Chesapeake, VA Homes for Sale under $300,000

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  /3

  $299,900

  • Land
  • 3.79 Acres
  • $79,234 per Acre

  737 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

  737 Bedford St, Chesapeake, VA 23322
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• 

  

  

  /3

  $299,900

  • Land
  • 3.49 Acres
  • $86,030 per Acre

  731 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

  731 Bedford St, Chesapeake, VA 23322
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  /23

  $224,900

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1004 Saint Andrews Way Unit D, Chesapeake, VA 23320

  Come check out this adorable townhome in Saint Andrews Condos before it's gone! This open floor plan home is 2 bedrooms & 2 bathrooms. The spacious living room features a cozy fireplace and flows seamlessly into the dining area and kitchen. Close to the YMCA, shopping, restaurants, and everything Greenbrier has to offer. Includes water, sewer, ground maintenance and trash! Welcome home!

  Stephen & Courtney Zawisa Atlantic Sotheby's International Realty

  1004 Saint Andrews Way Unit D, Chesapeake, VA 23320
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  /10

  $219,900

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft

  704 Shenandoah River Dr Unit C, Chesapeake, VA 23320

  Don’t let the square footage fool you! This beautiful 1 story (NO STAIRS) home located in the well sought after neighborhood of River Walk. Home offers 2 bedrooms, 2 bathrooms, Fireplace, updated Kitchen, new flooring throughout, washer/dryer, double vanity in main bathroom, stainless steel appliances, newer indoor and outdoor HVAC units. Relax and have your coffee and on your patio. HOA includes

  Debbie Crevier Kent Cottage Street Realty LLC

  704 Shenandoah River Dr Unit C, Chesapeake, VA 23320
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  /28

  $299,900

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

  1509 Waitsel Dr Unit 204, Chesapeake, VA 23320

  Enjoy the ease of one-level living in this beautifully designed 2-bedroom, 2-bath home. The owner’s suite offers a private bath and a walk-in closet with custom wood shelving. This interior unit features an open-concept floor plan with soaring ceilings, expansive windows that fill the space with natural light, and elegant interior finishes throughout. The spacious kitchen is ideal for both

  Andrew Christie Atlantic Sotheby's International Realty

  1509 Waitsel Dr Unit 204, Chesapeake, VA 23320
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  /27

  $230,000

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  1008 Saint Andrews Way Unit D, Chesapeake, VA 23320

  Welcome to this beautifully maintained condo in the heart of Chesapeake! This 2-bedroom, 2-bath home offers an open and airy layout with abundant natural light, perfect for both relaxing and entertaining. The spacious living room features a cozy fireplace and flows seamlessly into the dining area and kitchen. Enjoy a private patio ideal for morning coffee or evening wind-downs. The primary suite

  Alicia Ford The Agency

  1008 Saint Andrews Way Unit D, Chesapeake, VA 23320
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  /2

  $249,000

  • 3 Beds
  • 1.5 Baths
  • 1,465 Sq Ft

  3303 Rokeby Ave, Chesapeake, VA 23325

  Rare retreat in Norfolk Highlands! Tucked away on a private dead-end street high on a hill overlooking the Eastern Branch of the Elizabeth River, this aggressively priced 3 bed/1.5 bath ranch offers savvy creatives both privacy & instant equity potential. Wait until you see the Italian marble tilework in the bathrooms, each with oversized trough-style wall-mount sinks. Side patio entry doubles as

  Paul Pavon Exit Realty Professionals

  3303 Rokeby Ave, Chesapeake, VA 23325
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  /30

  $295,000

  • 4 Beds
  • 1 Bath
  • 1,587 Sq Ft

  185 George Washington Hwy S, Chesapeake, VA 23323

  Waterfront ranch home on almost half an acre of land! This home has been newly renovated with all new paint, lighting, fixtures, flooring, appliances, carpet and more! Open kitchen with granite countertops and stainless steel appliances. Beautifully remodeled bathroom. Spacious, finished attic serves as a bedroom. Big windows for great natural light. Backyard with covered porch and stone path.

