Chesapeake, VA Homes for Sale under $400,000

• 

  

  

  /5

  $285,000

  • 2 Beds
  • 2.5 Baths
  • 1,276 Sq Ft

  2351 Old Greenbrier Rd, Chesapeake, VA 23325

  This beautifully updated 2 bedroom, 2.5 baths, 2 story condo features 2 full primary ensuite bedrooms w/updated bathrooms including new sinks, counter, vanities, lighting, & toilets. In addition, brank new LPV flooring, new upgraded carpet 2nd floor, fresh paint throughout, new kitchen cabinets, new granite counters and new stainless-steel appliances create a clean and modern feel. There is a

  Nancy Myers EXIT Realty Central

  2351 Old Greenbrier Rd, Chesapeake, VA 23325
• 

  

  

  /43

  $284,000

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

  2806 Baldwin Dr, Chesapeake, VA 23321

  Located in one of the most private settings in The Woodlands, this condo offers a spacious, modern layout with wooded views and no buildings directly behind. The open first floor features a bright living area, dining space, and a well-equipped kitchen with abundant counter space, breakfast bar, stainless steel appliances, and a large pantry. Sliding doors open to a fenced patio with a storage

  Michelle Helmsderfer BHHS RW Towne Realty

  2806 Baldwin Dr, Chesapeake, VA 23321
• 

  

  

  /30

  $350,000

  • 2 Beds
  • 1.5 Baths
  • 1,293 Sq Ft

  2112 Paramont Ave, Chesapeake, VA 23320

  Beautifully updated home in the desirable Greenbrier area! Features include a renovated kitchen with new appliances, updated baths, bright open living spaces, new flooring and great curb appeal. Enjoy a private backyard perfect for relaxing or entertaining. Conveniently located near Greenbrier Mall, shopping, dining, parks, and major highways. Move-in ready and in a sought-after school zone —

  Amanda Martinez Gallery Realty LLC

  2112 Paramont Ave, Chesapeake, VA 23320
• 

  

  

  /43

  $349,900

  • 3 Beds
  • 2.5 Baths
  • 1,870 Sq Ft

  1523 Pucknall Dr, Chesapeake, VA 23320

  Easy living awaits in this 3-bedroom, 2.5-bath condo in the heart of Greenbrier. The living room is filled with natural light and offers a warm, inviting feel from the moment you walk in. The large kitchen features plenty of cabinet and counter space, a walk-in pantry, and opens to the dining area, making everyday living and entertaining easy. A first-floor bedroom adds flexibility and

  Jonathan Shepheard House Goals

  1523 Pucknall Dr, Chesapeake, VA 23320
• 

  

  /2

  $240,000

  • Land
  • 5.33 Acres
  • $45,054 per Acre

  B Taft Rd, Chesapeake, VA 23322

  Vacant cleared lot, road access via access easement via lot 1 adjacent to Taft road

  Tom Thrasher Greenbrier Real Estate & Appr.

  B Taft Rd, Chesapeake, VA 23322
• 

  

  /23

  $314,000

  $1K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 950 Sq Ft

  600 Mooney Rd, Chesapeake, VA 23325

  Welcome home to this beautifully renovated 3-bedroom, 2-bathroom all-brick ranch! This move-in-ready gem features a new roof, new windows, and a new hot water heater, providing peace of mind for years to come. Inside, you'll find a blend of refinished hard wood flooring and LVP flooring throughout. The stunning kitchen and updated bathrooms showcase custom tile work and modern finishes that add

  Alesha Smith Fathom Realty

  600 Mooney Rd, Chesapeake, VA 23325
• 

  

  /5

  $320,000

  • 3 Beds
  • 2.5 Baths
  • 1,610 Sq Ft

  709 Montrose Ct, Chesapeake, VA 23320

  Welcome to 709 Montrose Ct., Chesapeake, VA! This well- maintained two-story townhome offers 1,610 +/- sq. ft. of comfortable living space in a convenient location. Built in 1991, the home features 3 bedrooms, 2.5 baths, and a functional floor plan designed for everyday living. The spacious layout provides ample room for relaxing, entertaining, and working from home. Conveniently located near

