Homes for Sale near Western Branch High School

• 

  

  

  /5

  $255,000

  • 2 Beds
  • 2.5 Baths
  • 1,336 Sq Ft

  4443 Pepper Ridge Ct, Chesapeake, VA 23321

  Well maintained and updates throughout, you don't want to miss this opportunity to own this beautiful home in the sought after Western Branch area. French doors open to a large patio, with plenty of space for entertaining, and gardening. 2 primary suites with their own bath, and lots of closet space. Low maintenance!! Association pool and clubhouse.

  Adrian Pinkney LPT Realty LLC

  4443 Pepper Ridge Ct, Chesapeake, VA 23321
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  /11

  $199,700

  • Land
  • 5.00 Acres
  • $39,940 per Acre

  4729 Sunray Ave, Chesapeake, VA 23321

  Perfect opportunity to own 5 acres in the Western Branch zone of Chesapeake. 2 Acres in front are cleared and 3 acres in back are partially wooded. Property is zoned A1 - check with City of Chesapeake for endless possibilities for this property. Take a ride around the neighborhood, and you will find new country chic farm homes, horses, farm equipment, crops....lots of ways to be close to city

  LeAnn Amory BHHS RW Towne Realty

  4729 Sunray Ave, Chesapeake, VA 23321
• 

  

  

  /19

  $430,000

  • 4 Beds
  • 2 Baths
  • 2,073 Sq Ft

  4225 Terry Dr, Chesapeake, VA 23321

  Welcome to this meticulously maintained all brick ranch house waiting to become your home right across from sought after Western Branch High School. Brand new HVAC system. This beautiful home has an open floor plan and is equipped with hard wood floors throughout and stainless-steel appliances. Kitchen boasts plenty of counter space and cabinets. New composite deck in large back yard to relax or

  Aaron Lewis 1st Class Real Estate Riverside

  4225 Terry Dr, Chesapeake, VA 23321
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  /50

  $355,000

  • 4 Beds
  • 2.5 Baths
  • 2,301 Sq Ft

  3904 River Breeze Cir, Chesapeake, VA 23321

  Welcome to River Breeze! Located in the Western Branch section of Chesapeake, this beautiful home located in a condominium community features a beautiful open floor plan! Step inside to a gorgeous layout featuring LVP flooring throughout the first living level. The front sitting room flows right into the dining room before entering the open kitchen. Designed for entertaining, this kitchen is well

  Richard Febus Next Chapter VA Realty Inc

  3904 River Breeze Cir, Chesapeake, VA 23321
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  /47

  $475,000 Open Sat 12PM - 2PM

  • 5 Beds
  • 2 Baths
  • 3,119 Sq Ft

  4032 Georgia Rd, Chesapeake, VA 23321

  Welcome to your dream home in the heart of Western Branch! This beautifully updated 2-story all-brick home offers 5 spacious bedrooms, 2 full baths, and over 3,100 square feet of flexible living space—great for multigenerational living with a separate upstairs 2/1 layout! Enjoy peace of mind with wrapped exterior trim, a vinyl privacy fence, new windows, new LVP flooring downstairs, and fresh

  Betsy Thompson The Agency

  4032 Georgia Rd, Chesapeake, VA 23321
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  /38

  $410,000

  • 4 Beds
  • 3 Baths
  • 1,822 Sq Ft

  4237 Woodland Dr, Chesapeake, VA 23321

  Don’t miss this move-in-ready home in Western Branch! Features 2 large primary suites, 3 full bathrooms, updated kitchen with new appliances, new floors & carpet, and fresh paint throughout. Enjoy a 3-car garage, a bonus shed, and a spacious yard in a quiet neighborhood close to schools, shopping, and highways.? Highlights: • Appraised at $433K — $23K instant equity! • 2

