Chesapeake, VA Homes for Sale under $400,000

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  /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
• Explore Chesapeake

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  /35

  $314,000

  $66K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 2,354 Sq Ft

  1417 Gust Ln, Chesapeake, VA 23323

  This unique property offers a main home and a separate second residence, creating flexibility that's hard to find. Whether you're looking for multigenerational living, a private in-law suite, rental income, guest accommodations, or space to run a home-based business (where permitted), this property adapts to your lifestyle. The main home features 3 bedrooms and 2.5 baths, while the second home

  

  Candice Myers

  BHHS RW Towne Realty

  1417 Gust Ln, Chesapeake, VA 23323
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  /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
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  /18

  $385,000

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft

  2415 Chesapeake Cir, Chesapeake, VA 23324

  Stunning fully renovated 4-bed, 2-bath home featuring brand-new kitchen cabinets, premium granite countertops, and top-of-the-line stainless steel appliances. Includes a new roof, vinyl windows, and modern upgraded bathrooms with high-end finishes and extreme attention to detail. The master closet has been completely redone, offering a larger and more functional space, and the additional closets

  

  Steffanie Battles

  1st Class Real Estate Flagship

  2415 Chesapeake Cir, Chesapeake, VA 23324
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  /38

  $349,900

  • 3 Beds
  • 2.5 Baths
  • 2,070 Sq Ft

  1421 Chesapeake Ave, Chesapeake, VA 23324

  Timeless character meets modern comfort in this beautifully updated 1915 South Norfolk home. A spacious wraparound porch sets a welcoming tone, while the light-filled, open-concept interior showcases an original staircase and updated finishes throughout. The custom kitchen features gray shaker cabinetry, soft-close doors and drawers, granite countertops, a large center island, stainless steel

  

  Andy Nelson

  Iron Valley Real Estate HR

  1421 Chesapeake Ave, Chesapeake, VA 23324
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  /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
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  /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
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  /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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  /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
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  /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
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  /32

  $355,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,330 Sq Ft

  944 Bells Mill Rd, Chesapeake, VA 23322

  Welcome to 944 Bells Mill Road, a beautifully updated Craftsman-style bungalow in the highly desirable Great Bridge area of Chesapeake. This home blends timeless character with modern updates, featuring fresh paint throughout, brand-new kitchen countertops, new luxury vinyl plank flooring in the kitchen and laundry room, and a refreshed bathroom. Situated on a spacious 0.36-acre lot, the property

  

  Brenda Williams

  Howard Hanna Real Estate Svcs.

  944 Bells Mill Rd, Chesapeake, VA 23322
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  /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
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  /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
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  /34

  $385,000

  • 5 Beds
  • 3 Baths
  • 2,600 Sq Ft

  1518 Manson St, Norfolk, VA 23523

  Finding a home that feels like a retreat & gives you room to breathe is rare — but this brand-new 5-bedroom, 3-bath beauty delivers exactly that. Inside, an open-concept floorplan designed for real life: a spacious kitchen with a large island breakfast bar, stainless steel appliances, granite countertops, & durable LVP flooring that keeps everything looking crisp & clean.The primary suite & an

  

  Nichole Harrison

  Prodigy Realty

  1518 Manson St, Norfolk, VA 23523
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  /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
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  /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
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  /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
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  /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
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  /45

  $399,900

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

  624 Rock Dr, Chesapeake, VA 23323

  Make this your first stop! This beautifully updated brick ranch in the desirable Oak Manor neighborhood was fully remodeled in 2022 and offers the perfect combination of style, space, and functionality. Featuring 4 spacious bedrooms, 2 full bathrooms, and an attached garage, this move-in-ready home has room for everyone. The thoughtful renovation included updated flooring, paint, lighting, and

  

  Matthew Salway

  Iron Valley Real Estate HR

  624 Rock Dr, Chesapeake, VA 23323
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  /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
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  /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
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  /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
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  /33

  $345,000

  • 2 Beds
  • 2 Baths
  • 1,327 Sq Ft

  1509 Waitsel Dr Unit 206, Chesapeake, VA 23320

  Welcome home to this beautiful, like-new condo in the heart of Chesapeake! Built just 2 years ago, this home offers modern finishes, an open layout, and low-maintenance living.The open-concept floor plan connects the kitchen, dining, and living areas, creating a great space for everyday living or entertaining. The kitchen features quartz countertops, stainless steel appliances, upgraded

  

  Jermaine Anderson

  Keller Williams Coastal Virginia Chesapeake

  1509 Waitsel Dr Unit 206, Chesapeake, VA 23320
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  /30

  $305,000

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  2135 English Ave, Chesapeake, VA 23320