  Joshua Britt Prodigy Realty

  185 George Washington Hwy S, Chesapeake, VA 23323
• 

  

  /19

  $265,000

  • 2 Beds
  • 1.5 Baths
  • 1,292 Sq Ft

  824 Nottaway Dr, Chesapeake, VA 23320

  Move-in ready and perfectly located, this Knells Ridge townhouse offers a spacious, open layout designed for comfort and convenience. The bright eat-in kitchen flows seamlessly into the dining area and living room—for both everyday living and entertaining. Enjoy two oversized primary suites, each with generous closet space for all your storage needs. Step outside to your own private, fenced

  Chad Keeney Harrell Homes Real Estate

  824 Nottaway Dr, Chesapeake, VA 23320
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  /28

  $225,000

  • 3 Beds
  • 1 Bath
  • 825 Sq Ft

  2603 Berkley Ave, Chesapeake, VA 23325

  Come See this Renovated Ranch in the Heart of Chesapeake Today!!!!

  Joshua Chilton EXP Realty LLC

  2603 Berkley Ave, Chesapeake, VA 23325
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  /33

  $225,000

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

  4316 Hillingdon Bend Unit 303, Chesapeake, VA 23321

  Beautifully Maintained 2-Bedroom, 2-Bath, 1,367sqft Condo. Step into this spacious and thoughtfully designed condo featuring 9-foot ceilings and an open, modern floor plan perfect for both everyday living and entertaining. The large kitchen boasts 42" cabinets, a breakfast bar, and plenty of prep space. The primary suite offers comfort and convenience with two closets and a generous en-suite

  Mark Laino The Bryant Group

  4316 Hillingdon Bend Unit 303, Chesapeake, VA 23321
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  /16

  $295,000

  • 3 Beds
  • 1 Bath
  • 942 Sq Ft

  3613 Weiss Ln, Chesapeake, VA 23323

  Discover this charming home in Chesapeake featuring 3 bedrooms, 1 bathroom, living room, laundry room and updated kitchen with SS electric range, SS dishwasher and SS microwave situated on a large lot. New paint and flooring throughout, ceiling fans and updated lighting. This house has close proximityto schools, shopping and more. Don't miss out! Schedule your showing today!

  Debbie Crevier Kent Cottage Street Realty LLC

  3613 Weiss Ln, Chesapeake, VA 23323
• 

  

  /19

  $299,999

  • 4 Beds
  • 2 Baths
  • 1,747 Sq Ft

  2929 Hilton Ave, Chesapeake, VA 23324

  Spacious 4-bed, 2-bath ranch with generously sized bedrooms; including a large primary suite; Cook with ease in the updated kitchen featuring granite tops and ample cabinetry. Recent upgrades include double hung windows (approx. 8 yrs old) and new hot water heater. Step outside to a newly installed deck over looking a fully fenced, oversized back yard with fire pit; an in-ground trampoline and

  Stephanie Lane Keller Williams Realty Town Center

  2929 Hilton Ave, Chesapeake, VA 23324
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  /19

  $239,900

  • 3 Beds
  • 2.5 Baths
  • 1,201 Sq Ft

  1821 Spar St, Chesapeake, VA 23321

  This ranch-style home in the heart of Chesapeake offers space, flexibility, and potential—all at a price that reflects its current as-is condition. The layout includes a cozy living room, a spacious family room with a full bath (ideal as a fourth bedroom or in-law suite), and a large eat-in kitchen with generous counter space and cabinet storage. Enjoy a private, fenced backyard with a

  Lavette Bell ONYX Realty Professionals LLC

  1821 Spar St, Chesapeake, VA 23321
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  /29

  $220,000

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  918 Wickford Dr, Chesapeake, VA 23320

  *One or more photos have been virtually staged/altered. Discover this beautifully rehabilitated 2-bedroom, 1-bath end-unit townhouse offering modern comfort with timeless charm. The open main level features fresh updates throughout, including a bright living space and a stylishly refreshed kitchen designed for both function and flow. Upstairs, two spacious bedrooms provide versatility for restful

  Ethan Windish Iron Valley Real Estate Norfolk

  918 Wickford Dr, Chesapeake, VA 23320
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  /30

  $285,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  4232 Schooner Trail, Chesapeake, VA 23321

  Welcome to this beautifully updated 3-bedroom, 1-bathroom ranch, perfectly situated near Towne Park @Goose Creek neighborhood. You'll love the open eat-in kitchen, complete with granite countertops and stainless steel appliances, ideal for both everyday living and entertaining. Step outside to a spacious, fenced backyard that backs to an open field—offering peaceful views, and a perfect space for

  Judy Reed Judy Reed Realty

  4232 Schooner Trail, Chesapeake, VA 23321
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  /12

  $260,000

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  901 Washington Dr, Chesapeake, VA 23322

  Opportunity knocks! This .4-acre corner lot is located in the highly desirable Great Bridge area of Chesapeake. The existing home is being sold as-is, with the true value in the land itself. Surrounded by new construction and beautifully updated homes, this property offers incredible potential for builders, investors or anyone looking to create their dream home in a thriving neighborhood

