Homes for Sale near Jolliff Middle School

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  /4

  $495,000

  • 3 Beds
  • 2.5 Baths
  • 2,214 Sq Ft

  904 Flintfield Crescent, Chesapeake, VA 23321

  Beautiful traditional style home. Located on a large lot in the Western Branch area of Chesapeake. Home features include three large bedrooms. Large family room with a fireplace. Eat in kitchen with stainless steel wireless refrigerator, stove, microwave, and washer and dryer, all convey. Dining room leads to the enormous living room. Primary bedroom includes a walk in closet. Huge

  

  Adrienne Campbell

  Keller Williams Coastal Virginia Chesapeake

  (757) 296-8807

  904 Flintfield Crescent, Chesapeake, VA 23321
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  /50

  $562,500 Open Sun 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 2,352 Sq Ft

  4621 Old Woodland Dr, Chesapeake, VA 23321

  Prepare to fall in love with this immaculate, move-in ready home on a spacious corner lot just under 1 acre with **no HOA!** Enjoy an open floor plan with hardwood floors, a gas fireplace, and pre-wired surround sound. The beautiful kitchen features granite counters, stainless steel appliances, pantry, and a large island. All appliances convey, including washer & dryer. The generous primary suite

  

  Christina Fleck

  World Class Realty

  (757) 919-8308

  4621 Old Woodland Dr, Chesapeake, VA 23321
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  /50

  $303,000

  • 3 Beds
  • 2 Baths
  • 1,799 Sq Ft

  4128 Sunkist Rd, Chesapeake, VA 23321

  Discover this spacious ranch-style home in the sought-after Cedar Grove Acres neighborhood! Nestled on a peaceful street in the desirable Western Branch area, this home offers both comfort and privacy. Step out onto the serene back deck—no rear neighbors mean uninterrupted relaxation. HUD Case# 544-345609 IE (Insured Escrow), Subject to Appraisal. Seller makes no representations or warranties as

  Susan Jenkins Better Homes&Gardens R.E. Native American Grp

  4128 Sunkist Rd, Chesapeake, VA 23321
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  /33

  $549,900

  • 4 Beds
  • 2.5 Baths
  • 2,585 Sq Ft

  4252 Raleigh Rd, Chesapeake, VA 23321

  Fully renovated 4-bedroom, 2.5 bath home blending style and function! Enjoy peace of mind with a new roof, plumbing, electrical, HVAC, and more. Inside, you'll find new flooring, a sleek modern kitchen, updated baths, fresh lighting, and open living spaces. Outside features two new decks, a fresh driveway and walkway, plus a sparkling upgraded pool. Bonus: Finished room over the garage and a

  Naty Horev BHHS RW Towne Realty

  4252 Raleigh Rd, Chesapeake, VA 23321
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  /47

  $585,000

  • 4 Beds
  • 2.5 Baths
  • 3,026 Sq Ft

  4105 Dock Landing Rd, Chesapeake, VA 23321

  Welcome to this stunning 2-story home in the sought-after Western Branch area of Chesapeake! Boasting 3,026 sq ft, this spacious residence features 4 bedrooms, 2.5 baths, & beautiful new quartz countertops that elevate the kitchen's appeal. The first level shines w/original Hardwood & LVP flooring. Eat in Kitchen opens to the living & dining rooms, add in the front office & you have a fantastic

  Lori Gomoke BHHS RW Towne Realty

  4105 Dock Landing Rd, Chesapeake, VA 23321
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  /23

  $489,000

  • 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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  /24

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,419 Sq Ft

  3973 Grand Isle Dr, Chesapeake, VA 23323

  SPACIOUS RANCH WITH FORMAL DINING ROOM AND LARGE GREAT ROOM WITH FIREPLACE. LARGE EAT-IN-KITCHEN THAT OPENS TO GREAT ROOM. LOTS OF ADDED SPACE TO ENJOY WITH AND REAR COVERED SUNROOM AND NEWER ADDED TREX DECK WITH RETRACTABLE AWNING AND LIGHTS. SPACIOUS, PRIVATE PRIMARY BEDROOM SUITE WITH DEEP BATHTUB, SEPARATE SHOWER AND SEPARATE VANITIES WITH VIEWS OF CRYSTAL LAKE! FRONT YARD SPRINKLER SYSTEM.

  Lisa Moore CENTURY 21 Nachman Realty

  3973 Grand Isle Dr, Chesapeake, VA 23323
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  /49

  $524,999

  • 4 Beds
  • 2.5 Baths
  • 2,628 Sq Ft

  2158 Seastone Trace, Chesapeake, VA 23321

  Located in a sought-after Western Branch neighborhood, this 4-bedroom, 2.5-bath home offers a seamless blend of comfort and style. A distinctive split staircase adds architectural interest, starting as one and dividing into two separate ends—one leading to the kitchen, the other to the front entry. The open-concept kitchen flows into a spacious backyard with a gorgeous patio, perfect for

  Ciara Whedbee Keller Williams Coastal Virginia Chesapeake

  2158 Seastone Trace, Chesapeake, VA 23321
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  /30

  $530,000 Open Sun 1PM - 2PM

  • 4 Beds
  • 2 Baths
  • 2,658 Sq Ft

  2019 River Pearl Way, Chesapeake, VA 23321

  This beautiful one-story home with an open floor plan will not disappoint! Natural lighting, wooded backyard, and a quiet neighborhood. The home has been painted from floor to ceiling including outside trim. Brand new flooring throughout along with many other updates.

