Chesapeake, VA Homes for Sale under $300,000

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  /17

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,005 Sq Ft

  1330 Wingfield Ave, Chesapeake, VA 23325

  Fully remodeled 3-Bedroom, 2-bath Ranch situated on a corner lot in a quiet Chesapeake neighborhood. This home features durable LVP flooring throughout, recessed lighting, and brand-new windows. The open-concept kitchen and living area offers a functional and cozy space, complete with granite countertops and modern finishes. Both bathrooms have been tastefully updated with a clean, contemporary

  

  Alex Currie

  Long & Foster Real Estate Inc.

  (757) 601-5810

  1330 Wingfield Ave, Chesapeake, VA 23325
• Explore Chesapeake

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  /25

  $249,000

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  2005 Lockard Ave, Chesapeake, VA 23320

  Discover this charming one bedroom home perfectly situated just minutes from Greenbrier mall and Kempsville areas of Virginia Beach. Enjoy a rare blend of comfort, style and convenience - whether you're a first time buyer, downsizing, or searching for a great investment opportunity!! Step inside to find bright open living spaces, modern finishes and a cozy atmosphere, that instantly feels like

  

  Katie Burke

  Long & Foster Real Estate Inc

  (757) 512-6236

  2005 Lockard Ave, Chesapeake, VA 23320
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  /49

  $247,500

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

  1016 Thoroughgood Way Unit 307, Chesapeake, VA 23324

  Make this your first stop! Beautifully maintained, low maintenance, open concept, Third floor condo! Building is secured with intercom and fob access. This two bedroom, two bathroom unit will immediately feel like your new home. Beautiful Views and Plenty of Natural lighting. Primary bedroom has a spacious walk-in closet and en-suite bathroom with a walk-in shower. Near Bases. Shipyards. And

  

  Eric Hovik

  RE/MAX Alliance

  (757) 300-5128

  1016 Thoroughgood Way Unit 307, Chesapeake, VA 23324
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  /24

  $285,000

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

  1439 Orchard Grove Dr, Chesapeake, VA 23320

  $5,000 Buyer Allowance! Don’t miss this beautiful condo in the highly sought-after Orchard Grove community in Greenbrier. Perfectly located with a larger yard, 2 assigned parking spaces (#20 close by), and mailbox nearby. Features include NEW quartz kitchen countertops, New stove, 2 year old carpet, plus a screened in porch that backs up to trees for added privacy, and a flexible loft that can be

  

  Carlos Cardo

  RE/MAX Ultra

  (757) 703-8735

  1439 Orchard Grove Dr, Chesapeake, VA 23320
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  /25

  $269,900

  • 3 Beds
  • 2 Baths
  • 1,122 Sq Ft

  814 Hughes Ave, Chesapeake, VA 23324

  Welcome to this beautifully updated home in Chesapeake! From the moment you arrive, the welcoming front porch invites you in to explore a bright, open living area, perfect for gathering or relaxing. The dining area flows seamlessly into the newly renovated kitchen, featuring brand new appliances, perfect for your favorite recipes. A convenient mudroom off the kitchen leads to a spacious backyard,

  

  Brian Simon

  Fit Realty

  (757) 840-4047

  814 Hughes Ave, Chesapeake, VA 23324
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  /28

  $248,000

  • 2 Beds
  • 2 Baths
  • 1,169 Sq Ft

  1016 Thoroughgood Way Unit 100, Chesapeake, VA 23324

  Welcome to this spacious condo located in a well-maintained traditional-style building with secured entrance, elevator access, and an intercom system for added peace of mind. This beautifully designed unit features two oversized bedrooms and two generously sized bathrooms, offering both comfort and convenience. The open-concept kitchen includes a large breakfast bar with seating for 4–6, Great

  

  Michele Salyer

  A Better Way Realty Inc.

  (757) 290-8046

  1016 Thoroughgood Way Unit 100, Chesapeake, VA 23324
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  /11

  $295,000

  • 1,710 Sq Ft

  1215 Hoover Ave, Chesapeake, VA 23324

  

  Greg Garrett

  Garrett Realty Partners

  (757) 906-6964

  1215 Hoover Ave, Chesapeake, VA 23324
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  /18

  $239,900

  • 2 Beds
  • 2 Baths
  • 1,169 Sq Ft

  1016 Thoroughgood Way Unit 201, Chesapeake, VA 23324

  Make this your first stop! Beautifully maintained, low maintenance, open concept, second floor condo! Building is secured with intercom and fob access. This two bedroom, two bathroom unit will immediately feel like your new home. The bedrooms have dormers to bring in extra light and open up the space. Primary bedroom has a spacious walk-in closet and en-suite bathroom with a walk-in shower.