  Phil Taylor BHHS RW Towne Realty

  901 Washington Dr, Chesapeake, VA 23322
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  /40

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  2701 Omar St, Chesapeake, VA 23324

  A charming three-bedroom, two-bath single-story residence situated on a corner lot. The property features a detached garage. The kitchen has contemporary cabinetry, granite countertops, and stainless steel appliances. Common areas are (LVP) flooring, complemented by updated fixtures. Primary bedroom offers a modernized en-suite bathroom, a generous walk-in closet, and a sliding glass door

  Princess Stuckey World Class Realty & Property Management

  2701 Omar St, Chesapeake, VA 23324
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  /24

  $239,000

  • 2 Beds
  • 1 Bath
  • 1,025 Sq Ft

  513 E Lake Cir, Chesapeake, VA 23322

  Beautiful 2-bedroom condo in sought after Great Bridge area is move-in ready with many updates. The condo is an upstairs unit all on one level with cathedral ceilings and an open floor plan. Updated kitchen and bath (2020) with granite countertops, beautiful backsplash, stainless steel appliances, lots of cabinets, and eat-in kitchen area. New LVP flooring (2023). Roof (2024). Parking lot redone

  Dr. Mary Kraft Military Veterans Realty

  513 E Lake Cir, Chesapeake, VA 23322
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  /26

  $297,000

  • 3 Beds
  • 2.5 Baths
  • 1,470 Sq Ft

  522 Trolley Crossing, Chesapeake, VA 23320

  Welcome to 522 Trolley Crossing! This beautifully maintained end-unit townhome offers 3 spacious bedrooms, 2.5 baths, and nearly 1,500 square feet of living space. With soaring cathedral ceilings, abundant natural light, and a cozy gas fireplace, the main level feels open and inviting. **Seller willing to offer a carpet allowance for the right offer!**The kitchen includes all major

  Sonali Hutson Samson Properties

  522 Trolley Crossing, Chesapeake, VA 23320
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  /36

  $299,900 Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,461 Sq Ft

  501 Track Crossing, Chesapeake, VA 23320

  Well maintained end unit condo, the bright and airy living room showcases cathedral ceilings and a gas fireplace, creating the perfect backdrop for everyday living. The kitchen comes complete with appliances, ample storage, and easy flow to the dining area. The first-floor primary suite adds comfort with double vanities and a walk-in closet. Enjoy a private fenced patio, storage shed, and two

  Mike Zimmerman RE/MAX Ultra

  501 Track Crossing, Chesapeake, VA 23320
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  /50

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  1755 Oliver Ave, Chesapeake, VA 23324

  ATTENTION INVESTORS AND VISIONARIES! THIS CLASSIC OLDER HOME SITS ON 3 LOTS. THIS HOME OFFERS PLENTY OF CHARACTER AND SITS ALONGSIDE TWO ADDITIONAL CONNECTED LOTS. WHILE THE HOME REQUIRES SOME TLC, THE POSSIBILITIES ARE ENDLESS-RESTORE, REBUILD, OR EXPAND. THIS IS A RARE OPPORTUNITY TO OWN MULTIPLE LOTS TOGETHER IN A WELL-ESTABLISHED NEIGHBORHOOD. HOUSE SOLD AS IS. SHED SOLD AS IS. NO APPLIANCES

  Melanie Brown BHHS RW Towne Realty

  1755 Oliver Ave, Chesapeake, VA 23324
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  /21

  $295,000

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft

  2535 Dexter St E, Chesapeake, VA 23324

  ** AMAZING OPPORTUNITY ** This Beautiful Ranch Style Home offers 3 Bedrooms, 2 Full Bathrooms and is MOVE IN READY!! Has the Following FEATURES: Inviting Kitchen with Modern Styling Cabinets, Full Stainless Steel Appliance Package to include Refrigerator, Electric Range, Dishwasher & Microwave, LVP flooring in the Main Living Areas with Carpet in the Bedrooms, WONDERFUL Family Room, Separate

  Ryan Schoch Earl Sanders Realty Inc.

  2535 Dexter St E, Chesapeake, VA 23324
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  /38

  $244,900

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

  1322 Hoover Ave, Chesapeake, VA 23324

  This meticulously updated home is completely move-in ready and awaits its new owner. Fresh paint and new flooring create a pristine canvas throughout the living spaces. The heart of the home, a gourmet kitchen, features gleaming granite countertops and a suite of stainless steel appliances, perfect for any home chef. Both bathrooms have been stylishly updated, adding a touch of modern elegance.

