Chesapeake, VA Homes

• 

  

  

  /50

  $699,000

  $51K PRICE DROP Under Contract

  • 4 Beds
  • 3.5 Baths
  • 4,459 Sq Ft

  433 Truitt Rd, Chesapeake, VA 23321

  This home, on 5 acres, offers country living & modern updates. With 4-bedrooms, 2 living areas, 2 add'l flex rooms great for a home office, game room, guest space, or potential extra bedrooms, this property provides versatility today's buyers are searching for. There is new LVP flooring, updated bathrooms, & a remodeled kitchen completed in the last 6 years. The wood stove adds warmth & character

  

  Kevin Keogh

  BHHS RW Towne Realty

  (757) 992-8212

  433 Truitt Rd, Chesapeake, VA 23321
• Explore Chesapeake

• 

  

  

  /5

  $3,695 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,906 Sq Ft
  • House for Rent

  1516 Clearwater Ln, Chesapeake, VA 23322

  Absolutely gorgeous home with maximum space and great open concept! Offering 4 bedroom and 2.5 baths. Huge primary on first floor with trey ceilings, tons of storage with 3 closets, full on bath with garden tub and large separate shower. All other bedrooms are located on the 2nd floor, nicely sized and equipped with ceiling fans. Kitchen has lots of cabinet space, a pantry, eat at bar, breakfast

  

  Neal Wilson

  Patriot Property Management

  (757) 828-1946

  1516 Clearwater Ln, Chesapeake, VA 23322
• 

  $351,000

  Sold Jun 08, 2026

  2130 Berkley Ave, Chesapeake, VA 23324

  • 4 Beds
  • 3 Baths
  • 1,770 Sq Ft
  • Built 2026

  Last Sold Summary

  • $198/SF
  • 14 Days On Market

  Current Estimated Value $275,960

  Last Listing Agent Nichole Harrison Prodigy Realty

  2130 Berkley Ave, Chesapeake, VA 23324
• 

  

  

  /21

  Est $312,023

  Not Listed For Sale

  740 W Lake Cir, Chesapeake, VA 23322

  • 3 Beds
  • 2.5 Baths
  • 1,557 Sq Ft
  • Built 1997

  740 W Lake Cir, Chesapeake, VA 23322

  Last Sold Summary

  • 5 Days On Market
• 

  

  

  /27

  $305,500

  $5K PRICE DROP Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,442 Sq Ft

  585 Marc Smiley Rd, Chesapeake, VA 23324

  Welcome to this beautifully maintained 3-story condo in the Reunion neighborhood of Chesapeake! This home features 2 spacious bedrooms, including a primary suite with dual sink vanity and private bath. The first-floor flex room offers versatility as a home office, guest space, or optional third bedroom. Enjoy an open-concept second level with a bright living room featuring surround sound, dining

  

  Raquel Ricci

  BHHS RW Towne Realty

  (757) 255-7260

  585 Marc Smiley Rd, Chesapeake, VA 23324
• 

  

  /35

  Starting at $1,234

  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

  (757) 979-3366

  

  3537 Towne Pointe Rd, Chesapeake, VA 23321
• 

  $311,000

  Sold Jun 01, 2026

  12 Romsey Cir, Chesapeake, VA 23320

  • 3 Beds
  • 2.5 Baths
  • 1,248 Sq Ft
  • Built 1985

  Last Sold Summary

  • $249/SF
  • 18 Days On Market

  Current Estimated Value $285,861

  Last Listing Agent Mary Barclay Swell Realty Co.

  12 Romsey Cir, Chesapeake, VA 23320
• 

  

  /50

  Est $401,606

  Not Listed For Sale

  4233 Terry Dr, Chesapeake, VA 23321

  • 3 Beds
  • 2 Baths
  • 1,566 Sq Ft
  • Built 1975

  4233 Terry Dr, Chesapeake, VA 23321

  Last Sold Summary

  • 11 Days On Market
• 

  

  /46

  $399,900

  $5K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 1,950 Sq Ft

  2532 Lanier St, Chesapeake, VA 23324

  This move-in-ready 4-bedroom, 3.5-bath home offers incredible flexibility with two spacious primary suites—one on the first floor featuring an additional sunroom, great for a home office or sitting area, and a second private suite upstairs. Amazing for multi-generational living! Enjoy the convenience of 2 washer and dryer hookups. Lot's of closet and storage space. The home also features a

  

  Tina Dubois

  A Better Way Realty Inc.

