36

Deep Creek-Portsmouth Houses for Sale with Garage

Section Image Section Image
  • /46

    $619,900

    • 4 Beds
    • 2.5 Baths
    • 2,420 Sq Ft

    2115 Tall Pine Dr, Chesapeake, VA 23323

    Charming 4-bed, 2.5-bath home in Summerwood, located in the desirable Grassfield school district. This well-maintained home features an open-concept layout with granite countertops, stainless steel appliances, gas stove, 8-ft island, and pantry. The morning room overlooks a private wooded backdrop. The spacious primary suite includes a walk-in closet and en suite bath. Enjoy a fenced backyard

    Agent Photo

    Daniel Parrish

    Real Broker LLC

    (757) 505-7109

    2115 Tall Pine Dr, Chesapeake, VA 23323
  • /10

    $793,900

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

    1918 Mccoy Rd, Chesapeake, VA 23323

    STUNNING Spec Home TO BE BUILT by award-winning builder! This 4-bedroom beauty offers ensuite baths for all, upscale finishes throughout, and light-filled living spaces with oversized windows. Entertainers kitchen - Quartz counters, custom backsplash, GE Cafe; appliances, soft-close cabinetry, and a custom range hood. Enjoy 10' ceilings on the midlevel, an impressive stair tower with oak treads,

    Monique Darling BHHS RW Towne Realty

    1918 Mccoy Rd, Chesapeake, VA 23323
  • /50

    $579,900

    • 5 Beds
    • 3 Baths
    • 2,549 Sq Ft

    2130 Chesterfield Loop, Chesapeake, VA 23323

    Spacious and inviting, this 5-bedroom, 3-bath, 2-story home offers 2,549 sq ft of comfortable living. A desirable first-floor bedroom and full bath provide flexibility for guests or a home office. The updated kitchen and bath flooring, open kitchen-to-living room layout, and abundance of natural light create a warm and welcoming feel. Enjoy both an eat-in kitchen and a formal dining room, plus a

    Lori Gomoke BHHS RW Towne Realty

    2130 Chesterfield Loop, Chesapeake, VA 23323
  • /35

    $470,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 2,088 Sq Ft

    509 Lake Crest Dr, Chesapeake, VA 23323

    This spacious home is great for a large or growing family and wonderful for entertaining guests. Located in a desirable area with top-rated schools, it offers the comfort, convenience, and value you've been looking for! The home features bright, inviting, abundant natural lighting; brand new carpets upstairs; freshly painted; solid wood cabinets with stainless steel appliances, and pantry in the

    Patty Bills BHHS RW Towne Realty

    509 Lake Crest Dr, Chesapeake, VA 23323
  • /43

    $625,000

    • 5 Beds
    • 3 Baths
    • 2,733 Sq Ft

    1820 Rockwood Dr, Chesapeake, VA 23323

    Welcome to this modern, fully renovated home in Grassfield's Summer Park neighborhood! **Open House on Saturday, 10/13 from 12-2pm**This is a 5 bedroom, 3 bath home, is on a large open floor plan with built-in storage cubbies, a first floor primary, and an optional home office on the first floor. The second floor boasts a HUGE primary with walk in shower, 3 additional large bedrooms, and

    Courtney Harding Iron Valley Real Estate Prestige

    1820 Rockwood Dr, Chesapeake, VA 23323
  • /50

    $580,000

    • 5 Beds
    • 2.5 Baths
    • 2,839 Sq Ft

    2150 Docking Post Dr, Chesapeake, VA 23323

    Pride of ownership is evident throughout this beautiful transitional home in a quiet cul-de-sac. Large backyard ready for you to design and create your own private oasis! 5-BDRMS, 2.5-BATHS. Awesome open floor plan w/ cathedral ceilings in the foyer, spacious sun room, and a cozy breakfast nook w/ bay windows. The huge primary bdrm will be your own personal retreat w/ its recently updated ensuite

