Chesapeake County, VA Homes

• 

  

  

  /35

  $465,000

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,975 Sq Ft

  2744 Horseshoe Dr, Chesapeake, VA 23322

  Nestled in the sought-after Homestead Acres community of Chesapeake, this beautifully maintained brick ranch offers the perfect blend of comfort, charm, and functionality. Enjoy an inviting open floor plan with spacious living areas, an updated kitchen, bright sunroom, and screened-in porch to enjoy year-round. Step outside to a large backyard retreat complete with a built-in firepit, great for

  

  Jessica Haynes

  Keller Williams Capital Props.

  2744 Horseshoe Dr, Chesapeake, VA 23322
• 

  

  

  /21

  $1,500 Per Month

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft
  • House for Rent

  2604 Omar St, Chesapeake, VA 23324

  Discover comfortable living in this 672-square-foot home in Chesapeake's Providence Terrace, where bright interiors and an open flow create an inviting place to begin and end each day. Fresh finishes, a functional layout, and a detached garage provide everyday convenience, while the spacious yard offers room to relax, entertain, or enjoy the outdoors. The community offers Greenbrier Mall,

  

  Lea' Marie Ngowakl

  Atlantic Sothebys Int'l Realty

  2604 Omar St, Chesapeake, VA 23324
• 

  $226,000

  Sold Jul 29, 2026

  909 Decatur St, Chesapeake, VA 23324

  • 2 Beds
  • 1 Bath
  • 1,016 Sq Ft
  • Built 1924

  Last Sold Summary

  • 3% Above List Price
  • $222/SF
  • 16 Days On Market

  Current Estimated Value $206,559

  Last Listing Agent Todd Morton AtCoastal Realty

  909 Decatur St, Chesapeake, VA 23324
• 

  

  

  /31

  Est $680,187

  Not Listed For Sale

  2133 Summer Breeze Rd, Chesapeake, VA 23323

  • 6 Beds
  • 3.5 Baths
  • 2,929 Sq Ft
  • Built 2018

  2133 Summer Breeze Rd, Chesapeake, VA 23323

  Last Sold Summary

  • 131 Days On Market

  Last Listing Agent Wendy Saunders Keller Williams Williamsburg
• 

  

  

  /50

  $734,900

  • 5 Beds
  • 3 Baths
  • 2,756 Sq Ft

  1741 Watershed Ct, Chesapeake, VA 23323

  There is not enough space to explain how wonderful this home is! A rare sense of privacy meets thoughtful luxury in this upgraded 2022 Grassfield home. Near the end of a cul-de-sac and bordered by protected wetlands and unbuildable parcels on both sides, the lot offers a wooded backdrop that is hard to replicate. The flexible 5-bedroom, 3-bath layout includes two primary suites, one on the first

  

  Allison Samson

  Broadsight Realty

  1741 Watershed Ct, Chesapeake, VA 23323
• 

  

  /35

  Starting at $1,364

  Total Monthly Price

  • 1 - 3 Beds

  3537 Towne Pointe Rd, Chesapeake, VA 23321

  Welcome to Chesapeake Pointe Apartments in Chesapeake, VA. Our pet-friendly one, two, and three-bedroom apartment homes are well-designed and offer access to two resort pools – AION SPLASH. This sprawling park-like community is located in both Chesapeake, VA and Portsmouth, VA. Chesapeake Pointe is minutes to I-664, I-64, Downtown Norfolk, Old Dominion University, and less than 13 miles to the

  Chesapeake Pointe

  

  3537 Towne Pointe Rd, Chesapeake, VA 23321
• 

  $205,000

  Sold Mar 03, 2026

  1605 Stone Moss Reach Unit D, Chesapeake, VA 23320

  • 2 Beds
  • 2 Baths
  • 978 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Above List Price
  • $210/SF
  • 26 Days On Market

  Last Listing Agent Celia Romaine Keller Williams Coastal Virginia Chesapeake

  1605 Stone Moss Reach Unit D, Chesapeake, VA 23320
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  /4

  Not Listed For Sale

  Lot 39 Trinkle St, Chesapeake, VA 23322

  Lot 39 Trinkle St, Chesapeake, VA 23322

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Derek Greene The Greene Realty Group
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  /50

