Chesapeake County VA Homes for Sale

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  /10

  $925,000

  • 7 Beds
  • 4 Baths
  • 3,786 Sq Ft

  537 Margaret Dr, Chesapeake, VA 23322

  Welcome home! This beautifully updated 7 bedroom and 4 full bath property offers over 3 acres of land and ample parking. First floor primary suite features a fireplace and upgraded bathroom with sleek tile. The kitchen boasts a large island, all new countertops, stainless steel appliances, and tile backsplash. Two upstairs bedrooms include full baths and walk-in closets. Open layout with recessed

  Reagan Feuerhahn Prodigy Realty

  537 Margaret Dr, Chesapeake, VA 23322
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  /27

  $746,105

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,803 Sq Ft

  729 Crestfield Dr, Chesapeake, VA 23320

  Experience the perfect blend of comfort and functionality in this versatile ranch home. The heart of the residence features an expansive open-concept living area, overlooking the kitchen with oversized island. Retreat to the spacious owners suite, a private sanctuary complete with a generous walk-in closet & a spa-like ensuite featuring a soaking tub & separate walk-in shower. Two additional

  Dragas Companies Builder

  729 Crestfield Dr, Chesapeake, VA 23320
• 

  

  

  /22

  $659,990

  New Construction $19K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,250 Sq Ft

  976 Intracoastal Way, Chesapeake, VA 23322

  Welcome to the Denton, a beautifully designed 2,250 sq ft single-story home offering a modern open-concept living space with luxury finishes throughout. Perfect for those seeking one-level living, this home features a spacious living room, which opens to a dining area and a kitchen with a large center island, ideal for cooking and entertaining. The large primary suite is a true retreat, offering

  D.R. Horton Builder

  976 Intracoastal Way, Chesapeake, VA 23322
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  /31

  $679,600

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,652 Sq Ft

  704 Field Crest Ct, Chesapeake, VA 23322

  December Delivery. Elegant two-story home with approx. 2,652 square feet of meticulously designed living space. The main level boasts an open-concept layout with soaring 9-foot ceilings throughout. The heart of the home is the large kitchen, equipped w/tons of storage & countertops for meal prep & entertaining. A flex space on the first floor provides versatility for a home office, playroom, or

  Dragas Companies Builder

  704 Field Crest Ct, Chesapeake, VA 23322
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  /9

  $999,985

  • 6 Beds
  • 4 Baths
  • 4,090 Sq Ft

  1324 Simon Dr, Chesapeake, VA 23320

  White all-brick 2-story contemporary home with front porch, arches and large foyer. The backyard is a private oasis with trees, pond and flowing fountain. Enjoy the serenity of nature, including the blue herons, egrets, ducks and more, as you sip your morning coffee or have dinner on the patio.As you enter the first-floor foyer, notice the large formal dining room on the left and an archway

  Regina Fletcher Allison James Estates & Homes

  1324 Simon Dr, Chesapeake, VA 23320
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  /16

  $289,900

  $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,460 Sq Ft

  1236 Damyien Arch, Chesapeake, VA 23320

  A blank canvas awaiting your personal touch! 4-bedroom townhome with spacious open floorplan! No HOA fees! Downstairs bedroom with full bath. 3 bedrooms upstairs w 2 full bathrooms. Living room features high ceilings and open layout. Property includes a one car garage w/ driveway. Backyard features water views! Located in the heart of the Greenbrier area! Priced to sell!

  Janita Rucker Rucker Realty LLC

  1236 Damyien Arch, Chesapeake, VA 23320
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  /27

  $320,000

  • 3 Beds
  • 1.5 Baths
  • 1,207 Sq Ft

  1605 Laurel Ave, Chesapeake, VA 23325

  Single family two-story detached home located in the Norfolk Highlands section of Chesapeake. 3 bedrooms, 1.5 bathrooms. Spacious layout with a bedroom and half bathroom on the second floor. Many updates throughout completed in 2021. First floor laundry. Large lot with huge fenced in backyard with an oversized shed. Many updates completed in 2021.

