Chesapeake, VA Homes for Sale

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  /28

  $795,000

  • 6 Beds
  • 3.5 Baths
  • 3,955 Sq Ft

  804 River Strand, Chesapeake, VA 23320

  Well-maintained, spacious home on a prime lot in the beautiful Riverwalk community. New Roof, all new Windows, new paint interior and exterior, and new carpet in 2026! Beautiful wood floors in living and dining areas. Six bedrooms, 3 full and 1 half baths. Designed for those who love to entertain, the expansive floor plan offers elegant gathering spaces, abundant natural light, a formal butler

  Frank Mangum Frank Mangum Realty Inc.

  804 River Strand, Chesapeake, VA 23320
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  /3

  $60,000

  $15K PRICE DROP

  • Land
  • 3,920 Sq Ft
  • $666,667 per Acre

  29 Gale Ave, Chesapeake, VA 23323

  This 40’ x 105’ cleared buildable corner lot offers an excellent opportunity to build your dream home in the desirable Deep Creek area of Chesapeake. Zoned R6, the property has access to city utilities at the street, making the building process more convenient and efficient. No HOA! Ideally located near major highways and interstate access, as well as shopping, restaurants, and schools, this lot

  Vanda Kennedy World Class Realty & Prop Mgmt

  29 Gale Ave, Chesapeake, VA 23323
• 

  Price To Be Determined

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,737 Sq Ft

  The Willow Plan at Cedar Glen, Chesapeake, VA 23320

  Home Associates Of Virginia, Inc. Builder

  1053 Butte Ln Unit 39639151, Chesapeake, VA 23320
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  /46

  $569,900

  $5K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,414 Sq Ft

  1916 Orangewood Rd, Chesapeake, VA 23323

  Located in the highly sought-after Grassfield School District, this spacious home offers over 2,400 square feet of comfortable living space with 4 bedrooms, a dedicated study, and 2.5 bathrooms. The thoughtfully designed floor plan features a bright and inviting sunroom sitting area just off the kitchen. Continue outside to enjoy the large backyard, offering plenty of room for gardening, pets, or

  Steve Marable Iron Valley Real Estate HR

  1916 Orangewood Rd, Chesapeake, VA 23323
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  /46

  $916,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,734 Sq Ft

  109 Ballahack Rd, Chesapeake, VA 23322

  HURRY; THIS HOME WON’T LAST!!! If you are looking for privacy this single family home situated on a spacious 1-acre lot with “no” HOA fee & convenient interstate access is for you!!! The attention to detail & custom upgrades are simply “impeccable”! Home features double door front entrance, 3 bedrooms including that much sought after “first floor primary” with a luxurious spa inspired bath,

  Judy Duke Wainwright Real Estate

  109 Ballahack Rd, Chesapeake, VA 23322
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  /39

  $649,900

  • 4 Beds
  • 3 Baths
  • 2,993 Sq Ft

  413 Wickwood Dr, Chesapeake, VA 23322

  Nestled on a quiet double cul-de-sac in the heart of Great Bridge, this beautifully maintained all-brick home offers the perfect blend of timeless character and modern comfort. Situated on a lush corner lot this custom 4-bedrm, 3-bath home features spacious bedrooms, hardwood floors, & custom updates designed for today's lifestyle. The renovated kitchen serves as the heart of the home, while the

  Thais Sebastia Atlantic Sothebys Int'l Realty

  413 Wickwood Dr, Chesapeake, VA 23322
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  /38

  $449,900

  New Construction

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

  4605 Longleaf Place, Chesapeake, VA 23321

  Toss the lawn mower! It's too hot for that. It's time for low-maintenance living and relaxing by the pool at The Retreat at WesternBranch. This move-in ready, new construction Lafayette floor plan features a first-floor primary suite, a huge island kitchen opento the living room, and a first-floor office or guest room with a full bath. Upstairs you'll find a spacious loft plus two

  Monique McClellan BHHS RW Towne Realty

  4605 Longleaf Place, Chesapeake, VA 23321
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  /50

  $494,500

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,248 Sq Ft

  1431 Thistlewood Ln, Chesapeake, VA 23320

  Welcome to The Retreat at Greenbrier in Chesapeake, a 55+ community! This beautiful home offers incredible value with a fresh, move-in-ready feel, featuring new Coretec tiles in the kitchen and a desirable first-floor primary suite, spacious en-suite bath, and large walk-in closets. Tons of natural light with an easy, level floor plan provides comfortable accessibility and everyday convenience.