  Tracy Tomovik COVA Home Realty

  2019 River Pearl Way, Chesapeake, VA 23321
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  /42

  $600,000

  • 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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  /35

  $530,000

  • 4 Beds
  • 3.5 Baths
  • 2,472 Sq Ft

  3925 Grand Isle Dr, Chesapeake, VA 23323

  This stunning 4 bedroom, 3.5 bath, transitional style home which has been completely updated in the past 2 years is nestled on a serene lake in the beautiful Nassau Subdivision.  This home is perfect for entertaining, featuring a spacious deck with tranquil water views with an open-concept first floor. The open kitchen has new granite countertops, kitchen island and stainless steel

  Lisabelén Sanchez Aweigh Real Estate

  3925 Grand Isle Dr, Chesapeake, VA 23323
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  /45

  $599,900 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 EXP Realty LLC

  5015 Oriole Dr, Chesapeake, VA 23321
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  /2

  $609,775 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,416 Sq Ft

  MM Sorrento Rd, Suffolk, VA 23435

  The Sorrento floorplan, from 2416 sq ft to 3133 sq ft, offers ranch-style convenience with spacious, elegant design. A dramatic 2-story Family Room with sloped ceilings is the heart of the home, seamlessly connecting to the Foyer, Dining Room, Kitchen, and Breakfast Nook, ideal for everyday living and entertaining. Add an optional Sunroom with open fireplace for even more natural light and

  Kelly Moran BHHS RW Towne Realty

  MM Sorrento Rd, Suffolk, VA 23435
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  /24

  $696,900 New Construction

  • 5 Beds
  • 3.5 Baths
  • 4,005 Sq Ft

  MM Rosewood 2, Chesapeake, VA 23321

  The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike/walking paths, a community center, a swimming pool, and tree-lined sidewalks. The Rosewood floor plan, offers grand features like James Hardie Plank siding, a covered porch, gourmet

  Steve Freeman RHOAD & CO.

  MM Rosewood 2, Chesapeake, VA 23321
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  /49

  $529,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,209 Sq Ft

  MM Bayberry, Chesapeake, VA 23321

  Welcome to the Bayberry, which offers open-concept living without compromising comfort. With features like a large gourmet kitchen with granite countertops & stainless steel appliances. Walk-in closets in 3 bedrooms, family room with open loft, fireplace, downstairs master bedroom and so much more. You also have the option to build any variety of our models and completely customize them to suit

  Christian Ramirez RHOAD & CO.

  MM Bayberry, 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 primary

  Jennifer Smithson Light Box Realty

  4237 Woodland Dr, Chesapeake, VA 23321
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  /23

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,735 Sq Ft

  5208 Askew Rd, Chesapeake, VA 23321

  Rare opportunity. 1 owner brick ranch on double lot in Western Branch. Property needs cosmetic updates and is sold "as is". Hardwood floors under carpets. 3 bedroom and 2 full bathrooms. Spacious living, dining and family rooms. Masonry fireplace and sunroom access in family room. Propane heating system approximately 10 years old. Central AC. 2 car attached garage has pull down ladder to attic.

  Sandy Preiser BHHS RW Towne Realty

  5208 Askew Rd, Chesapeake, VA 23321
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  /16

  $255,000

  • 3 Beds
  • 2 Baths
  • 1,323 Sq Ft

  3904 Starboard Rd, Chesapeake, VA 23321

  This charming single family home located at 3904 Starboard Rd in Chesapeake, VA was built in 1964 and boasts 2 bathrooms with a total of 1,323 sq.ft. of finished living space. Situated on a spacious lot spanning 9,104 sq.ft., this property offers plenty of room for outdoor enjoyment. With its convenient location and classic design, this home is perfect for those seeking a comfortable and

  Debbie Crevier Kent Cottage Street Realty LLC

  3904 Starboard Rd, 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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  /31

  $349,900

  • 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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  /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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  /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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  /11

  $225,000

  • Land
  • 5.00 Acres
  • $45,000 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 - 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 necessities and still enjoy country privacy. There is a septic in front of

  LeAnn Amory BHHS RW Towne Realty

  4729 Sunray Ave, Chesapeake, VA 23321
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  /3

  $24,900

  • Land

  .29ac Coffman Blvd, Chesapeake, VA 23321

  Potential for Farmers Market, Green House, Garden and Light Storage.