  Tracy Thayer Own Real Estate LLC

  1605 Laurel Ave, Chesapeake, VA 23325
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  /50

  $580,000

  Open Sun 11AM - 2PM

  • 4 Beds
  • 3 Baths
  • 3,072 Sq Ft

  2600 Saint Brides Rd W, Chesapeake, VA 23322

  Retreat to the expansive second-level primary suite, featuring a private sunroom, spacious loft, luxurious garden tub, separate tiled shower, and beautiful cherry hardwood flooring. The main level offers three additional bedrooms, two full bathrooms, and a generous sunroom complete with a built-in bar—perfect for entertaining or relaxing. Enjoy 3.16 acres of peaceful outdoor living, featuring a

  Jannice Chambers Atlantic Sothebys Int'l Realty

  2600 Saint Brides Rd W, Chesapeake, VA 23322
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  /25

  $509,000

  • 4 Beds
  • 2.5 Baths
  • 2,121 Sq Ft

  405 S Monterey Dr, Chesapeake, VA 23320

  This home is a Wellspring gem with valuable upgrades. The front lawn and spacious 2 car garage create a warm and inviting first impression. Inside, the thoughtfully designed first floor offers multiple living spaces including a formal living room, dining room, eat in kitchen and cozy den featuring a gas fireplace. A convenient half bath makes everyday living and entertaining a breeze. Upstairs

  

  Jackie Feagin

  BHHS RW Towne Realty

  405 S Monterey Dr, Chesapeake, VA 23320
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  /34

  $309,000

  • 3 Beds
  • 2.5 Baths
  • 1,571 Sq Ft

  1404 River Birch Run S, Chesapeake, VA 23320

  Welcome home to this charming and spacious interior townhome, perfectly located in the heart of everything! Offering nearly 1,600 sq ft of well-maintained living space, this home has 3 spacious sized bedrooms & 2.5 baths, providing the perfect blend of comfort and functionality. Filled with character and warmth, the thoughtfully designed floor plan offers plenty of room to relax and entertain.

  Carmon Pizzanello BHHS RW Towne Realty

  1404 River Birch Run S, Chesapeake, VA 23320
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  /50

  $775,000

  • 5 Beds
  • 5 Baths
  • 3,583 Sq Ft

  1833 Benefit Rd, Chesapeake, VA 23322

  A Full Acre. Two Primary Suites. Room for Everyone — 1833 Benefit Rd, Chesapeake VA. Over 3,600 sf. Renovated 5-bedroom home on a full acre in Chesapeake — brand new carpet, all freshly painted. The space, privacy, and flexibility that rarely come together at this price point. Two primary suites, one up and one down, give you real options: multigenerational living, long-term guests, or a

  Nelene Gibbs Gibbs Realty Group

  1833 Benefit Rd, Chesapeake, VA 23322
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  /50

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,064 Sq Ft

  529 Royal Grant Dr, Chesapeake, VA 23322

  Welcome to 529 Royal Grant Drive in the desirable Cheshire Meadows area of Chesapeake. This well-maintained 4-bedroom, 2-bath ranch offers approximately 2,064 square feet of living space with a comfortable layout, office/study, finished room over the garage, and attached 2-car garage. The updated kitchen features granite countertops and stainless appliances, along with cathedral ceilings,

  Debbie Marable The Real Estate Group

  529 Royal Grant Dr, Chesapeake, VA 23322
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  /49

  $1,750,000

  • 4 Beds
  • 4 Baths
  • 5,707 Sq Ft

  2505 Sylvia Ct, Chesapeake, VA 23322

  Set at the end of a quiet Hunters Ridge cul-de-sac, this custom brick estate rests on three private, gated acres, held by a single owner since its 2006 build. Beyond its 5,707 square feet of main finished living space, the home offers approximately 1,800 additional square feet of year-round conditioned space. A two-story foyer with a curved staircase opens to formal rooms and a two-story great

