Chesapeake, VA Homes for Sale under $500,000

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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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  /24

  $444,000

  $6K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,228 Sq Ft

  450 Asuza St, Chesapeake, VA 23323

  Juniper Model built in 2021. 1st floor has flex room, can be used as office, mud room, or rec room. Also, separate bedroom with full bath. 2nd floor has huge open floor plan. Kitchen has large island, SS appliances, lots of cabinets, and large pantry. Great room with gas electric fireplace. Deck off front. Lots of windows for natural lighting. Please call night before to see.

  Victoria Schiano The Real Estate Group

  450 Asuza St, Chesapeake, VA 23323
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  /35

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 2,058 Sq Ft

  711 Pile Ave, Chesapeake, VA 23320

  Welcome home to this beautifully maintained 3 bedroom, 2.5 bath home featuring an open-concept layout with soaring ceilings and a versatile loft. Luxury vinyl plank flooring flows throughout the first floor, creating a stylish and low-maintenance living space. The spacious primary suite offers a private en suite bath, while generously sized secondary bedrooms provide flexibility for a variety of

  Tonia Kovach Coastal Towne Realty

  711 Pile Ave, Chesapeake, VA 23320
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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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  /36

  $424,900

  $2K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,349 Sq Ft

  713 Tiffany Green Ct, Chesapeake, VA 23320

  Welcome to your dream home in Chesapeake! This meticulously maintained end-unit condo blends modern luxury with effortless living, offers 4 bedrooms, 2.5 bathrooms, and beautifully upgraded living spaces. Go inside to an airy open-concept layout with vaulted ceilings, crown molding, and luxury vinyl flooring. Enjoy upgraded recessed lighting, pendant lights, and modern ceiling fans. The chef's

  Stephanie Fortunat BHHS RW Towne Realty

  713 Tiffany Green Ct, Chesapeake, VA 23320
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  /14

  $349,900

  Pre-Foreclosure

  • 4 Beds
  • 2 Baths
  • 1,346 Sq Ft

  1205 Aaron Ct, Chesapeake, VA 23323

  This renovated ranch is nestled in the neighborhood and boasts new paint and LVP and lighting throughout. Brand new kitchen (with new SS appliances) with eye-catching quartz countertops, overlooks the dining room . Updated bathrooms with new ceramic tile and vanities. All this plus a new roof! Walk in and enjoy the open floor plan of your new home! Both sheds sold "as is".

  Marcella Montagna CoastalVA Realty Inc.

  1205 Aaron Ct, Chesapeake, VA 23323
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  /43

  $349,900

  • 4 Beds
  • 2 Baths
  • 1,587 Sq Ft

  3568 Dunedin Dr, Chesapeake, VA 23321

  Welcome home to this beautifully renovated, move-in-ready home where the big-ticket updates are already DONE! Featuring a NEW roof, NEW HVAC, NEW windows and NEW hot water heater. The gorgeous new kitchen offers granite countertops, a large breakfast bar, stainless steel appliances and a stainless steel farmhouse sink. Enjoy custom tiled bathrooms, spacious walk-in closets, new flooring, fresh

  Bridget Combs COVA Home Realty

  3568 Dunedin Dr, Chesapeake, VA 23321
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  /27

  $339,900

  Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,577 Sq Ft

  4376 Pickney Ln, Chesapeake, VA 23324

  MOVE-IN READY and packed with upgrades! Fresh paint and brand-new flooring throughout make this newer 3-story condo truly shine. this energy-efficient home offers modern style, low-maintenance living, and exceptional versatility. The open floor plan features high ceilings, recessed lighting, and surround sound speakers in the living room. The gourmet kitchen boasts a breakfast bar, tile

  Danielle Sticha Howard Hanna Real Estate Svcs.

  4376 Pickney Ln, 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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  /30

  $409,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,654 Sq Ft

  897 Railroad Ave, Chesapeake, VA 23324

  Full appliance package (including washer/dryer & refrigerator) on all existing inventory! Seller will pay up to $12,000 for closing cost assistance orto be used at buyer's discretion using our preferred lender and our attorney. Stunning New Construction! Welcome to this beautiful 3-bedroom,2.5-bath home offering 1,654 square feet of modern living space. Designed with a spacious open floor

  Laura Rowe BHHS RW Towne Realty

  897 Railroad Ave, Chesapeake, VA 23324
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  /33

  $425,000

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  2122 English Ave, Chesapeake, VA 23320