  Make this your first stop! This beautifully maintained 3-bedroom, 2-bath ranch in Norfolk Highlands offers the perfect combination of comfort, convenience, and value. Updated in 2022 and well cared for since, this move-in-ready home features an eat-in kitchen with granite countertops, stainless steel appliances, and plenty of cabinet space. The spacious primary suite includes a private ensuite

  

  Matthew Salway

  Iron Valley Real Estate HR

  2135 English Ave, Chesapeake, VA 23320
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  /28

  $335,000

  $15K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  2701 Bainbridge Blvd, Chesapeake, VA 23324

  Welcome to this charming Cape Cod offering 4 bedrooms and 2 full bathrooms, thoughtfully designed to provide comfortable living with flexible spaces to suit a variety of needs. The inviting layout features bright living areas, functional room configurations, and plenty of opportunities to make the home your own.Step outside to enjoy the fully fenced backyard, offering a private outdoor

  

  Victoria Reasor Nelson

  Real Broker LLC

  2701 Bainbridge Blvd, Chesapeake, VA 23324
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  /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
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  /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
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  /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
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  /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
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  /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
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  /40

  $309,000

  • 3 Beds
  • 1.5 Baths
  • 1,139 Sq Ft

  424 Shell Rd, Chesapeake, VA 23323

  Welcome to 424 Shell Rd, where warmth, versatility, and everyday comfort come together. Beautiful wood floors add timeless character, while the kitchen feels fresh with new LVT flooring and a freshly painted ceiling. A repaired crawlspace dehumidifier adds another thoughtful update, plus have peace of mind with all new electrical receptacles, new electrical panel, and new service line to the

  Natalie Carrier Redfin Corporation

  424 Shell Rd, Chesapeake, VA 23323
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  /41

  $359,800

  $50K PRICE DROP

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

  4205 Nautilus Ave, Chesapeake, VA 23325

  Discover one of the best values in Chesapeake! This spacious 5-bedroom, 2-bath home offers over 2,100 square feet of versatile living space with room for everyone. Recent updates include a newer roof, updated HVAC, replacement windows, luxury vinyl plank flooring, fresh paint, and updated lighting, providing peace of mind and modern appeal. The bright kitchen features ample cabinet and counter

  John Conard Redfin Corporation

  4205 Nautilus Ave, Chesapeake, VA 23325
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  /21

  $394,900

  New Construction $33K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,847 Sq Ft

  674 Allery Rd, Chesapeake, VA 23320

  Now preselling by appointment. The Bristol plan offers 2 spacious owner suites on 3rd floor with convenient 3rd floor laundry. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. First floor flex space with 2-car rear-loading garage. Community will feature pool, playground, dog park and grilling

  Clarice Savereux Dragas Companies Realty Inc

  674 Allery Rd, Chesapeake, VA 23320
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  /17

  $390,000

  • 3 Beds
  • 2.5 Baths
  • 1,729 Sq Ft

  1324 Hawthorne Dr, Chesapeake, VA 23325

  The moment you walk through the door, you'll feel right at home. The spacious open layout is perfect for everyday living, whether you're enjoying a quiet evening or hosting friends and family. The thoughtfully designed primary suite offers a private retreat with a full bath and generous walk-in closet, while luxury vinyl plank flooring flows throughout the home. Recent improvements, including the

  Kris Weaver Atlantic Sothebys Int'l Realty

  1324 Hawthorne Dr, Chesapeake, VA 23325
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  /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
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  /38

  $358,900

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

  3232 Sir Meliot Dr, Chesapeake, VA 23323

  WELCOME TO CAMELOT - WELL ESTABLISHED COMMUNITY IN DEEP CREEK AREA OF CHESAPEAKE - NEIGHBORHOOD CAMELOT ELEMENTARY SCHOOL AND PARK - DON'T MISS THIS FOUR (4) BEDROOMS - TWO (2) BATHROOMS - RANCHER MOVE IN READY! INTERIOR FRESHLY PAINTED - NEW CARPET - NEW MICROWAVE - PLUS MORE! FOYER - LIVING ROOM - DINING ROOM PLUS ADDITIONAL ROOM OFF KITCHEN AND FIREPLACE! EASY ACCESS TO INTERSTATES - SHOPPING

  Jackie Thomas Jackie Thomas Real Estate LLC

  3232 Sir Meliot Dr, Chesapeake, VA 23323
• 

  /2

  $370,000

  Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 1,428 Sq Ft

  100 Alice St, Chesapeake, VA 23323

  Tranika Starks Swell Real Estate Co

  100 Alice St, Chesapeake, VA 23323
• 

  

  /19

  $331,900

  New Construction Open Sun 1PM - 3PM

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

  4983 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

  4983 Boone Rd, Chesapeake, VA 23321
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  /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

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