  $575,000

  $15K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 2,780 Sq Ft

  776 Big Bear Ln, Chesapeake, VA 23323

  $10,000 IN CLOSING COST ASSISTANCE OFFERED - use it to lower your interest rate or reduce your cash to close! Built in 2022 and move-in ready, this meticulously maintained Culpepper Landing home offers modern finishes and an open-concept layout. The gourmet kitchen features quartz countertops, a large island with seating, gas cooktop, double ovens, stainless steel appliances, under-cabinet

  

  Maritza Brandon

  The Real Estate Group

  776 Big Bear Ln, Chesapeake, VA 23323
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  /41

  $2,600 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,248 Sq Ft
  • Townhouse for Rent

  10 Warwick Cir, Chesapeake, VA 23320

  Welcome home to this beautifully updated 3-bedroom end unit townhome with an attached garage! Bursting with style and warmth, this move-in ready gem features fresh paint, luxury LVP flooring, and brand-new carpet throughout. The stunning kitchen is a true showstopper with crisp white cabinetry, quartz countertops, and sleek stainless steel appliances, perfect for everything from busy mornings to

  

  Marie DePedro

  World Class Realty & Prop Mgmt

  10 Warwick Cir, Chesapeake, VA 23320
• 

  $293,000

  Sold Feb 09, 2026

  4331 Oneford Place, Chesapeake, VA 23321

  • 2 Beds
  • 2.5 Baths
  • 1,875 Sq Ft
  • Built 2006

  Last Sold Summary

  • 1% Below List Price
  • $156/SF
  • 30 Days On Market

  Current Estimated Value $292,564

  Last Listing Agent Juanita Alexander EXIT Realty Central

  4331 Oneford Place, Chesapeake, VA 23321
• 

  

  /49

  Est $479,795

  Not Listed For Sale

  1213 Eagle Pointe Way, Chesapeake, VA 23322

  • 3 Beds
  • 2.5 Baths
  • 2,397 Sq Ft
  • Built 2008

  1213 Eagle Pointe Way, Chesapeake, VA 23322

  Last Sold Summary

  • 83 Days On Market

  Last Listing Agent Sharon Baker BHHS RW Towne Realty LLC
• 

  

  /31

  $210,000

  • 2 Beds
  • 2 Baths
  • 978 Sq Ft

  2201 Rock Cliff Reach Unit A, Chesapeake, VA 23320

  You do not want to miss this stunning condo! It features fresh paint throughout, professionally cleaned carpets, and appliances, making it move-in ready. Nestled right in the heart of Greenbrier, this location offers ultimate convenience with quick access to a selection of entertainment, dining, and shopping. Don't wait schedule your tour today and see this property for yourself!

  

  Keisha Rorie

  Shipmate Real Estate +JPAR

  2201 Rock Cliff Reach Unit A, Chesapeake, VA 23320
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  /42

  Starting at $1,768

  Total Monthly Price

  • 1 - 3 Beds

  150 Coveside Ln, Chesapeake, VA 23320

  Welcome home to Hideaway at Greenbrier Luxury Apartment Homes, perfectly located in the prestigious Greenbrier area of Chesapeake, Virginia. Hideaway at Greenbrier offers one, two, and three-bedroom apartments, each well-appointed with a breakfast bar, den/study area and spectacular views. The apartment home also comes with either a sunroom or patio/balcony, plus and hardwood flooring in

  Hideaway at Greenbrier

  

  150 Coveside Ln, Chesapeake, VA 23320
• 

  $580,000

  Sold Jun 05, 2026

  1316 Head of River Rd, Chesapeake, VA 23322

  • 3 Beds
  • 2 Baths
  • 2,626 Sq Ft
  • Built 1962

  Last Sold Summary

  • 1% Above List Price
  • $221/SF
  • 19 Days On Market

  Current Estimated Value $590,668

  Last Listing Agent James Williams Atlantic Connection Real Est.