  Honey stop the car! This completely move in ready, newer built home is ready for new owners! Downstairs features an open concept kitchen and living space featuring granite countertops and stainless steel appliances. Fresh paint and new carpets throughout! Enjoy relaxing in your fenced in backyard with freshly painted deck. Centrally located in Chesapeake close to military bases, freeways and

  Cassidy Juarez 1st Class Real Estate Elevate

  2122 English Ave, Chesapeake, VA 23320
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  /29

  $497,500

  • 5 Beds
  • 3 Baths
  • 3,590 Sq Ft

  4624 Westborough Dr, Chesapeake, VA 23321

  Ben Rego Gallery of Homes Real Estate

  4624 Westborough Dr, Chesapeake, VA 23321
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  /31

  $399,999

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

  1117 Winsford Ln, Chesapeake, VA 23320

  Welcome home! This move-in ready townhome offers low-maintenance living in a convenient Chesapeake location near Greenbrier. Enjoy a fully renovated primary bath, a low-maintenance patio with AstroTurf, and community amenities including a pool and park. Conveniently located near shopping, dining, entertainment, and major roadways, this home offers the perfect blend of comfort, convenience, and

  Lexi Pace RE/MAX Alliance

  1117 Winsford Ln, Chesapeake, VA 23320
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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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  /32

  $343,000

  $7K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,462 Sq Ft

  3036 Bomar Dr, Chesapeake, VA 23321

  Updated ranch in Western Branch with open floor plan. Kitchen has beautiful granite countertops and stainless steel appliances. Large bonus room that could be used as an extra bedroom, playroom, office, entertainment room, or family room. Fully fenced back yard with detached garage. Close to interstates, shopping, restaurants, and Military bases.

  Catherine Blythe The Real Estate Group

  3036 Bomar Dr, Chesapeake, VA 23321
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  /33

  $340,000

  • 3 Beds
  • 1.5 Baths
  • 1,224 Sq Ft

  815 Rutledge Rd, Chesapeake, VA 23320

  Welcome home to this well-maintained 3-bedroom, 1.5-bath ranch located in an established neighborhood with convenient access to major military bases, shopping, dining, and interstate access. Inside, you’ll find beautifully refinished hardwood floors, a recently updated kitchen with new cabinets and countertops, newer HVAC, newer roof, and updated dishwasher. The bonus room just off the kitchen

  Angela Kennedy 1st Class Real Estate Integrity

  815 Rutledge Rd, Chesapeake, VA 23320
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  /31

  $344,900

  New Construction

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

  1540 Eldwick Drive #101, 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 1st floor corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes.

  Clarice Savereux Dragas Companies Realty Inc

  1540 Eldwick Drive #101, Chesapeake, VA 23320
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  /32

  $397,000

  $38K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,315 Sq Ft

  2113 Quaker Place, Chesapeake, VA 23325

  This lovely Rancher style home has lots of room for you! Upon entrance you will see some of the wood laminated floors. The family room (18 X 16) with vaulted ceiling, has an open feeling plus gas fireplace. Roomy kitchen with lots of cabinet & counter space. Recently renovated Florida room (18 X 15). Lots of fresh painting, some new carpet and more! All bedrooms in this 4 bedroom rancher are

  Larry Townsend BHHS RW Towne Realty

  2113 Quaker Place, Chesapeake, VA 23325
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  /36

  $374,900

  $20K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,124 Sq Ft

  1421 Ardmore Cir, Chesapeake, VA 23324

  Welcome to 1421 Ardmore Circle! This charming cape cod home offers 5 bedrooms and 3 full bathrooms nestled on almost 1/2 an acre. Step inside to find a welcoming layout designed for both everyday living and entertaining. The spacious kitchen has been completely updated with white shaker style cabinets, quartz countertops, new stainless steel appliances, new faucet, new light fixture and new

  Kim McGlone Keller Williams Coastal Virginia Chesapeake

  1421 Ardmore Cir, Chesapeake, VA 23324
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  /16

  $349,900

  • 4 Beds
  • 2.5 Baths
  • 1,656 Sq Ft

  844 Parapet Rd, Chesapeake, VA 23323

  Welcome to this spacious two-story home offering a fantastic layout and incredible potential! The first floor features a formal living room, separate dining room, a cozy den, and a convenient half bath. Upstairs, you will find three comfortably sized bedrooms alongside a primary suite complete with its own private en suite bath. Excellent storage and parking are provided by the attached two-car