  Jennifer Smithson Light Box Realty

  4237 Woodland Dr, Chesapeake, VA 23321
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  /33

  $419,400

  • 3 Beds
  • 2 Baths
  • 1,771 Sq Ft

  2309 Drum Creek Rd, Chesapeake, VA 23321

  Experience modern elegance in this beautifully renovated 3-bedroom, 2-bath brick ranch located in the coveted Western Branch area of Chesapeake. Completely transformed in 2021, this home boasts meticulous updates throughout, showcasing exquisite finishes and attention to detail. The open floor plan seamlessly integrates living and entertaining spaces, creating an inviting atmosphere for family

  Andy Nelson Iron Valley Real Estate Hampton Roads

  2309 Drum Creek Rd, Chesapeake, VA 23321
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  /48

  $445,000

  • 4 Beds
  • 2 Baths
  • 2,087 Sq Ft

  2400 Deerfield Crescent, Chesapeake, VA 23321

  Welcome home to this beautiful 4 bedroom, 2 bath home located in the well-established neighborhood of Taylorwood Estates in sought after Western Branch. It has been updated with a new kitchen, and all new appliances in 2023. Updated furnishings including new light fixtures, and ceiling fans all throughout the home. Freshly painted. New HVAC in 2024. The backyard is fully fenced in and equipped

  Tom Busciglio Howard Hanna Real Estate Services

  2400 Deerfield Crescent, Chesapeake, VA 23321
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  /5

  $284,900

  • 2 Beds
  • 2.5 Baths
  • 1,329 Sq Ft

  2801 Baldwin Dr, Chesapeake, VA 23321

  Gorgeous condo in the highly desirable Woodlands at Western Branch community! The first floor offers an open floor plan with a spacious living room and dining area. The kitchen features a breakfast bar, ample cabinet and counter space, and stainless steel appliances. Sliding doors off the living room lead to a fully fenced backyard with a patio and storage shed. Upstairs, you’ll find two large

  Michael Daugherty Own Real Estate LLC

  2801 Baldwin Dr, Chesapeake, VA 23321
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  /27

  $234,900

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

  2469 Leytonstone Dr Unit 207, Chesapeake, VA 23321

  Well maintained 2-Bed, 2-Bath Condo in Chesapeake. This beautifully kept condo offers two spacious bedrooms, two full baths, and an open layout with modern finishes. Conveniently located near shopping, dining, and major highway ideal for easy access to military bases and everyday essentials.

  Eric Edwards Iron Valley Real Estate Prestige

  2469 Leytonstone Dr Unit 207, Chesapeake, VA 23321
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  /50

  $699,000

  • 5 Beds
  • 4.5 Baths
  • 4,100 Sq Ft

  4208 McKenna Close, Chesapeake, VA 23321

  Welcome home to well established Miars Plantation! This beautifully maintained one-owner custom home offers 5 spacious bedrooms and 4.5 baths, including a first-floor bedroom with full bath perfect for guests or multigenerational living. Freshly painted with brand-new carpet and a new roof (May 2025), this home also features a newer HVAC system, new refrigerator, and new microwave. First-floor

  Heather Bass BHHS RW Towne Realty

  4208 McKenna Close, Chesapeake, VA 23321
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  /50

  $1,060,000

  • 4 Beds
  • 2.5 Baths
  • 3,900 Sq Ft

  3321 Tyre Neck Rd, Chesapeake, VA 23321

  Rare opportunity for country living on 3.5 acres in the heart of Western Branch! This 1876 farmhouse beauty retains the integrity of the old with original tongue & groove ceilings in the eat-in kitchen to the crown molding & heart-pine floors...even the original front porch steps & railings have creatively been brought into the renovations! Along with the character & charm of the old, the updates

  Tommy Holland The Real Estate Group

  3321 Tyre Neck Rd, Chesapeake, VA 23321
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  /23

  $475,000

  • 5 Beds
  • 3 Baths
  • 2,541 Sq Ft

  4901 Lake Shore Dr, Chesapeake, VA 23321

  Brick ranch with open floor plan fresh paint ready for your family. Fireplace with built -ins. Living and dining room open to the large gourmet kitchen. Granite counters stainless appliances and lots of storage space. Large island. Bay windows overlook the fenced back yard. Finished room over the converted garage gives additional space . Converted garage with 2 large rooms,bath and separate

