Chesapeake, VA Homes for Sale under $300,000

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  /20

  $249,990

  • 3 Beds
  • 1 Bath
  • 1,019 Sq Ft

  200 Velva Dr, Chesapeake, VA 23325

  This 3-bedroom, 1-bath single-family home sits in a well-established Chesapeake neighborhood with fresh carpet in the bedrooms and a functional layout that works for everyday living. The standout feature is the oversized detached garage — a rare find that offers real flexibility for parking, storage, hobbies, or a workshop. The surrounding yard gives you plenty of outdoor space to work with.

  

  Jake Maines

  Iron Valley Real Estate HR

  (757) 960-3446

  200 Velva Dr, Chesapeake, VA 23325
• Explore Chesapeake

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  /44

  $255,000

  • 2 Beds
  • 2 Baths
  • 1,274 Sq Ft

  4301 Oneford Place, Chesapeake, VA 23321

  Welcome to easy, low-maintenance living in this beautifully designed single-story condo built in 2005! Offering 2 spacious bedrooms and 2 full bathrooms, this thoughtfully laid-out home combines comfort and functionality. The inviting primary suite features elegant trey ceilings and a private en-suite bath complete with a walk-in tub and separate shower for relaxation and convenience. Enjoy

  

  Susan Jenkins

  Better Homes & Gdns Ntv Am Grp

  (757) 601-4684

  4301 Oneford Place, Chesapeake, VA 23321
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  /8

  $284,500

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

  2415 Chesapeake Cir, Chesapeake, VA 23324

  Easy Fixer Upper. Very Nice 1 Level ranch. 5 bedrooms and 2 full baths.. PRICED BELOW MARKET VALUE. ARV $375k to $400k. **Perfect for Handyman, Investor or Landlord. **Selling As-Is. No Contingencies. Cash preferred .

  

  Tierra Walker

  Walker One Property Group LLC

  (757) 239-3543

  2415 Chesapeake Cir, Chesapeake, VA 23324
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  /7

  $259,300

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  1416 Martin Ave, Chesapeake, VA 23324

  Easy Fixer Upper. Very Nice 2 story home. 3 bedrooms and 2.5 baths.. PRICED BELOW MARKET VALUE. ARV $360k to $375k. **Perfect for Handyman, Investor or Landlord. **Selling As-Is. No Contingencies. Cash preferred .

  

  Tierra Walker

  Walker One Property Group LLC

  (757) 367-8261

  1416 Martin Ave, Chesapeake, VA 23324
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  /16

  $270,000

  • 3 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  1229 Decatur St, Chesapeake, VA 23324

  This is such a lovely home with a fantastic backyard and oversized detached garage conveniently located close to bases, highways, shipyards, shopping & restaurants. Seller offering flooring allowance. Ask agent for more details. Quick access to Norfolk & Portsmouth without going through the tunnel.

  

  Patrick Istilart

  1st Advantage Realty LLC

  (757) 780-8421

  1229 Decatur St, Chesapeake, VA 23324
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  /11

  $294,500

  • 2 Beds
  • 2.5 Baths
  • 1,471 Sq Ft

  523 Nesbit Dr Unit 101, Chesapeake, VA 23323

  Want WALK IN EQUITY? This is it, identical unit next door listed for 309,900. This one needs some elbow grease for cosmetics but the seller is offering generous allowances on full price offer for paint, flooring and anything you see that needs to be taken care of. A little work on your part earns you instant equity. 1$ down to VA buyer if qualified.

  

  Janice Myers-Hollowell

  World Class Realty

  (757) 832-8195

  523 Nesbit Dr Unit 101, Chesapeake, VA 23323
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  /38

  $249,700

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

  511 Appomattox St, Norfolk, VA 23523

  This renovated home is move-in-ready and absolutely adorable! New LVP flooring in living spaces, new carpet in bedrooms and tile in the bathrooms. Stunning kitchen with new cabinets, granite countertops and new Stainless-Steel appliances. All new lighting and plumbing fixtures, new siding, new roof, new HVAC. Lovely front porch and a great back yard.

