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

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  /36

  $269,000

  • 3 Beds
  • 2 Baths
  • 1,313 Sq Ft

  1414 Loose Strife Place, Chesapeake, VA 23320

  Beautifully remodeled 3BR/2BA home is ready for its new owner! Bright, open, spacious, this two-story home offers the kind of layout that feels impressive the moment you walk in. Two-story foyer, high ceilings, skylights, large windows, and open living/dining area create a light and airy feel throughout. Home was refreshed in 2026 with new water heater, new flooring on both levels, finished walls

  

  Val Milan

  Swell Real Estate Co

  1414 Loose Strife Place, Chesapeake, VA 23320
• Explore Chesapeake

• 

  

  

  /24

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,812 Sq Ft

  1233 Transylvania Ave, Chesapeake, VA 23324

  

  Andy Nelson

  Iron Valley Real Estate HR

  1233 Transylvania Ave, Chesapeake, VA 23324
• 

  

  

  /31

  $210,000

  • 2 Beds
  • 2 Baths
  • 978 Sq Ft

  2201 Rock Cliff Reach Unit A, Chesapeake, VA 23320

  You do not want to miss this stunning condo! It features fresh paint throughout, professionally cleaned carpets, and appliances, making it move-in ready. Nestled right in the heart of Greenbrier, this location offers ultimate convenience with quick access to a selection of entertainment, dining, and shopping. Don't wait schedule your tour today and see this property for yourself!

  

  Keisha Rorie

  Shipmate Real Estate +JPAR

  2201 Rock Cliff Reach Unit A, Chesapeake, VA 23320
• 

  

  

  /23

  $239,900

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

  4332 Hillingdon Bend Unit 206, Chesapeake, VA 23321

  Located in the Western Branch North area of Chesapeake, Virginia, 4332 Hillingdon Bend, Unit 206, is a second-floor condominium built in 2014. The residence offers approximately 1,367 square feet of single-level living space with an open floor plan and nine-foot ceilings. It features two bedrooms and two full bathrooms, including a primary suite equipped with dual closets. The kitchen includes

  

  Jon Bourque

  Verian Realty

  4332 Hillingdon Bend Unit 206, Chesapeake, VA 23321
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  /46

  $269,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,314 Sq Ft

  1312 Hull St, Chesapeake, VA 23324

  Beautifully renovated 3-bedroom, 2-bath home in the historic South Norfolk neighborhood! Blending classic character with fresh, modern updates throughout, we start just past the brick porch and swing with a 2-story foyer. Just off the stairs, the first of three bedrooms has fresh paint, carpet, and 6-inch baseboards. Through the living room, the home boasts an expansive eat-in kitchen with new

  

  Daniel Patton

  Prodigy Realty

  1312 Hull St, Chesapeake, VA 23324
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  /2

  $124,000

  • Land
  • 10,628 Sq Ft
  • $508,197 per Acre

  1721 Faulk St, Chesapeake, VA 23323

  Attention Builders and Visionaries: Beautiful large lot in the Deep Creek area of Chesapeake. Lot is ready for all your ideas of a new home.

  

  Adrienne Campbell

  Keller Williams Coastal Virginia Chesapeake

  1721 Faulk St, Chesapeake, VA 23323
• 

  /2

  $45,000

  • Land
  • 2.15 Acres
  • $20,911 per Acre

  000 Shell Rd, Chesapeake, VA 23323

  Discover 2.15 acres of beautifully wooded residential land tucked away in the Deep Creek area of Chesapeake. This serene parcel offers a peaceful natural setting with mature trees for a long-term investment. The property is currently landlocked with no established road access, and buyers will need to explore access options independently. Property to be sold as-is where-is. Located near the Oak

  

  John Horton

  Samson Properties

  000 Shell Rd, Chesapeake, VA 23323
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  /8

  $250,000

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  2425 Lofurno Rd, Chesapeake, VA 23323

  Great starter home with huge backyard and easy access to highway, military bases & shopping.