  (757) 349-1733

  2532 Lanier St, Chesapeake, VA 23324
• 

  

  /27

  $2,550 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,159 Sq Ft
  • House for Rent

  1231 Stewart St, Chesapeake, VA 23324

  Welcome to 1231 Stewart Street, an immaculate single-family home built in 2018, offering modern amenities and a prime location! Conveniently located near military bases, downtown Chesapeake, interstates, and shopping centers, this home has 4 spacious bedrooms and 2.5 bathrooms, with approximately 2,159 square feet of living space. The expansive open kitchen is equipped with granite countertops

  

  Kristen Boyd

  Next Chapter VA Realty Inc

  (757) 979-6173

  1231 Stewart St, Chesapeake, VA 23324
• 

  $274,900

  Sold Jun 18, 2026

  902 Annette St, Chesapeake, VA 23324

  • 3 Beds
  • 1.5 Baths
  • 1,444 Sq Ft
  • Built 1985

  Last Sold Summary

  • $190/SF
  • 11 Days On Market

  Current Estimated Value $282,154

  Last Listing Agent Andy Nelson Iron Valley Real Estate HR

  902 Annette St, Chesapeake, VA 23324
• 

  

  /35

  Est $397,537

  Not Listed For Sale

  1724 Defiance Dr, Chesapeake, VA 23323

  • 3 Beds
  • 4 Baths
  • 1,760 Sq Ft
  • Built 2021

  1724 Defiance Dr, Chesapeake, VA 23323

  Last Sold Summary

  • 3 Days On Market
• 

  

  /20

  $314,999

  • 4 Beds
  • 1.5 Baths
  • 1,350 Sq Ft

  1602 Willow Ave, Chesapeake, VA 23325

  Welcome home to this beautifully updated 3-bedroom, 1.5-bath property offering the perfect blend of comfort, style, and space. Fresh paint throughout, newer LVP flooring, and updated kitchen and bathrooms give this home a modern feel while maintaining warmth and charm. Enjoy multiple living and dining areas that provide plenty of room for entertaining, relaxing, or everyday living. The spacious

  

  Jessica Lewis

  Iron Valley Real Estate HR

  (757) 720-4698

  1602 Willow Ave, Chesapeake, VA 23325
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  /154

  Starting at $1,803 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

  (757) 432-3453

  

  504 Cap Stone Arcade, Chesapeake, VA 23323
• 

  $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
• 

  

  /31

  Est $674,132

  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
• 

  

  /38

  $299,000

  $14K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft

  1002 Mayfield Ave, Chesapeake, VA 23324

  This magazine cover worthy home can be YOURS! Welcome to this gorgeously remodeled from top to bottom 2BR/2BA house. It has EVERYTHING you've been searching for: open concept layout, with large windows, new luxury LVP flooring throughout, light fixtures, custom tile work, freshly painted, you name it! Completely NEW spacious chef’s kitchen shines with expensive QUARTZ countertops, large island

  

  Val Milan

  Swell Real Estate Co

  (757) 832-8163

  1002 Mayfield Ave, Chesapeake, VA 23324
• 

  

  /25

  $1,995 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

  (757) 601-5422

  935 Still Harbor Cir, Chesapeake, VA 23320
• 

  $230,000

  Sold Aug 01, 2025

  2547 Old Greenbrier Rd, Chesapeake, VA 23325

  • 2 Beds
  • 2 Baths
  • 1,230 Sq Ft
  • Built 2004

  Last Sold Summary

  • $187/SF
  • 25 Days On Market

  Current Estimated Value $235,229

  Last Listing Agent Jay Hassell Keller Williams Realty Twn Ctr

  2547 Old Greenbrier Rd, Chesapeake, VA 23325
• 

  /2

  Est $382,899

  Not Listed For Sale

  2501 Southern Pines Dr, Chesapeake, VA 23323

  • 4 Beds
  • 2 Baths
  • 1,656 Sq Ft
  • Built 1999

  2501 Southern Pines Dr, Chesapeake, VA 23323
• 

  

  /22

  $285,000

  • 2 Beds
  • 2.5 Baths
  • 1,350 Sq Ft

  1507 Hambledon Loop, Chesapeake, VA 23320

  Beautiful home in the desirable Brighton Park at Greenbrier. Incredible location right at Virginia Beach city line. This home has a private feel with ample natural light. Two suites each with walk-in closets. Private patio and shed. Amenities include two community pools and beautiful landscaping. Water, sewer and trash included. Call for your private showing.

  

  John West

  Haworth Realty LLC

  (757) 356-6358

  1507 Hambledon Loop, Chesapeake, VA 23320
• 

  

  /100

  Starting at $1,769 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

  (757) 563-1907

  

  1805 Kerwyck Place, 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 $293,320

  Last Listing Agent Juanita Alexander EXIT Realty Central

  4331 Oneford Place, Chesapeake, VA 23321
• 

  

  /49

  Est $463,316

  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
• 

  

  /18

  $579,900

  New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,522 Sq Ft

  Swan Plan, Chesapeake, VA

  

  Classic Design Builders

  Builder

  0 Shell Place St Unit 37905457, Chesapeake, VA
• 

  

  /36

  $1,950 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,131 Sq Ft
  • Townhouse for Rent

  2008 Fawnwood Common, Chesapeake, VA 23320

  Welcome to 2008 Fawnwood Common in Chesapeake’s Woodgate Commons, a 1,131 sq ft end-unit townhome designed for everyday ease and low-maintenance living. Inside you'll find a bright, open layout with durable laminate flooring, a welcoming living space, and a functional kitchen that connects seamlessly to dining and entertaining areas. Upstairs, three spacious bedrooms offer flexibility for restful

  

  Lea' Marie Ngowakl

  Atlantic Sothebys Int'l Realty

  (757) 356-6104

  2008 Fawnwood Common, 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 $608,032

  Last Listing Agent James Williams Atlantic Connection Real Est.