  Karen Swaney Salty Dog Realty LLC

  .29ac Coffman Blvd, Chesapeake, VA 23321
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  /19

  $420,000

  • 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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  /3

  $337,500

  • 2 Beds
  • 2 Baths
  • 1,711 Sq Ft

  4262 Schooner Trail, Chesapeake, VA 23321

  For sale: This original brick house sits on over two acres of picturesque, navigable waterfront. The property offers a tranquil setting with a private drive and ample space to enjoy nature. The house features: 2 bedrooms with potential for third, a large kitchen and den, a formal living, 2 bathrooms, one which has been completely renovated, and a full basement for additional storage or potential

  Candy Dennis Long & Foster Real Estate Inc.

  4262 Schooner Trail, 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

  $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
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  /19

  $419,900 New Construction

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

  4934 Breck Ln, 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/ granite countertops & subway tile backsplash. Easily maintained & durable LVP

  Angela McCaskill Corinth Realty LLC

  4934 Breck Ln, Chesapeake, VA 23321
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  /19

  $421,900 New Construction

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

  4938 Breck Ln, 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/ soft-close cabinetry & drawers, quartz countertops, subway tile backsplash, & under

  Angela McCaskill Corinth Realty LLC

  4938 Breck Ln, Chesapeake, VA 23321
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  /27

  $856,953 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,098 Sq Ft

  1248 Jolliff Rd, Chesapeake, VA 23321

  WALK OUT ATTIC NOW ADDED! The Lee model is under construction and will be ready for a Fall move in. This home will have an extensive list of included features. A few highlights: 3rd car garage. Primary suite on first floor with sitting room. Extended kitchen to include an @6'x9' walk in pantry. Front and Rear covered porch overlooking 2.9 acres! The interior of the home will be embellished with

  Deana Renn AtCoastal Realty

  1248 Jolliff Rd, Chesapeake, VA 23321
• 

  

  /19

  $431,900 New Construction

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

  4933 Apricot Way, Chesapeake, VA 23321

  Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake.

  Angela McCaskill Corinth Realty LLC

  4933 Apricot Way, Chesapeake, VA 23321
• 

  

  /19

  $426,900 New Construction

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

  4929 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 tri-level Ashbury plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ soft-close cabinetry & drawers, granite countertops, subway tile backsplash, & under cabinet lighting.

  Angela McCaskill Corinth Realty LLC

  4929 Apricot Way, Chesapeake, VA 23321
• 

  

  /19

  $382,900 New Construction

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

  4923 Apricot Way, De Soto, 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 tile backsplash, soft-close drawers & under cabinet lighting. Easily

  Angela McCaskill Corinth Realty LLC

  4923 Apricot Way, De Soto, VA 23321
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  /4

  $449,900 New Construction

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

  MM Nansemond, Chesapeake, VA 23321

  Welcome to the Nansemond! A beautifully designed home that blends comfort and functionality! This three-bedroom, 2.5-bath layout offers a first-floor primary suite, providing convenience and privacy. The open-concept family room with a cozy gas fireplace flows seamlessly into a well-appointed kitchen, creating the perfect space for everyday living and entertaining. With first-floor laundry to add

  Donna Lakoski BHHS RW Towne Realty

  MM Nansemond, Chesapeake, VA 23321
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  /5

  $615,900 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,060 Sq Ft

  MM Magnolia 2 W, Chesapeake, VA 23321

  The Magnolia II is a grand floor plan with a 2 story foyer as you enter! Formal Living room, large family room that opens to the Kitchen and Eating Area. Downstairs utility space that allows for the perfect 'Mudroom. 5 spacious bedrooms & 3 baths on the 2nd & 3rd floor with a finished room over the garage. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with

  Steve Freeman RHOAD & CO.

  MM Magnolia 2 W, Chesapeake, VA 23321
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  /40

  $585,900 New Construction

  • 5 Beds
  • 3.5 Baths
  • 2,745 Sq Ft

  MM Bradford 2, Chesapeake, VA 23321

  If you enjoy a timeless, classic, or traditional design... our Bradford model may be the one for you. The Bradford is designed with the focus of everyday living and functionality. Enjoy 3-story living with 5BR's & 3.5 baths @2745 sq ft w/3rd-floor option added to our standard Bradford. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches,

  Christian Ramirez RHOAD & CO.

  MM Bradford 2, Chesapeake, VA 23321
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  /46

  $576,900 New Construction

  • 5 Beds
  • 3 Baths
  • 2,755 Sq Ft

  MM Dogwood 2, Chesapeake, VA 23321

  Welcome to The Dogwood, our most popular ranch model! This highly desired floor plan offers 4 bedrooms, 2 baths, and 2335 sq ft. Perfect first home or forever home! The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, a community playground, water features, a sports

  Christian Ramirez RHOAD & CO.

  MM Dogwood 2, Chesapeake, VA 23321
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  /17

  $559,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  MM Bayberry 2, Chesapeake, VA 23321

  Welcome to the Bayberry II, offering open-concept living without compromising comfort. Features include a large gourmet kitchen with w/granite countertops & stainless steel appliances. Walk-in closets in 3 bedrooms, family room with open loft, fireplace, downstairs primary bedroom and so much more. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered

  Steve Freeman RHOAD & CO.

  MM Bayberry 2, Chesapeake, VA 23321

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