  

  Rachel Beasley

  Shoreline Realty

  (757) 997-2197

  511 Appomattox St, Norfolk, VA 23523
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  /34

  $268,999

  • 2 Beds
  • 2.5 Baths
  • 1,255 Sq Ft

  1816 Willow Point Arch, Chesapeake, VA 23320

  Gorgeous 2-bedroom, 2.5-bath condo in the highly desirable Willow Point (River Walk) community! This home has been thoughtfully updated with granite countertops, cabinets, newer appliances, and recent upgrades including the hot water heater, furnace, and HVAC. The open and inviting layout offers comfortable living with modern finishes throughout. Low-maintenance living in a convenient location

  Lisa Mayes Redfin Corporation

  1816 Willow Point Arch, Chesapeake, VA 23320
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  /32

  $264,999

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft

  420 Cobblewood Bend, Chesapeake, VA 23320

  Welcome home! Beautifully updated 2-bedrooms, 1-full bath located in desirable Cobblewood community! New roof 2024, new HVAC 2024, new water heater 2024, fresh interior paint, new solar panel 2024 loan to be paid off by seller at closing a tremendous amount of savings in your electric bill! This well maintained home offers comfortable living with a functional layout, spacious bedrooms and plenty

  Adela Savino BHHS RW Towne Realty

  420 Cobblewood Bend, Chesapeake, VA 23320
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  /44

  $279,000

  • 3 Beds
  • 2 Baths
  • 1,317 Sq Ft

  1333 Great Bridge Blvd, Chesapeake, VA 23320

  Welcome to Crestwood Gardens in Chesapeake! This home features major updates made within the last 10 years such as the roof, windows, HVAC, and kitchen. With a total of three bedrooms, one of the rooms is a Primary Suite with a view of the expansive backyard. Two additional bedrooms provide enough space for multi-purpose rooms and the second bathroom is conveniently located near the living room

  Jaine Lindo The Real Estate Group

  1333 Great Bridge Blvd, Chesapeake, VA 23320
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  /28

  $298,000

  • 3 Beds
  • 1.5 Baths
  • 1,525 Sq Ft

  1400 River Birch Run S, Chesapeake, VA 23320

  Welcome home to this charming three bedroom end-unit townhome in the sought after Greenbrier area! Open living area with good natural light, functional kitchen and dining layout along with a spacious backyard perfect for entertaining and relaxing outdoors. Updated laminate flooring downstairs, carpet upstairs ($3000 flooring credit with full price offer). Roof replaced 2025 and crawl space

  Jewel Dyson Garrett Realty Partners

  1400 River Birch Run S, Chesapeake, VA 23320
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  /16

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,364 Sq Ft

  2717 Omar St, Chesapeake, VA 23324

  Welcome to 2717 Omar Street - a charming gem ready for its new owner to call home! This inviting property offers a spacious primary bedroom with a private ensuite bathroom, great for relaxing at the end of the day. The layout provides comfortable living spaces and plenty of natural light, giving the home a warm and welcoming feel. Step outside to enjoy a back deck, great for gatherings or quiet

  Pervis Blake MR Rivera Realty Group

  2717 Omar St, Chesapeake, VA 23324
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  /9

  $210,000

  • 2 Beds
  • 1 Bath
  • 918 Sq Ft

  6468 Duquesne Place, Virginia Beach, VA 23464

  CLOSING COST Assistance AND 1yr Home Warranty w/Full Price Offer! Enjoy low maintenance living in this 2-bed 1-full bath home in the Tallwood/Brandon school district of Virginia Beach. Inside, you’ll find an open layout with spacious rooms and a dedicated laundry area that accommodates a stackable washer and dryer. Newer Carpet and Electric Panel. The kitchen opens to the living room with

  Natalie Giles Boyd Realty Partners

  6468 Duquesne Place, Virginia Beach, VA 23464
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  /23

  $280,000

  • 3 Beds
  • 2.5 Baths
  • 1,524 Sq Ft

  1314 Perry St, Chesapeake, VA 23324

  Welcome home to this three-bedroom beauty that pairs historic charm with modern convenience. Enjoy bright, cozy living spaces refreshed with new paint and flooring. The primary suite is a retreat featuring a sun-drenched skylight, a renovated ensuite bathroom and walk-in closet. Outside, a newly paved driveway and fresh landscaping invites you home. The backyard provides a great outdoor space

  Eric Overmyer Own Real Estate LLC

  1314 Perry St, Chesapeake, VA 23324
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  /25

  $227,500

  • 2 Beds
  • 2 Baths
  • 989 Sq Ft

  701 Meherrin River Ct Unit D, Chesapeake, VA 23320

  Experience effortless living in this meticulously maintained 2BR, 2BA home in Chesapeake’s sought-after Riverwalk. This 989 sq ft unit features an open-concept layout and floor-to-ceiling windows leading to a private balcony with recently refinished wood and dedicated storage. Move in with total peace of mind—the HVAC was replaced in March 2026.The interior boasts clean carpeting, an updated

  Marlan Church Creed Realty

  701 Meherrin River Ct Unit D, Chesapeake, VA 23320
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  /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
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  /28

  $274,900

  • 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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  /40

  $259,900

  • 1,790 Sq Ft

  1101 Park Ave, Chesapeake, VA 23324

  Great investment! This 2-story duplex sits on a large corner lot in a quiet residential community. Private backyard, with privacy fence. Both tenants have off street parking with a wide driveway and detached garage, PLUS a nice big shed. Separate heat pumps and electric meters. Each apartment has a sitting area, dining room, 2 bedrooms and a full bathroom. They also both have washer and dryer

