Affordable Homes for Sale in Chesapeake, VA under $322,000

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  /15

  $249,000

  • 4 Beds
  • 2 Baths
  • 1,528 Sq Ft

  3604 Bosun Dr, Chesapeake, VA 23321

  This 4-bedroom, 2-bathroom single-family home at 3604 Bosun Dr, Chesapeake, VA 23321, is a prime opportunity for investors looking for steady rental income or a value-add project in the highly desirable Western Branch submarket. Situated in Western Branch, a neighborhood known for its low turnover and reliable tenant base. It is conveniently close to major military hubs like the Portsmouth Naval

  Charles Cornwell 1EXP Realty, LLC

  3604 Bosun Dr, Chesapeake, VA 23321
• 

  

  

  /23

  $149,900

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  3529 Clover Meadows Dr, Chesapeake, VA 23321

  This FIRST FLOOR condo offers 2 bedrooms and 1 full bath, great for those seeking convenient one-level living in a prime location. The functional layout provides comfortable living and dining spaces with great natural light, while the bedrooms offer flexibility for a guest room, or home office. Enjoy the benefit of low exterior maintenance, making this an ideal option for first-time buyers, down

  Tracey Caddy Southside Real Estate

  3529 Clover Meadows Dr, Chesapeake, VA 23321
• 

  

  /2

  $12,000

  • Land
  • 9,583 Sq Ft
  • $54,545 per Acre

  1430 Trinkle St, Chesapeake, VA 23322

  Three adjoining wooded residential lots (Lots 28, 30 & 32) available in the established Hillcrest area of South Chesapeake. Each parcel is approximately 50’ x 200’, offering a unique opportunity to purchase individually or together for added flexibility and potential.Interior lots located near Arthur’s Court with convenient access to S. Battlefield Blvd and Johnstown Road. Ideal for builders,

  Connie Bowe Fathom Realty

  1430 Trinkle St, Chesapeake, VA 23322
• 

  

  

  /50

  $297,900

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft

  5 Harbor Watch Dr Unit 419, Chesapeake, VA 23320

  Life along the Intracoastal Waterway begins here—where mornings start with a cup of coffee on your private balcony and evenings end in a serene, relaxed atmosphere. The open-concept layout seamlessly transitions from the kitchen to the dining area, creating a space designed for effortless mornings and entertaining guests. A sliding glass door floods the space with natural light, extending your

  Paulette Harris Howard Hanna Real Estate Svcs.

  5 Harbor Watch Dr Unit 419, Chesapeake, VA 23320
• 

  

  

  /31

  $305,000

  • 3 Beds
  • 2.5 Baths
  • 1,776 Sq Ft

  2628 Leytonstone Dr Unit 352, Chesapeake, VA 23321

  This stunning condo features an ideal floor plan, spacious bedrooms, and oversized closets with custom built-ins. The desirable primary first-floor bedroom offers convenience and flexibility while fresh paint and brand-new carpet make this home move-in ready. Enjoy relaxing on your private patio and a thoughtfully designed layout with three spacious bedrooms, two full bathrooms, and a convenient

  Haley Rosario LPT Realty LLC

  2628 Leytonstone Dr Unit 352, Chesapeake, VA 23321
• 

  /2

  $12,000

  • Land
  • 9,583 Sq Ft
  • $54,545 per Acre

  1432 Trinkle St, Chesapeake, VA 23322

  Three adjoining wooded residential lots (Lots 28, 30 & 32) available in the established Hillcrest area of South Chesapeake. Each parcel is approximately 50’ x 200’, offering a unique opportunity to purchase individually or together for added flexibility and potential.Interior lots located near Arthur’s Court with convenient access to S. Battlefield Blvd and Johnstown Road. Ideal for builders,

  Connie Bowe Fathom Realty

  1432 Trinkle St, Chesapeake, VA 23322
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  /36

  $275,000

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

  712 Inlet Quay Unit A, Chesapeake, VA 23320

  Move-in ready and one-level living! This spacious 2-bedroom, 2-bath home offers 1,304 sq ft with large living areas and a massive primary suite featuring a walk-in closet and full bath. Enjoy an outdoor patio with an exterior storage closet and the ease of low-maintenance living. The home features many thoughtful upgrades throughout that you don't want to miss out on. Schedule a showing today!