  1316 Head of River Rd, Chesapeake, VA 23322
• 

  

  /46

  Est $593,218

  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
• 

  

  /25

  $263,000

  $2K PRICE DROP Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,144 Sq Ft

  1614 Willow Point Arch, Chesapeake, VA 23320

  Move in ready home in Chesapeake featuring fresh interior paint, new carpet, new laminate flooring, and a new electric fireplace that adds a modern touch to the main living area. Kitchen offers new countertops along with ample cabinet and prep space. Functional floor plan provides comfortable everyday living with easy access to shopping, dining, parks, and major interstates. A great opportunity

  

  Jacob Bronk

  Own Real Estate LLC

  (757) 347-8127

  1614 Willow Point Arch, Chesapeake, VA 23320
• 

  

  /35

  Starting at $1,868 Plus Fees

  • 1 - 3 Beds

  101 Sabal Palm Ln, Chesapeake, VA 23320

  TOUR YOUR WAY! We have a tour to fit your needs- virtual, self-guided, or agent-guided. Find your next home at a luxury hideaway in Chesapeake, VA. MAA Adalay Bay is nestled away in a quiet neighborhood, yet within reach of all the conveniences you want. Each one-, two-, and three-bedroom apartment home features its own washer/dryer, while select units feature sunrooms, garden tubs, stainless

  MAA Adalay Bay

  (757) 394-8272

  

  101 Sabal Palm Ln, 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 $525,768

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

  1308 Fairhaven Rd, Chesapeake, VA 23322
• 

  

  /16

  Est $380,561

  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
• 

  

  /45

  $644,900

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft

  941 Painted Lady Place, Chesapeake, VA 23323

  This home shows pride of ownership located in sought after Grassfield area! This spacious 4 bedroom, 2.5 bath home offers an open & inviting layout filled w/ natural light. The first floor features an eat in kitchen open to the living room, formal dining area, guest half bath, & a flexible sitting room can be used for a home office, playroom, or study. Upstairs you'll find a large primary suite

  

  Mary Barclay

  Swell Realty Co.

  (757) 699-4583

  941 Painted Lady Place, Chesapeake, VA 23323
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  /101

  Starting at $1,750 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

  (757) 432-3733

  

  728 Tapestry Park Loop, Chesapeake, VA 23320
• 

  $289,000

  Sold Jul 08, 2025

  934 Brigantine Ct, Chesapeake, VA 23320

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1982

  Last Sold Summary

  • $241/SF
  • 61 Days On Market

  Current Estimated Value $286,951

  Last Listing Agent Brian Wurst A Better Way Realty Inc.

  934 Brigantine Ct, Chesapeake, VA 23320
• 

  /2

  Est $378,501

  Not Listed For Sale

  608 Appaloosa Trail, Chesapeake, VA 23323

  • 4 Beds
  • 2 Baths
  • 1,476 Sq Ft
  • Built 1992

  608 Appaloosa Trail, Chesapeake, VA 23323
• 

  

  /33

  $674,900

  $30K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft

  3618 Point Elizabeth Dr, Chesapeake, VA 23321

  Experience refined living in this exceptional Western Branch residence. Boasting over 3,000 sq ft, this fully turnkey home blends elegance and comfort at every turn. The heart of the home is a breathtaking 10x5 imported quartz island—an unforgettable centerpiece designed for elevated entertaining and everyday luxury. The open-concept design flows seamlessly into a custom fireplace with built-ins,

  

  Kayleigh Jo St. Clair

  Swell Realty Co.

  (757) 909-6106

  3618 Point Elizabeth Dr, Chesapeake, VA 23321
• 

  

  /33

  Starting at $1,303 Plus Fees

  • 2 - 3 Beds

  908 Lake Village Dr, Chesapeake, VA 23323

  Our apartment homes offer comfortable living with thoughtful floor plans to fit your lifestyle. Choose from our classic or newly renovated 2 & 3-bedroom homes. Each apartment home combines scenic views with modern amenities. Enjoy the convenience of nearby shopping, dining, and entertainment in a welcoming community just minutes from some of Chesapeake's famous waterways.

  Lake Village

  (757) 821-5923

  

  908 Lake Village Dr, Chesapeake, VA 23323
• 

  $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 $479,058

  Last Listing Agent Marquetta Brown 1st Class Real Estate Norfolk

  4125 Lakeview Dr, Chesapeake, VA 23323
• 

  

  /16

  Est $273,046

  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

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