Chesapeake, VA Homes for Sale under $300,000

• 

  

  

  /28

  $284,000

  Open House 9/26 $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,328 Sq Ft

  1106 Maryview Ave, Chesapeake, VA 23324

  Welcome home to this charming ranch that's full of warmth, character, and timeless appeal! Nestled at the end of your street with no through traffic, this adorable home offers the perfect blend of privacy, comfort, and convenience. Enter to discover soaring vaulted ceilings that create an open, airy feel throughout the main living spaces. With two inviting fireplaces and two separate dens,

  

  Katie Burke

  Long & Foster Real Estate Inc.

  1106 Maryview Ave, Chesapeake, VA 23324
• Explore Chesapeake

• 

  

  

  /36

  $269,000

  • 3 Beds
  • 2 Baths
  • 1,313 Sq Ft

  1414 Loose Strife Place, Chesapeake, VA 23320

  Beautifully remodeled 3BR/2BA home is ready for its new owner! Bright, open, spacious, this two-story home offers the kind of layout that feels impressive the moment you walk in. Two-story foyer, high ceilings, skylights, large windows, and open living/dining area create a light and airy feel throughout. Home was refreshed in 2026 with new water heater, new flooring on both levels, finished walls

  

  Val Milan

  Swell Real Estate Co

  1414 Loose Strife Place, Chesapeake, VA 23320
• 

  

  

  /16

  $285,000

  Open Sun 11AM - 1PM

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  1128 Wright Ave, Chesapeake, VA 23324

  Come Fall In Love with this Absolutely Gorgeous Like New Professionally Renovated Home! Stunning All New Kitchen with Granite counters and Soft close cabinets. All New Stainless Steel Appliances. Enjoy Entertaining in the Open living space. Beautiful All New Bathroom. All New HVAC and Ducting, New Roof, siding, windows, water heater and even all new insulation. Every light fixture and socket is

  

  Jim Leland

  LPT Realty LLC

  1128 Wright Ave, Chesapeake, VA 23324
• 

  

  

  /29

  $274,900

  • 2 Beds
  • 2.5 Baths
  • 1,146 Sq Ft

  102 Ford St, Chesapeake, VA 23323

  Move-in ready! This 2-bedroom home offers a rare dual-ensuite layout — each bedroom has its own full bath, plus a powder room downstairs for guests. Brand-new LVP flooring and carpet, fresh paint throughout, and a new hot water heater. Kitchen and bath cabinetry has been freshly painted in a soft sage tone, paired with a brand-new stainless steel appliance package — refrigerator, range,

  

  Chris Faircloth

  Swell Realty Co

  102 Ford St, Chesapeake, VA 23323
• 

  

  

  /24

  $184,900

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,812 Sq Ft

  1233 Transylvania Ave, Chesapeake, VA 23324

  

  Andy Nelson

  Iron Valley Real Estate HR

  1233 Transylvania Ave, Chesapeake, VA 23324
• 

  

  /24

  $220,000

  • 2 Beds
  • 2 Baths
  • 1,116 Sq Ft

  3521 Sugar Run, Chesapeake, VA 23321

  Welcome to 3521 Sugar Run! Step inside and you’ll immediately notice the high ceilings and open, inviting feel. Offering 2 bedrooms, 2 full baths, and over 1,100 square feet, all living spaces are conveniently located on one level, with exterior stairs providing access to the home. Both bathrooms have been updated, while thoughtful touches like the barn door entrance to the pantry add character

  

  Jermaine Anderson

  Keller Williams Coastal Virginia Chesapeake

  3521 Sugar Run, Chesapeake, VA 23321
• 

  

  /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
• 

  

  /26

  $220,000

  • 3 Beds
  • 1 Bath
  • 921 Sq Ft

  2501 Harling Dr, Chesapeake, VA 23325

  Welcome to 2501 Harling Drive! Step inside this freshly painted 3-bedroom home, where beautiful new flooring flows throughout and creates a bright, polished, move-in-ready atmosphere. The eat-in kitchen offers a comfortable space for morning coffee, casual meals, and memorable gatherings. Set on a corner lot with landscaping, the property provides plenty of outdoor space to enjoy. Conveniently

  

  Brenda Williams

  Howard Hanna Real Estate Svcs.