  Lizzy Zetlin Taylor BHHS RW Towne Realty

  712 Inlet Quay Unit A, Chesapeake, VA 23320
• 

  

  /19

  $187,000

  • 3 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  3860 Schooner Trail, Chesapeake, VA 23321

  Come see this one first—it won’t last long at this price. This Chesapeake townhome is vacant and move-in ready, offering a great opportunity for both first-time buyers and investors. Featuring a new roof, new HVAC, and new appliances, this home has major updates already completed. Easy to rent and a strong addition to any investment portfolio. Conveniently located with access to Western Branch

  Melissa Gibbs Howard Hanna Real Estate Svcs.

  3860 Schooner Trail, Chesapeake, VA 23321
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  /17

  $247,500

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  102 Diamond Ave Unit D, Chesapeake, VA 23323

  A Diamond Condo with NO FEES! Located in the highly sought-after Grassfield school district, this condo has had a complete transformation. come into a beautiful cathedral ceiling and unique reading nook under the stairs. New SS Appliances in the kitchen, new luxury vinyl floors, all new bathroom and bedroom/office downstairs with laundry. Private upstairs bedroom with spacious closet space and

  Kara Louk Iron Valley Real Est Norfolk

  102 Diamond Ave Unit D, Chesapeake, VA 23323
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  /2

  $7,334

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

  15 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.

  15 Binford St, Chesapeake, VA 23322
• 

  

  /39

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,523 Sq Ft

  712 Inlet Quay Unit F, Chesapeake, VA 23320

  Welcome to this spacious condo in the desirable Riverwalk community!! This home features an open-concept floor plan with a convenient first-floor bedroom. The kitchen and bathrooms were fully renovated in 2022, showcasing modern cabinetry and elegant granite countertops .New Carpet and LVP , Water heater replaced 2024. Step outside to a large private balcony—great for entertaining or relaxing.

  Constance Simms Keffer Realty

  712 Inlet Quay Unit F, Chesapeake, VA 23320
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  /2

  $7,334

  • Land
  • 20,037 Sq Ft
  • $15,943 per Acre

  19-20 Caddie 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.

  19-20 Caddie St, Chesapeake, VA 23322
• 

  

  /23

  $245,000

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

  4348 Stafford Dr, Chesapeake, VA 23321

  Move-in ready 2-bedroom, 1.5-bath townhouse with no association fees—a rare find! Major updates have already been taken care of, including a roof, HVAC system, replacement windows, and vinyl siding all just 2 years old. The kitchen features granite countertops and a brand-new range, perfect for everyday cooking and entertaining. Enjoy a spacious family room with a cozy wood-burning fireplace, and

  Tammy Patel Garrett Realty Partners

  4348 Stafford Dr, Chesapeake, VA 23321
• 

  

  /18

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  2041 Lockard Ave, Chesapeake, VA 23320

  Great investment opportunity! This 3 bedroom, 1 bath ranch comes with a tenant in place through January 2027, offering immediate rental income. Enjoy a bright front sunroom that adds extra living space and screen-in side porch - a cozy, private spot to relax. The fenced backyard and storage shed provide versatility for tenants or future updates. Single-level living in a convenient location near

  Andreia Worst Wainwright Real Estate

  2041 Lockard Ave, Chesapeake, VA 23320
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  /16

  $179,900

  • 3 Beds
  • 1.5 Baths
  • 1,280 Sq Ft

  4061 Holly Cove Dr, Chesapeake, VA 23321

  Great Investment! 3 bedroom, 1 1/2 bath townhouse located in the Western Branch section of Chesapeake. Nearby shopping, restaurants and interstate. Property is being sold as part of a portfolio - 10628174 and 10628119.