  Jamey Fereday World Class Realty

  1322 Hoover Ave, Chesapeake, VA 23324
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  /25

  $295,000

  • 2 Beds
  • 2 Baths
  • 1,405 Sq Ft

  500 Judah Way Unit 121, Chesapeake, VA 23320

  Beautiful 2-bedroom and two full bathroom condo in the centrally located Greenbriar neighborhood. This gated community includes an elevator, fitness center, ground maintenance, security, and trash pickup. This condo features beautiful cherry cabinets with granite countertops and stainless steel appliances, a custom television entertainment unit with a gas fireplace, and assigned covered parking,

  Angela Jernigan Realty One Group Unified

  500 Judah Way Unit 121, Chesapeake, VA 23320
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  /20

  $239,000

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  1319 Decatur St, Chesapeake, VA 23324

  Don't miss out on this one. Charming 3-Bedroom Cape Cod in Chesapeake. This inviting 3-bedroom, 1-bath Cape Cod offers comfort, convenience, and recent updates. Inside, you’ll find newer carpet, fresh paint, and a kitchen equipped with a newer stove and dishwasher—making it move-in ready.Situated in a prime location, this home is just minutes from the naval base, outlet mall, shopping, and

  Tom Busciglio Howard Hanna Real Estate Services

  1319 Decatur St, Chesapeake, VA 23324
• 

  

  /17

  $229,000

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

  4309 Hillingdon Bend Unit 303, Chesapeake, VA 23321

  Welcome to Unit 303 at Kings Pointe, a perfect blend of comfort and convenience! Located just off I-64, Exit 11B in Western Branch, this newer community offers easy access to dining, shopping, and local amenities. The 2-bedroom, 2-bathroom condo sits on the top floor, providing stunning, unobstructed views. Enjoy the luxury of a clubhouse, pool, trails, grills, firepits, and plenty of guest

  Judy Reed Judy Reed Realty

  4309 Hillingdon Bend Unit 303, Chesapeake, VA 23321
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  /18

  $234,000

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

  4308 Colindale Rd Unit 206, Chesapeake, VA 23321

  Move in ready - Beautiful 2nd floor condo. Walk into an open floor plan with new LVP in the kitchen and foyer. Kitchen has 42 in cabinets, stainless steel appliances, large pantry and a breakfast bar. Large primary bedroom with two closets and spacious second bedroom with hallway bath. The condo fee includes water, sewer, trash pick-up, ground maintenance and master insurance policy. Amenities to

  Steve Freeman RHOAD & CO.

  4308 Colindale Rd Unit 206, Chesapeake, VA 23321
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  /38

  $295,000

  • 2 Beds
  • 2.5 Baths
  • 1,613 Sq Ft

  603 Sail Fish Quay, Chesapeake, VA 23320

  This beautifully renovated condo in the highly desired Riverwalk community boasts an open floor plan with high end finishes throughout. The 1st floor is home to two primary suites each with stylish ensuite baths and conveniently located laundry area. The 2nd floor features a vaulted ceiling and skylights in the great room offering an abundance of natural light which flows into the dining area

  Rhonda Shelton BHHS RW Towne Realty

  603 Sail Fish Quay, Chesapeake, VA 23320
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  /38

  $290,000

  • 3 Beds
  • 1 Bath
  • 1,309 Sq Ft

  708 Stalham Rd, Chesapeake, VA 23325

  Renovated Ranch!!!! Home was taken down to the studs. Newly installed Plumbing, Electrical, Zoned Heat/A/C,Roof, Vinyl Siding, LVP Floors, Appliances, Water Heater, Patio, Most of The Windows, Sliding Glass Door & More!!!! Too Many Upgrades to List! Home has an Open Feel and gets Tons of Light!!!! Come See Today!!!!