  

  Janez Hargrove

  Verian Realty

  2425 Lofurno Rd, Chesapeake, VA 23323
• 

  

  /20

  $169,900

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,321 Sq Ft

  1608 Ohio St, Chesapeake, VA 23324

  Uncover the potential in this 3-bedroom, 1-bathroom cottage located in the heart of South Norfolk. Spanning approximately 1,321 square feet, this 1953 home serves as a blank canvas for investors or ambitious homeowners looking to build equity through a full renovation. The interior features a functional layout and an original fireplace, awaiting your modern touch. A standout feature of this

  

  Jon Bourque

  Verian Realty

  1608 Ohio St, Chesapeake, VA 23324
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  /43

  $319,000

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

  362 Faire Chase, Chesapeake, VA 23322

  Updated and Move-In ready 3BR/2.5BA townhome in Great Bridge Area, in the HIGHLY RATED school district, with NO HOA Fees! RECENT UPDATES 2026: New HVAC, FULLY New Kitchen, Bathrooms, Flooring thoughout the house, Light Fixtures, Freshly Painted Walls & Ceilings, and so much more! House offers Open Concept layout with a lot of space and natural light. Gorgeous Eat-In Kitchen with New tall

  

  Val Milan

  Swell Real Estate Co

  362 Faire Chase, Chesapeake, VA 23322
• 

  /2

  $85,000

  • Land
  • 15,681 Sq Ft
  • $236,111 per Acre

  L38 40 Norfolk St, Suffolk, VA 23435

  Rare chance to acquire a .36-acre (15,682 sq ft) vacant lot in the established Pughsville area. Zoned single-family residential, this parcel is great for builders, investors, or custom home buyers looking create a tailored residence in a growing location. Enjoy a balance of privacy and convenience with easy access to major routes, shopping, dining, and nearby Chesapeake and Portsmouth. With

  

  Xavier Bryan

  EXP Realty LLC

  L38 40 Norfolk St, Suffolk, VA 23435
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  /8

  $265,000

  $31K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  813 Shenandoah River Rd, Chesapeake, VA 23320

  Easy Fixer Upper. Great Neighborhood (desirable Kingsford section of the Riverwalk community). **Priced well below market value! **ARV $315k+. **Selling As-Is. **No Contingencies. **Cash Preferred. **Excellent opportunity for Handyman, Investor or Landlord. **Condo fee includes exterior building maintenance, community pool, trash collection, and much more!

  

  Tierra Walker

  Walker One Property Group LLC

  813 Shenandoah River Rd, Chesapeake, VA 23320
• 

  /2

  $20,000

  • Land
  • 10,018 Sq Ft
  • $86,957 per Acre

  .229AC Trinkle St, Chesapeake, VA 23322

  Vacant lot currently being used as Camp site.

  

  Jason Dunaway

  Howard Hanna Real Estate Svcs.

  .229AC Trinkle St, Chesapeake, VA 23322
• 

  

  /31

  $305,000

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

  2135 English Ave, Chesapeake, VA 23320

  Make this your first stop! This beautifully maintained 3-bedroom, 2-bath ranch in Norfolk Highlands offers the perfect combination of comfort, convenience, and value. Updated in 2022 and well cared for since, this move-in-ready home features an eat-in kitchen with granite countertops, stainless steel appliances, and plenty of cabinet space. The spacious primary suite includes a private ensuite

  

  Matthew Salway

  Iron Valley Real Estate HR

  2135 English Ave, Chesapeake, VA 23320
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  /44

  $299,000

  Open Sat 10AM - 12PM

  • 3 Beds
  • 1.5 Baths
  • 1,244 Sq Ft

  1346 River Birch Run S, Chesapeake, VA 23320

  Move in ready-well maintained Townhouse in desirable Greenbrier. LVT/Vinyl flooring throughout, carpet upstairs. Open floor plan with Large Livingroom, Kitchen, and Dining Area. Fenced in back yard and storage shed. Do not miss this move in ready home.

  

  Eric Hovik

  RE/MAX Alliance

  1346 River Birch Run S, Chesapeake, VA 23320
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  /28

  $289,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,328 Sq Ft

  1106 Maryview Ave, Chesapeake, VA 23324

  Welcome home to this charming ranch that's full of warmth, character, and timeless appeal! Nestled at the end of your street with no through traffic, this adorable home offers the perfect blend of privacy, comfort, and convenience. Enter to discover soaring vaulted ceilings that create an open, airy feel throughout the main living spaces. With two inviting fireplaces and two separate dens,

  

  Katie Burke

  Long & Foster Real Estate Inc.