  Tana Hipp LPT Realty LLC

  1431 Thistlewood Ln, Chesapeake, VA 23320
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  /30

  $795,425

  New Construction $11K PRICE INCREASE

  • 5 Beds
  • 3.5 Baths
  • 3,089 Sq Ft

  2032 Charwood Dr, Chesapeake, VA 23320

  Location backing mature tree line, ready early 2027, still time to customize. The Hawthorne floor plan offers flexibility & spacious living, making it the largest & most adaptable 2-story home at Crestfield. With an impressive 3,089 square feet, this open-concept home offers 5 bedrooms, including dual owner’s suites & 3.5 baths. The kitchen features quartz countertops, stainless steel appliances,

  Morgan Xenos Dragas Companies Realty Inc

  2032 Charwood Dr, Chesapeake, VA 23320
• 

  

  /43

  $335,000

  • 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
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  /8

  $375,000

  • 4 Beds
  • 2 Baths
  • 2,029 Sq Ft

  305 Providence Rd, Chesapeake, VA 23325

  Welcome to this charming 4 bedroom brick ranch located in Chesapeake's desirable Georgetown neighborhood. This home offers a spacious backyard, creating the perfect space for relaxing or entertaining family and friends. Inside you will find stylish updates including tile in secondary bathroom, ceiling fans, warm wood flooring, and a newer furnace (2020). Seller is offering $20,000.00 towards

  Drucilla Griffin The James Allen Group

  305 Providence Rd, Chesapeake, VA 23325
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  /5

  $750,000

  Coming Soon

  • 6 Beds
  • 3.5 Baths
  • 4,811 Sq Ft

  1548 Waterside Dr N, Chesapeake, VA 23320

  Spacious 4,899 sf lakefront home offering 6 bedrooms and 3.5 baths with an exceptional floor plan designed for comfortable living and entertaining. The expansive 1st floor primary suite provides a private retreat, while a 2nd floor ensuite is great for guests or multigenerational living. A massive great room with stunning lake views serves as the heart of the home, flowing seamlessly to a large

  Rhonda Shelton BHHS RW Towne Realty

  1548 Waterside Dr N, Chesapeake, VA 23320
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  /49

  $515,000

  • 4 Beds
  • 2.5 Baths
  • 2,018 Sq Ft

  801 Winter King Ct, Chesapeake, VA 23323

  WELCOME HOME TO THIS BEAUTIFULLY UPDATED WATERFRONT PROPERTY TUCKED AWAY ON A QUIET CULDESAC. RECENT UPDATES INCLUDE LVP FLOORS, SOLID OAK STAIRS, FRESH PAINT THROUGHOUT. NEW 6 BURNER GAS RANGE WITH BEAUTIFUL HAND MADE BUTCHER BLOCK COUNTERS SURROUNDING. NEWER GAS FIREPLACE COMPONENTS, WATER FILTRATION SYSTEM AND RECENTLY SERVICED HVAC. BACKYARD FEATURES AN ABOVE GROUND POOL WITH POOL HOUSE AND

  Sheri Pynn Creed Realty

  801 Winter King Ct, Chesapeake, VA 23323
• 

  /2

  $16,700

  • Land
  • 10,018 Sq Ft
  • $72,609 per Acre

  1536 Tuck St St, Chesapeake, VA 23322

  Three adjoining wooded residential lots available as a package in the established Hillcrest area of South Chesapeake. Includes 1534, 1536 & 1538 Tuck St. These contiguous parcels offer a unique opportunity for builders, investors, or buyers looking to get multiple lots for future development or personal use. Conveniently located near S. Battlefield Blvd and Johnstown Road with access to nearby

  Nancy Bui Keller Williams Realty Twn Ctr

  1536 Tuck St St, Chesapeake, VA 23322
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  /43

  $750,000

  • 3 Beds
  • 3 Baths
  • 2,464 Sq Ft

  3536 Riverwood Crescent, Chesapeake, VA 23322

  Updated farmhouse charm on nearly 4 acres! This traditional home offers 3 bedrooms, 3 full baths, and a spacious finished room over the garage. Outside, enjoy designated pastures, a barn, and a detached two-car garage with a framed upper level ready for future expansion or flexible use. A unique property with room to enjoy the outdoors and endless possibilities. Back on Market due to no fault of

