Chesapeake, VA Homes for Sale under $300,000

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  /34

  $289,900

  New Construction

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

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

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

  Dragas Companies Builder

  1516 Elbow Rd Unit 36469973, Chesapeake, VA 23320
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  /2

  $275,000

  $45K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 905 Sq Ft

  843 Quail Ave, Chesapeake, VA 23324

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

  Paula Moore Keffer Realty

  843 Quail Ave, Chesapeake, VA 23324
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  /6

  $49,900

  $15K PRICE DROP

  • Land
  • 2,613 Sq Ft
  • $831,667 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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  /14

  $239,995

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

  516 Rue Marseille, Chesapeake, VA 23320

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

  Deanna Crook Signature Properties

  516 Rue Marseille, Chesapeake, VA 23320
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  /17

  $235,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 989 Sq Ft

  701 Rapidan River Ct Unit A, Chesapeake, VA 23320

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

  Eddie Gerardo-Ferrer RE/MAX Allegiance

  701 Rapidan River Ct Unit A, Chesapeake, VA 23320
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  /26

  $235,000

  $25K PRICE DROP

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

  1002 Willow Green Ct, Chesapeake, VA 23320

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

  Pamela Boone-Skeeter BHHS RW Towne Realty

  1002 Willow Green Ct, Chesapeake, VA 23320
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  /20

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,039 Sq Ft

  1302 Portlock Rd, Chesapeake, VA 23324

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

  Kim Stanley Green Tree Real Estate Inc

  1302 Portlock Rd, Chesapeake, VA 23324
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  /3

  $225,000

  • 2 Beds
  • 2 Baths
  • 962 Sq Ft

  401 Bracknell Arch Unit F, Chesapeake, VA 23320

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

  Malcolm Jenkins Swell Realty Co

  401 Bracknell Arch Unit F, Chesapeake, VA 23320
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  /7

  $249,000

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

  608 Edinburg Ave, Chesapeake, VA 23324

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

  Melissa Gibbs Howard Hanna Real Estate Svcs.

  608 Edinburg Ave, Chesapeake, VA 23324
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  /12

  $260,000

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

  1914 Woodgate Arch, Chesapeake, VA 23320

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

  Ashley Faulk Wainwright Real Estate

  1914 Woodgate Arch, Chesapeake, VA 23320
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  /5

  $289,900

  New Construction

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

  1540, Chesapeake, VA 23320

  Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details.Our Addison model features an open-concept floorplan & high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with center island,

  Clarice Savereux Dragas Companies Realty Inc

  1540, Chesapeake, VA 23320
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  /9

  $240,000

  $10K PRICE DROP

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

  4809 Sondej Ave, Chesapeake, VA 23321

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

  LeAnn Amory BHHS RW Towne Realty

  4809 Sondej Ave, Chesapeake, VA 23321
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  /42

  $285,000

  $13K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 996 Sq Ft

  1225 Jackson Ave, Chesapeake, VA 23324

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

  Ron Sawyer RE/MAX Prime

  1225 Jackson Ave, Chesapeake, VA 23324
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  /45

  $225,000

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

  4316 Hillingdon Bend Unit 305, Chesapeake, VA 23321

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

  Bridgette Hamm The Real Estate Group

  4316 Hillingdon Bend Unit 305, Chesapeake, VA 23321
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  /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
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  /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
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  /2

  $7,900

  • Land
  • 10,018 Sq Ft
  • $34,348 per Acre

  14 blk Tuck St, Chesapeake, VA 23322

  Vacant Land in Hillcrest subdivision. Zoned for great schools! Drive by anytime. Seller has never occupied the land, has no information to share. Buyer to perform all due diligence.