  1106 Maryview Ave, Chesapeake, VA 23324
• 

  

  /23

  $285,000

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

  1305 Quail Creek Hollow Unit A, Chesapeake, VA 23320

  Enjoy easy, one-level living in this charming end-unit condo located in a highly desirable golf course community! The bright, open floor plan features vaulted ceilings in the great room & kitchen, creating a spacious feel. The kitchen offers ample cabinet & counter space, a breakfast bar, & pantry, while the dining area showcases beautiful built-in cabinetry providing additional storage. Relax or

  

  Stephanie Kelly

  Swell Real Estate Co

  1305 Quail Creek Hollow Unit A, Chesapeake, VA 23320
• 

  

  /22

  $227,500

  • 2 Beds
  • 2 Baths
  • 1,326 Sq Ft

  4301 Colindale Rd Unit 208, Chesapeake, VA 23321

  Resort-style living in Kings Pointe at Western Branch! This bright, open-concept 2 BR/2 BA second-floor corner condo features 1,367 sq ft of modern space, serene water views, and a private balcony. Low-maintenance living covers water, sewer, trash, and ground maintenance. Enjoy incredible community perks like a pool, clubhouse and walking trails. Conveniently located near shopping, dining, and

  

  Candace Jones

  Atlantic Sothebys Int'l Realty

  4301 Colindale Rd Unit 208, Chesapeake, VA 23321
• 

  

  /20

  $277,000

  • 3 Beds
  • 2.5 Baths
  • 1,275 Sq Ft

  1806 Beckwood Common, Chesapeake, VA 23320

  Well maintained, tenant occupied 1,275 sf, 3-bedroom, 2.5 bath Townhouse in Chesapeake's Woodgate Commons community. Ideally located near restaurants, shopping, interstate access, military bases, and a nearby golf course, this home offers both convenience and value. Recent updates include new first-floor flooring, remodeled bathrooms, fresh interior and exterior paint, updated kitchen appliances

  

  Judy Boone

  Judy Boone Realty Inc.

  1806 Beckwood Common, Chesapeake, VA 23320
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  /41

  $292,000

  $3K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft

  1002 Mayfield Ave, Chesapeake, VA 23324

  Welcome HOME to this gorgeously remodeled, from top to bottom 2BR/2BA one-story ranch house. It has EVERYTHING you've been searching for: open concept layout, large updated windows, new luxury LVP flooring throughout, modern light fixtures, custom tile work, freshly painted, you name it! Completely NEW spacious chef’s kitchen shines with expensive QUARTZ countertops, large island with built-in

  

  Val Milan

  Swell Real Estate Co

  1002 Mayfield Ave, Chesapeake, VA 23324
• 

  

  /16

  $270,000

  $39K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  4310 Cromwell Ave, Chesapeake, VA 23325

  PRICE IMPROVEMENT. This charming 3-bedroom, 1 bath home is now offered at an exceptional value, and the seller will consider contributing toward buyer's closing costs with an acceptable offer. Inside you will find an open floor plan with cathedral ceilings that create a bright, spacious feel throughout. The efficient layout makes the most of every square foot, providing comfortable single level

  

  Phyllis Mihalas

  Swell Real Estate Co

  4310 Cromwell Ave, Chesapeake, VA 23325
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  /20

  $272,000

  $2K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,025 Sq Ft

  449 E Lake Cir, Chesapeake, VA 23322

  Welcome home to this bright and inviting condo conveniently located just off Cedar Rd, placing you minutes from shopping, local restaurants, entertainment, and everything the area has to offer. Whether you’re relaxing by the pool, grabbing dinner, meeting friends, or enjoying a night out, you’ll appreciate having so many amenities nearby. Inside, you’ll find soaring vaulted ceilings and arched

  

  Timothy Eure

  COVA Home Realty

  449 E Lake Cir, Chesapeake, VA 23322
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  /14

  $200,000

  $25K PRICE DROP

  • Land
  • 24,262 Sq Ft
  • $359,066 per Acre

  Par B George Washington Hwy S, Chesapeake, VA 23323

  Commercial Building Lot in the Deep Creek area of Chesapeake. Located on the Dismal Swamp Canal & George Washington Hwy across the street from a Shopping Center. Property is on the navigable Dismal Swamp Canal. Property Zoning is B-1 with over 250 feet of road frontage.