  

  Matthew Salway

  Iron Valley Real Estate HR

  (757) 914-9584

  1016 Thoroughgood Way Unit 201, Chesapeake, VA 23324
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  /25

  $269,800

  • 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. Make this lovely home yours before ethe

  

  Rachel Beasley

  Own Real Estate LLC

  (757) 863-6645

  511 Appomattox St, Norfolk, VA 23523
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  /25

  $274,800

  • 3 Beds
  • 2 Baths
  • 1,235 Sq Ft

  308 Taft Dr, Portsmouth, VA 23701

  Renovated Brick Ranch Home- so many beautiful new features to include New Roof, HVAC, Kitchen, Bathrooms and more. Enter this fresh home into the living room which is open to the dining and kitchen. Kitchen boasts all new cabinets, granite countertops and new SS appliances. The Hallway leads you to the bedrooms where you will find bedroom 2 & 3 and the hall bathroom. The primary suite is large -

  

  Rachel Beasley

  Own Real Estate LLC

  (757) 530-7306

  308 Taft Dr, Portsmouth, VA 23701
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  /28

  $265,000

  • 3 Beds
  • 1.5 Baths
  • 1,633 Sq Ft

  87 Dahlgren Ave, Portsmouth, VA 23702

  

  Chris Lloyd

  Coast to Coast Real Estate Inc

  (757) 982-2874

  87 Dahlgren Ave, Portsmouth, VA 23702
• 

  

  /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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  /45

  $250,000

  • 2 Beds
  • 2 Baths
  • 1,223 Sq Ft

  725 Inlet Quay Unit C, Chesapeake, VA 23320

  Come see this beautiful first-floor condo in the sought-after Riverwalk area! This home offers 2 bedrooms, 2 baths, and 1,223 sq. ft. of comfortable living space. The inviting living room features an electric fireplace, great for relaxing or entertaining. The kitchen opens to the dining and living areas, creating a nice flow for everyday living. The primary bedroom is very large with room for a

  Susan Jenkins Better Homes & Gdns Ntv Am Grp

  725 Inlet Quay Unit C, Chesapeake, VA 23320
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  /49

  $255,000

  • 2 Beds
  • 1.5 Baths
  • 993 Sq Ft

  919 Captains Ct, Chesapeake, VA 23320

  Welcome home to this well-maintained 2-story townhouse offering 2 spacious bedrooms and 1.5 baths. Enjoy a bright, open layout with a cozy breakfast area for morning coffee and casual dining. The private fenced yard provides the space for pets, gardening, or outdoor relaxation. Convenient off-street parking adds ease to your daily routine. Nestled in a prime location near Greenbrier Mall,

  Susan Jenkins Better Homes & Gdns Ntv Am Grp

  919 Captains Ct, Chesapeake, VA 23320
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  /50

  $275,400

  • 2 Beds
  • 2 Baths
  • 1,311 Sq Ft

  823 Rivanna River Reach, Chesapeake, VA 23320

  Welcome to this home featuring 1 bedroom and full bathroom upstairs with a loft, and a full bedroom and bathroom downstairs. As an end unit, it includes a large concrete patio with shade. Cathedral ceilings with lots of natural light. HUD Case# 541-733417 IE (Insured Escrow), Subject to Appraisal. Seller makes no representations or warranties as to property condition. HUD Homes are Sold “As-Is”.