  Patrick Clark Byler Realty

  2505 Sylvia Ct, Chesapeake, VA 23322
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  /48

  $775,000

  • 5 Beds
  • 2.5 Baths
  • 4,200 Sq Ft

  112 Station Rd, Chesapeake, VA 23322

  One of a kind property in Hickory area of Chesapeake with 2 (YES TWO) SFH that are legally deeded, WATERFRONT (ocean access) ~3.5 ac lot, with no neighbors in sight! Main house is over 3,000 sqft 5/2.5. Smaller house about 1200 sqft, 2/. Both have newer systems and New Roofs. Each home has its own Septic/Well system & pumped in 2024-large house/2025-small house. Property backs to 60 ft of

  Alexandra Serrano The Real Estate Group

  112 Station Rd, Chesapeake, VA 23322
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  /27

  $245,000

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  700 New River Ct Unit C, Chesapeake, VA 23320

  Welcome to 700 New River Court #C, a refreshed Chesapeake condo offering comfort, style, and low-maintenance living in a convenient Greenbrier-area location. Step inside to bright neutral finishes, updated wood-look flooring, and an inviting layout.The spacious living room features natural light, a cozy fireplace with a bold black mantle, and room to relax or entertain. The dining area offers

  Courtney Watkins

  Iron Valley Real Estate HR

  700 New River Ct Unit C, Chesapeake, VA 23320
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  /25

  $259,999

  $3K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,462 Sq Ft

  2510 King Ct, Chesapeake, VA 23324

  This remodeled townhome shines with a brand-new water heater, sleek new appliances, a semi-custom kitchen, a modern HVAC system, and thoughtful, beautiful finishes throughout.

  Leonel Vasquez Coalesce Real Estate Inc

  2510 King Ct, Chesapeake, VA 23324
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  /48

  $335,000

  Open Sun 3PM - 6PM

  • 3 Beds
  • 2.5 Baths
  • 1,862 Sq Ft

  1513 Braishfield Ct, Chesapeake, VA 23320

  Welcome to this beautifully maintained condo featuring two spacious primary suites, each complete with a private ensuite bathroom, generous walk-in closet, and additional sitting area for added comfort and flexibility. The open-concept floor plan is great for everyday living and entertaining, highlighted by an updated kitchen with stainless steel appliances, modern cabinetry, and durable LVP

  Racheal Pridgen Keller Williams Town Center

  1513 Braishfield Ct, Chesapeake, VA 23320
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  /30

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,750 Sq Ft

  2415 Fieldsway Dr, Chesapeake, VA 23320

  Embrace a life of vibrant neighborhood and comfort within this meticulously updated Chesapeake real estate standout. This pristine condition attached home features 3 spacious beds, 2.5 baths, a private one-car garage, and a spectacular master suite complete with a massive walk-in closet. Relax out back on your peaceful privacy-fenced patio. Schedule a showing today!

  Warren Neal Real Broker LLC

  2415 Fieldsway Dr, Chesapeake, VA 23320
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  /34

  $639,000

  $5K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,192 Sq Ft

  2828 Seven Eleven Rd, Chesapeake, VA 23322

  Welcome to your private country retreat! Nestled on 3 beautiful acres in the desirable Grassfield School District, this custom-built 2014 home offers the perfect blend of space, comfort, and privacy. Featuring 4 spacious bedrooms, 2.5 baths, and an open-concept layout for entertaining, this property is designed for both everyday living and peaceful relaxation. Enjoy the charm of country living

  Jessica Lucas Keller Williams Coastal Virginia Chesapeake

  2828 Seven Eleven Rd, Chesapeake, VA 23322
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  /39

  $459,000

  • 3 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  440 Fleming Cir, Chesapeake, VA 23323

