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

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  /12

  $293,000

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  1207 Kay Ave, Chesapeake, VA 23324

  Charming well-built 3-bedroom home in Chesapeake. This property offers comfortable living spaces and plenty of natural sunlight. The owners have maintained this home with love and it shows. Original hardwood floors and pristine original tile in the bathroom make this home special. The large back yard and covered patio are perfect for entertaining. The long driveway and detached garage will

  Deanna Crook Signature Properties

  1207 Kay Ave, Chesapeake, VA 23324
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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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  /5

  $290,130

  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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  /45

  $220,000

  $5K PRICE DROP

  • 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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  /43

  $224,900

  • 2 Beds
  • 2.5 Baths
  • 1,244 Sq Ft

  2359 Old Greenbrier Rd, Chesapeake, VA 23325

  Take advantage of this SWEET DEAL!! Sizable, Double-Primary-Bedroom Condo, each with their own En-suite! Brand new hot water heater and garbage disposal. Association is repairing gutters. Owner receives one reserved parking space, and there is an ABUNDANCE of visitor parking available. Amenities include Pool, Clubhouse, Grounds Maintenance and Trash Collection. 2 Pets under 30 lbs. each allowed!

  Kathy Hershy The Real Estate Group

  2359 Old Greenbrier Rd, Chesapeake, VA 23325
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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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  /8

  $285,000

  • 3 Beds
  • 1.5 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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  /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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  /30

  $229,900

  $20K 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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  /36

  $268,000

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

  1414 Loose Strife Place, Chesapeake, VA 23320

  Experience airy, sun-drenched living in this beautifully updated two-story home. Enjoy an open living and dining space elevated by soaring ceilings, architectural skylights, and expansive windows that maximize natural light. Refreshed in 2026, the interior showcases brand-new flooring across both levelsfresh paint, and a new water heater. The fully serviced HVAC ensures year-round comfort. The

  Jamey Fereday World Class Realty

  1414 Loose Strife Place, Chesapeake, VA 23320
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  /32

  $320,130

  New Construction

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

  1540 Eldwick Dr Unit 301, 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 Rowen model is a corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with

  Dragas Companies Builder

  1540 Eldwick Dr Unit 301, Chesapeake, VA 23320
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  /31

  $320,130

  New Construction

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

  1540 Eldwick Drive #302, 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 Rowen model is a corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen

  Clarice Savereux Dragas Companies Realty Inc

  1540 Eldwick Drive #302, Chesapeake, VA 23320
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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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  /24

  $190,000

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,070 Sq Ft

  3520 Sugar Run, Chesapeake, VA 23321

  $3000 Carpet Allowance! This well-maintained 2-bedroom, 2-bath first-floor condo in desirable Miars Farm offers comfortable single-level living in the heart of Western Branch. Move-in ready with a new HVAC system and hot water heater, plus newer stainless steel appliances. The spacious layout features two full baths and easy access to the rear patio with additional outdoor storage. Community

  Raymond Barnett A Better Way Realty Inc.

  3520 Sugar Run, Chesapeake, VA 23321
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  /23

  $246,500

  • 2 Beds
  • 1.5 Baths
  • 1,000 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. Walk into a beautiful cathedral ceiling and unique reading nook under the stairs. New SS Appliances in the kitchen, new luxury vinyl floors, bedroom/office downstairs with laundry,Beautifully renovated full bathroom. Private upstairs bedroom with half bath

  Kara Louk Iron Valley Real Est Norfolk

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

  $129,000

  • Land
  • 10,018 Sq Ft
  • $560,870 per Acre

  37 Darden St, Chesapeake, VA 23322

  37 DARDEN, ONE OF TWO 50' x 200' BUILDABLE LOTS IN HICKORY. 1/4 ACRE +/-. NO HOA. Power, phone, internet available. Darden St. is a paved street unlike others in this subdivision. Quiet neighborhood surrounded by a sea of mature trees and protected wetlands. NO WETLANDS CREDITS REQUIRED FOR CONSTRUCTION. Preliminary plat attached, boundary and topo survey performed. This site is septic and well.

  Dustin Floyd Howard Hanna Real Estate Svcs.