  Christy Cole United Country - A B Cole&Asc

  709 Montrose Ct, Chesapeake, VA 23320
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  /3

  $239,900

  $40K PRICE DROP

  • Land
  • 3.77 Acres
  • $63,702 per Acre

  743 Bedford St, Chesapeake, VA 23322

  This is a 3+ acre lot zoned A1 for agriculture use and barns. Build your own barn for your personal equipment or animals. Potential for commercial office/warehouse use with a conditional use variance from the Chesapeake City Council and Navy. Septic and well approvals are available. This lot cannot be used for a residential building site and air rights have been sold off. Owner will consider

  Robert Wadsworth Pungo Realty LLC

  743 Bedford St, Chesapeake, VA 23322
• 

  

  /22

  $319,000

  $9K PRICE INCREASE

  • 2 Beds
  • 2.5 Baths
  • 2,790 Sq Ft

  2462 Leytonstone Dr, Chesapeake, VA 23321

  See showing instructions. Amazing value for the size! Huge 2,790 sq.ft. home in Kings Pointe at Western Branch. This 3 bedroom, 2 bath home features ensuites for both bedrooms and a flexible bonus room downstairs that could serve as a third bedroom, office, media room, or additional living space. Gourmet kitchen with lots of custom cabinets for storage, a walk-in Pantry, and SS Appliances.

  Julie Resh Atlantic Coast Realty Corp

  2462 Leytonstone Dr, Chesapeake, VA 23321
• 

  

  /10

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,128 Sq Ft

  817 Dana Dr, Chesapeake, VA 23321

  Instant equity!!!!Welcome home to this charming, single-level ranch that blends comfort and functionality! Nestled in a quiet, established neighborhood zoned for highly desirable schools, this 3-bedroom, 2-bathroom, 1,120 sqft home offers a cozy yet efficient footprint. The heart of the home features a bright and open eat-in kitchen, making meal prep and entertaining a breeze. You will love the

  Erika Ingram COVA Home Realty

  817 Dana Dr, Chesapeake, VA 23321
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  /14

  $275,000

  • Land
  • 4.87 Acres
  • $56,468 per Acre

  3725 Cornland Rd, Chesapeake, VA 23322

  Centrally located. QUIET, SECLUDED LIVING on 4.87 ACRES IN THE COUNTRY PART OF CHESAPEAKE. Located off RT 17 near the North Carolina line in a growing area. Less than 10 minutes to GREAT BRIDGE and minutes from I-64 for access to all S Hampton Roads and the Peninsula. PRIVACY, SECLUDED LOCATION. THE CITY OF CHESAPEAKE TAX RECORDS DOCUMENT LAND USE AS RESIDENTIAL ACREAGE. THIS IS A GOOD TIME TO

  Ronda Galko Howard Hanna Real Estate Svcs.

  3725 Cornland Rd, Chesapeake, VA 23322
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  /28

  $269,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,372 Sq Ft

  1331 Hull St, Chesapeake, VA 23324

  This home offers a well-maintained and move-in-ready home offering comfort, functionality, and modern updates. It strikes a balance between style, space, and convenience, offering a bright, inviting floor plan with spacious living areas. Outside, you'll find a private yard that's perfect for relaxing or entertaining. Additionally, Lakeside Park is perfect for a walk, just one block away, offering

  Christina Sherrill Creed Realty

  1331 Hull St, Chesapeake, VA 23324
• 

  

  /37

  $389,000

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft

  1421 Glendale Ave, Chesapeake, VA 23323

  Welcome home to 1421 Glendale Avenue! Designed for effortless living, where quality craftsmanship, modern style & everyday convenience come together in this beautifully updated 4-Bedroom, 2 Bathroom Ranch home w/exceptional indoor & outdoor living spaces in the heart of Chesapeake! The high-end custom eat-in kitchen features abundant cabinetry, granite countertops, stainless steel appliances,