  Beautiful 3 bedroom 2.5 bath home in the desirable Grassfield area of Chesapeake. This home offers a spacious layout with plenty of room for everyday living and entertaining. The kitchen has lots of cabinet and counter space and opens to the dining and living areas. The primary bedroom features a private bath and a walk-in closet. Roof replaced in 2017, windows replaced in 2021 and HVAC in 2025

  Cindy Powell Iron Valley Real Est Norfolk

  440 Fleming Cir, Chesapeake, VA 23323
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  /50

  $889,000

  • 3 Beds
  • 2 Baths
  • 2,863 Sq Ft

  2410 Centerville Turnpike S, Chesapeake, VA 23322

  If these walls could talk, they would tell you 175 years of stories. Rare pre-Civil War farmhouse charm meets modern comfort in this private retreat that feels like a vacation every day. This 2-story home is filled with character, featuring 4 fireplaces, gorgeous original hardwood floors, 10-foot ceilings, hand-sawed original moldings, intricate ceiling details, and antique lighting. The living

  Shawna Hulen Own Real Estate LLC

  2410 Centerville Turnpike S, Chesapeake, VA 23322
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  /22

  $335,000

  • 1,799 Sq Ft

  2216 Decatur St, Chesapeake, VA 23324

  Welcome to 2216 Decatur Street in Chesapeake! This brick ranch duplex is a great addition to any investors rental portfolio of the perfect place to house hack! Both units feature two bedrooms, one full bathroom, a living room, eat in kitchen and a large basement with plenty of room for storage. Both units are separately metered for power and paid for by the tenants while the owner pays for the

  Samantha Janisch Own Real Estate LLC

  2216 Decatur St, Chesapeake, VA 23324
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  /40

  $590,000

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

  1045 Winchester Way, Chesapeake, VA 23320

  Beautifully updated and impeccably maintained, this exceptional 4BR/2.5BA home offers thoughtfully designed living space in the highly sought-after Kemp Woods neighborhood of Chesapeake. Nestled on a quiet, tree-lined street, this move-in ready home perfectly blends timeless elegance, quality craftsmanship, & modern updates. Step inside to an inviting floor plan filled with natural light, with

  

  Val Milan

  Swell Real Estate Co

  1045 Winchester Way, Chesapeake, VA 23320
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  /43

  $535,000

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,831 Sq Ft

  940 Saddleback Trail Rd, Chesapeake, VA 23322

  Welcome to this charming brick-front ranch offering 3 bedrooms plus a spacious room over the garage that can serve as a fourth bedroom, home office, hobby room, or flexible living space. Situated on just under an acre, this property provides an expansive backyard with plenty of room to enjoy outdoor activities, gardening, or simply relaxing.Unwind on the inviting front porch or entertain on the

  Jobel Daugherty Howard Hanna Real Estate Svcs.

  940 Saddleback Trail Rd, Chesapeake, VA 23322
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  /37

  $229,999

  • 2 Beds
  • 2 Baths
  • 1,326 Sq Ft

  4332 Hillingdon Bend Unit 208, Chesapeake, VA 23321

  Don't miss this great 2nd floor unit. Updates have been done and its ready to go. Close to shopping center, Highway, Hospital, Military Bases, Shipyard and more. Get it before its gone.

  Armin Harris EXIT Realty Central

  4332 Hillingdon Bend Unit 208, Chesapeake, VA 23321
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  /30

  $370,000

  Open Sat 2PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 1,994 Sq Ft

  1601 Thomason Trail, Chesapeake, VA 23320

  Welcome to this exceptional end-unit luxury townhome, original owner bought as the community's model home. Built in 2014 and thoughtfully upgraded throughout, Thomason Trail offers nearly 1,900 square feet of living space, combining timeless finishes with everyday comfort. You'll appreciate the warmth of rich hardwood flooring, abundant natural light, and the attention to detail that sets this