  2501 Harling Dr, Chesapeake, VA 23325
• 

  

  /13

  $275,000

  Open House 9/19

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft

  2916 Mintwood Dr, Chesapeake, VA 23321

  REAL ESTATE AUCTION – PRICE SHOWN IS THE ADVERTISED STARTING BID, NOT THE SELLER’S RESERVE OR GUARANTEED SALE PRICE. This single-story brick ranch offers approximately 1,564 square feet with 3 bedrooms, 2 full bathrooms, an attached garage and a 0.332-acre lot. Live on-site auction Saturday, October 24, 2026, at 11:00 a.m. Reserve auction subject to seller confirmation. A 10% buyer’s premium will

  

  Becky Lyons

  Coastal Real Estate & Auction Group LLC

  2916 Mintwood Dr, Chesapeake, VA 23321
• 

  

  /20

  $259,999

  $14K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,025 Sq Ft

  449 E Lake Cir, Chesapeake, VA 23322

  Affordable Great Bridge lake-view living! Enjoy low-maintenance condo living just off Cedar Road, a short drive from shopping, restaurants, entertainment and everything Great Bridge has to offer.Inside, vaulted ceilings, arched windows and abundant natural light give the home an open, inviting feel. The living room features a cozy fireplace and opens to a private balcony overlooking the

  

  Timothy Eure

  COVA Home Realty

  449 E Lake Cir, Chesapeake, VA 23322
• 

  

  /40

  $290,000

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft

  2502 Livesay Rd, Chesapeake, VA 23323

  Welcome home to this charming 1,224-square-foot home with a comfortable layout and plenty to offer. Inside, you'll find an updated kitchen and bathrooms, inviting living spaces, and a home that's been freshly cleaned and is ready for its next chapter. A little fresh paint gives the new owner an easy opportunity to add their own style. Outside, enjoy a manageable yard and convenient driveway

  

  Rachel Beasley

  KW Allegiance Shoreline

  2502 Livesay Rd, Chesapeake, VA 23323
• 

  

  /7

  $150,000

  • Land
  • 41,817 Sq Ft
  • $156,250 per Acre

  1136 Sunlight Dr, Chesapeake, VA 23322

  AMAZING OPPORTUNITY TO BUILD NEW CONSTRUCTION HOMES IN A PEACEFUL SETTING, YET CONVENIENTLY LOCATED AND CLOSE TO SHOPPING, SCHOOLS AND INTERSTATE. TO BE SOLD TOGETHER WITH 1148 SUNLIGHT DR, THIS ALLOWS FOR 3 BUILDABLE LOTS AT 0.64 AC EACH. ALL THE WORK IS DONE, YOU JUST NEED TO BUILD!

  

  Tyler Broker/Owner

  Prodigy Realty

  1136 Sunlight Dr, Chesapeake, VA 23322
• 

  

  /14

  $200,000

  $25K PRICE DROP

  • Land
  • 24,262 Sq Ft
  • $359,066 per Acre

  Par B George Washington Hwy S, Chesapeake, VA 23323

  Commercial Building Lot in the Deep Creek area of Chesapeake. Located on the Dismal Swamp Canal & George Washington Hwy across the street from a Shopping Center. Property is on the navigable Dismal Swamp Canal. Property Zoning is B-1 with over 250 feet of road frontage.

  

  John Horton

  Samson Properties

  Par B George Washington Hwy S, Chesapeake, VA 23323
• 

  /2

  $124,000

  • Land
  • 10,628 Sq Ft
  • $508,197 per Acre

  1721 Faulk St, Chesapeake, VA 23323

  Attention Builders and Visionaries: Beautiful large lot in the Deep Creek area of Chesapeake. Lot is ready for all your ideas of a new home.

  

  Adrienne Campbell

  Keller Williams Coastal Virginia Chesapeake

  1721 Faulk St, Chesapeake, VA 23323
• 

  /2

  $45,000

  • Land
  • 2.15 Acres
  • $20,911 per Acre

  000 Shell Rd, Chesapeake, VA 23323

  Discover 2.15 acres of beautifully wooded residential land tucked away in the Deep Creek area of Chesapeake. This serene parcel offers a peaceful natural setting with mature trees for a long-term investment. The property is currently landlocked with no established road access, and buyers will need to explore access options independently. Property to be sold as-is where-is. Located near the Oak

  

  John Horton

  Samson Properties

  000 Shell Rd, Chesapeake, VA 23323
• 

  

  /33

  $295,000

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

  1 Sandy Point Ln Unit 216, Chesapeake, VA 23320

  Welcome to easy, low maintenance living at 1 Sandy Point Lane #216! This beautifully refreshed condo offers an open layout, fresh paint, and a 2025 kitchen remodel that brings a modern feel to the heart of the home. Major systems are already in place with a 2019 HVAC and 2021 water heater, giving you added peace of mind.The HOA takes care of the details that make condo living truly

  

  Christina Fleck

  Swell Realty Co.