  Maria Smoot The Real Estate Group

  4901 Lake Shore Dr, Chesapeake, VA 23321
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  /40

  $445,000 Open Sun 10AM - 12PM

  • 3 Beds
  • 2 Baths
  • 1,997 Sq Ft

  2836 Greenwood Rd, Chesapeake, VA 23321

  Beautifully renovated ranch, located in the heart of Western Branch on a spacious 0.38-acre lot along the Elizabeth River. From the moment you enter the home, you'll appreciate the stunning luxury vinyl plank flooring that flows throughout the main living areas. The thoughtfully redesigned open floor plan seamlessly connects the great room, dining area, and kitchen, creating an ideal space for

  Bethany White Keller Williams Coastal Virginia Chesapeake

  2836 Greenwood Rd, Chesapeake, VA 23321
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  /38

  $349,900

  • 4 Beds
  • 2 Baths
  • 1,689 Sq Ft

  3316 Pine Hill Crescent, Chesapeake, VA 23321

  This lovingly kept home has so much to offer; amazing living spaces, four big bedrooms, an expansive yard and backyard deck, and plenty of parking in your extra large driveway. Located in a desired school district with a geothermal HVAC system installed in 2010 (expected 50 year lifespan), the water heater is 3 years old, mini-split in sunroom installed 2021. Roof is approx 3-5 years and solar

  Kim Finley KFinCo Realty

  3316 Pine Hill Crescent, Chesapeake, VA 23321
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  /45

  $395,000

  • 3 Beds
  • 2.5 Baths
  • 2,268 Sq Ft

  4141 Sunkist Rd, Chesapeake, VA 23321

  Change your life in this beautifully maintained 3-bedroom, 2.5-bath home offering bright, open living in the highly sought-after Western Branch area of Chesapeake. The spacious layout includes a dedicated office/study and generous attic storage. Enjoy an updated kitchen, modern HVAC system, and a large backyard with a deck—great for outdoor entertaining. Conveniently located near shopping,

  Jordan L. Williams Keller Williams Coastal Virginia Chesapeake

  4141 Sunkist Rd, Chesapeake, VA 23321
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  /24

  $355,000

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft

  3217 Bangor Dr, Chesapeake, VA 23321

  Beautiful, updated brick home featuring new luxury vinyl flooring, new carpet, and fresh paint throughout. All new appliances, fixtures, doors, and windows. The kitchen features stainless-steel appliances, white cabinets, and tile backsplash. Fully updated bathrooms with tile and new vanities. Primary bedroom with bathroom. Sliding glass doors lead to a new wood deck and spacious backyard with a

  Reagan Feuerhahn Prodigy Realty

  3217 Bangor Dr, Chesapeake, VA 23321
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  /42

  $585,000

  • 4 Beds
  • 2.5 Baths
  • 2,725 Sq Ft

  2011 River Pearl Way, Chesapeake, VA 23321

  Have you ever wanted to live in a pristine HOA neighborhood without the expense of the HOA? This is the house! RARE is an understatement. This almost-new home, built in 2021 is nestled in the established Waterstone neighborhood in desirable Western Branch school district. This home is unlike any other. Amazing kitchen with loads of space and a floor plan that flows perfectly. Backyard is huge

  Samuel Sansalone Wainwright Real Estate

  2011 River Pearl Way, Chesapeake, VA 23321
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  /31

  $345,000

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

  4200 Airline Blvd, Chesapeake, VA 23321

  Come see this fantastic two-story brick home in the heart of the Bowers Hill neighborhood of Western Branch, Chesapeake! This move-in ready gem features a first-floor primary suite and two generously sized bedrooms upstairs. The oversized lot offers endless possibilities—ideal for entertaining, expanding, or adding additional outbuildings. Already on the property is a detached 2+ car garage,