  Crystal Lance BHHS RW Towne Realty

  3536 Riverwood Crescent, Chesapeake, VA 23322
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  /45

  $649,900

  Open Sat 12PM - 3PM $29K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,114 Sq Ft

  2008 Burson Dr, Chesapeake, VA 23323

  Welcome Home! A Stephen Alexander build where timeless design meets the comfort of everyday living. Tucked away on nearly half an acre in sought-after Grassfield, this beautifully cared-for home has been lovingly maintained by its original owners since day one. 4 spacious bedrooms, 2.5 baths, and nearly 3,200 sqft of inviting space with room for both quiet mornings and lively gatherings. The

  Emily Cockrell Lee S Halyard & Assoc Realtor

  2008 Burson Dr, Chesapeake, VA 23323
• 

  Price To Be Determined

  New Construction

  • 5 Beds
  • 3 Baths
  • 2,725 Sq Ft

  The Ashford Plan at Riverview Landing, Chesapeake, VA 23322

  Wetherington Homes Builder

  324 Riverview Rd Unit 39644726, Chesapeake, VA 23322
• 

  

  /21

  $437,400

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,076 Sq Ft

  670 Allery Rd, Chesapeake, VA 23320

  Now accepting presale reservations, pending state condo document approval. Estimated Fall delivery. The Bristol plan offers 2 spacious owner suites on 3rd floor with convenient 3rd floor laundry. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. First floor flex space with 2-car rear-loading garage.

  Dragas Companies Builder

  670 Allery Rd, Chesapeake, VA 23320
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  /29

  $425,000

  $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,225 Sq Ft

  808 Monroe Ct, Chesapeake, VA 23320

  Welcome to this beautifully maintained open-concept home in the heart of Greenbrier! This move-in-ready home offers a spacious layout with separate living and dining rooms, plus a warm family room that opens to the updated kitchen—perfect for everyday living and entertaining.Recent 2025 updates include a new HVAC system, granite countertops throughout, LED recessed lighting, upgraded ceiling

  Jeannette Johnson Swell Realty Co

  808 Monroe Ct, Chesapeake, VA 23320
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  /27

  $399,900

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,794 Sq Ft

  1400 Fentress Rd, Chesapeake, VA 23322

  Step into a timeless sanctuary nestled on a serene 1-acre lot, this charming 4-bedroom, 2-bathroom home offers the perfect blend of tranquility and convenience. Enjoy the privacy and peace of country living while still being within easy reach of city amenities. Step inside to find spacious interiors filled with natural light and cozy ambiance. Originally built circa 1898, this property exudes

  David Perry David Perry Realty LLC

  1400 Fentress 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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  /14

  $982,800

  • Land
  • 12.29 Acres
  • $80,000 per Acre

  1928 Moses Grandy Trail, Chesapeake, VA 23323

  Parcel A- residential lot on the waterway. Condemned home & small cemetery on premises. 12.285 ac in the heart of grassfield, perfect for building a home on a 15,000 sq foot lot and have privacy all around you. Parcels B,C & D are also available

  Carmon Pizzanello BHHS RW Towne Realty

  1928 Moses Grandy Trail, Chesapeake, VA 23323
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  /49

  $645,000

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,681 Sq Ft

  2101 Beeblossom Ln, Chesapeake, VA 23323

  Experience the lifestyle you've been searching for in one of Chesapeake's most desirable communities, just minutes from top-rated Grassfield High School. This beautifully maintained home welcomes you with a charming front porch and gleaming hardwood floors throughout the main level. A versatile flex room that can be used for a home office, playroom, or sitting area, while the formal dining room

  Allen Boone Redfin Corporation

  2101 Beeblossom Ln, Chesapeake, VA 23323
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  /26

  $320,000

  $5K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,620 Sq Ft

  1535 Lyons Ave, Chesapeake, VA 23324

  Charming ranch home with 3 bedrooms and 1.5 bathrooms, new LVP flooring and paint, and overlooking a pond in the fenced backyard. Inquire today!