  Alexandra Serrano The Real Estate Group

  14 blk Tuck St, Chesapeake, VA 23322
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  /2

  $285,000

  Coming Soon

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

  2016 Rokeby Ave, Chesapeake, VA 23320

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

  Renee Perry BHHS RW Towne Realty

  2016 Rokeby Ave, Chesapeake, VA 23320
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  /38

  $299,000

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

  2454 Whitman St, Chesapeake, VA 23321

  This like-new beauty is a rare find, featuring THREE en-suite bedrooms (one on the first floor, and two on the second floor) each with their own bathrooms and walk-in closets. There is an additional bonus/flex room upstairs as well- perfect for an office, media room, workout space, or just extra storage space. Downstairs boasts an open kitchen with a breakfast bar, recessed & pendant lighting and

  Amanda Ackiss Triumph Realty

  2454 Whitman St, Chesapeake, VA 23321
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  /30

  $275,000

  • 4 Beds
  • 1.5 Baths
  • 1,624 Sq Ft

  708 B St, Chesapeake, VA 23324

  Updated 4-bedroom, 1.5-bath traditional two-story home featuring a welcoming front porch. Recent upgrades include a brand-new HVAC system with new ductwork, updated plumbing, and modernized electrical systems. The bathrooms have stylish tile finishes, a shower, and a tub. The stunning kitchen boasts granite countertops and stainless steel appliances. Convenient first-floor living includes a

  Kelly Liedtke AMW Real Estate Inc

  708 B St, Chesapeake, VA 23324
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  /39

  $290,000

  $35K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,430 Sq Ft

  1403 Algona Rd, Chesapeake, VA 23324

  Brick ranch, 3 bedrooms 1 1/2 baths. fresh pain throughout, newer flooring, new appliances. Large backyard. New HVAC.Termite and moisture report has been done.

  Amanda Martinez Gallery Realty LLC

  1403 Algona Rd, Chesapeake, VA 23324
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  /3

  $239,900

  • 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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  /29

  $287,000

  $2K PRICE DROP

  • 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, 1.5 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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  /23

  $264,000

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,304 Sq Ft

  708 Inlet Quay Unit B, Chesapeake, VA 23320

  Well desired community. First Floor corner unit, move-in ready. Beautiful wood flooring, updatedappliances, large primary bedroom with bathroom. Condo amenities include a pool, clubhouse, tennis courtsand close to trails.

  Lynn Atkison BHHS RW Towne Realty

  708 Inlet Quay Unit B, Chesapeake, VA 23320
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  /42

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,250 Sq Ft

  2704 Misty Point Rd, Chesapeake, VA 23323

  Room to garden, create, and entertain. A home designed for real use! Located at the end of a dead-end street on a cul-de-sac, this 3-bedroom, 1.5-bath home offers hardwood floors, a comfortable living area, and a full kitchen suite with all the countertop space, cabinets, and storage you need. The house only gets better outside, with an exceptional amount of usable outdoor space. In the front,

  Corey Hubbard Barn Door Homes

  2704 Misty Point Rd, Chesapeake, VA 23323
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  /41

  $295,000

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

  3714 Whitechapel Arch, Chesapeake, VA 23321

  Welcome to 3714 Whitechapel Arch! This move-in-ready townhouse features a new 2026 HVAC, tankless water heater, fresh paint throughout, cathedral ceilings, large closets, and an open floor plan. Enjoy the flexibility of two primary suites, each with an attached full bathroom: one upstairs and one downstairs. The upstairs also offers a versatile landing area. Additional features include an

  Daisy Phillips Atlantic Sothebys Int'l Realty

  3714 Whitechapel Arch, Chesapeake, VA 23321
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  /30

  $233,500

  $16K PRICE DROP

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

  1603 Seaboard Ave, Chesapeake, VA 23324

  Two-story traditional in Chesapeake's Quincy Place. 3 beds, 1.5 baths, ~1,360 sq ft. The new roof carries a 30-year warranty that transfers to the buyer—peace of mind for years to come. Updated light fixtures throughout, central air with forced hot air heat, and a partially finished attic for bonus living space. Two-space driveway on a low-maintenance ~0.07-acre lot. Single-family home in the

  Debbie Crevier Kent Cottage Street Realty LLC

  1603 Seaboard Ave, Chesapeake, VA 23324
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  /2

  $290,000

  • 4 Beds
  • 1.5 Baths
  • 1,176 Sq Ft

  3209 Dunworken Dr, Chesapeake, VA 23321

  AS IS, extra-large garage w/electricity & workshop area

  Michelle Harris 1st Class Real Estate Flagship

  3209 Dunworken Dr, Chesapeake, VA 23321
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  /8

  $165,000

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  3524 Clover Meadows Dr, Chesapeake, VA 23321

  Welcome home to this charming first-floor 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 storage.