  1 Sandy Point Ln Unit 216, Chesapeake, VA 23320
• 

  

  /8

  $230,000

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  2425 Lofurno Rd, Chesapeake, VA 23323

  Great starter home with huge backyard and easy access to highway, military bases & shopping.

  

  Janez Hargrove

  Verian Realty

  2425 Lofurno Rd, Chesapeake, VA 23323
• 

  

  /33

  $282,500

  $7K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,340 Sq Ft

  1535 Hambledon Loop, Chesapeake, VA 23320

  Well maintained townhouse-style condo in the highly sought-after Brighton Park at Greenbrier community! Bright and open two-story home features an open-concept layout, fresh paint and all appliances convey to include washer and dryer. Kitchen features a brand new microwave and the home is freshly painted and cleaned. New roof installed in this year. Two primary suites each offer a private

  

  Terry Smith

  BHHS RW Towne Realty

  1535 Hambledon Loop, Chesapeake, VA 23320
• 

  /2

  $85,000

  • Land
  • 15,681 Sq Ft
  • $236,111 per Acre

  L38 40 Norfolk St, Suffolk, VA 23435

  Rare chance to acquire a .36-acre (15,682 sq ft) vacant lot in the established Pughsville area. Zoned single-family residential, this parcel is great for builders, investors, or custom home buyers looking create a tailored residence in a growing location. Enjoy a balance of privacy and convenience with easy access to major routes, shopping, dining, and nearby Chesapeake and Portsmouth. With

  

  Xavier Bryan

  EXP Realty LLC

  L38 40 Norfolk St, Suffolk, VA 23435
• 

  /2

  $20,000

  • Land
  • 10,018 Sq Ft
  • $86,957 per Acre

  .229AC Trinkle St, Chesapeake, VA 23322

  Vacant lot currently being used as Camp site.

  

  Jason Dunaway

  Howard Hanna Real Estate Svcs.

  .229AC Trinkle St, Chesapeake, VA 23322
• 

  

  /44

  $289,900

  $9K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,244 Sq Ft

  1346 River Birch Run S, Chesapeake, VA 23320

  Move in ready-well maintained Townhouse in desirable Greenbrier. LVT/Vinyl flooring throughout, carpet upstairs. Open floor plan with Large Livingroom, Kitchen, and Dining Area. Fenced in back yard and storage shed. Do not miss this move in ready home.

  

  Eric Hovik

  RE/MAX Alliance

  1346 River Birch Run S, Chesapeake, VA 23320
• 

  

  /22

  $285,000

  • 2 Beds
  • 2 Baths
  • 1,141 Sq Ft

  1305 Quail Creek Hollow Unit A, Chesapeake, VA 23320

  Enjoy easy, one-level living in this charming end-unit condo located in a highly desirable golf course community! The bright, open floor plan features vaulted ceilings in the great room & kitchen, creating a spacious feel. The kitchen offers ample cabinet & counter space, a breakfast bar, & pantry, while the dining area showcases beautiful built-in cabinetry providing additional storage. Relax or

  

  Stephanie Kelly

  Swell Real Estate Co

  1305 Quail Creek Hollow Unit A, Chesapeake, VA 23320
• 

  

  /20

  $277,000

  • 3 Beds
  • 2.5 Baths
  • 1,275 Sq Ft

  1806 Beckwood Common, Chesapeake, VA 23320

  Well maintained, tenant occupied 1,275 sf, 3-bedroom, 2.5 bath Townhouse in Chesapeake's Woodgate Commons community. Ideally located near restaurants, shopping, interstate access, military bases, and a nearby golf course, this home offers both convenience and value. Recent updates include new first-floor flooring, remodeled bathrooms, fresh interior and exterior paint, updated kitchen appliances

  

  Judy Boone

  Judy Boone Realty Inc.