  Joshua Britt Prodigy Realty

  1535 Lyons Ave, Chesapeake, VA 23324
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  /16

  $231,900

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  919 Decatur St, Chesapeake, VA 23324

  Welcome home to this charming 3 bedroom, 2 full bath single-family home! It offers over 1,000 square feet of comfortable living space. Situated on a 0.12-acre lot, this home features a functional floor plan. Conveniently located with quick access to major highways, military bases, shopping, dining, and entertainment, you'll enjoy an easy commute and all the conveniences of the area. Whether

  Jonathan Melvin Benham Real Estate LLC

  919 Decatur St, Chesapeake, VA 23324
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  /38

  $450,000

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  2904 Sir Walter Crescent, Chesapeake, VA 23321

  Fantastic large brick home in Point Elizabeth! 4 bedrooms and 2 and a half bathrooms! Large Family room with cathedral ceilings. Lots of storage space. Hardwood floors underneath the carpet. Two gas fireplaces in separate living areas. Beautiful big screened porch to relax in the evenings! Large, fenced backyard with shed. Woods and walking trails located behind the privacy fence! Located in

  Cheryl Huotte Metro Brokers of Hampton Roads

  2904 Sir Walter Crescent, Chesapeake, VA 23321
• 

  /2

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,668 Sq Ft

  2008 Girard Ave, Chesapeake, VA 23323

  Own the end of the street! Tucked away in Deep Creek, this rare 7 parcel package spans both sides of Girard Avenue and offers a surprising sense of privacy within an established Chesapeake neighborhood. This residential listing represents 2 of the 7 parcels and includes the existing home, which conveys strictly as is. The remaining 5 parcels are offered through the coordinated land listing

  Nichole Douillard RE/MAX Ultra

  2008 Girard Ave, Chesapeake, VA 23323
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  /35

  $345,900

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

  4107 River Breeze Cir, Chesapeake, VA 23321

  Beautifully updated detached end-unit condo in the desirable River Breeze community! Enjoy the privacy and feel of a single-family home with the convenience of low-maintenance condo living. This move-in-ready home features a new roof (2026), luxury vinyl plank flooring (2026), fresh interior paint, and a new privacy fence. The open, bright interior offers a welcoming atmosphere with modern

  Chaidra Garcia Iron Valley Real Est Norfolk

  4107 River Breeze Cir, Chesapeake, VA 23321
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  /37

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,374 Sq Ft

  3136 Joseph Ave, Chesapeake, VA 23324

  Welcome to 3136 Joseph Ave, a charming single-level home offering 3 bedrooms, 2 full bathrooms, and 1,374 square feet of comfortable living space in Chesapeake's established South Norfolk community. This well-maintained ranch features a functional floor plan designed for both everyday living and entertaining. The spacious living areas flow seamlessly into the kitchen and dining space, while the

  Brandon Allen River City Elite Properties - Real Broker

  3136 Joseph Ave, Chesapeake, VA 23324
• 

  

  /50

  $625,000

  $75K PRICE DROP

  • 6 Beds
  • 3.5 Baths
  • 2,802 Sq Ft

  3504 Old Mill Rd, Chesapeake, VA 23323

  This Six Bedroom, Three and a Half Bathroom, Near New Construction Ranch Home is Move In Ready for its Next Owner. Located on 1.53 Acres of Waterfront Land, it is Perfect for Multi-Generational Living, Having Two First Floor Bedrooms with Full Ensuite Baths. The Beautiful Primary Bedroom Features Double Sinks in the Bath, Tiled Shower, a Large Walk-In Closet, and Direct Access to the Back Deck.

  Angela Kennedy 1st Class Real Estate Integrity

  3504 Old Mill Rd, Chesapeake, VA 23323
• 

  

  /35

  $439,900

  • 4 Beds
  • 2 Baths
  • 1,864 Sq Ft

  4117 Hawksley Dr, Chesapeake, VA 23321

  Do not look any further, this wonderful brick ranch is just waiting for you! Make this your home with 4 spacious bedrooms, 2 full baths, large living room with electric F/P and HW floors, dining room for all your family meals, family room with electric F/P. The kitchen has breakfast bar and all appliances convey, Large 2 car garage. You will be delighted with the backyard deck or enjoy the 4

  Kelle Foster The Real Estate Group

  4117 Hawksley Dr, Chesapeake, VA 23321
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  /42

  $597,900

  New Construction

  • 5 Beds
  • 2.5 Baths
  • 3,351 Sq Ft

  The Everest Plan at Walker Grove, Chesapeake, VA 23321

  The Everest floor plan lives up to its name, allowing every member of the family to experience spacious living. This prominent 3,351-square-foot home gives you an open-concept living area. It includes a great room connected to the kitchen, which includes a large island and a roomy pantry to the side. Just past the pantry is a separate dining room that can be used and personalized to your