  Michelle Adcock Swell Realty Co

  1601 Thomason Trail, Chesapeake, VA 23320
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  /26

  $999,999

  • 6 Beds
  • 4 Baths
  • 4,700 Sq Ft

  821 Redleafe Cir, Chesapeake, VA 23320

  Welcome to the Greystone Community, one of Chesapeake's most coveted custom luxury home communities. This beautifully maintained home offers numerous upgrades and exceptional outdoor living spaces. Major improvements include three HVAC systems replaced within the past four years, a new roof installed in April, encapsulated crawl space, new hardwood flooring throughout the second floor and

  Alison Rehpelz LPT Realty LLC

  821 Redleafe Cir, Chesapeake, VA 23320
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  /41

  $399,800

  $10K PRICE DROP

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

  4205 Nautilus Ave, Chesapeake, VA 23325

  Renovated and move-in ready! This beautifully updated home offers modern style and everyday comfort with a stunning new kitchen featuring stylish cabinetry, quartz countertops, stainless steel appliances, and updated lighting. The open floor plan flows into spacious living areas with fresh paint, new flooring, and renovated bathrooms. Major updates provide peace of mind, making this home truly

  John Conard Redfin Corporation

  4205 Nautilus Ave, Chesapeake, VA 23325
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  /44

  $554,500

  $5K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,510 Sq Ft

  3421 Anita Cir, Chesapeake, VA 23321

  Welcome to Miars Farm in sought-after Western Branch! This beautifully maintained 4BR, 3.5BA home offers ~2,500 sq ft of inviting living space on a .25-acre lot with timeless curb appeal and modern farmhouse touches. Enjoy a classic front porch, spacious driveway, and attached garage. Inside, the open layout features a stunning eat-in kitchen with granite countertops, stainless steel appliances,

  Jennifer Smithson Light Box Realty

  3421 Anita Cir, Chesapeake, VA 23321
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  /40

  $725,000

  Open Sat 11AM - 2PM $25K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,811 Sq Ft

  136 Bella Dr, Chesapeake, VA 23322

  Welcome to this beautifully maintained 5-bedroom, 3-bath home in the highly sought-after Viridian Reserve at Hickory. From the moment you step inside, you'll appreciate the hardwood floors, open-concept design, and spacious living room anchored by a cozy gas fireplace with wired surround sound. The kitchen is the heart of the home, featuring granite countertops, stainless steel appliances, a gas

  Racheal Pridgen Keller Williams Town Center

  136 Bella Dr, Chesapeake, VA 23322
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  /36

  $499,999

  • 5 Beds
  • 2.5 Baths
  • 2,267 Sq Ft

  517 Whisper Walk, Chesapeake, VA 23322

  Lakefront 5 bedroom home in Grassfield High and Middle School District! Fully updated $60k of premium upgrades intended for a forever home! Quiet, sought-after neighborhood. Just minutes from shopping and interstate. Large property features a 30-yrnew architectural roof, all-new hardwood floors, and a new driveway. Interior boasts an office, formal dining, eat-in-kitchen with a new refrigerator,

  Michael Miller RE/MAX Allegiance

  517 Whisper Walk, Chesapeake, VA 23322
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  /23

  $452,900

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,044 Sq Ft

  4904 Apricot Way, Chesapeake, VA 23321

  Unbelievable Incentives! Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This tri-level Ashbury plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ upgraded quartz countertops & glass subway tile backsplash. Easily maintained &

  Angela McCaskill Corinth Realty LLC

  4904 Apricot Way, Chesapeake, VA 23321
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  /30

  $624,900

  • 6 Beds
  • 4.5 Baths
  • 4,500 Sq Ft

  501 Thornloe Ln, Chesapeake, VA 23320

  Rare opportunity to own a beautifully updated 6-bedroom, 4.5-bath home featuring a private, fully equipped in-law suite for multigenerational living, extended family, guests, rental income, or a private home office. The main residence offers 5 spacious bedrooms, 3 full baths, and a stunning remodeled kitchen with quartz countertops, sleek high-gloss cabinetry, stainless steel appliances, and