  Rachael Podruchny Vylla Home

  844 Parapet Rd, Chesapeake, VA 23323
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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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  /42

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,250 Sq Ft

  2704 Misty Point Rd, Chesapeake, VA 23323

  Room to garden, create, and entertain. A home designed for real use! Located at the end of a dead-end street on a cul-de-sac, this 3-bedroom, 1.5-bath home offers hardwood floors, a comfortable living area, and a full kitchen suite with all the countertop space, cabinets, and storage you need. The house only gets better outside, with an exceptional amount of usable outdoor space. In the front,

  Corey Hubbard Barn Door Homes

  2704 Misty Point Rd, Chesapeake, VA 23323
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  /41

  $295,000

  • 2 Beds
  • 2.5 Baths
  • 1,436 Sq Ft

  3714 Whitechapel Arch, Chesapeake, VA 23321

  Welcome to 3714 Whitechapel Arch! This move-in-ready townhouse features a new 2026 HVAC, tankless water heater, fresh paint throughout, cathedral ceilings, large closets, and an open floor plan. Enjoy the flexibility of two primary suites, each with an attached full bathroom: one upstairs and one downstairs. The upstairs also offers a versatile landing area. Additional features include an

  Daisy Phillips Atlantic Sothebys Int'l Realty

  3714 Whitechapel Arch, Chesapeake, VA 23321
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  /30

  $233,500

  $16K 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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  /10

  $431,000

  $29K PRICE DROP

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

  1028 Ramsgate Ln, Chesapeake, VA 23322

  Opportunity awaits! Whether you're an investor, renovator, or buyer looking to build equity, this property offers incredible potential. With the right updates and vision, this home could truly shine again. Great for someone ready to renovate and make it their own or transform it into a great investment property. Bring your ideas and creativity, this is a chance to add value and create something

  Matthew Monaco BHHS RW Towne Realty

  1028 Ramsgate Ln, Chesapeake, VA 23322
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  /2

  $290,000

  • 4 Beds
  • 1.5 Baths
  • 1,176 Sq Ft

  3209 Dunworken Dr, Chesapeake, VA 23321

  AS IS, extra-large garage w/electricity & workshop area

  Michelle Harris 1st Class Real Estate Flagship

  3209 Dunworken Dr, Chesapeake, VA 23321
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  /44

  $415,000

  • 5 Beds
  • 3 Baths
  • 2,256 Sq Ft

  2624 Powell Cir, Chesapeake, VA 23323

  Updated top to bottom and built for flexibility — this home offers two separate entrances, making it ideal for extended family living or rental income potential. The main residence features 3 bedrooms and 2 full baths, plus a charming bonus space that works beautifully as a home office, mudroom, or whatever your needs call for. The secondary living quarters include 2 bedrooms, a living room, 1

  Betsy Thompson The Agency

  2624 Powell Cir, Chesapeake, VA 23323
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  /29

  $469,000

  $1K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,136 Sq Ft

  4126 Scotfield Dr, Chesapeake, VA 23321

  In a quiet cul-de-sac, this brick-front home features high ceilings in the entryway, a formal living room, and family room. It also offers a two-car garage, a spacious yard, and a large storage shed with electricity. New HVAC installed in 2021. Flooring allowance with acceptable offer.

  Laura Rynkiewicz Vylla Home

  4126 Scotfield Dr, Chesapeake, VA 23321
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  /36

  $374,900

  • 4 Beds
  • 2 Baths
  • 1,368 Sq Ft

  1522 Lilac Ave, Chesapeake, VA 23325

  This beautiful ranch-style home offers an inviting open floor plan, renovated kitchen and bathrooms, and numerous recent updates like roof and HVAC system. Step outside and enjoy the brand-new deck with pergola, overlooking the spacious fenced backyard and above-ground pool—perfect for relaxing or entertaining. The spacious primary suite features a WIC and updated private bathroom. A finished

  Ron Sawyer RE/MAX Prime

  1522 Lilac Ave, Chesapeake, VA 23325
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  /34

  $419,000

  Open Sat 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,853 Sq Ft

  1601 Lilac Ave, Chesapeake, VA 23325

  Charming Cape Cod situated on a desirable corner lot in Norfolk Highlands! This 4-bedroom, 2 full bath home offers a fresh, move-in-ready feel with newly painted interiors and new carpet throughout. The renovated kitchen provides an updated and inviting space for everyday living and entertaining. The spacious bedroom count offers flexibility for guests, a home office, or additional living needs.