  Jacob Sloop 1st Class Real Estate Flagship

  4061 Holly Cove Dr, Chesapeake, VA 23321
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  /2

  $7,334

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

  Lot 22 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 22 Trinkle St, Chesapeake, VA 23322
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  /26

  $219,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  948 Saint Andrews Reach Unit B, Chesapeake, VA 23320

  Welcome home! This tastefully renovated condo has recently been updated with fresh flooring, and upgraded bathroom, redesigned kitchen, and fresh paint throughout. The converted loft space can be used as an office or bedroom. Centrally located in Greenbrier near shopping, restaurants, parks, and highway access. Enjoy the peace and quiet of Saint Andrew's Reach while only being a stones throw from

  Joseph Bergamino Real Broker LLC

  948 Saint Andrews Reach Unit B, Chesapeake, VA 23320
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  /27

  $258,000

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

  720 Inlet Quay Unit A, Chesapeake, VA 23320

  First floor unit in desirable Riverwalk community. Enjoy all of the amenities of the community; Clubhouse, boat slip, tennis courts, pool, paths, playground and more. Close to restaurants, shopping, entertainment and interstate. This well maintained unit includes an AC system less than three years old. Refrigerator is less than three years old. Updated flooring, and sliding glass doors. Very

  Kenneth Holt The Real Estate Group

  720 Inlet Quay Unit A, Chesapeake, VA 23320
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  /35

  $235,000

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

  616 Ridge Cir, Chesapeake, VA 23320

  Knells Ridge in Greenbrier area and close to Chesapeake hospital. 2 primary bedrooms/2.5 bath corner unit. Freshly painted. LVP downstairs and carpet upstairs. Open floor plan with great room with fireplace and kitchen area. Kitchen has bar counter top, all appliances including washer & dryer and convey "as is." Both bedrooms have walk-in closets & private baths. Private fenced courtyard &

  Jorge Gonzalez RE/MAX Allegiance

  616 Ridge Cir, Chesapeake, VA 23320
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  /26

  $270,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 1.5 Baths
  • 1,064 Sq Ft

  901 Seabreeze Ct, Chesapeake, VA 23320

  Completely remodeled end-unit townhome next to the water. New flooring throughout, new paint, new bathrooms, updated kitchen with stainless appliances and granite countertops, backyard space perfect for gardening or relaxing outdoors, 2 parking spaces, fireplace as-is

  Kathryn Sharpe Howard Hanna Real Estate Svcs.

  901 Seabreeze Ct, Chesapeake, VA 23320
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  /35

  $278,000

  • 2 Beds
  • 2.5 Baths
  • 1,642 Sq Ft

  140 Springer Ln Unit 232, Chesapeake, VA 23320

  Charming 2-Bedroom Condo with Dual Balconies, a large walk-in closet and a private bathroom in each room, along with a half-bath in the common area for your guests. This Community is a safe haven with a security code for the front gate & your building entrance. Just minutes from Greenbrier shopping, city parks, dining, and local attractions, for convenient travel. If you love a clean, pristine

  Kishma Merritt Iron Valley Real Est Norfolk

  140 Springer Ln Unit 232, Chesapeake, VA 23320
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  /26

  $225,000

  • 2 Beds
  • 2 Baths
  • 978 Sq Ft

  1718 Rock Bridge Mews Unit B, Chesapeake, VA 23320

  JUST PLAIN CUTE. WELCOME TO THIS BEAUTIFULLY UPDATED FIRST FLOOR 2 BED/2 BATH CONDO WITH THE SWEETEST COASTAL INSPIRED KITCHEN WITH CUSTOM MOSIAC TILE. ITS COZY. LOW MAINTNANCE AND PERFECTLY LOCATED NEAR SHOPPING, RESTAURANTS AND INTERSTATE! CONDO ASSN COVERS MASTER INSURANCE POLICY, GROUNDS MAINTENANCE, WATER, SEWER.