  Kim Wilkins RE/MAX Ultra

  1421 Glendale Ave, Chesapeake, VA 23323
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  /40

  $299,900

  • 2 Beds
  • 2.5 Baths
  • 1,334 Sq Ft

  1313 Quail Creek Hollow Unit C, Chesapeake, VA 23320

  Private end-unit in desirable Greenbrier Fairways with a first-floor primary suite and spacious second bedroom. Versatile loft with closet overlooks the great room, great for an office, flex space, or potential third bedroom. Kitchen features ample cabinetry, pantry, and breakfast bar. Enjoy a backyard patio and attached storage shed. HVAC & roof (2019), flooring (2017), paint (2023). FHA/VA

  Cindy Mayberry BHHS RW Towne Realty

  1313 Quail Creek Hollow Unit C, Chesapeake, VA 23320
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  /18

  $285,000

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft

  4000 Kilbride Dr, Chesapeake, VA 23325

  All Brick Ranch with a detached garage on a fenced corner lot. The home is almost waterfront, neighbors just a few doors down are waterfront. Established area centrally located to interstates, schools, and shopping. Three bedrooms, one bath and no power bill. This home boasts a Solar system that cuts the power bill to the connection fee. Pavers off the back door offer added area for relaxing. The

  Charles Beeson Wainwright Real Estate

  4000 Kilbride Dr, Chesapeake, VA 23325
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  /2

  $285,000

  • 3 Beds
  • 2.5 Baths
  • 1,703 Sq Ft

  4606 Old Fox Trail, Chesapeake, VA 23321

  Tucked-Away Condo Charm in Western Branch!Located in the back of the community away from the street, this 3-bedroom, 2.5-bath townhomeoffers 1,703 square feet of comfortable living surrounded by peaceful green space and mature trees. Step inside to an open-concept layoutfeaturing a bright and airy eat-in kitchen with abundant storage, generous counter space, and an oversized pantry —

  Katherine Durbin Shaffer Real Estate Inc.

  4606 Old Fox Trail, Chesapeake, VA 23321
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  /17

  $265,000

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft

  2317 Wildwood Rd, Chesapeake, VA 23323

  Move-in ready and beautifully updated, this home offers the perfect blend of modern style and everyday functionality. Step inside to a bright, inviting interior featuring a beautifully renovated kitchen with soft-close shaker cabinetry, granite countertops, and brand-new stainless steel appliances—perfect for cooking, gathering, and entertaining. Outside, the spacious backyard provides plenty of

  Brian Wurst A Better Way Realty Inc.

  2317 Wildwood Rd, Chesapeake, VA 23323
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  /38

  $264,900

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,215 Sq Ft

  500 Judah Way Unit 123, Chesapeake, VA 23320

  Gated Community! Elevator! Move in ready for serene living. Bright and modern condo with elevator access to the 2nd floor. Open floor plan, family room with fireplace, kitchen with granite counter tops and upgraded cabinetry, stainless steel appliances, pantry and utility room. Two primaries with en-suites and balcony. Hardwood floors. Upgraded custom built-ins throughout. Private storage room on

  Paul Bauer The Bauer Group-RE Solutions

  500 Judah Way Unit 123, Chesapeake, VA 23320
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  /28

  $239,900

  • 3 Beds
  • 1.5 Baths
  • 1,268 Sq Ft

  824 Huntly Dr, Chesapeake, VA 23320

  Tyler Keffer Keffer Realty

  824 Huntly Dr, Chesapeake, VA 23320
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  /11

  $165,000

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  3301 Clover Meadows Dr, Chesapeake, VA 23321

  Welcome home to this charming first-floor end-unit condo in the desirable Clover Meadows community of Western Branch! Offering 2 bedrooms and 1 full bath, this well-maintained condo features an open and functional layout with abundant natural light and added privacy as an end unit. Enjoy easy one-level living with a spacious living area, cozy dining space, and a bright kitchen with ample cabinet