  

  John Horton

  Samson Properties

  Par B George Washington Hwy S, Chesapeake, VA 23323
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  /2

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,020 Sq Ft

  34 Frailey Place, Portsmouth, VA 23702

  STOP HERE FIRST...if you're looking for a move-in ready home with value! As you approach the home, you'll notice a wraparound screened in porch ready for summer. Home features newer roof (2020) and newer HVAC, paint and LVP flooring (2022). Kitchen and bath features newer cabinets and counter tops (2022). New gas hot water heater installed in 2023. Generational living with a detached converted

  

  Sharon Rand Voogd

  1st Class RE-Signature Prop

  34 Frailey Place, Portsmouth, VA 23702
• 

  

  /41

  $250,000

  • 2 Beds
  • 2.5 Baths
  • 1,386 Sq Ft

  3613 Cinnamon Ct, Chesapeake, VA 23321

  This beautifully updated home features an open floor plan with durable luxury vinyl plank (LVP) flooring throughout the main level. Enjoy the community's beautiful pool and clubhouse, perfect for relaxing and socializing. Conveniently located near shopping, the mall, and major interstates, this move-in-ready home offers both comfort and convenience!

  Cameron Elliott AtCoastal Realty

  3613 Cinnamon Ct, Chesapeake, VA 23321
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  /2

  $295,000

  $30K PRICE DROP

  • Land
  • 1.99 Acres
  • $148,615 per Acre

  2524 Battlefield Blvd S, Chesapeake, VA 23322

  Excellent development opportunity in the Hickory area of Chesapeake. This mostly wooded parcel offers the opportunity to build a custom home in a well-established area with convenient access to shopping, dining, recreation, and major commuter routes. The residence originally built in 1957 was demolished and cleared in 2020. City water is available. Buyer to perform all due diligence regarding

  Cherrie Platt BHHS RW Towne Realty

  2524 Battlefield Blvd S, Chesapeake, VA 23322
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  /7

  $165,000

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  3337 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

  3337 Clover Meadows Dr, Chesapeake, VA 23321
• 

  

  /4

  $75,000

  • Land

  4999 Clifton St, Chesapeake, VA 23321

  Imagine the possibilities! This vacant lot offers the flexibility to build your dream home and create a space designed to fit your needs.

  Michael Daugherty Own Real Estate LLC

  4999 Clifton St, Chesapeake, VA 23321
• 

  

  /26

  $199,900

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  717 Inlet Quay Unit H, Chesapeake, VA 23320

  Move-in ready and ideally located in the heart of Chesapeake! This well-maintained home features a spacious layout, two private terraces, and convenient access to shopping, dining, and major commuter routes. Property is being sold as-is. Home could use some TLC, offering a great opportunity to make it your own in a prime location.** SOME PHOTOS ARE VIRTUALLY STAGED.

  Danielle Morse The Bryant Group

  717 Inlet Quay Unit H, Chesapeake, VA 23320
• 

  

  /50

  $245,000

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

  1016 Thoroughgood Way Unit 302, Chesapeake, VA 23324

  Welcome to Village at Gateway in the heart of South Norfolk! This beautifully maintained third-floor condo is easily accessed via elevator and features an open-concept floor plan with oversized rooms and abundant natural light from skylights. The upgraded kitchen provides ample cabinetry, a pantry, and bar seating for four for casual dining or entertaining. Enjoy indoor-outdoor living with a

  Lauren Harrigan Better Homes & Gdns Ntv Am Grp

  1016 Thoroughgood Way Unit 302, Chesapeake, VA 23324
• 

  

  /26

  $309,000

  $6K PRICE DROP

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

  502 Hermit Thrush Way, Chesapeake, VA 23323

  Meticulously maintained 2-bedroom, 2.5-bath condo with newer HVAC and LVP flooring on the main level. Spacious floor plan with tons of natural light, bonus room/office and 2 Primaries with en-suite baths. Enjoy an olympic sized pool, dog park, playgrounds, community center, and lake, all just minutes from shopping, dining, and interstate access. Don't miss this opportunity to live in a

