Chesapeake County, VA Homes

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  /36

  $824,500

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

  1105 Waters Rd, Chesapeake, VA 23322

  Come see this enchanting storybook house! Leave cookie cutter homes behind! Acreage right where you want it, convenient to everything. This home SCREAMS "HOME", exceptionally tranquil with many possibilities. ORIGINAL and BEAUTIFUL hardwood floors, very solid old school construction. Two very large bedrooms downstairs, 2 more upstairs. In ground pool with pool house just down a charming walkway

  

  Janice Myers-Hollowell

  World Class Realty

  (757) 847-5780

  1105 Waters Rd, Chesapeake, VA 23322
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  /40

  $1,510 - $1,799 per month

  Woodbriar Apartment Homes

  1 - 2 Beds

  208 Crosswinds Dr, Chesapeake, VA 23320

  The Breeden Company invites you to enjoy quality living where charm and the imaginative design of contemporary architecture are yours. Peacefulness of country living yet conveniences of the city are afforded you at Woodbriar, just minutes from Greenbrier Mall. Each spacious one and two bedroom apartment is designed for your living comfort and enjoyment. Vaulted ceilings and washers/dryers are

  208 Crosswinds Dr, Chesapeake, VA 23320
• 

  $370,000 Sold Jul 23, 2025

  1521 Tallwood Cir, Chesapeake, VA 23320

  • 3 Beds
  • 2.5 Baths
  • 1,875 Sq Ft
  • Built 1999

  Last Sold Summary

  • $197/SF
  • 4 Days On Market

  Current Estimated Value $378,983

  Last Listing Agent Debbie Crevier Kent Cottage Street Realty LLC

  1521 Tallwood Cir, Chesapeake, VA 23320
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  /5

  Est $482,025 Not Listed For Sale

  2157 Arbutus Cir, Chesapeake, VA 23323

  • 5 Beds
  • Built 2022

  2157 Arbutus Cir, Chesapeake, VA 23323

  Last Sold Summary

  • 666% Above List Price
  • $27/SF
  • 108 Days On Market

  Last Sold Price $62,900

  Last Listing Agent Robert Poff Johnston and Rhodes Real Estate
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  /36

  $429,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,810 Sq Ft

  728 Luther St, Chesapeake, VA 23322

  This beautiful home is nestled into a cozy neighborhood in the heart of Great Bridge. Boasting open floor plan with family/ great room and gas fireplace is great for rest and relaxation. Beautiful hardwood floors throughout, and lovely gourmet kitchen with stainless-steel appliances, and lots of cabinet space. Breakfast nook overlooks the deck and backyard. Great size laundry room as well. This

  

  Carmen Anthony

  BHHS RW Towne Realty

  (757) 505-8584

  728 Luther St, Chesapeake, VA 23322
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  /17

  $2,295 per month

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • House for Rent

  3332 Kinsington Dr, Chesapeake, VA 23321

  3 bedrooms, 2 full-bath Ranch with 1 car attached garage, located between shopping at Churchland and I-664. Home has separate living room and family room, Laundry room with washer/dryer hook-ups, Eat-in kitchen has electric stove, refrigerator, dishwasher. Large fenced back yard. One dog ok (some breeds excluded) with additional $400 pet deposit. No cats. Minimum One year lease. SORRY, NO

  Steve Barbour Barbour Realty Inc.

  3332 Kinsington Dr, Chesapeake, VA 23321
• 

  $260,000 Sold May 23, 2025

  25 Gale Ave, Chesapeake, VA 23323

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 2004

  Last Sold Summary

  • $250/SF
  • 24 Days On Market

  Current Estimated Value $267,078

  Last Listing Agent J Adam Harris LPT Realty LLC

  25 Gale Ave, Chesapeake, VA 23323
• 

  /2

  Est $393,037 Not Listed For Sale

  2123 Steiner St, Chesapeake, VA 23321

  • 3 Beds
  • 3 Baths
  • 1,870 Sq Ft
  • Built 2019

  2123 Steiner St, Chesapeake, VA 23321

  Last Sold Summary

  • 11% Below List Price
  • $190/SF

  Last Sold Price $355,000

  Last Listing Agent Melissa Edwards Rivers Edge Realty, LLC
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  /41