  Jessica Cecchini RE/MAX Alliance

  3301 Clover Meadows Dr, Chesapeake, VA 23321
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  /14

  $227,900

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  2041 Lockard Ave, Chesapeake, VA 23320

  Great starter home! This charming 3-bedroom, 1-bath ranch offers comfortable single-level living with plenty of potential. Enjoy the bright front sunroom, perfect for relaxing or creating additional living space, plus a screened-in side porch that provides a cozy, private retreat. The fenced backyard and storage shed offer room for hobbies, pets, gardening or future improvements. Conveniently

  Andreia Worst Wainwright Real Estate

  2041 Lockard Ave, Chesapeake, VA 23320
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  /8

  $250,000

  • Land

  2716 Seven Eleven Rd, Chesapeake, VA 23322

  Excellent building opportunity. Great location. Surrounded by several custom built homes. Very private and priced below market.

  Fred Helm BHHS RW Towne Realty

  2716 Seven Eleven Rd, Chesapeake, VA 23322
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  /30

  $237,500

  $8K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,255 Sq Ft

  1016 Thoroughgood Way Unit 307, Chesapeake, VA 23324

  Beautifully maintained, one-owner, 3rd-floor condo with elevator access in a secure-entry building. This open-concept home offers a bright, airy layout with a private balcony—great for relaxing. Gated parking adds convenience and peace of mind. Ideally located near downtown Norfolk, Waterside District, military bases, shipyard, interstates, dining, shopping, and entertainment venues. Adjacent to

  Sherri Bryant The Bryant Group

  1016 Thoroughgood Way Unit 307, Chesapeake, VA 23324
• 

  

  /13

  $275,000

  • 4 Beds
  • 2 Baths
  • 1,550 Sq Ft

  1321 Seaboard Ave, Chesapeake, VA 23324

  Beautifully updated 4 bedroom, 2 bath home in Chesapeake! Spacious home that features modern updates throughout and offers easy access to nearby interstates for a quick commute. Don’t miss the amazing blend of style, comfort, and convenience!

  Tavion Baker World Class Realty & Prop Mgmt

  1321 Seaboard Ave, Chesapeake, VA 23324
• 

  

  /20

  $385,000

  • 3 Beds
  • 2.5 Baths
  • 1,592 Sq Ft

  208 Oak Grove Run, Chesapeake, VA 23320

  Well cared for 3 bedroom 2.5 bathroom hoe in sought after neighborhood of Knells Ridge/Oak Lake Estates Freshly painted, new deck, new LVP flooring in hall bathroom, LG smart washer 2024, ADT touchscreen smart alarm system 2024, google nest protect smart smoke & carbon monoxide detector 2024, LG smart dishwasher 2023, LG smart dryer 2021, LG smart refrigerator 2021, hot water heater 2021, ring

  Kim Groff Dominion Property Management

  208 Oak Grove Run, Chesapeake, VA 23320
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  /39

  $299,000

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft

  746 Sendero Ct, Chesapeake, VA 23322

  Welcome to Sendero Ct! Located with-in a Cul-de-sac. Spacious End unit townhome has 2 bedrooms, Loft and 2 baths. Head inside and notice the bold, beautiful new flooring and freshly paint, updated Kitchen and 2 updated bathrooms. Fenced Backyard Oasis with Hot Tub and Grilling area. Located near Hwy 17 and easy access to Downtown Norfolk, VA Beach, Suffolk, Military Bases, Shopping, Restaurants

  Corinne Zedd The Real Estate Group

  746 Sendero Ct, Chesapeake, VA 23322
• 

  

  /20

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,593 Sq Ft

  1109 Hearthstone Landing, Chesapeake, VA 23320

  You will love coming home to this comfortable ranch home with cozy rooms. Located near the intersection of Greenbrier Parkway and Volvo Parkway in Turtle Rock on a cul-de-sac. Enjoy the floor plan which includes living room, dining room, den with fireplace, eat-in kitchen, laundry room, primary bedroom with bathroom, two other bedrooms and hall bathroom. Walking trails & playgrounds nearby. Lots