  1316 Head of River Rd, Chesapeake, VA 23322
• 

  

  /46

  Est $595,038

  Not Listed For Sale

  718 Firethorn Rd, Chesapeake, VA 23320

  • 4 Beds
  • 2.5 Baths
  • 2,956 Sq Ft
  • Built 1996

  718 Firethorn Rd, Chesapeake, VA 23320

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Alison Mazzuca RE/MAX Capital
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  /50

  $774,900

  $75K PRICE DROP Under Contract

  • 4 Beds
  • 3.5 Baths
  • 2,800 Sq Ft

  1124 Saint Brides Rd W, Chesapeake, VA 23322

  Set on over 3 acres and tucked back from the road, this meticulously updated 4-bedroom, 3.5-bath Chesapeake property offers a rare blend of space, privacy, and modern finishes. Renovated with care and attention to detail, updates include a new roof, all-new kitchen cabinetry, upgraded stainless steel appliances, quartz countertops, engineered hardwood flooring, fresh paint, and beautifully

  

  Andy Nelson

  Iron Valley Real Estate HR

  1124 Saint Brides Rd W, Chesapeake, VA 23322
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  /25

  $1,850 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft
  • Townhouse for Rent

  935 Still Harbor Cir, Chesapeake, VA 23320

  Everything is NEW, NEW, NEW! New flooring, new paint throughout, new cabinets, new granite counters, new vanities, new fixtures and finishes. NEW, NEW, NEW!!! Live in the heart of Chesapeake’s Greenbrier area at 935 Still Harbor Cir, a 1,064 SqFt townhome offering comfort, convenience, and connected living near Greenbrier Mall, Chesapeake Regional Medical Center, and major commuter routes

  

  Lea' Marie Ngowakl

  Atlantic Sothebys Int'l Realty

  935 Still Harbor Cir, Chesapeake, VA 23320
• 

  $530,000

  Sold Apr 10, 2026

  1308 Fairhaven Rd, Chesapeake, VA 23322

  • 4 Beds
  • 2.5 Baths
  • 2,233 Sq Ft
  • Built 1995

  Last Sold Summary

  • 1% Below List Price
  • $237/SF
  • 16 Days On Market

  Current Estimated Value $535,235

  Last Listing Agent Michael Morisi Better Homes & Gdns Ntv Am Grp

  1308 Fairhaven Rd, Chesapeake, VA 23322
• 

  

  /16

  Est $374,590

  Not Listed For Sale

  1210 Macdonald Rd, Chesapeake, VA 23325

  • 3 Beds
  • 1 Bath
  • 1,729 Sq Ft
  • Built 1958

  1210 Macdonald Rd, Chesapeake, VA 23325

  Last Sold Summary

  • 189 Days On Market

  Last Listing Agent Susan Jenkins Better Homes and Gardens Native American Group
• 

  

  /23

  $239,900

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

  4332 Hillingdon Bend Unit 206, Chesapeake, VA 23321

  Located in the Western Branch North area of Chesapeake, Virginia, 4332 Hillingdon Bend, Unit 206, is a second-floor condominium built in 2014. The residence offers approximately 1,367 square feet of single-level living space with an open floor plan and nine-foot ceilings. It features two bedrooms and two full bathrooms, including a primary suite equipped with dual closets. The kitchen includes

  

  Jon Bourque

  Verian Realty

  4332 Hillingdon Bend Unit 206, Chesapeake, VA 23321
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  /44

  Starting at $1,095 Plus Fees

  • 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,

  Arbor Glen Apartments

  

  2616 Arbor Glen Dr, Chesapeake, VA 23324
• 

  $480,000

  Sold Aug 22, 2025

  4125 Lakeview Dr, Chesapeake, VA 23323

  • 4 Beds
  • 4 Baths
  • 2,920 Sq Ft
  • Built 1993

  Last Sold Summary

  • $164/SF
  • 41 Days On Market

  Current Estimated Value $490,125

  Last Listing Agent Marquetta Brown 1st Class Real Estate Norfolk

  4125 Lakeview Dr, Chesapeake, VA 23323
• 

  

  /16

  Est $274,933

  Not Listed For Sale

  619 Pine Bend, Chesapeake, VA 23320

  • 3 Beds
  • 1.5 Baths
  • 1,220 Sq Ft
  • Built 1979

  619 Pine Bend, Chesapeake, VA 23320

  Last Sold Summary

  • 84 Days On Market

  Last Listing Agent Susan Jenkins Better Homes and Gardens Native American Group
• 