  $695,000 Under Contract

  • 5 Beds
  • 3.5 Baths
  • 2,686 Sq Ft

  416 Middleton Way, Chesapeake, VA 23322

  $100,945 in upgrades (see attachment). Practically new, built in 2024 and ideally situated on one of the community’s scenic lakes, this impressive 5-bedroom home offers space, style, and modern comfort. Enjoy dual owner’s suites—one on the main level and one upstairs—each featuring tiled showers and quartz vanity tops. The open-concept living area showcases a spacious kitchen with quartz

  

  Greg Garrett

  Garrett Realty Partners

  (757) 551-2743

  416 Middleton Way, Chesapeake, VA 23322
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  /15

  $1,420 - $2,225 per month

  Stonebridge Apartments

  1 - 3 Beds

  4152 Prindle Ct, Chesapeake, VA 23321

  Experience the best of apartment living at Stonebridge Apartments. Our pet-friendly community offers a range of amenities, including spacious floor plans, fitness center, and swimming pool. With exceptional service and a convenient location, Stonebridge is the perfect place to call home.

  4152 Prindle Ct, Chesapeake, VA 23321
• 

  $260,000 Sold Aug 04, 2025

  2025 Allison Dr, Chesapeake, VA 23325

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1985

  Last Sold Summary

  • $217/SF
  • 18 Days On Market

  Current Estimated Value $257,342

  Last Listing Agent Jessica Bailey The Real Estate Group

  2025 Allison Dr, Chesapeake, VA 23325
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  /40

  Not Listed For Sale

  2409 Lena Ct, Chesapeake, VA 23323

  • 4 Beds
  • 2.5 Baths
  • 2,385 Sq Ft
  • Built 2018

  2409 Lena Ct, Chesapeake, VA 23323

  Last Sold Summary

  • 385 Days On Market
• 

  

  /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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  /43

  $3,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,511 Sq Ft
  • House for Rent

  5205 Pughsville Rd, Chesapeake, VA 23321

  Please Read Carefully: TOURING TO BE SCHEDULED AFTER APPLICATION. CHECK OUT THE 43 PHOTOS, WALKTHROUGH VIDEOS & DRIVE BY THE PROPERTY @ YOUR CONVENIENCE. Security Deposit=$3,000+1st Mo Rent Of $3,000 & Move In Cost=$6,000 with Excellent Credit & Rental History. Welcome home to this beautiful home with ultra modern open floor plan with traditional dining area comes with a ton of new upgrades and

  Boldstar Property Management Boldstar Real Estate

  5205 Pughsville Rd, Chesapeake, VA 23321
• 

  $235,000 Sold Aug 06, 2025

  335 Gainsborough Square, Chesapeake, VA 23320

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 1996

  Last Sold Summary

  • $205/SF
  • 30 Days On Market

  Current Estimated Value $234,532

  Last Listing Agent Zena Ward BHHS RW Towne Realty

  335 Gainsborough Square, Chesapeake, VA 23320
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  /21

  Not Listed For Sale

  4332 Hillingdon Bend, Chesapeake, VA 23321

  • 2 Beds
  • 2 Baths
  • 1,367 Sq Ft
  • Built 2014

  4332 Hillingdon Bend, Chesapeake, VA 23321

  Last Sold Summary

  • $102/SF
  • 107 Days On Market

  Last Sold Price $140,000

  Last Listing Agent Dina Thomas Howard Hanna William E. Wood
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  /24

  $290,000 Pending

  • 1,620 Sq Ft

  4109 5th St, Chesapeake, VA 23324

  Exclusive Showing Thursday, 2/26/26 from 10am to 11am! Exceptional Investment Opportunity! One unit is vacant; one is occupied by a tenant. Tenant needs 48 hours notice to approve showings for the occupied unit. DO NOT DISTURB TENANT. LARGE side-yard and backyard lot. Onsite driveway for parking in the front, with backyard access. Wonderfully situated near major interstates, military bases, and a