  Susan Jenkins Better Homes & Gdns Ntv Am Grp

  823 Rivanna River Reach, Chesapeake, VA 23320
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  /49

  $259,000

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

  952 Saint Andrews Reach Unit A, Chesapeake, VA 23320

  Charming water-view home in sought-after Chesapeake! This inviting 3-bedroom, 2-bath residence offers comfort, style, and convenience in a beautiful setting. Enjoy a spacious kitchen featuring granite countertops, ample cabinetry, and modern finishes — great for cooking and entertaining. The open layout flows seamlessly into bright living and dining areas filled with natural light. A first-floor

  Kim McCabe Better Homes & Gdns Ntv Am Grp

  952 Saint Andrews Reach Unit A, Chesapeake, VA 23320
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  /37

  $280,000

  • 3 Beds
  • 1.5 Baths
  • 1,377 Sq Ft

  1023 Nelson St, Chesapeake, VA 23324

  Welcome to this beautifully staged and move-in ready, inviting home which offers new lighting fixtures throughout, spacious bedrooms, and a versatile extra room great for a second living area, den, office, study, playroom, or entertainment space. The dedicated laundry room comes with a washer and dryer that convey. The primary bedroom includes its own private bathroom. Outside, enjoy a manicured

  Ivy Obasi Allison James Estates & Homes

  1023 Nelson St, Chesapeake, VA 23324
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  /17

  $275,000

  • 3 Beds
  • 1 Bath
  • 1,005 Sq Ft

  1004 Mayfield Ave, Chesapeake, VA 23324

  Indulge in an elevated lifestyle where tranquility meets utility in this distinguished residence, privately situated within a friendly and quiet neighborhood. Experience the pleasure of owning a home that perfectly accommodates both grand entertaining and peaceful repose. Picture yourself beginning each day with a moment of calm on the beautiful front porch, a stately entrance to your sanctuary.

  Deborah Reynolds Keller Williams Richmond West

  1004 Mayfield Ave, Chesapeake, VA 23324
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  /6

  $280,000

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft

  2029 Stonehurst St, Chesapeake, VA 23324

  Look no further! This seller is very motivated to sell and get you in your new home before the holidays. This wonderfully maintained family home is located on a desired street in the South Norfolk area of Chesapeake. Inside picture will be posted in a few days. It features an open front porch, deck, and a large storage shed in the backyard. Plenty of driveway space, spacious bedrooms, inviting

  Jazmine Hall LPT Realty LLC

  2029 Stonehurst St, Chesapeake, VA 23324
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  /45

  $290,000

  • 2 Beds
  • 1 Bath
  • 834 Sq Ft

  708 Sparrow Rd, Chesapeake, VA 23325

  Don’t let the square footage fool you—this home feels spacious with a bright living area and beautiful hardwood floors. A long driveway leads to a large detached garage that also has an additional bathroom (per seller; not included in permitted living space). Enjoy the charming front porch and a huge backyard perfect for relaxing or entertaining. Conveniently located near bases, the interstate,

  Sally Powell 1st Class R E - Equity Group

  708 Sparrow Rd, Chesapeake, VA 23325
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  /22

  $290,000

  • 4 Beds
  • 2 Baths
  • 1,868 Sq Ft

  1308 Chesapeake Ave, Chesapeake, VA 23324

  Step into the timeless charm of South Norfolk’s Historic District with this 1908 home! Boasting 4 bedrooms, 2 baths, and flexible living spaces, this residence blends character and comfort. Enjoy morning coffee on the inviting wraparound porch before stepping inside to a bright living room with a decorative fireplace and architectural details and built-ins. The kitchen features granite

  Elaina Kirk KW Coastal Virginia Chesapeake

  1308 Chesapeake Ave, Chesapeake, VA 23324
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  /32

  $275,000

  • 2 Beds
  • 2.5 Baths
  • 1,278 Sq Ft

  418 Middle Oaks Dr, Chesapeake, VA 23322

  Charming townhome in the desirable Middle Oaks community, located in the highly sought-after Great Bridge school district! This home features 2 spacious bedrooms and 2.5 baths, offering plenty of room to relax or entertain. Recent updates include a new HVAC system (indoor and outdoor units replaced in 2021) and a fully replaced privacy fence in 2022. With just a little TLC, this home is ready to

  Imani Overton-Santos Iron Valley Real Est. Prestige

  418 Middle Oaks Dr, Chesapeake, VA 23322
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  /38

  $275,000

  • 3 Beds
  • 1 Bath
  • 1,309 Sq Ft

  708 Stalham Rd, Chesapeake, VA 23325

  Renovated Ranch! 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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  /29

  $275,000

  • 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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  /48