  Joshua Chilton EXP Realty LLC

  708 Stalham Rd, Chesapeake, VA 23325
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  /14

  $285,000 Open Sun 12PM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 1,330 Sq Ft

  303 Middle Oaks Dr, Chesapeake, VA 23322

  Nicely appointed townhome, great location, and amenities. No HOA, POA or condo fees. Come see this home before it's gone. All upgrades are approx. 7 yrs old. HVAC was replaced 2019, New fence in 2025

  Merrill Getto Keffer Realty

  303 Middle Oaks Dr, Chesapeake, VA 23322
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  /33

  $275,000

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  4429 Pepper Ridge Ct, Chesapeake, VA 23321

  Welcome to this Western Branch 3 Bedroom, 2.5 Bath Brick condo in Miars Farm. Great investment the roof was replaced by Stublen, HVAC in 2020, Hot water large tank system with alarm & auto shut off in 2020, top of the line windows in 2024, metal lite pull down attic steps, back entrance and front entrance (more parking) new antibacterial carpet 2021, painted 2020, top of the line wood laminate

  LeAnn Amory BHHS RW Towne Realty

  4429 Pepper Ridge Ct, Chesapeake, VA 23321
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  /29

  $290,000

  • 3 Beds
  • 1.5 Baths
  • 1,196 Sq Ft

  2114 Mclain St, Chesapeake, VA 23324

  This beautifully renovated ranch in Avalon blends classic charm with modern updates—offering more value than new construction! Step through the stone-accented sun porch into a cozy cottage filled with character, including refinished hardwood floors and a thoughtful layout. 2020 updates include HVAC and water heater as well as a full roof replacement. The spacious, powered workshop, privacy-fenced

  Logan Cooper EXP Realty LLC

  2114 Mclain St, Chesapeake, VA 23324
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  /35

  $299,000

  • 3 Beds
  • 2.5 Baths
  • 1,639 Sq Ft

  707 Sailfish Quay, Chesapeake, VA 23320

  Welcome to your move-in ready home, designed for easy living and modern comfort. This beautifully updated residence features new flooring and fresh paint throughout, creating a clean and inviting atmosphere. Enjoy the efficiency of a brand-new HVAC system and the charm of a white kitchen complete with granite countertops and stainless steel appliances. The bathrooms have been thoughtfully

  Jamey Fereday World Class Realty

  707 Sailfish Quay, Chesapeake, VA 23320
• 

  /2

  $299,900

  • Land
  • 3.77 Acres
  • $79,634 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
• 

  

  /28

  $207,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  1009 Saint Andrews Way Unit B, Chesapeake, VA 23320

  Looking for a condo in a great location? We have one! It's conveniently located in the Greenbrier Section of Chesapeake. It's a 2-story townhome style condo on the golf course. Comes with 1 bedroom, an oversized loft, and an open floorplan, in a quiet neighborhood. Maintenance free living with new roof! It's next to the YMCA. There's a dog park down the street and it's near shopping &

  Kimberly Bedsole BHHS RW Towne Realty

  1009 Saint Andrews Way Unit B, Chesapeake, VA 23320
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  /48

  $299,000

  • 3 Beds
  • 2.5 Baths
  • 1,492 Sq Ft

  2042 Berkley Ave, Chesapeake, VA 23324

  Step into this charming gem! Completely remodeled! This beautifully maintained home offers timeless character blended with thoughtful updates – making it move-in ready and full of potential. Plenty of natural light and updated light fixtures! Enjoy the HUGE private balcony from the primary bedroom on the 2nd floor. Custom tile work with granite countertops, and all new stainless-steel appliances.

  Angela Kennedy 1st Class Real Estate Integrity

  2042 Berkley Ave, Chesapeake, VA 23324
• 

  

  /19

  $245,000

  • 2 Beds
  • 1.5 Baths
  • 950 Sq Ft

  918 Seabreeze Ct, Chesapeake, VA 23320

  Enjoy a great location near shopping and lots of restaurants, especially the new Towne Place at Greenbrier! Close to the interstate for quick access to anywhere in Hampton Roads. Well maintained and move-in ready with updated flooring, updated lights, and updated ceiling fans. Patio provides a great space to entertain, and newly rebuilt shed gives you extra storage! Second floor has two spacious

  Kimberly Dykes Aweigh Real Estate

  918 Seabreeze Ct, Chesapeake, VA 23320
• 

  

  /11

  $250,000

  • 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 Keller Williams Coastal Virginia Chesapeake

  1317 Yeadon Rd, Chesapeake, VA 23324
• 

  

  /15

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  3108 Aaron Dr, Chesapeake, VA 23323

  The seller offers a $600.00 credit towards the buyer's choice of dishwasher.This ranch-style home was fully remodeled in 2013 with quality upgrades throughout. Featuring a newer roof, windows, and siding updated in 2013. Step inside to find ceramic flooring, a stylish kitchen with granite countertops, modern cabinets, and stainless steel appliances.Both bathrooms were updated in 2013 with

  Darrell Moore CENTURY 21 Top Producers

  3108 Aaron Dr, Chesapeake, VA 23323

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