  

  Linda Brandon

  BHHS RW Towne Realty

  (757) 353-4334

  4109 5th St, Chesapeake, VA 23324
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  /35

  $1,303 per month

  Arbor Glen Apartments

  1 - 2 Beds

  2616 Arbor Glen Dr, Chesapeake, VA 23324

  As a resident of Arbor Glen Apartments you will be treated to pleasant amenities both indoors and outside. Not only are our floor plans spacious, they are also energy efficient. We’ve helped you to save money on your monthly heating bill by installing energy efficient windows, appliances and a 15 SEER Trane heat pump. You will also find a washer and dryer is included in your rent. At Arbor Glen,

  2616 Arbor Glen Dr, Chesapeake, VA 23324
• 

  $560,000 Sold Oct 20, 2025

  854 Jo Anne Cir, Chesapeake, VA 23322

  • 4 Beds
  • 3 Baths
  • 2,450 Sq Ft
  • Built 1980

  Last Sold Summary

  • $229/SF
  • 10 Days On Market

  Current Estimated Value $555,808

  Last Listing Agent Diane Pearman The Real Estate Group

  854 Jo Anne Cir, Chesapeake, VA 23322
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  /25

  Est $678,591 Not Listed For Sale

  3329 Conservancy Dr, Chesapeake, VA 23323

  • 3 Beds
  • 3.5 Baths
  • 2,406 Sq Ft
  • Built 2018

  3329 Conservancy Dr, Chesapeake, VA 23323

  Last Sold Summary

  • 70% Above List Price
  • $166/SF
  • 6 Days On Market

  Last Sold Price $398,195

  Last Listing Agent Sidney James HHHunt Realty Inc
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  /42

  $225,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 900 Sq Ft

  2717 Thomas St, Chesapeake, VA 23323

  Charming move in ready Bungalow on a oversized lot. Covered front porch. New carpet and freshly painted throughout. Newer vinyl replacement windows. Kitchen remodeled two years ago with new appliances just replaced - stainless refrigerator and gas stove. Primary bedroom with 1/2 bathroom. Heating/Air 2021 and Water Heater 2020.

  

  David Cacace

  BHHS RW Towne Realty

  (757) 801-2721

  2717 Thomas St, Chesapeake, VA 23323
• 

  

  /25

  $2,400 per month

  • 3 Beds
  • 2.5 Baths
  • 1,757 Sq Ft
  • Townhouse for Rent

  529 Bright Red Run, Chesapeake, VA 23323

  You will love this contemporary townhouse featuring foyer, great room with ceiling fan open to dining area and kitchen. Kitchen features lots of counter space, all appliances(refrigerator, electric range, dishwasher, microwave, disposal) plus bar eating area. Great room back door opens to small patio in the backyard. 1 car garage. Upstairs there is a primary bedroom big enough for king size bed,

  Kathy Elliott RE/MAX Allegiance

  529 Bright Red Run, Chesapeake, VA 23323
• 

  $310,000 Sold Jul 18, 2025

  2816 Gavin Rd Unit 14, Chesapeake, VA 23323

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft
  • Built 2016

  Last Sold Summary

  • $170/SF
  • 9 Days On Market

  Last Listing Agent Betsy Thompson The Agency

  2816 Gavin Rd Unit 14, Chesapeake, VA 23323
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  /30

  Est $536,887 Not Listed For Sale

  3344 Conservancy Dr, Chesapeake, VA 23323

  • 3 Beds
  • 3.5 Baths
  • 2,178 Sq Ft
  • Built 2018

  3344 Conservancy Dr, Chesapeake, VA 23323

  Last Sold Summary

  • 42% Above List Price
  • $174/SF
  • 29 Days On Market

  Last Sold Price $378,685

  Last Listing Agent Sidney James HHHunt Realty Inc
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  /45

