

  718 Osborn Ave, Chesapeake, VA 23325
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  /28

  $265,000

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

  2306 Bainbridge Blvd, Chesapeake, VA 23324

  Welcome to this beautifully updated 2 bedroom, 1.5 bath home located in South Norfolk! Renovated in 2023, this home offers a fresh, modern feel throughout. The updates included a fully remodeled kitchen featuring new cabinets, granite countertops, and new appliances, as well as both bathrooms upgraded with stylish tile surrounds. Upon entering, you’ll find an open and inviting space featuring

  Vernon Sims Keller Williams Realty Twn Ctr

  2306 Bainbridge Blvd, Chesapeake, VA 23324
• 

  

  /8

  $288,500

  $12K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  106 Greenbrier Rd, Chesapeake, VA 23320

  Cute 1 story cottage in the heart of Greenbrier Chesapeake on almost an acre of private wooded property. This charming 2 bedroom home with a bonus room that has been used as a 3rd bedroom (no closet). Bright and Airy vintage appeal. Galley Kitchen opens to dining room with arched opening to living room. Open concept with character.The property is zoned Industrial and the current legal use is

  Jay Hassell Keller Williams Realty Twn Ctr

  106 Greenbrier Rd, Chesapeake, VA 23320

Showing Results 81 - 120, Page 3 of 4