  

  /48

  $665,000

  $25K PRICE DROP Pending

  • 5 Beds
  • 3 Baths
  • 3,466 Sq Ft

  3932 Colony Pointe Dr, Chesapeake, VA 23321

  All-brick 5BR home with 3,466 SF on a cul-de-sac - no HOA. Rich hardwood floors flow through the main level and into the primary suite on the second, anchoring a home that balances timeless character with everyday livability. The Large Living areas open up to the expansive backyard featuring a covered outdoor kitchen, screened gazebo, and sprawling composite deck. Lovingly maintained by one owner

  

  Michael Rowland

  Rowland RE

  3932 Colony Pointe Dr, Chesapeake, VA 23321
• 

  

  /13

  $2,895 Per Month

  • 4 Beds
  • 2 Baths
  • 1,825 Sq Ft
  • House for Rent

  3339 Dietz Dr, Chesapeake, VA 23323

  Welcome home to this beautifully maintained home in the desirable Deep Creek area of Chesapeake! Featuring a spacious and functional floor plan, this property offers comfortable living with generous bedrooms, an open living area, and a well-appointed kitchen with ample cabinet and counter space. Enjoy a private backyard perfect for relaxing or entertaining, plus an attached garage and convenient

  

  Troy Brimmer

  1st Class Real Estate Flagship

  3339 Dietz Dr, Chesapeake, VA 23323
• 

  $295,000

  Sold Aug 27, 2025

  1108 Santeetlah Ave, Chesapeake, VA 23325

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • Built 1959

  Last Sold Summary

  • $236/SF
  • 21 Days On Market

  Current Estimated Value $305,112

  Last Listing Agent Jason Winger Swell Realty Co

  1108 Santeetlah Ave, Chesapeake, VA 23325
• 

  

  /11

  Est $328,078

  Not Listed For Sale

  3404 Port Chambers Ct, Chesapeake, VA 23321

  • 3 Beds
  • 1.5 Baths
  • 1,442 Sq Ft
  • Built 1969

  3404 Port Chambers Ct, Chesapeake, VA 23321

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Susan Jenkins Better Homes and Gardens Native American Group
• 

  

  /40

  $444,000

  $1K PRICE DROP Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft

  927 Thatcher Way, Chesapeake, VA 23320

  Welcome to your golfer’s paradise on the 14th hole of Greenbrier Country Club! Meticulously updated, this stunning homeblends modern elegance with everyday comfort. Come into a breathtaking living area showcasing soaring cathedral ceilings,high-end LVP flooring, and massive, picturesque windows that bathe the space in natural light while framing panoramicfairway views. Retreat to the

  

  Danielle Rosetti Lopez

  Better Homes & Gdns Ntv Am Grp

  927 Thatcher Way, Chesapeake, VA 23320
• 

  

  /154

  Starting at $1,798 Plus Fees

  • 1 - 3 Beds

  504 Cap Stone Arcade, Chesapeake, VA 23323

  Tattersall Chesapeake Apartments offers the perfect blend of small-town charm and everyday convenience in historic Chesapeake, VA. Our spacious one-, two-, and three-bedroom apartment homes feature modern kitchens with islands, oversized bathroom vanities, and private patios or balconies designed for comfortable living.Enjoy resort-style amenities including a sparkling swimming pool with sundeck,

  Tattersall Chesapeake

  

  504 Cap Stone Arcade, Chesapeake, VA 23323
• 

  $532,500

  Sold Sep 24, 2025

  904 Will Scarlet Way, Chesapeake, VA 23322

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft
  • Built 1996

  Last Sold Summary

  • $242/SF
  • 33 Days On Market

  Current Estimated Value $522,156

  Last Listing Agent Brian Wurst A Better Way Realty Inc.