  1806 Beckwood Common, Chesapeake, VA 23320
• 

  /2

  $239,000

  Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 1,860 Sq Ft

  164 Whitlock Ct, Chesapeake, VA 23324

  

  Joyce Cooper

  Cooper Realty Group LLC

  164 Whitlock Ct, Chesapeake, VA 23324
• 

  /2

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,020 Sq Ft

  34 Frailey Place, Portsmouth, VA 23702

  STOP HERE FIRST...if you're looking for a move-in ready home with value! As you approach the home, you'll notice a wraparound screened in porch ready for summer. Home features newer roof (2020) and newer HVAC, paint and LVP flooring (2022). Kitchen and bath features newer cabinets and counter tops (2022). New gas hot water heater installed in 2023. Generational living with a detached converted

  

  Sharon Rand Voogd

  1st Class RE-Signature Prop

  34 Frailey Place, Portsmouth, VA 23702
• 

  /2

  $274,000

  $51K PRICE DROP

  • Land
  • 1.99 Acres
  • $138,035 per Acre

  2524 Battlefield Blvd S, Chesapeake, VA 23322

  Excellent development opportunity in the Hickory area of Chesapeake. This mostly wooded parcel offers the opportunity to build a custom home in a well-established area with convenient access to shopping, dining, recreation, and major commuter routes. The residence originally built in 1957 was demolished and cleared in 2020. City water is available. Buyer to perform all due diligence regarding

  Cherrie Platt BHHS RW Towne Realty

  2524 Battlefield Blvd S, Chesapeake, VA 23322
• 

  

  /4

  $75,000

  • Land

  4999 Clifton St, Chesapeake, VA 23321

  Imagine the possibilities! This vacant lot offers the flexibility to build your dream home and create a space designed to fit your needs.

  Michael Daugherty Own Real Estate LLC

  4999 Clifton St, Chesapeake, VA 23321
• 

  

  /34

  $280,000

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

  2704 Faulkner Dr, Chesapeake, VA 23321

  Welcome home! This beautifully maintained 2 BR 2.5 bath condo is located in the heart of Western Branch. The open concept main living area offers a spacious and inviting layout, featuring a breakfast bar stylish pendant lighting, and flexible space for entertaining, working or every day living. The gourmet kitchen is designed with functionality in mind, showcasing stainless steel appliances,

  KIMBERLY FOSTER Iron Valley Real Estate Prestige

  2704 Faulkner Dr, Chesapeake, VA 23321
• 

  

  /26

  $190,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  717 Inlet Quay Unit H, Chesapeake, VA 23320

  Move-in ready and ideally located in the heart of Chesapeake! This well-maintained home features a spacious layout, two private terraces, and convenient access to shopping, dining, and major commuter routes. Property is being sold as-is. Home could use some TLC, offering a great opportunity to make it your own in a prime location.** SOME PHOTOS ARE VIRTUALLY STAGED.

  Danielle Morse The Bryant Group

  717 Inlet Quay Unit H, Chesapeake, VA 23320
• 

  

  /23

  $236,950

  • 2 Beds
  • 1.5 Baths
  • 1,020 Sq Ft

  3202 Clover Rd E, Chesapeake, VA 23321

  Opportunity to love this affordable updated 2-bedroom, 1.5 bath townhome in desirable Western Branch! Features an updated kitchen, updated baths, luxury vinyl plank flooring (LVP), HVAC and water heater all replaced within the last 5 years. Improvements also include energy efficient vinyl windows, 30-year architectural shingles, custom brick backyard with privacy fence and shed. Located at end of

  Marvin Smith KW Coastal Chesapeake Virginia

  3202 Clover Rd E, Chesapeake, VA 23321
• 

  

  /50

  $240,000

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,285 Sq Ft

  1016 Thoroughgood Way Unit 302, Chesapeake, VA 23324

  Welcome to Village at Gateway in the heart of South Norfolk! This beautifully maintained third-floor condo is easily accessed via elevator and features an open-concept floor plan with oversized rooms and abundant natural light from skylights. The upgraded kitchen provides ample cabinetry, a pantry, and bar seating for four for casual dining or entertaining. Enjoy indoor-outdoor living with a

  Lauren Harrigan Better Homes & Gdns Ntv Am Grp

  1016 Thoroughgood Way Unit 302, Chesapeake, VA 23324
• 

  

  /26

  $299,900

  $15K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,456 Sq Ft

  502 Hermit Thrush Way, Chesapeake, VA 23323

  Meticulously maintained 2-bedroom, 2.5-bath condo with newer HVAC and LVP flooring on the main level. Spacious floor plan with tons of natural light, bonus room/office and 2 Primaries with en-suite baths. Enjoy an olympic sized pool, dog park, playgrounds, community center, and lake, all just minutes from shopping, dining, and interstate access. Don't miss this opportunity to live in a