  Jacob Sloop 1st Class Real Estate Flagship

  1101 Park Ave, Chesapeake, VA 23324
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  /8

  $250,000

  • 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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  /22

  $299,000

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  2703 Cayce Dr, Chesapeake, VA 23324

  Completely renovated and packed with versatility, this home offers more than just a place to live, it creates opportunity. The main home features 3 bedrooms, 1 fully updated bath, granite countertops, and brand-new stainless steel appliances, all wrapped in a bright, modern feel. What truly sets this property apart is the fully finished garage conversion with its own bedroom, full bath, and

  Jamison Nicolaison Iron Valley Real Est Norfolk

  2703 Cayce Dr, Chesapeake, VA 23324
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  /9

  $200,000

  • 3 Beds
  • 1 Bath
  • 1,112 Sq Ft

  704 Burrow Ave, Chesapeake, VA 23324

  Great opportunity for investors or buyers looking to add value! This 3-bedroom, 1-bath home offers 1,112 sq ft of potential and is ready for your vision. With the right updates and improvements, this property could truly shine. Seller’s loan is assumable at a low 3% interest rate, providing a unique financing advantage. Bring your ideas and make this property your next success!

  Tracey Patrick Coldwell Banker Premier

  704 Burrow Ave, Chesapeake, VA 23324
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  /38

  $270,000

  • 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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  /42

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,013 Sq Ft

  5023 Booker St, Chesapeake, VA 23320

  Beautifully renovated rancher in the heart of Chesapeake! This 3BR/2BA home offers convenient one-level living with numerous updates throughout. Features include shaker-style cabinets, granite countertops, and fully remodeled bathrooms with modern finishes. Fresh paint, new LVP flooring, new carpet, updated lighting, and contemporary fixtures. Spacious backyard ideal for entertaining and extended

  Raquel Sayago Iron Valley Real Est Norfolk

  5023 Booker St, Chesapeake, VA 23320
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  /26

  $299,999

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft

  1321 Eagles Trace Path Unit E, Chesapeake, VA 23320

  Enjoy peaceful golf course views from this bright and spacious 2 bedroom, 2 bath condo located in the desirable Greenbrier area of Chesapeake. Situated along the 10th fairway of Greenbrier Country Club, this home offers comfortable living with beautiful scenery right outside your door. The open layout and natural light create a welcoming space great for everyday living or

  Tiffany Doyon LPT Realty LLC

  1321 Eagles Trace Path Unit E, Chesapeake, VA 23320
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  /23

  $200,000

  • 3 Beds
  • 1 Bath
  • 1,254 Sq Ft

  1317 Yeadon Rd, Chesapeake, VA 23324

  A brick house in the center of Plymouth Park neighborhood.

  Travis Bouldin KW Coastal Virginia Chesapeake

  1317 Yeadon Rd, Chesapeake, VA 23324
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  /19

  $218,900

  • 2 Beds
  • 1 Bath
  • 822 Sq Ft

  1601 Stone Moss Reach Unit C, Chesapeake, VA 23320

  This is it! Move-in ready at a phenomenal price! Step into this second-level condo that features an open concept floorplan w/vaulted ceiling and a wood-burning fireplace. Kitchen has modern shaker cabinetry and stainless-steel appliances. Primary bedroom w/ample closet space and direct access to upgraded bath. Spare bedroom w/great closet space as well. All that's left to do is move in as

  Conner Walters World Class Realty & Prop Mgmt

  1601 Stone Moss Reach Unit C, Chesapeake, VA 23320
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  /22

  $275,000

  • 3 Beds
  • 1 Bath
  • 1,140 Sq Ft

  1310 Elder Ave, Chesapeake, VA 23325

  This centrally located 3 bedroom 1 bathroom ranch style home is ready for you! Fresh paint and new flooring throughout. Schedule your showing today!

  Ryan Forsberg Swell Realty Co

  1310 Elder Ave, Chesapeake, VA 23325
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  /28

  $229,900

  • 2 Beds
  • 2 Baths
  • 1,061 Sq Ft

  333 Gainsborough Square, Chesapeake, VA 23320

  Welcome to your new home in the heart of Greenbrier! Two primary suites with a spacious family room and separate dining area. Just rehabbed with fresh paint, new flooring, modern lighting, a chef's kitchen complete with new granite counters and stainless appliance package. Enjoy your own private outdoor space on the enclosed patio. The association fee covers water, trash, and landscaping.

  Judy Farris Howard Hanna Real Estate Svcs.