  Trey Vineyard Vineyard Homes Real Estate

  502 Hermit Thrush Way, Chesapeake, VA 23323
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  /21

  $295,000

  $34K PRICE DROP

  • Land

  15.+AC Johnson Ln, Chesapeake, VA 23322

  LIST PRICE SIGNIFICANTLY UNDER TAX VALUE-Imagine owning a little over 22 acres of beautifully wooded agricultural land where privacy, nature, and possibility come together. This expansive parcel offers an ideal backdrop for creating your own homestead, with plenty of room for a homesite, gardens, animals, or a self sufficient lifestyle. Mature trees provide natural beauty and seclusion, making

  Autumn Dunn BHHS RW Towne Realty

  15.+AC Johnson Ln, Chesapeake, VA 23322
• 

  /2

  $16,500

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

  LOT 6 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 6 Tuck St, Chesapeake, VA 23322
• 

  

  /50

  $287,500

  $10K PRICE DROP

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

  5 Harbor Watch Dr Unit 419, Chesapeake, VA 23320

  Enjoy low-maintenance living at Harbor Watch in Great Bridge. This well-maintained third-floor condo with elevator access offers 3 bedrooms, 2 baths, and 1,764 sq ft of comfortable living space. The open-concept layout connects the kitchen, dining, and living areas, with sliding glass doors leading to a private balcony and filling the home with natural light. The spacious primary suite includes a

  Paulette Harris Howard Hanna Real Estate Svcs.

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

  

  /14

  $239,000

  • 3 Beds
  • 2 Baths
  • 1,179 Sq Ft

  1800 Portlock Rd, Chesapeake, VA 23324

  Charming 3-bedroom, 2-bath single-family home offering 1,179 sq ft of potential! Bring your vision and make this home shine! Conveniently located near the interstate and more! Call today for more information and to schedule your tour! Case#544-376530 IE (Insurable with escrow) Subject to Appraisal. Property is Owned by the US Dept. of HUD. Seller makes no representations or warranties as to the

  Jonathan Melvin Benham Real Estate LLC

  1800 Portlock Rd, Chesapeake, VA 23324
• 

  

  /25

  $225,000

  • 2 Beds
  • 2 Baths
  • 919 Sq Ft

  1012 Rue Marseille, Chesapeake, VA 23320

  Hard to find single level living! Newer LVP flooring in main living area, carpet in bedrooms less than 2 years old, galley kitchen and updated light fixtures. End unit tucked away but right across from the pool! All new windows and sliding glass door, move in ready.

  Christine Ornoff Long & Foster Real Estate Inc.

  1012 Rue Marseille, Chesapeake, VA 23320
• 

  

  /23

  $238,900

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft

  928 Saint Andrews Reach Unit A, Chesapeake, VA 23320

  Discover the perfect blend of modern updates and prime location in this spacious 3-bedroom, 2-bath home, fully remodeled in 2024. Enjoy the luxury of renovated bathrooms and luxury vinyl flooring throughout the entire first floor. The home features a reserved parking spot right at your front door for added convenience. Nestled in the heart of Greenbrier, this home offers unparalleled convenience.

  Deanna Wilson RE/MAX Country to Coast

  928 Saint Andrews Reach Unit A, Chesapeake, VA 23320
• 

  /2

  $7,000

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

  Lot 22 Trinkle St, Chesapeake, VA 23322

  One of four parcels adjacent to each other offered at just above tax value. Makes for great holding investment opportunity as the tax value has doubled to 6000 for the upcoming year, or for recreational use, riding fourwheelers, camping, etc. Come take a look! Roughly 900' from the paved section of Arthurs Ct.Ten minutes to the heart of Great Bridge or Edinburgh.

  Dustin Floyd Howard Hanna Real Estate Svcs.

  Lot 22 Trinkle St, Chesapeake, VA 23322
• 

  

  /26

  $312,500

  $2K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,380 Sq Ft

  1313 Willow Ave, Chesapeake, VA 23325

  Welcome home to this beautiful, move-in-ready ranch style property in Chesapeake! Featuring a bright and airy open-concept floor plan, this home offers an effortless flow is great for entertaining. The interior boasts 3 bedrooms, 1 full bath and tasteful modern updates throughout. Step outside to your private outdoor retreat, complete with a newer deck that leads to a generously sized backyard,

  Rachael Podruchny Vylla Home

  1313 Willow Ave, Chesapeake, VA 23325
• 

  /2

  $16,500

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

  Lot 8 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 8 Tuck St, Chesapeake, VA 23322

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