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

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  /43

  $305,000

  Open Sat 12:30PM - 2:30PM

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft

  816 Shenandoah River Rd, Chesapeake, VA 23320

  Welcome to 816 Shenandoah River Road! Spacious 2 bedroom 2 bathroom condo tucked away in established Riverwalk! This move in ready home offers a cool modern feel with many updates throughout. Main living area welcomes you with fresh paint and LVP flooring. Kitchen has been updated to include custom cabinetry, quartz countertops and tile backsplash. One bedroom / bath occupy first floor and One

  Shana Mitchell Creed Realty

  816 Shenandoah River Rd, Chesapeake, VA 23320
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  /16

  $270,000

  • 3 Beds
  • 2 Baths
  • 1,276 Sq Ft

  1605 Hawthorne Dr, Chesapeake, VA 23325

  This 3-bedroom, 2-bathroom property offers nearly 1,300 square feet of living space and is ready for a complete transformation. The home requires some updating, providing an opportunity for buyers, investors, or rehabbers to bring their vision to life. With a functional bedroom and bath count and plenty of potential, this property is ready for someone with the vision and experience to turn it

  Jonathan Melvin Benham Real Estate LLC

  1605 Hawthorne Dr, Chesapeake, VA 23325
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  /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
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  /2

  $214,000

  $1K PRICE DROP

  • 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

  $230,000

  $15K 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

  $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
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  /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
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  /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
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  /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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  /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. Inside, discover a residence that feels brand new. The kitchen shines with new Harbour Town slow-close cabinets and quartz countertops, plus fresh appliances — including a refrigerator, electric range, and

  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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  /37

  $290,000

  • 2 Beds
  • 2 Baths
  • 1,383 Sq Ft

  1547 Orchard Grove Dr, Chesapeake, VA 23320

  Welcome home to easy living in Orchard Grove! This spacious 2-bedroom, 2-bath condo offers a flexible layout designed for both everyday comfort and entertaining. Start your morning at the dedicated coffee bar before settling into the light-filled living room, where soaring ceilings and skylights create an open, airy feel. When the weather cools down, the gas fireplace makes the perfect spot to

  Kelly Liedtke AMW Real Estate Inc

  1547 Orchard Grove Dr, 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

  $305,000

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

  2453 Leytonstone Dr, Chesapeake, VA 23321

  Short sale subject to lender approval. This home offers a functional first-floor layout with a spacious living room, dining area, kitchen, half bath, and a 12x14 bonus room that can serve as an office, playroom, game room, or potential third bedroom. The kitchen features Corian countertops, Frigidaire appliances, and a large walk-in pantry with ample shelving. Upstairs are two generously sized

  Joshua Wilborne Own Real Estate LLC

  2453 Leytonstone Dr, Chesapeake, VA 23321
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  /45

  $304,999

  $15K 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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  /27

  $245,000

  $5K PRICE DROP

  • 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

  $214,900

  $13K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  2041 Lockard Ave, Chesapeake, VA 23320

  Great starter home! This charming 2-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

  $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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  /27

  $225,000

  $15K PRICE DROP

  • 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
• 

  /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
• 

  

  /17

  $216,000

  • 4 Beds
  • 2 Baths
  • 1,173 Sq Ft

  2514 Narrow St, Chesapeake, VA 23324

  Opportunity awaits! This 4-bedroom, 2-bath brick ranch in the heart of Chesapeake offers 1,173 square feet of living space on a 0.15-acre lot. With a practical single-level layout and classic brick exterior, this property presents an excellent opportunity for buyers looking to renovate and create a home tailored to their vision. The home needs updating and renovation, making it ideal for those

  Jonathan Melvin Benham Real Estate LLC

  2514 Narrow St, 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
• 

  /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
• 

  /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
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  /32

  $294,500

  • 2 Beds
  • 2 Baths
  • 1,153 Sq Ft

  1028 Livingston Ave, Chesapeake, VA 23324

  Charming cottage-style single-family home on a quiet street in South Norfolk! This 2-bedroom, 2-bath gem offers 1,153 sq ft of comfortable living with a spacious eat-in kitchen and formal dining room. Enjoy the covered front porch and wood deck great for morning coffee or evening relaxing. Detached 1.5-car garage provides excellent storage. No HOA! Bonus: a heated and cooled second-floor space

  Connie Bowe Fathom Realty

  1028 Livingston Ave, Chesapeake, VA 23324
• 

  /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
• 

  

  /21

  $310,000

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

  719 Creekside Crescent, Chesapeake, VA 23320

  Welcome home to this well-maintained End unit 3-bedroom, 2.5-bath townhome located in the Riverwalk community. The inviting open floor plan provides a comfortable flow between the living, dining, and kitchen areas, making it ideal for everyday living and entertaining. Step outside to enjoy the private rear patio, complete with a storage shed for added convenience. Upstairs, you’ll find three

  Tawni Walker Atlantic Realty&Prop Mgmt Grp

  719 Creekside Crescent, Chesapeake, VA 23320
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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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  /39

  $319,000

  $6K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,582 Sq Ft

  1213 Killington Square, Chesapeake, VA 23320

  MOVE-IN READY end-unit townhome in highly desirable Greenbrier! Fresh paint and brand-new carpet throughout give this home a clean, modern feel. The bright eat-in kitchen features stainless steel appliances and granite countertops, perfect for everyday living and entertaining. The spacious great room includes a dining area, cozy fireplace, and direct access to a large fenced backyard with storage

  Maribeth Dunlap Long & Foster Real Estate Inc.

  1213 Killington Square, Chesapeake, VA 23320
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  /6

  $30,000

  $35K PRICE DROP

  • Land
  • 2,613 Sq Ft
  • $500,000 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
• 

  

  /15

  $234,900

  $5K PRICE DROP

  • 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
• 

  

  /13

  $304,999

  • 3 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, Updated new LVP flooring, 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
• 

  

  /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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