  Sheri Pynn Creed Realty

  1718 Rock Bridge Mews Unit B, Chesapeake, VA 23320
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  /4

  $289,900

  • Land
  • 14,810 Sq Ft
  • $852,647 per Acre

  904 Brice Ct, Chesapeake, VA 23322

  You finally found a lot for sale in Great Bridge - in a subdivision - in a cul-de-sac-ready for your house to be platted - need a builder - no problem - got it covered yourself - no problem - give us a call - Great Bridge School District at every level -Whether you're an investor, builder, or future homeowner, this is a rare opportunity to secure a premium piece of land in a desirable

  Patty Cohen RE/MAX Allegiance

  904 Brice Ct, Chesapeake, VA 23322
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  /27

  $310,000

  • 3 Beds
  • 2.5 Baths
  • 1,300 Sq Ft

  1 Newstead Cir, Chesapeake, VA 23320

  Beautiful home tucked away on a tree-lined street on a cul-de-sac. This Home offers privacy, space, and smart updates throughout. Enjoy a spacious backyard with a patio and large shed, perfect for unwinding. The heavy lifting is done HVAC (2022), kitchen remodel (2025), hall bath (2022), 2nd-floor flooring (2022), enlarged laundry room + sliding door (2022), primary bath remodel (2024), windows

  Brent Montella Sea Shore Realty & Prop. Mgmt.

  1 Newstead Cir, Chesapeake, VA 23320
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  /2

  $7,334

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

  36 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.

  36 Trinkle St, Chesapeake, VA 23322
• 

  

  /16

  $70,000

  • Land
  • 3,920 Sq Ft
  • $777,778 per Acre

  435 Freeman Ave, Chesapeake, VA 23324

  Prime opportunity in Chesapeake’s South Norfolk/Money Point area! This vacant parcel is zoned M-2 (Heavy Industrial), offering excellent potential for a wide range of commercial or industrial uses. The lot is approx. 3,920 sq ft and ideally positioned with convenient access to major thoroughfares, interstates, and the Port of Virginia.The value here is in the land and its flexible zoning, making

  Robert Rogers Real Broker LLC

  435 Freeman Ave, Chesapeake, VA 23324
• 

  

  /31

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,327 Sq Ft

  204 Velva Dr, Chesapeake, VA 23325

  Located in Chesapeake, this beautiful updated 3-bedroom, 2-bath home offers a spacious layout designed for comfortable living. The interior features an open-concept main living area that flows into a large eat-in kitchen with a center island, granite countertops, stainless steel appliances, recessed lighting, and generous cabinet space. A sizable additional living area with vaulted ceilings

  Madison Sherwood Swell Realty Co.

  204 Velva Dr, Chesapeake, VA 23325
• 

  

  /13

  $228,000

  • 2 Beds
  • 2 Baths
  • 1,367 Sq Ft

  2469 Leytonstone Dr Unit 106, Chesapeake, VA 23321

  Welcome to beautiful Kings Pointe ! Just a convenient quick walk from an assigned parking space through a covered breezeway to open-concept living with 9 foot ceilings & newer LVP flooring (2023). Enjoy the refreshing community swimming pool this summer and take advantage of grilling with friends on the pool deck. Located in the Western Branch area of Chesapeake near restaurants and shops - plus

  Nancy Morefield Real Broker LLC

  2469 Leytonstone Dr Unit 106, Chesapeake, VA 23321
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  /24

  $310,000

  • 2 Beds
  • 2 Baths
  • 1,462 Sq Ft

  728 W Lake Cir, Chesapeake, VA 23322

  Step into easy, modern living with this turn-key 2 bedroom condo Designed for both comfort and convenience, Each spacious bedroom features its own private en-suite bathroom-ideal for privacy guests or a roommate setup.The open -concept layout creates a bright and inviting atmosphere, seamlessly connecting the living, dining, and kitchen areas-ideal for entertaining or relaxing at

  Willie Farmer Weichert Realtors-KBL Company

  728 W Lake Cir, Chesapeake, VA 23322
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  /2

  $7,334

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

  Lot 35 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 35 Trinkle St, Chesapeake, VA 23322
• 

  /2

  $7,334

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

  LOT 40 Caddie 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 40 Caddie St, Chesapeake, VA 23322
• 

  

  /15

  $290,000

  • Land
  • 7.4 Acres
  • $39,189 per Acre

  1813 Shillelagh Rd, Chesapeake, VA 23323

  Great opportunity to own approx 7.4 acres in Hickory! This city-approved building site has already been cleared and is ready for your dream home. All preliminary site work and necessary approvals are complete, to including surveying, engineered septic system with a successful perc test, wetlands mitigation, and full compliance with Corps of Engineers requirements. Bring the builder of your choice!