  $275,000

  • 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 RealEstate Integrity

  2042 Berkley Ave, Chesapeake, VA 23324
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  /26

  $275,000 Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,216 Sq Ft

  929 Still Harbor Cir, Chesapeake, VA 23320

  This unique 3-bedroom, 1.5-bathroom townhouse offers modern living with charming kitchen featuring stainless steel appliances, granite countertops, and vintage cabinets. Enjoy a private backyard with no homes directly behind and a peaceful greenspace. Located within walking distance to shopping, dining, and just minutes from major highways and military bases. Low POA fees, no condo fees—perfect

  Rowan Whitenack LPT Realty LLC

  929 Still Harbor Cir, Chesapeake, VA 23320
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  /50

  $280,000

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

  6465 Duquesne Place, Virginia Beach, VA 23464

  Updated 3 bed, 1.5 bath townhouse with major systems already taken care of! Upgrades include roof (2010), windows & patio doors with transferable warranty (2010/11), HVAC (2013) with air scrubber (2024), hot water heater (2022), and ductwork cleaned/sealed (2024). Interior updates: remodeled kitchen with 2023 appliances, LVP flooring (2023), recessed lighting (2023), new front door and gate

  Debra Gutekunst Iron Valley Real Estate HR

  6465 Duquesne Place, Virginia Beach, VA 23464
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  /27

  $294,900

  • 3 Beds
  • 3 Baths
  • 1,776 Sq Ft

  609 Sail Fish Quay, Chesapeake, VA 23320

  Welcome to this stunning condo nestled in the highly desirable Riverwalk community of Chesapeake. Featuring 3 spacious bedrooms and 3 full bathrooms, this home offers comfort, style, and convenience just minutes from I-664/I-64, Greenbrier, and Great Bridge. Expansive loft ideal for a home office or flex space. Well-sized walk-in closets for ample storage. Bright, open layout with modern

  Sonya Brown Wainwright Real Estate

  609 Sail Fish Quay, Chesapeake, VA 23320
• 

  

  /29

  $295,000

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

  1 Sandy Point Ln Unit 218, Chesapeake, VA 23320

  Experience relaxed coastal living in this beautifully maintained 3-bedroom, 2-bath, one-level condo located on the third floor of an elevator building. Offering nearly 1,800 sq ft in a highly desirable Intracoastal Waterway community, this home features refreshed baths, brand-new carpet and paint, and an open-concept living area. The kitchen includes generous counter space, a pantry, and a

  Kris Weaver Atlantic Sothebys Int'l Realty

  1 Sandy Point Ln Unit 218, Chesapeake, VA 23320
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  /28

  $230,000

  • 2 Beds
  • 2.5 Baths
  • 1,190 Sq Ft

  2453 Old Greenbrier Rd Unit 124, Chesapeake, VA 23325

  Welcome to this meticulously maintained and tastefully updated condo in Providence Pointe! This home features two beds, two and a half baths, with the primary bedroom containing an in-suite. You’ll love the open living space with its sleek, updated flooring, modern light fixtures, and access to a private patio right off the side. The kitchen features newer counters, stainless steel appliances,

  Garrett Williams The Real Estate Group

  2453 Old Greenbrier Rd Unit 124, Chesapeake, VA 23325
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  /31

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,245 Sq Ft

  4605 Woodmark Trail, Chesapeake, VA 23321

  Welcome to Western Branch Commons, Don't miss this Lovely 3 Bedroom , 2 Bath one level end unit Condo in the Western Branch School District. Large Great Room with tray ceiling, gas fireplace leading to private patio and a 8x10 storage unit. Spacious eat in Kitchen with pantry. Large primary bedroom with large walk in closet. Assigned 2 parking spaces and low condo fees. HVAC 2023 Hot water 2019

  Brenda Lewis Realty Source

  4605 Woodmark Trail, Chesapeake, VA 23321
• 

  

  /21

  $259,900

  • 4 Beds
  • 2 Baths
  • 1,278 Sq Ft

  2044 Christian Ave, Chesapeake, VA 23324

  4-bedroom, 2-bath home with a functional two-story layout and modern finishes throughout. The kitchen and bathrooms feature updated materials and fixtures. Bedrooms are located on the upper and lower levels. The floor plan offers a straightforward flow.