  Jessica Cecchini RE/MAX Alliance

  3524 Clover Meadows Dr, Chesapeake, VA 23321
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  /2

  $7,334

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

  Lot 37 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 37 Trinkle St, Chesapeake, VA 23322
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  /13

  $249,000

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft

  2918 Berkley Ave, Chesapeake, VA 23325

  Great opportunity to own a 3 bedroom/2 bath ranch fixer upper/investment property being sold as-is. Needs updates and some TLC. Make this one your own. Large front porch and fully fenced yard. Storage shed out back.

  James Williams Atlantic Connection Real Estate

  2918 Berkley Ave, Chesapeake, VA 23325
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  /32

  $199,000

  • 2 Beds
  • 1.5 Baths
  • 1,262 Sq Ft

  3437 Bruin Dr, Chesapeake, VA 23321

  Welcome to this charming 2-bedroom, 1.5-bath townhome in the desirable Western Branch area of Chesapeake! This home offers a comfortable and functional layout with plenty of opportunity to add your own personal touches. Conveniently located near shopping, dining, schools, entertainment, and major roadways, making commuting throughout Hampton Roads easy. Whether you’re a first-time buyer,

  Hillary Kaufman Barn Door Homes

  3437 Bruin Dr, Chesapeake, VA 23321
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  /34

  $289,900

  New Construction

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

  1540 Eldwick Dr Unit 203, 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 203, Chesapeake, VA 23320
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  /4

  $189,900

  $190K PRICE INCREASE

  • 2 Beds
  • 1 Bath
  • 860 Sq Ft

  1811 Hoover Ave, Chesapeake, VA 23324

  Great beginning! A solid well-built affordable house with a large multi-level deck, screened porch area, and a large back yard with some trees. This house offers a spacious great room and loft area, with washer, dryer and refrigerator; located in a quiet Chesapeake neighborhood. The house is vacant and ready for you to move in right away. This affordable house is cheaper than some rental. You

  Eddie Franklin New Direction Real Estate Co.

  1811 Hoover Ave, Chesapeake, VA 23324
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  /21

  $162,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  3504 Clover Meadows Dr, Chesapeake, VA 23321

  Welcome home to this move-in ready, two-bedroom, two-bathroom condo located in the heart of Western Branch! Whether you are looking for your first home, or looking to downsize, you will enjoy low maintenance living in this first-floor unit that is conveniently accessible to Harbor View, Interstate 664, Interstate 64, shopping, dining, entertainment, and military bases! This condo comes with a

  Leia Dotson Keller Williams Coastal Virginia Chesapeake

  3504 Clover Meadows Dr, Chesapeake, VA 23321
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  /25

  $299,990

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,586 Sq Ft

  3834 Whitechapel Arch, Chesapeake, VA 23321

  Welcome home to this lovely, well-maintained 3 bedroom 2.5 bathroom townhome located in the heart of Western Branch! No HOA! Desirable school district! Freshly painted inside and out! New carpet on stairs! Primary suite features a walk-in closet! Loft area is ideal for a game room, fitness room or office! Screened-in patio is the perfect place for entertaining and relaxing! Centrally located for

  Ted Townsley Jason Mitchell Real Estate

  3834 Whitechapel Arch, Chesapeake, VA 23321
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  /2

  $7,334

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

  Lot 16 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 16 Binford St, Chesapeake, VA 23322
• 

  

  /5

  $294,900

  New Construction

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

  1540 Eldwick Drive #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,

  Clarice Savereux Dragas Companies Realty Inc

  1540 Eldwick Drive #303, Chesapeake, VA 23320
• 

  /2

  $7,334

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

  34 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.

  34 Trinkle St, Chesapeake, VA 23322
• 

  /2

  $16,700

  • Land
  • 10,018 Sq Ft
  • $72,609 per Acre

  1534 Tuck St, Chesapeake, VA 23322

  Three adjoining wooded residential lots available as a package in the established Hillcrest area of South Chesapeake. Includes 1534, 1536 & 1538 Tuck St. These contiguous parcels offer a unique opportunity for builders, investors, or buyers looking to get multiple lots for future development or personal use. Conveniently located near S. Battlefield Blvd and Johnstown Road with access to nearby

  Nancy Bui Keller Williams Realty Twn Ctr

  1534 Tuck St, Chesapeake, VA 23322

Showing Results 121 - 160, Page 4 of 5