  Trey Vineyard Vineyard Homes Real Estate

  502 Hermit Thrush Way, Chesapeake, VA 23323
• 

  

  /3

  $50,000

  • Land

  29 Gale Ave, Chesapeake, VA 23323

  This 40’ x 105’ cleared corner lot offers an excellent opportunity to build your dream home in the desirable Deep Creek area of Chesapeake. Zoned R6, the property has access to city utilities at the street. No HOA! Ideally located near major highways and interstate access, as well as shopping, restaurants, and schools, this lot provides easy access to everything Chesapeake has to offer. Don’t

  Vanda Kennedy World Class Realty & Prop Mgmt

  29 Gale Ave, Chesapeake, VA 23323
• 

  /2

  $16,500

  • Land
  • 10,018 Sq Ft
  • $71,739 per Acre

  LOT 6 Tuck St, Chesapeake, VA 23322

  Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on

  Dustin Floyd Howard Hanna Real Estate Svcs.

  LOT 6 Tuck St, Chesapeake, VA 23322
• 

  

  /14

  $215,100

  $24K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,179 Sq Ft

  1800 Portlock Rd, Chesapeake, VA 23324

  Charming 3-bedroom, 2-bath single-family home offering 1,179 sq ft of potential! Bring your vision and make this home shine! Conveniently located near the interstate and more! Call today for more information and to schedule your tour! Case#544-376530 IE (Insurable with escrow) Subject to Appraisal. Property is Owned by the US Dept. of HUD. Seller makes no representations or warranties as to the

  Jonathan Melvin Benham Real Estate LLC

  1800 Portlock Rd, Chesapeake, VA 23324
• 

  

  /17

  $222,000

  $3K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 919 Sq Ft

  1012 Rue Marseille, Chesapeake, VA 23320

  Hard to find single level living! Newer LVP flooring in main living area, carpet in bedrooms less than 2 years old, galley kitchen and updated light fixtures. End unit tucked away but right across from the pool! All new windows and sliding glass door, move in ready.

  Christine Ornoff Long & Foster Real Estate Inc.

  1012 Rue Marseille, Chesapeake, VA 23320
• 

  /2

  $7,000

  • Land
  • 10,018 Sq Ft
  • $30,435 per Acre

  Lot 22 Trinkle St, Chesapeake, VA 23322

  One of four parcels adjacent to each other offered at just above tax value. Makes for great holding investment opportunity as the tax value has doubled to 6000 for the upcoming year, or for recreational use, riding fourwheelers, camping, etc. Come take a look! Roughly 900' from the paved section of Arthurs Ct.Ten minutes to the heart of Great Bridge or Edinburgh.

  Dustin Floyd Howard Hanna Real Estate Svcs.

  Lot 22 Trinkle St, Chesapeake, VA 23322
• 

  /2

  $16,500

  • Land
  • 10,018 Sq Ft
  • $71,739 per Acre

  Lot 8 Tuck St, Chesapeake, VA 23322

  Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on

  Dustin Floyd Howard Hanna Real Estate Svcs.

  Lot 8 Tuck St, Chesapeake, VA 23322
• 

  

  /12

  $229,900

  $5K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,275 Sq Ft

  401 Henley Ct Unit K, Chesapeake, VA 23320

  Affordable living in the largest condo model available in Wimbledon Chase. Easy access to I64, the Chesapeake Expressway, Greenbrier and Great Bridge. No car needed for access to shopping & restaurants; adjacent to Chesapeake Regional Medical Complex. Summertime living is easy with the community pool. All appliances convey including washer & dryer, as-is.Besides the generous ensuite, the

  Rob Waring Creed Realty

  401 Henley Ct Unit K, Chesapeake, VA 23320
• 

  

  /4

  $199,900

  • 2 Beds
  • 1.5 Baths
  • 792 Sq Ft

  1804 Portlock Rd, Chesapeake, VA 23324

  Charming, move-in ready bungalow nestled on an large 60 x 120 lot! Inside, you will find beautiful original hardwood floors flowing throughout a bright and welcoming layout. The property also features jack & jill 1/2 bath, a detached 1-car garage and includes all appliances conveying as-is. Ideally located for an easy commute, you are just minutes from major expressways, Greenbriar area, downtown

  Melody Cespedes 1st Class Real Estate Flagship

  1804 Portlock Rd, Chesapeake, VA 23324

Showing Results 1 - 40, Page 1 of 5