  John Conard Redfin Corporation

  501 Thornloe Ln, Chesapeake, VA 23320
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  /8

  $288,500

  $12K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  106 Greenbrier Rd, Chesapeake, VA 23320

  Cute 1 story cottage in the heart of Greenbrier Chesapeake on almost an acre of private wooded property. This charming 2 bedroom home with a bonus room that has been used as a 3rd bedroom (no closet). Bright and Airy vintage appeal. Galley Kitchen opens to dining room with arched opening to living room. Open concept with character.This Single family residence has Business/Commercial

  Jay Hassell Keller Williams Realty Twn Ctr

  106 Greenbrier Rd, Chesapeake, VA 23320
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  /49

  $624,900

  • 4 Beds
  • 2.5 Baths
  • 2,211 Sq Ft

  1229 Waters Rd, Chesapeake, VA 23322

  Welcome home to this stunning like new construction in the highly sought-after Great Bridge School District! Move-in ready and thoughtfully designed, this beautiful home offers the freedom of no HOA and all the modern finishes today's buyers are looking for.Step inside to discover a bright, open-concept floor plan perfect for both everyday living and entertaining. The spacious first-floor office

  Tom Busciglio Howard Hanna Real Estate Svcs.

  1229 Waters Rd, Chesapeake, VA 23322
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  /42

  $570,000

  $15K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,992 Sq Ft

  1213 Lakeford Place, Chesapeake, VA 23322

  Rare find in sought after neighborhood. Spacious and flexible floor plan features 5 bedrooms and 3 full baths, 4 closets in primary bedroom, huge family room and a flex room with fireplace that would be perfect for an office, library or study. Large back bedroom has its own entrance with easy, close access to full bath. Workshop has electricity. Well maintained by original owners. Make an

  Renee Joseph The Real Estate Group

  1213 Lakeford Place, Chesapeake, VA 23322
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  /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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  /33

  $569,900

  • 5 Beds
  • 3 Baths
  • 2,431 Sq Ft

  529 Wittington Dr, Chesapeake, VA 23322

  Located on a quiet cul-de-sac in desirable Southern Pines, this well-kept 5BDRM/3BA home offers 2,491sq ft of comfortable living on a 1/2 acre wooded lot. Features include a gas log / wood-burning fireplace, open front porch, and large wooden deck overlooking the spacious backyard. Fully finished room over garage is ideal as a fourth bedroom, playroom, or office. The 5th bedroom and attached

  Derek Greene The Greene Realty Group

  529 Wittington Dr, Chesapeake, VA 23322
• 

  

  /50

  $640,000

  • 4 Beds
  • 2.5 Baths
  • 2,518 Sq Ft

  445 Middleton Way, Chesapeake, VA 23322

  Welcome to the popular Wells Model in Hickory Manor, offering 4 bedrooms, 2.5 baths, and a versatile upstairs loft. This home features exceptional storage throughout, including a double-door pantry, hall closet, under-stair storage, two upstairs linen closets, and dual closets in the spacious primary suite. The oversized 8-foot-long island has quartz countertops, perfect for entertaining and

  Lauren Harrigan Better Homes & Gdns Ntv Am Grp

  445 Middleton Way, Chesapeake, VA 23322
• 

  

  /50

  $975,000

  • 5 Beds
  • 6 Baths
  • 4,680 Sq Ft

  3000 Miars Green, Chesapeake, VA 23321

  Experience this exceptional waterfront home, built by Sasser, in person—photos simply can't capture its beauty, scale, or breathtaking setting. From the moment you arrive, you'll be captivated by panoramic views, an abundance of natural light, and picturesque scenery surrounding the home. Inside, you'll find an expansive kitchen designed for gathering, along with the rare convenience of a full

  Laura McGuire VA Realty Professionals

  3000 Miars Green, Chesapeake, VA 23321

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