  333 Gainsborough Square, Chesapeake, VA 23320
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  /38

  $232,700

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

  4332 Hillingdon Bend Unit 104, Chesapeake, VA 23321

  Discover this BEAUTIFUL 2-bedroom home in the sought-after Western Branch area! This gem features NEW carpet, modern flooring, paint and bathrooms, and a spacious, open floor plan connecting the living room, kitchen and breakfast bar. Enjoy generously sized bedrooms, ample closet space, and storage. Its prime location offers convenience to military bases, shipyards, major hospitals, popular

  Reigne Brown RE/MAX Ultra

  4332 Hillingdon Bend Unit 104, Chesapeake, VA 23321
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  /36

  $290,000

  • 2 Beds
  • 2.5 Baths
  • 1,329 Sq Ft

  2314 Alcott Way, Chesapeake, VA 23321

  Welcome to this beautifully maintained condo built in 2021, offering modern finishes and low-maintenance living in a prime location. This home features two spacious primary suites, each with its own private bathroom—perfect for flexibility, guests, or shared living. The open-concept layout creates a bright and inviting space, while the immaculate condition makes it truly move-in ready.

  Genna Vannoy Triumph Realty

  2314 Alcott Way, Chesapeake, VA 23321
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  /40

  $255,000

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

  717 Inlet Quay Unit G, Chesapeake, VA 23320

  Welcome home to this beautifully refreshed 2-bedroom, 2-bath condo in the Riverwalk community! Featuring a newly remodeled kitchen with shaker cabinets, quartz countertops, Bosch dishwasher and Frigidaire refrigerator. Upgraded flooring throughout. Conveys with a stacked, full-size Kenmore washer/dryer. This original-owner home is truly move-in ready. The second floor bedroom offers a private

  Ron Sawyer RE/MAX Prime

  717 Inlet Quay Unit G, Chesapeake, VA 23320
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  /37

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,509 Sq Ft

  1717 Orchard Way, Chesapeake, VA 23320

  Beautifully Renovated Condo - Looks like New! 3 Bedrooms with First Floor Primary Bedroom! Eat-In Kitchen with New Appliances, huge breakfast bar, large great room w/Cathedral Ceilings & Fireplace. Spacious Bedrooms and Screened in Porch! Windows on Order!

  Michael Miller RE/MAX Allegiance

  1717 Orchard Way, Chesapeake, VA 23320
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  /26

  $280,000

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

  1462 Titchfield Dr, Chesapeake, VA 23320

  Welcome to effortless living in this beautifully maintained 2-bedroom, 2.5-bath condo nestled in the heart of Chesapeake’s desirable Greenbrier area. Enjoy unbeatable convenience with quick access to premier shopping, dining, parks, major interstates, and military bases. Inside, you’ll find a bright, open layout with a spacious living area that flows into the dining space, creating a warm and

  Tilman Dunbar Keller Williams Realty Twn Ctr

  1462 Titchfield Dr, Chesapeake, VA 23320
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  /6

  $245,900

  • 2 Beds
  • 2 Baths
  • 1,263 Sq Ft

  304 Gainsborough Square, Chesapeake, VA 23320

  charming 2 bedroom 2 full baths condo located near Chesapeake General Hospital. Well maintained home has an open layout. The primary suite features a private en-suite bath. an open office space with built in desk and cabinets next to primary suite. The appliances convey, and sold as is. fenced in patio w/storage closet. Easy access to the interstate, and major retail stores and restaurants.

  Robert McBride Harbor Associates Real Estate

  304 Gainsborough Square, Chesapeake, VA 23320
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  /17

  $250,000

  • 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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  /25

  $299,900

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

  213 Cedar Creek Terrace, Chesapeake, VA 23322

  SOLAR PANEL LOAN TO BE PAID AT SETTLEMENT!!!Townhouse in the heart of Great Bridge with many new updates to include, updated bathrooms, upstairs carpet, downstairs stamped concrete, hot water heater, asphalt roof, doors, ceiling fans, attic insulation, HVAC in 2021 and a new sewer line. Conveniently located to shopping, and sought after Great Bridge school district. Appliances work but convey as

  Michael Morgan Iron Valley Real Est. Prestige

  213 Cedar Creek Terrace, Chesapeake, VA 23322
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  /29

  $249,800

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  830 Partridge Ave, Chesapeake, VA 23324

  Fully-renovated and move-in ready, this beautiful updated 2-bedroom home offers efficient living and incredible value. Step inside to find fresh paint, updated flooring, and a bright open layout that makes the most of every square foot. The kitchen features new appliances, cabinetry, and a clean, modern look, great for everyday living or entertainment. Outside, enjoy a spacious yard and garage

  Angela Kennedy 1st Class Real Estate Integrity

  830 Partridge Ave, Chesapeake, VA 23324
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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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  /29

  $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
• 

  

  /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

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