  Marco Rivas 757 Realty

  1813 Shillelagh Rd, Chesapeake, VA 23323
• 

  

  /11

  $317,000

  • 3 Beds
  • 1.5 Baths
  • 1,431 Sq Ft

  4108 Wake Ave, Chesapeake, VA 23324

  Beautifully and fully remodeled ranch-style home offered by the original owners. Located in a quiet, well-established neighborhood and conveniently close to shopping, dining, and amenities. This three-bedroom, two-and-a-half-bath home features a spacious layout with numerous updates throughout and all new appliances.Enjoy a large backyard ideal for outdoor living and gatherings, along with a

  Christina Edmonds Paragon Real Estate Group

  4108 Wake Ave, Chesapeake, VA 23324
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  /47

  $234,999

  • 2 Beds
  • 2 Baths
  • 1,285 Sq Ft

  1016 Thoroughgood Way Unit 104, Chesapeake, VA 23324

  Step into comfort and style at this beautifully refreshed 2 bed/2 bath first-floor condo in a secured building with a private key fob entrance! This inviting home features new flooring, an updated kitchen with modern cabinets, and a bright open-concept layout great for relaxing or entertaining. Both bedrooms are generously sized, including a spacious primary suite with a large ensuite bathroom

  Kristina Price EXP Realty LLC

  1016 Thoroughgood Way Unit 104, Chesapeake, VA 23324
• 

  /2

  $7,334

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

  Lot 17 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 17 Binford St, Chesapeake, VA 23322
• 

  

  /4

  $259,900

  • Land
  • 3.79 Acres
  • $68,666 per Acre

  737 Bedford St, Chesapeake, VA 23322

  This is one out of four available 3+ acre lots 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.

  Robert Wadsworth Pungo Realty LLC

  737 Bedford St, Chesapeake, VA 23322
• 

  

  /10

  $298,200

  • 5 Beds
  • 2 Baths
  • 1,600 Sq Ft

  1138 Seaboard Ave, Chesapeake, VA 23324

  Welcome to this FULLY RENOVATED gem, boasting NEW modern comfort! From the moment you arrive, you'll be captivated by the BRAND-NEW METAL ROOF, designed for both style & durability. Step inside to discover bright, open-concept living spaces with all NEW finishes- perfect for family gatherings or entertaining guests. Enjoy optimal comfort year round with a NEW state of the art HVAC system. Each

  Marquis Bynum A Better Way Realty Inc.

  1138 Seaboard Ave, Chesapeake, VA 23324
• 

  /2

  $12,000

  • Land
  • 9,583 Sq Ft
  • $54,545 per Acre

  1428 Trinkle St, Chesapeake, VA 23322

  Three adjoining wooded residential lots (Lots 28, 30 & 32) available in the established Hillcrest area of South Chesapeake. Each parcel is approximately 50’ x 200’, offering a unique opportunity to purchase individually or together for added flexibility and potential.Interior lots located near Arthur’s Court with convenient access to S. Battlefield Blvd and Johnstown Road. Ideal for builders,

  Connie Bowe Fathom Realty

  1428 Trinkle St, Chesapeake, VA 23322
• 

  

  /6

  $225,000

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

  516 Rue Marseille, Chesapeake, VA 23320

  Spacious 2 bedroom/2bath condo featuring an open floor plan and soaring cathedral ceilings. Bright end unit that allows an abundant of natural sunlight throughout. We-designed layout for entertaining. Prime location with easy access to interstate, shopping and restaurants.

  Deanna Crook Signature Properties

  516 Rue Marseille, Chesapeake, VA 23320
• 

  

  /29

  $320,000

  • 3 Beds
  • 2 Baths
  • 1,894 Sq Ft

  1222 Jackson Ave, Chesapeake, VA 23324

  Welcome to 1222 Jackson Ave. This home is located in Historic Chesapeake and offers the perfect blend of charm and updates. This home features granite countertops, stainless steel appliances, and modern lighting throughout, along with a functional layout and spacious yard ideal for relaxing or entertaining.

  Amy Platt Iron Valley Real Estate Prestige

  1222 Jackson Ave, Chesapeake, VA 23324

Showing Results 41 - 80, Page 2 of 4