  Meredith Liverman Signature Homes

  1601 Lilac Ave, Chesapeake, VA 23325
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  /18

  $385,000

  • 3 Beds
  • 2.5 Baths
  • 1,704 Sq Ft

  2130 Lockard Ave, Chesapeake, VA 23320

  Step inside this inviting 3-bedroom Chesapeake home offering plenty of space both inside and out! The first floor welcomes you with a bright, open layout that brings the living, dining, and kitchen areas together, making the space great for everyday living and entertaining. The kitchen is equipped with abundant cabinetry, ample counter space, a large pantry, and a convenient breakfast bar.

  Le'Montez Jones Own Real Estate LLC

  2130 Lockard Ave, Chesapeake, VA 23320
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  /32

  $319,900

  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

  $319,900

  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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  /17

  $334,900

  New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,464 Sq Ft

  4987 Boone Rd, Chesapeake, VA 23321

  Welcome to Piney Grove, an exquisite community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level plan beautifully showcases an open floorplan w/ luxurious upgrades. The kitchen stuns guests w/ upgraded quartz countertops, subway tile backsplash, & soft-close drawers. Easily maintained & durable LVP flooring & crown molding throughout 1st

  Lisa Kyriakides Corinth Realty LLC

  4987 Boone Rd, Chesapeake, VA 23321
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  /25

  $469,900

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,852 Sq Ft

  145 Hurdle Dr, Chesapeake, VA 23322

  Welcome to this spacious 4-bed, 2-bath home situated on a beautiful half-acre lot in the heart of Great Bridge! Offering a flexible floor plan, this home features 2 oversized living areas, 2 spacious primary bedrooms, & 2 additional bedrooms—ideal for multigenerational living, a home office, playroom, or the potential for a 5th bedroom. Updates include fresh interior paint, new flooring, restored

  Casey Preston Keller Williams Coastal Virginia Chesapeake

  145 Hurdle Dr, Chesapeake, VA 23322
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  /13

  $450,000

  • Land
  • 23,304 Sq Ft
  • $841,121 per Acre

  341 Scone Castle Loop, Chesapeake, VA 23322

  This is a rare chance to own a vacant lakefront lot in a prestigious, established community of luxury custom homes valued between $1,300,000 and $2,000,000 a former HOMEARAMA neighborhood. Enjoy serene water views, mature landscaping, with proximity to top schools and convenient shopping. A soil report is available for your builder's review, and the seller is willing to provide custom house plans

  Jennifer Cool BHHS RW Towne Realty

  341 Scone Castle Loop, Chesapeake, VA 23322
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  /2

  $426,000

  • Land
  • 6.93 Acres
  • $61,472 per Acre

  3912 Savannah Dr, Chesapeake, VA 23322

  Rare opportunity to own a vacant homesite in this established Chesapeake estate neighborhood! This wooded 6.93-acre parcel offers a unique combination of privacy, space, and a desirable residential setting surrounded by established homes. A creek along the rear of the property adds to its character. Whether you're looking to create a private estate or build your dream home with plenty of room to

  April Dickson 1st Class Real Estate Flagship

  3912 Savannah Dr, Chesapeake, VA 23322
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  /33

  $383,000

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,640 Sq Ft

  4113 Taylor Rd, Chesapeake, VA 23321

  Charming all brick home with major system updates already completed! Step inside to find beautiful hardwood floors and a warm, inviting layout filled with character. Enjoy peace of mind with a roof replaced in 2021, along with the durability and timeless appeal of brick construction. Outside, you'll love the expansive, fully fenced backyard perfect for entertaining, pets, gardening, or simply

  Raechel Geiss Own Real Estate LLC

  4113 Taylor Rd, Chesapeake, VA 23321
• 

  

  /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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  /37

  $499,900

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

  3248 Battlefield Blvd S, Chesapeake, VA 23322

  Amazing property in the heart of Hickory. Home is dated before 1850, that is when they started record keeping! 3 beds up with 2 baths, and 1/2 bath down. 2 wood burning fireplaces. Owner willing to make minor repairs with acceptable offer. Large barn/garage, that was a former auto-mechanic shop! Large, covered deck with additional open-air deck. All appliances convey. Must see to appreciate the

  Kim Mills Kirkby The Real Estate Group

  3248 Battlefield Blvd S, Chesapeake, VA 23322

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