  Chesapeake Homes Builder

  1905 Paw Place Unit 41447394, Chesapeake, VA 23321
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  /26

  $499,990

  New Construction $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,462 Sq Ft

  2213 Edwin Dr, Chesapeake, VA 23322

  The Asheville is a beautifully designed quad-style home offering 1,462 square feet of single-level living at its finest. Featuring two spacious bedrooms and two full bathrooms, this home exudes a charming cottage-like feel that’s perfect for comfortable living. A welcoming covered front porch leads into a spacious living room with a cozy fireplace, setting the tone for relaxation. The heart of

  D.R. Horton Builder

  2213 Edwin Dr, Chesapeake, VA 23322
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  /48

  $530,000

  Open Fri 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,106 Sq Ft

  1417 Blairwood Ln, Chesapeake, VA 23320

  Beautiful move in ready home in an established neighborhood. Lots of recent upgrades - hardwood floors, countertops, HVAC, Water heater, and more! Perfect home for the 55 and up client - all one level, detached home, clubhouse, pool, water view from the back patio. Two car garage and so much more!

  Frances Germanos Own Real Estate LLC

  1417 Blairwood Ln, Chesapeake, VA 23320
• 

  

  /4

  $190,000

  • 2 Beds
  • 2.5 Baths
  • 1,254 Sq Ft

  747 Ridge Cir, Chesapeake, VA 23320

  Unlock incredible potential with this two-bedroom, two-bathroom condo, offering a fantastic blank canvas for investors, flippers, or homeowners looking to customize their own space. The main living area features a bright, open-concept layout with wood floors, a cozy fireplace, and sliding glass doors that open to a private patio. The adjacent kitchen features white cabinetry and a convenient

  Robert Thompson EXP Realty LLC

  747 Ridge Cir, Chesapeake, VA 23320
• 

  Price To Be Determined

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,623 Sq Ft

  The Bayberry Plan at Riverview Landing, Chesapeake, VA 23322

  Wetherington Homes Builder

  324 Riverview Rd Unit 39644644, Chesapeake, VA 23322
• 

  

  /27

  $465,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,011 Sq Ft

  MM Mesa Loop, Chesapeake, VA 23320

  2-B-built: Customize Your New LuxuryTownhome w/2-car garage, covered entry,fenced front yard w/gate to multi trail,covered entry.LVP floors select areas. 2nd floor:Kitchen center island w/shiplap, GE Profile Stainless appliances w/ refrigerator,pantry,living area w/linear fireplace and shiplap surround w/ built ins,dining area access to covered front deck.3rd flr: Primary:tile shower , dual

  Donna Melzer The Real Estate Group

  MM Mesa Loop, Chesapeake, VA 23320
• 

  

  /50

  $550,000

  $15K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,063 Sq Ft

  1113 Crystalwood Cir, Chesapeake, VA 23320

  Looking for space? This spacious home offers over 3,000 sq ft of living space 5 bedrooms and 3.5 baths. There is a first-floor primary suite and an oversized bonus room which could be a 6th bedroom. The downstairs flooring and carpet was installed in 2024. The family room has a cozy stone gas fireplace. The large eat-in kitchen features stainless steel appliances and plenty of cabinet space.

  Heather Meyers LPT Realty LLC

  1113 Crystalwood Cir, Chesapeake, VA 23320
• 

  /2

  $7,334

  • Land
  • 10,018 Sq Ft
  • $31,887 per Acre

  Lot 35 Trinkle St, Chesapeake, VA 23322

  Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the

  Dustin Floyd Howard Hanna Real Estate Svcs.

  Lot 35 Trinkle St, Chesapeake, VA 23322
• 

  

  /25

  $239,000

  • 2 Beds
  • 2 Baths
  • 1,236 Sq Ft

  724 Sail Fish Quay, Chesapeake, VA 23320

  Back on market at no fault due to seller! Fantastic first floor condo in sought after Riverwalk. This 2 bed, 2 bath condo features a gas fire place,private patio, and fresh paint throughout. Seller offering $500 home warranty. This home provides ease of living while offering incredibleamenities for activity and relaxation. You will love the huge pool, gorgeous clubhouse,

  Jazmine Hall LPT Realty LLC

  724 Sail Fish Quay, Chesapeake, VA 23320

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