  Taylor Madison C O R E Real Estate + Design

  2044 Christian Ave, Chesapeake, VA 23324
• 

  

  /22

  $270,000

  • 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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  /34

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,372 Sq Ft

  714 B St, Chesapeake, VA 23324

  A charming 2 story home nestled near the historic area of South Norfolk. This delightful residence features 3 bedrooms with 2 full bathrooms and an open floorplan. Home was updated in 2023 with new windows, countertops, tub/shower/vanities, dual zone HVAC, flooring and paint. Detached garage with a carport for additional off street parking. Located in a convenient neighborhood, this home is close

  Ryan Harkins Real Estate USA

  714 B St, Chesapeake, VA 23324
• 

  

  /22

  $259,900

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

  705 Creekside Crescent, Chesapeake, VA 23320

  This 2-bedroom townhome in Chesapeake’s desirable Riverwalk has much to offer a new owner. Downstairs you will find the kitchen with dedicated dining space, living room with fireplace, half bath, and laundry room. Upstairs are the bedrooms including the primary with ensuite bath and walk-in closet. The backyard with shed and fence offer space for adults, kids, and pets to relax and play.

  Brian Shelton CapCenter

  705 Creekside Crescent, Chesapeake, VA 23320
• 

  

  /21

  $230,000

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  1105 Kay Ave, Chesapeake, VA 23324

  Welcome to 1105 Kay Avenue in Chesapeake. This 3 bedroom 1 bathroom home has 912 square feet of living space inside and plenty of yard space outside. The sale of this home includes all the essentials you need to move right in including washer, dryer, stove, refrigerator, microwave, and a huge 100 inch projector screen with projector. To keep the heating and cooling costs down new energy efficient

  Roger McCann Atlantic Connection Real Est.

  1105 Kay Ave, Chesapeake, VA 23324
• 

  

  /23

  $260,000

  • 3 Beds
  • 1 Bath
  • 1,014 Sq Ft

  1217 Cleona Dr, Chesapeake, VA 23324

  Charming 3-bed, 1-bath ranch in Chesapeake’s Indian River neighborhood at 1217 Cleona Dr! This 1,014 sq ft single-family home sits on a spacious 5,837 sq ft lot, offering cozy curb appeal and endless potential. It’s immaculately maintained with fresh updates, hardwood floors, and a bright open layout. Enjoy a modern kitchen, generous bedrooms, and a full bath. Prime location near shopping, parks,

  Jasmina West Triumph Realty

  1217 Cleona Dr, Chesapeake, VA 23324
• 

  

  /35

  $289,900 Open Sun 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft

  412 Tekoa Rd, Chesapeake, VA 23325

  Welcome home to this cozy brick ranch that's been well cared for & thoughtfully updated. Enjoy peace of mind with a new roof & tankless water heater. Move right in without lifting a finger. This spacious fenced backyard is ready for your house warming party and comes with a storage shed, lawn mower, and grill all staying for the new owner. Bright rooms, a practical layout, and pride of ownership

  Jessica Burnette Swell Realty Co

  412 Tekoa Rd, Chesapeake, VA 23325
• 

  

  /35

  $280,000

  • 2 Beds
  • 2 Baths
  • 1,127 Sq Ft

  1023 Winged Foot Ct Unit A, Chesapeake, VA 23320

  Welcome home to this charming Fairways Villas condo perfectly positioned on the golf course! Enjoy single-story living with a bright, open floor plan featuring vaulted ceilings in both the great room and the primary bedroom, adding a spacious and airy feel. The primary suite offers a walk-in closet with shelving and a decorative display ledge. The dining area is just off the kitchen, providing

  Cynthia Inniss RE/MAX Alliance

  1023 Winged Foot Ct Unit A, Chesapeake, VA 23320
• 

  

  /17

  $282,000

  • 3 Beds
  • 2 Baths
  • 1,586 Sq Ft

  1007 Holly Ave, Chesapeake, VA 23324

  Charming Historic Gem in South Norfolk - Lakeside Park Views & Downtown Convenience! Step into this 3-bed, 2-full-bath single-family home nestled in the heart of South Norfolk's historic district. Spanning nearly 1,600 SF of thoughtfully designed living space, this residence blends classic charm with modern comfort, offering the perfect backdrop for your next chapter. Enjoy views of Lakeside Park

  Douglas Livermon Atlantic Sothebys Int'l Realty

  1007 Holly Ave, Chesapeake, VA 23324

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