  $399,900 Pending

  • 4 Beds
  • 3 Baths
  • 2,080 Sq Ft

  2016 Jefferson St, Chesapeake, VA 23324

  Eight years young and thoughtfully designed, this beautifully maintained four-bedroom home offers flexible living with two primary suites, one on the first floor and the one on the second. The oversized kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and generous prep space. Freshly installed carpet enhances the interior, and updated light fixtures add a

  

  Anna Staylor

  BHHS RW Towne Realty

  (757) 520-7922

  2016 Jefferson St, Chesapeake, VA 23324
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  /35

  $1,295 - $1,880 per month

  The Birches

  1 - 2 Beds

  1700 Birch Trail Cir, Chesapeake, VA 23320

  Welcome home to The Birches! Our garden-style apartment community features amenities and floor plans that are sure to satisfy your needs. Located in the Greenbrier area, The Birches is moments from 1-64, giving you access to military installations, beaches, downtown Norfolk and more. Our community is even close to the 168 Bypass, a scenic route to North Carolina's Outer Banks! At The Birches, you

  1700 Birch Trail Cir, Chesapeake, VA 23320
• 

  $1,003,214 Sold Jul 07, 2025

  183 Hessian Loop, Chesapeake, VA 23322

  • 6 Beds
  • 5 Baths
  • 3,892 Sq Ft
  • Built 2025

  Last Sold Summary

  • $258/SF
  • 1 Day On Market

  Last Listing Agent Judy Duke Wainwright Real Estate

  183 Hessian Loop, Chesapeake, VA 23322
• 

  /2

  Est $714,071 Not Listed For Sale

  2211 Orange Root Dr, Chesapeake, VA 23323

  • 6 Beds
  • 3 Baths
  • 3,500 Sq Ft
  • Built 2018

  2211 Orange Root Dr, Chesapeake, VA 23323

  Last Sold Summary

  Last Listing Agent Pat Davis BHHS RW Towne Property Mgmt
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  /26

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft

  3980 Port Rd, Chesapeake, VA 23321

  Charming brick ranch offering comfortable single-level living with approximately 1,485 square feet, 3 bedrooms, and 2 full bathrooms. This home features a spacious and functional layout with inviting living areas and generously sized bedrooms. The kitchen provides ample cabinet and counter space and flows easily into the main living areas, making everyday living and entertaining

  

  LJ Hunt

  Iron Valley Real Est Norfolk

  (757) 834-9614

  3980 Port Rd, Chesapeake, VA 23321
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  /12

  $1,850 per month

  • 2 Beds
  • 2 Baths
  • 1,214 Sq Ft
  • Townhouse for Rent

  1816 Carrollwood Common, Chesapeake, VA 23320

  Chesapeake Townhome in Woodgate Commons - Move-In Ready! Welcome to this charming 2-primary-bedroom townhome in the desirable Woodgate Commons community of Chesapeake. Thoughtfully designed for comfort & convenience, this home features a first-floor primary suite complete w/ a private bath-perfect for easy, single-level living. Upstairs, you’ll find a second spacious primary bedroom w/ its own

  AJ Williamson RE/MAX Alliance

  1816 Carrollwood Common, Chesapeake, VA 23320
• 

  $594,000 Sold May 16, 2025

  925 Saddleback Trail Rd, Chesapeake, VA 23322

  • 4 Beds
  • 2.5 Baths
  • 2,317 Sq Ft
  • Built 1991

  Last Sold Summary

  • $256/SF
  • 23 Days On Market

  Current Estimated Value $602,512

  Last Listing Agent Diane Keeley BHHS RW Towne Realty

  925 Saddleback Trail Rd, Chesapeake, VA 23322
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  /2

  Est $349,866 Not Listed For Sale

  614 Muddy Creek Rd, Chesapeake, VA 23324

  • 3 Beds
  • 4 Baths
  • 1,760 Sq Ft
  • Built 2018

  614 Muddy Creek Rd, Chesapeake, VA 23324

  Last Sold Summary
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  /38

  $399,900

  • 4 Beds
  • 3 Baths
  • 1,720 Sq Ft

  4225 Coffman Blvd, Chesapeake, VA 23321

  This beautifully updated 4-bedroom, 3-bathroom home offers an ideal blend of space, comfort, and modern updates. The spacious kitchen features granite countertops, ample cabinetry, and generous prep space, making it functional for everyday living and entertaining. Fresh interior paint throughout the home creates a clean, inviting feel, while the remodeled bathrooms add a polished, updated

  

  Michele Salyer

  A Better Way Realty Inc.