  Nate Carl Keller Williams Realty Town Center

  4200 Airline Blvd, Chesapeake, VA 23321
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  /48

  $490,000

  • 5 Beds
  • 4.5 Baths
  • 3,006 Sq Ft

  2329 Drum Creek Rd, Chesapeake, VA 23321

  Welcome to 2329 Drum Creek Rd in sought-after Drum Creek Estates! This spacious ranch-style home offers two primary suites plus two additional bedrooms, cathedral ceilings in the rear living room, a formal dining room, breakfast nook, large front sitting room/foyer, oversized laundry/utility room, and a bonus office off the garage. The primary suite in the main home offers vaulted ceilings, a

  Samantha Janisch Own Real Estate LLC

  2329 Drum Creek Rd, Chesapeake, VA 23321
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  /21

  $325,000

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

  3917 Sextant St, Chesapeake, VA 23321

  This beautifully remodeled ranch offers 4 spacious bedrooms and 2 full bathrooms, thoughtfully updated for modern living. The brand-new kitchen features granite countertops, soft-close cabinets, stainless steel appliances, and modern recessed lighting that continues into the living room, which is enhanced by a stunning tray ceiling for added charm and dimension. Throughout the home, you’ll find

  Megan Oldfield World Class Realty & Property Management

  3917 Sextant St, Chesapeake, VA 23321
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  /38

  $438,900

  • 4 Beds
  • 2 Baths
  • 2,021 Sq Ft

  4621 Helensburgh Dr, Chesapeake, VA 23321

  Your Dream Home Awaits! Step into style in this beautifully updated 4-bed, 2-bath brick ranch, boasting 2,000+ sq. ft. of chic, functional living space. Whip up your next culinary masterpiece in the open-concept eat-in kitchen, decked out with sleek stainless steel appliances. Multiple living spaces—including a bright living room, cozy family room, and dedicated dining area—offer room to relax,

  Tara Haynes Green Tree Real Estate Inc

  4621 Helensburgh Dr, Chesapeake, VA 23321
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  /29

  $364,900

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  2428 Taylorwood Blvd, Chesapeake, VA 23321

  Hurry to see this lovely brick ranch home located in the desirable Taylorwood Estates neighborhood in Western Branch area of Chesapeake! Situated on a spacious wooded lot, this home features 3 bedroom, 2 baths, formal living and dining room, family room with a fireplace, custom cabinetry in large eat-in kitchen with a bay window, hardwood floors and more! Interior could use updating, but has

  Judy Farris Howard Hanna Real Estate Services

  2428 Taylorwood Blvd, Chesapeake, VA 23321
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  /23

  $229,000

  • 2 Beds
  • 2 Baths
  • 1,367 Sq Ft

  4309 Hillingdon Bend Unit 303, Chesapeake, VA 23321

  Welcome to Unit 303 Kings Pointe! Location, location, location! This beautiful, newer community is tucked right off of I-64, Exit 11B in Western Branch. Gorgeous 2 Bedroom, 2 Bathroom third/top unit with unobstructed views of nature and the community! Condo is close to all restaurants, shops and amenities! Luxury living enhanced with a clubhouse, pool, trails, grills and firepits and plenty of

  Judy Reed Judy Reed Realty

  4309 Hillingdon Bend Unit 303, Chesapeake, VA 23321
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  /43

  $525,000

  • 4 Beds
  • 3 Baths
  • 2,842 Sq Ft

  4646 Longleaf Place, Chesapeake, VA 23321

  Welcome to easy living in this beautifully upgraded, nearly new condo in a vibrant 55+ community! This home is packed with upgrades and thoughtful touches throughout featuring custom Closet Factory closets, built-in bookcases, high-end appliances, and decorative molding. Bright open-concept layout with a gourmet kitchen, oversized island, upgraded cabinetry and upgraded lighting. Spacious living

  Danielle Brinson Keller Williams Coastal Virginia Chesapeake

  4646 Longleaf Place, Chesapeake, VA 23321
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  /50

  $595,000

  • 4 Beds
  • 3 Baths
  • 2,759 Sq Ft

  5029 Cape May Loop, Chesapeake, VA 23321

  This beautiful home exudes “Pride in Ownership!” Why wait for fall when you can enjoy this beautiful home all summer? Upgrades throughout include a subway tile backsplash, granite counters, SS appliances, upgraded lighting, & a fenced-in yard perfect for your family and furry friends. Enjoy a fire on the extended outdoor patio or “dine al fresco.” The custom-made shed blends perfectly with the