  Kathy Elliott RE/MAX Allegiance

  1109 Hearthstone Landing, Chesapeake, VA 23320
• 

  

  /23

  $375,000

  $25K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft

  1073 Scenic Blvd, Chesapeake, VA 23322

  Welcome to 1073 Scenic Boulevard! This beautifully updated ranch-style home offers modern finishes, flexible living space, and a private setting on approximately .4 acres in the desirable Great Bridge area. Step inside to an open and inviting floor plan featuring updated flooring, fresh paint, modern fixtures, and a stunning kitchen w/ white shaker cabinetry, granite countertops, stainless steel

  Chris Jenkins Better Homes & Gdns Ntv Am Grp

  1073 Scenic Blvd, Chesapeake, VA 23322
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  /25

  $299,900

  Open Thu 1PM - 3PM $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  508 Mooney Rd, Chesapeake, VA 23325

  Move-in ready Chesapeake ranch with major system updates buyers will appreciate. The roof was replaced in 2025, and the water heater is less than 5 years old. This 3 bedroom, 2 bath brick home offers a comfortable floor plan with a spacious kitchen, family room addition, and flexible living spaces for everyday living and entertaining. The fenced backyard provides outdoor space for relaxation,

  Missy Abrams L'Hoste Keller Williams Realty Twn Ctr

  508 Mooney Rd, Chesapeake, VA 23325
• 

  

  /18

  $249,999

  $125K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,170 Sq Ft

  604 Amick Rd, Chesapeake, VA 23325

  Beautiful property offering both investment and owner-occupant potential. Located in a desirable area. Sold As-Is. Seller will not make repairs . 4bedrooms 2full baths.

  Norman Domingo XRealty.NET LLC

  604 Amick Rd, Chesapeake, VA 23325
• 

  

  /11

  $255,000

  • 3 Beds
  • 1.5 Baths
  • 1,292 Sq Ft

  74 Colonial Way, Chesapeake, VA 23325

  BEAUTIFUL ALL-BRICK END-UNIT TOWNHOME!Don't miss this exceptional opportunity to own this beautifully maintained all-brick end-unit townhome in a well-established neighborhood that truly reflects pride of ownership.Features include:Beautiful all-brick constructionDesirable end-unit locationNO HOA!Conveniently located near major interstates for an easy commuteMinutes from hospitals, shopping,

  Willie Farmer Weichert Realtors-KBL Company

  74 Colonial Way, Chesapeake, VA 23325
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  /25

  $325,000

  Open Fri 4PM - 6PM Coming Soon

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

  1553 Forest Cove Dr, Chesapeake, VA 23323

  Discover single-level living at its finest in this charming Chesapeake ranch! Perfectly positioned on a generous corner lot, this 3-bedroom, 2-bath home boasts a bright and open atmosphere. The spacious living area flows seamlessly into a fully updated kitchen featuring modern appliances, a moveable island, and a cheerful breakfast nook. Down the hall, the primary suite offers a peaceful everyday

  Deven Burns Keller Williams Capital Props.

  1553 Forest Cove Dr, Chesapeake, VA 23323
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  /2

  $310,000

  $10K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 905 Sq Ft

  843 Quail Ave, Chesapeake, VA 23324

  **Excellent investment opportunity! This tenant-occupied home is situated on a quiet street and offers cozy living with a large rear yard, great for children, pets, gardening, or outdoor entertaining. A property with great potential for investors or future homeowners alike.**

  Paula Moore Keffer Realty

  843 Quail Ave, Chesapeake, VA 23324
• 

  

  /50

  $334,900

  Open Sun 1PM - 3PM $10K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,582 Sq Ft

  1213 Killington Square, Chesapeake, VA 23320

  MOVE-IN READY! Desirable END UNIT townhome in sought after Greenbrier. Fresh paint and new carpet throughout make this beautifully updated home shine. The bright eat-in kitchen features stainless steel appliances and granite countertops. The spacious great room offers a dining area, cozy fireplace, and access to the large, fenced backyard with utility room and storage shed (shed conveys As-Is). A

  Maribeth Dunlap Long & Foster Real Estate Inc.