  (757) 280-3731

  4225 Coffman Blvd, Chesapeake, VA 23321
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  /35

  $1,120 - $1,550 per month

  Marina Point

  1 - 3 Beds

  1301 Canal Dr, Chesapeake, VA 23323

  With gorgeous views of the Elizabeth River all around you, private access to your own boat ramp and fishing at your back door, Marina Point Apartments brings you the best of living life on the water in Chesapeake! Find your escape from the hustle and bustle in a quiet corner of Chesapeake that’s still nearby businesses, shopping, schools, recreation areas and military installations. Tucked away

  1301 Canal Dr, Chesapeake, VA 23323
• 

  $218,000 Sold Mar 12, 2026

  4309 Hillingdon Bend Unit 303, Chesapeake, VA 23321

  • 2 Beds
  • 2 Baths
  • 1,367 Sq Ft
  • Built 2017

  Last Sold Summary

  • 5% Below List Price
  • $159/SF
  • 18 Days On Market

  Current Estimated Value $224,680

  Last Listing Agent Judy Reed Judy Reed Realty

  4309 Hillingdon Bend Unit 303, Chesapeake, VA 23321
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  /2

  Est $659,823 Not Listed For Sale

  1311 McRowland Ln, Chesapeake, VA 23320

  • 4 Beds
  • 3 Baths
  • 2,542 Sq Ft
  • Built 2017

  1311 McRowland Ln, Chesapeake, VA 23320

  Last Sold Summary
• 

  

  /29

  $354,000

  • 3 Beds
  • 2 Baths
  • 1,591 Sq Ft

  1301 Tuckaway Reach Unit D, Chesapeake, VA 23320

  This second-level condo offers an open-concept layout with 3 bedrooms and 2 full bathrooms, highlighted by cathedral ceilings. Features include newer LVP flooring in the main living areas, newly carpeted bedrooms, updated lighting fixtures, and a renovated kitchen with granite countertops. New roof, a newer deck, and an updated HVAC system (compressor and air handler). The property includes an

  

  Katie Burke

  Long & Foster Real Estate Inc.

  (757) 517-3351

  1301 Tuckaway Reach Unit D, Chesapeake, VA 23320
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  /36

  $2,650 per month

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • House for Rent

  1249 Sir Kay Dr, Chesapeake, VA 23323

  Welcome to this waterfront ranch in Chesapeake, VA! This home offers 3 traditional bedrooms plus a versatile bonus room that can function as a 4th bedroom, home office, or guest space. The primary bedroom includes a private full bath, and the layout provides comfortable, functional living throughout. Enjoy a screened-in porch and a spacious backyard that leads to a private rear deck positioned

  Kandey Wilson EXIT Realty Central

  1249 Sir Kay Dr, Chesapeake, VA 23323
• 

  $497,000 Sold Jun 05, 2025

  808 Pleasant Way, Chesapeake, VA 23322

  • 4 Beds
  • 2.5 Baths
  • 2,085 Sq Ft
  • Built 1988

  Last Sold Summary

  • $238/SF
  • 19 Days On Market

  Current Estimated Value $509,891

  Last Listing Agent Loretta Killen Howard Hanna Real Estate Svcs.

  808 Pleasant Way, Chesapeake, VA 23322
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  /53

  Est $810,293 Not Listed For Sale

  1894 Bancroft Rd Unit 37563655, Chesapeake, VA 23320

  • 4 Beds
  • 2.5 Baths
  • 2,619 Sq Ft
  • Built 2022

  1894 Bancroft Rd Unit 37563655, Chesapeake, VA 23320

  Last Sold Summary

  • 108 Days On Market

Showing Results 241 - 280, Page 7 of 18