  37 Darden 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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  /19

  $225,000

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

  4332 Hillingdon Bend Unit 205, Chesapeake, VA 23321

  Well-maintained 2-bedroom condo with tenant in place through March 2027, offering immediate rental income and long-term stability. Ideal for investors, buyers planning a future move, or buyers seeking a potentially assumable 3.25% VA loan. Features include an open floor plan, spacious living areas, stainless steel appliances, ample cabinet space, and a primary suite with two closets. Conveniently

  Sarah Grace Doyle Sand & Sea Realty

  4332 Hillingdon Bend Unit 205, Chesapeake, VA 23321
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  /34

  $290,130

  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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  /30

  $314,800

  $10K PRICE DROP

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

  1416 Martin Ave, Chesapeake, VA 23324

  Welcome Home! Enjoy thoughtful updates throughout, including a new HVAC and new water heater. The freshly painted interior features new laminate and carpet flooring, creating a fresh and inviting feel. A spacious living room welcomes you upon entry and flows into the beautifully updated kitchen, complete with all-new cabinetry, granite countertops, and stainless steel appliances. The home offers

  Michael Daugherty Own Real Estate LLC

  1416 Martin Ave, Chesapeake, VA 23324
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  /18

  $252,000

  • 4 Beds
  • 2 Baths
  • 1,659 Sq Ft

  1307 Perry St, Chesapeake, VA 23324

  Spacious 4-bedroom, 1.5-bath home in the heart of South Norfolk offering over 1,600 sq ft of living space on a 0.23-acre lot. Property needs some updating and TLC but presents tremendous potential for investors or buyers looking to build equity. Bring your vision and really make this home shine! Conveniently located near dining, shopping, the interstate, and more! Call today for more information

  Jonathan Melvin Benham Real Estate LLC

  1307 Perry St, Chesapeake, VA 23324
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  /25

  $280,000

  • 3 Beds
  • 1.5 Baths
  • 1,318 Sq Ft

  1208 Basswood Ct, Chesapeake, VA 23320

  Welcome home to this well-maintained 3-bedroom, 1.5-bath townhome! All major systems have been replaced within the last 8 years, including the roof, offering valuable updates already taken care of. The home features a functional layout with comfortable living spaces and plenty of potential to make it your own. Best of all, there are NO HOA, giving you the benefits of townhome living without the

  John Leu LPT Realty LLC

  1208 Basswood Ct, Chesapeake, VA 23320
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  /29

  $199,000

  • 3 Beds
  • 1.5 Baths
  • 1,155 Sq Ft

  1214 Holly Ave, Chesapeake, VA 23324

  Great investment property to add to your portfolio or great for a first time home buyer. New windows just installed along with new hot water heater and new carpet as well as some new light fixtures. New HVAC system scheduled to be installed as well. This home is move in ready! Come by today!

  Matthew Zachary BHHS RW Towne Realty

  1214 Holly Ave, Chesapeake, VA 23324
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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

  $295,130

  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
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  /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
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  /7

  $195,000

  • 2 Beds
  • 1.5 Baths
  • 1,164 Sq Ft

  509 Harbour North Dr, Chesapeake, VA 23320

  Affordable home in Great Bridge minutes to Greenbrier mall $10K+ below fair market for TLC. Central heat pump less than 5 years old. Stainless appliances with new counter-depth energy saving refrigerator. Home has Living room, large combo Family room and dining room, a laundry room and a half bath on first floor. 2nd floor has 2 over-size bedrooms and a full bath.

  Norman Domingo XRealty.NET LLC

  509 Harbour North Dr, Chesapeake, VA 23320
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  /14

  $275,000

  • 2 Beds
  • 1 Bath
  • 906 Sq Ft

  5105 Deep Creek Blvd, Portsmouth, VA 23702

  Move-In Ready Bungalow with Metal Roof & Modern Updates! Welcome home! This charming fully refreshed bungalow on the boarder of Chesapeake & Portsmouth blends modern upgrades with classic character. From the street, you will immediately notice the durability and sleek look of the brand-new metal roof, offering peace of mind for years to come. Step inside to find a blend of original hardwood

  Jonathan Minerick homecoin.com

  5105 Deep Creek Blvd, Portsmouth, VA 23702
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  /20

  $300,000

  • 3 Beds
  • 1 Bath
  • 1,239 Sq Ft

  1009 Emporia Ave, Virginia Beach, VA 23464

  Welcome to this charming home at Virginia Beach offering comfort, convenience, and a location that keeps you close to everything the area has to offer. Situated on a spacious lot in an established neighborhood, this property provides easy access to shopping, dining, schools, parks, and major commuter routes. Inside, you’ll find inviting living spaces with plenty of natural light and a layout

  Zackery Britt World Class Realty & Prop Mgmt

  1009 Emporia Ave, Virginia Beach, VA 23464
• 

  /2

  $289,000

  $100K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft

  1506 Manson St, Norfolk, VA 23523

  INVESTOR SPECIAL – SOLD AS-IS! Prime opportunity to add value in Norfolk’s Campostella neighborhood. This all-brick 4-bedroom, 2-bathroom home offers a spacious layout and plenty of potential for renovation and value-add improvements. The generous floor plan provides a solid foundation for an investor looking to renovate, hold, or potentially resell. Bring your contractor, investor mindset, and

  Dustin Olverson EXP Realty LLC

  1506 Manson St, Norfolk, VA 23523

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