  904 Will Scarlet Way, Chesapeake, VA 23322
• 

  

  /39

  Est $868,266

  Not Listed For Sale

  326 Greens Edge Dr, Chesapeake, VA 23322

  • 5 Beds
  • 3.5 Baths
  • 3,994 Sq Ft
  • Built 2003

  326 Greens Edge Dr, Chesapeake, VA 23322

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Kathie David Howard Hanna William E. Wood
• 

  

  /46

  $269,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,314 Sq Ft

  1312 Hull St, Chesapeake, VA 23324

  Beautifully renovated 3-bedroom, 2-bath home in the historic South Norfolk neighborhood! Blending classic character with fresh, modern updates throughout, we start just past the brick porch and swing with a 2-story foyer. Just off the stairs, the first of three bedrooms has fresh paint, carpet, and 6-inch baseboards. Through the living room, the home boasts an expansive eat-in kitchen with new

  

  Daniel Patton

  Prodigy Realty

  1312 Hull St, Chesapeake, VA 23324
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  /100

  Starting at $1,719 Plus Fees

  • 1 - 3 Beds

  1805 Kerwyck Place, Chesapeake, VA 23320

  Embrace Luxury Living in Greenbrier, ChesapeakeExperience the elegance and luxury of resort-style living at Fenwyck Manor Apartments, where your comfort and satisfaction are at the top of our list. Built on 32 alluring acres with an attractive assortment of recreational and entertainment options, these apartments in Chesapeake, VA, feature a beautiful lake and everything you need to leave

  Fenwyck Manor Apartments

  

  1805 Kerwyck Place, Chesapeake, VA 23320
• 

  $703,000

  Sold Apr 22, 2026

  1101 Fairway Dr, Chesapeake, VA 23320

  • 4 Beds
  • 4 Baths
  • 3,630 Sq Ft
  • Built 1989

  Last Sold Summary

  • 5% Above List Price
  • $194/SF
  • 23 Days On Market

  Current Estimated Value $700,684

  Last Listing Agent Gayle Upchurch BHHS RW Towne Realty

  1101 Fairway Dr, Chesapeake, VA 23320
• 

  

  /27

  Est $243,087

  Not Listed For Sale

  1800 Westgate St, Chesapeake, VA 23324

  • 4 Beds
  • 1 Bath
  • 1,308 Sq Ft
  • Built 1952

  1800 Westgate St, Chesapeake, VA 23324

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Kelly Henson RE/MAX Supercenter
• 

  

  /20

  $299,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,701 Sq Ft

  3906 Peppercorn Way, Chesapeake, VA 23321

  Beautifully updated end-unit condo located in the desirable Miars Farm community in the heart of Western Branch! This spacious home features 3 bedrooms and a versatile loft perfect for a home office, media room, or additional living space. The first-floor primary suite offers convenience and privacy with an updated en-suite bath. Enjoy cooking in the renovated kitchen featuring stainless steel

  

  Rhonda Vaughn

  Cherished Destiny Real Estate

  3906 Peppercorn Way, Chesapeake, VA 23321
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  /101

  Starting at $1,778 Plus Fees

  • 1 - 3 Beds

  728 Tapestry Park Loop, Chesapeake, VA 23320

  We are NEW and IMPROVED! As we evolve, our homes should too. Tapestry Park is happy to announce that our thoughtfully designed floorplans now feature brand NEW granite countertops in both the kitchen and bathrooms of each apartment home, plus upgraded fixtures throughout! Nestled off the beaten path, yet conveniently located in the heart of Chesapeake, Virginia, our community is the

  Tapestry Park

  

  728 Tapestry Park Loop, Chesapeake, VA 23320
• 

  $625,000

  Sold Jan 30, 2026

  4044 Devon Dr, Chesapeake, VA 23321

  • 4 Beds
  • 2.5 Baths
  • 3,072 Sq Ft
  • Built 1994

  Last Sold Summary

  • $203/SF
  • 21 Days On Market

  Current Estimated Value $639,126

  Last Listing Agent Debbie Gutekunst Iron Valley Real Estate HR

  4044 Devon Dr, Chesapeake, VA 23321
• 

  /2

  Est $381,449

  Not Listed For Sale

  1346 Cypress Place, Chesapeake, VA 23320

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft
  • Built 1979

  1346 Cypress Place, Chesapeake, VA 23320

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