  Kathy Fink BHHS RW Towne Realty

  5029 Cape May Loop, Chesapeake, VA 23321
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  /50

  $500,000

  • 4 Beds
  • 2.5 Baths
  • 2,513 Sq Ft

  4650 Longleaf Place, Chesapeake, VA 23321

  Welcome to 4650 Longleaf Pl in the Retreat at Western Branch—where modern design meets easy living. Built in 2022, this beautifully maintained home features over 2,500 sq ft, a first-floor primary suite, and a dedicated office/flex space. Enjoy an open-concept layout with neutral colors, fresh paint, and new carpet throughout. The kitchen flows seamlessly into the living and dining areas, great

  Mario Dove EXP Realty LLC

  4650 Longleaf Place, Chesapeake, VA 23321
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  /19

  $160,000

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft

  3603 Clover Meadows Dr, Chesapeake, VA 23321

  Perfect for downsizers, investors, or those needing a starter home, this 2nd-story end unit condo is being sold in AS IS condition. No repairs by seller. Includes all kitchen appliances and a stack washer/dryer. Stairway and deck to enter the unit. Driveway parking. Condo fee is $210. Per month. Quiet area located off Taylor Road in Western Branch near I-664 - minutes to shopping in Western

  Caroline McCartney BHHS RW Towne Realty

  3603 Clover Meadows Dr, Chesapeake, VA 23321
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  /29

  $2,100,000

  • Land
  • 19 Acres
  • $107,914 per Acre

  2133 Portsmouth Blvd, Chesapeake, VA 23321

  Attention Investors! Don't miss this one! 19.456 Acres of B-1 property (Neighborhood Business District) on the Chesapeake side of the GROWING Portsmouth Blvd corridor. Large New Construction Residential presence across the street & corner of Jolliff and Ports Blvd. Site road frontage 598.04 feet. Wonderful opportunity for your business! Retail, Brewery, Offices, etc. Amazon ORF2 Fulfillment

  Genine Cooper The Real Estate Group

  2133 Portsmouth Blvd, Chesapeake, VA 23321
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  /17

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  5533 Willow Lake Rd, Chesapeake, VA 23321

  Unique Opportunity in Western Branch, Chesapeake, Discover a rare opportunity to own a piece of land in the tranquil setting of Western Branch, Chesapeake. Nestled on a quiet dead-end street, this property is surrounded by beautiful wildlife, providing a serene atmosphere for nature lovers. The lot features a detached garage next to the house and a spacious barn in the back, complete with large

  Kelly Ayers Keller Williams Realty Town Center

  5533 Willow Lake Rd, Chesapeake, VA 23321
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  /19

  $415,000

  • 5 Beds
  • 2 Baths
  • 3,333 Sq Ft

  3861 Ahoy Dr, Chesapeake, VA 23321

  Take a look at this beautifully updated 3,333 sq. ft. home features 5 spacious bedrooms, 2 stylish bathrooms, and a modern kitchen with granite countertops, dark cabinetry, and updated appliances. Relax or entertain on the deck outside. Move-in ready with elegant upgrades throughout—schedule your showing today!

  Patrick Olds Long & Foster Real Estate Inc.

  3861 Ahoy Dr, Chesapeake, VA 23321
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  /2

  $160,000

  • 3 Beds
  • 1.5 Baths
  • 1,505 Sq Ft

  4072 Sloop Trail, Chesapeake, VA 23321

  A great investment opportunity. Will a little TLC this townhome could be an excellent rental property or starter home. Property is being sold "AS IS". No repairs will be done by seller.