  1213 Killington Square, Chesapeake, VA 23320
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  /18

  $337,500

  $12K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  812 S Lake Cir, Chesapeake, VA 23322

  REMODELED, NEW TILE IN BATHROOM, NEW GRANITE COUNTER TOPS IN BATHROOMS, NEW GRANITE KITCHEN COUNTER TOPS, NEW FLOORS, NEW FIXTURE LIGHTS, NEW HVAC, NEW WATER TANK AND MUCH MORE.

  Nelson Vedia World Class Realty

  812 S Lake Cir, Chesapeake, VA 23322
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  /16

  $255,000

  $5K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,168 Sq Ft

  1002 Willow Green Ct, Chesapeake, VA 23320

  Located in the Riverwalk section of Chesapeake, this corner unit offers added privacy and a great position tucked toward the backside of the building. Enjoy a quiet serene lifestyle. The functional floor plan provides comfortable everyday living. 2 Bedrooms on the 2nd floor along with 2 Full-Baths with a convenient powder room on the 1st floor. Generous closet space and plenty of storage

  Pamela Boone-Skeeter BHHS RW Towne Realty

  1002 Willow Green Ct, Chesapeake, VA 23320
• 

  

  /39

  $329,500

  • 3 Beds
  • 3 Baths
  • 1,776 Sq Ft

  605 Sail Fish Quay, Chesapeake, VA 23320

  Be the first to see this stunning 3 bedroom, 3 full bath condo in sought after Riverwalk on the Elizabeth River. Offering 1,776 square feet of living space, this home features soaring cathedral ceilings, skylights, a dramatic two story great room with gas fireplace, and a spacious loft with potential for a fourth bedroom conversion. Recent updates include new carpet, luxury vinyl plank flooring,

  Diane Keeley BHHS RW Towne Realty

  605 Sail Fish Quay, Chesapeake, VA 23320
• 

  

  /43

  $379,999

  • 4 Beds
  • 2 Baths
  • 1,762 Sq Ft

  832 Parapet Rd, Chesapeake, VA 23323

  Nestled in Chesapeake’s established Camelot neighborhood, this beautifully updated vinyl and brick ranch offers 4 bedrooms, 2 full baths, and 1,762 square feet of comfortable single-level living. Luxury vinyl plank flooring flows throughout the main living areas, while the freestanding wood-burning stove creates a warm focal point for gathering. The kitchen features an oversized island, abundant

  Cristian Juarez ONYX Realty Professionals LLC

  832 Parapet Rd, Chesapeake, VA 23323
• 

  

  /20

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,245 Sq Ft

  4626 Old Fox Trail, Chesapeake, VA 23321

  Welcome home to this well-maintained 3-bedroom, 2-bath end-unit condo in the sought-after Western Branch area. The bright and inviting living room features a tray ceiling, natural light, and a gas fireplace. The spacious primary suite offers a walk-in closet and private en-suite bath. The kitchen includes newer appliances, a convenient bar-height counter, and a breakfast nook for casual dining.

  Jonathan Shepheard House Goals

  4626 Old Fox Trail, Chesapeake, VA 23321
• 

  

  /12

  $260,000

  • 2 Beds
  • 2 Baths
  • 1,214 Sq Ft

  1914 Woodgate Arch, Chesapeake, VA 23320

  Open House Saturday 7/18/26, 10 am - 2 pm. Welcome to this beautifully renovated 2-bedroom, 2 bathroom townhome featuring impressive high ceilings that create an open, airy feel throughout. The updated interior boasts modern finishes, refreshed flooring, and a stylish kitchen perfect for both everyday living and entertaining. Spacious bedrooms offer comfort and privacy, while the thoughtfully

  Ashley Faulk Wainwright Real Estate

  1914 Woodgate Arch, Chesapeake, VA 23320

Showing Results 121 - 160, Page 4 of 6