  Jacqueline Kahle J & K Realty Group

  4072 Sloop Trail, Chesapeake, VA 23321
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  /19

  $160,000

  • 3 Beds
  • 2 Baths
  • 1,335 Sq Ft

  3568 Dunedin Dr, Chesapeake, VA 23321

  Alden Lawrence LPT Realty LLC

  3568 Dunedin Dr, Chesapeake, VA 23321
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  /27

  $455,000

  • 3 Beds
  • 2.5 Baths
  • 2,555 Sq Ft

  4639 Longleaf Place, Chesapeake, VA 23321

  Anna Paduhovich EXP Commercial LLC

  4639 Longleaf Place, Chesapeake, VA 23321
• 

  

  /22

  $579,900 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,661 Sq Ft

  2212 Sanibel Ln, Chesapeake, VA 23321

  UNBELIEVABLE INCENTIVES! This beautiful 5 bdrm Buxton model is MOVE-IN READY! Throughout this charming, tree-lined neighborhood are an assortment of exceptional amenities including a resort-style pool, community trails, pocket parks & plazas w/ outdoor seating, a playground, natural preservation areas & state-of-the-art clubhouse w/ kitchen, conference room & fitness center. This homes gourmet

  Kathy Nelms Corinth Realty LLC

  2212 Sanibel Ln, Chesapeake, VA 23321
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  /45

  $594,900 New Construction

  • 5 Beds
  • 3 Baths
  • 2,497 Sq Ft

  5015 Oriole Dr, Chesapeake, VA 23321

  Brand new construction completed in 2025! This stunning 5-bedroom, 3 full bath home offers a spacious open floor plan with soaring 9-foot ceilings that flood the space with natural light. Great for multi-generational living or guests, the first floor includes a bedroom and full bath. The heart of the home is the gourmet kitchen, featuring a massive granite center island with a large farm sink,

  Laura Rowe BHHS RW Towne Realty

  5015 Oriole Dr, Chesapeake, VA 23321
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  /5

  $529,790 New Construction

  • 4 Beds
  • 3 Baths
  • 2,880 Sq Ft

  4613 Longleaf Place, Chesapeake, VA 23321

  Discover the Lafayette floor plan in our vibrant 55+ community! This thoughtfully designed home features a spacious first floor layout with two bedroom suites, and a convenient first floor laundry room. With luxury vinyl plank flooring and an open concept living space, it's perfect for hosting and relaxing. Enjoy community amenities like lawn care, clubhouse with a pool, fitness center, cozy

  Donna Lakoski BHHS RW Towne Realty

  4613 Longleaf Place, Chesapeake, VA 23321
• 

  

  /19

  $390,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,642 Sq Ft

  4917 Apricot Way, Chesapeake, VA 23321

  Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level Laurel plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ upgraded quartz countertops, subway glass tile backsplash, soft-close drawers & under cabinet lighting. Easily

  Angela McCaskill Corinth Realty LLC

  4917 Apricot Way, Chesapeake, VA 23321
• 

  

  /4

  $512,179 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,555 Sq Ft

  3511 Elaina Way, Chesapeake, VA 23321

  Welcome to the Nansemond! A stylish 3-bedroom, 2.5-bath home designed for comfort and convenience! Enjoy a spacious first-floor primary suite, open-concept living with a cozy gas fireplace, and a well-equipped kitchen perfect for entertaining. First-floor laundry adds everyday ease, while upstairs features two bedrooms, a full bath, and a large attic for storage. Located in a vibrant community

  Donna Lakoski BHHS RW Towne Realty

  3511 Elaina Way, Chesapeake, VA 23321
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  /5

  $525,104 New Construction

  • 4 Beds
  • 3 Baths
  • 2,880 Sq Ft

  3509 Elaina Way, Chesapeake, VA 23321

  Step into comfort and style with the Lafayette! A beautifully designed 4-bedroom, 3-bath home that blends functionality with modern flair! Enjoy the ease of main-level living with a spacious first-floor primary suite and an additional bedroom with a full bath, perfect for guests or flexible use. The inviting family room, featuring a cozy gas fireplace, flows effortlessly into a well-appointed

  Donna Lakoski BHHS RW Towne Realty

  3509 Elaina Way, Chesapeake, VA 23321

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