    Jennifer Johnson Signature Homes

    2150 Docking Post Dr, Chesapeake, VA 23323
  • /49

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 2,551 Sq Ft

    1725 Burson Dr, Chesapeake, VA 23323

    Beautiful two-story single-family home located in the Parkview subdivision. Built in 2014, this residence offers 2,400 square feet of living space on a 0.31-acre lot. It features 4 bedrooms and 2.5 bathrooms, with a layout that includes an open-concept kitchen, dining, and family room area. The kitchen is equipped with granite countertops, stainless steel appliances, a large pantry, and a center

    Megann Dewey Signature Homes

    1725 Burson Dr, Chesapeake, VA 23323
  • /47

    $559,500

    • 4 Beds
    • 2.5 Baths
    • 2,114 Sq Ft

    1758 Watershed Ct, Chesapeake, VA 23323

    Solar-powered savings, fresh updates, and an assumable VA loan opportunity—this home delivers on every detail. Located in the Grassfield School District, this 4-bedroom, 2.5-bath house blends comfort and efficiency with solar panels (will convey paid-off). A versatile front room offers flexible use, while the kitchen features white cabinetry, quartz countertops, a subway tile backsplash, and

    Allison Samson Broadsight Realty

    1758 Watershed Ct, Chesapeake, VA 23323
  • /50

    $510,000

    • 4 Beds
    • 2.5 Baths
    • 2,068 Sq Ft

    2139 Sunset Maple Ln, Chesapeake, VA 23323

    Welcome to 2139 Sunset Maple, located in beautiful Deer Crossing neighborhood. Feels like country, looks like HOME SWEET HOME. Some features that make this premier living include; OPEN FLOOR PLAN, NEW TANKLESS WATER HEATER, HEATED FLOOR in the primary bathroom and REMOTE CONTROL WINDOW SHADE in the living room. EXTENSIVE SHELVING in the garage. LOTS of storage space! Updated and ready for you to

    Ray Duncan ERA Real Estate Professionals

    2139 Sunset Maple Ln, Chesapeake, VA 23323
  • /20

    $480,000

    • 5 Beds
    • 3.5 Baths
    • 2,354 Sq Ft

    1415 Gust Ln, Chesapeake, VA 23323

    Explore the many possibilities of this unique property. It is comprised of 2 houses, 2 garages, 2 sheds, 2 electric meters, a deck, a patio & plenty of parking. House #1 has 3 bedrooms and 2.1 baths. House #2 has 2 bedrooms and 1 bath. Qualified buyers call to make an appointment for a private showing.

    Sandy Nance BHHS RW Towne Realty

    1415 Gust Ln, Chesapeake, VA 23323
  • /40

    $489,900

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    2505 Calonia Arch, Chesapeake, VA 23323

    Welcome to this charming 3-bedroom, 2.5-bath home in Deep Creek! A versatile FROG can serve as a 4th bedroom, office, or man cave. The roof is just 5 years old, and a new water heater (2024) adds modern efficiency. Enjoy a peaceful pond view in the backyard and relax. Inside, the home offers a bright, spacious layout with cozy living areas. Conveniently located within minutes of shopping, dining,

    Ken Capps World Class Realty

    2505 Calonia Arch, Chesapeake, VA 23323
  • /42

    $474,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    2152 Millville Rd, Chesapeake, VA 23323

    READY TO IMPRESS! This modern 4 bedroom, 2.5 bathroom home offers 2,200 sqft of open, thoughtfully designed living. Enjoy durable luxury vinyl plank floors and a bright, airy layout that's ideal for both everyday comfort and chic entertaining. The chef-inspired kitchen boasts sleek cabinetry, gleaming granite countertops, and an oversized center island that flows into the dining and living zones.

    Shynara Manley ONYX Realty Professionals LLC

    2152 Millville Rd, Chesapeake, VA 23323
  • /2

    $465,000

    • 3 Beds
    • 2 Baths
    • 2,246 Sq Ft

    2001 Kelsey Bay Ct, Chesapeake, VA 23323

    Welcome to Mill Creek Harbor- a well established neighborhood you will discover this charming, ranch-style gem. It's a 2,246 sq ft single-family home featuring 3 spacious bedrooms and 2 full baths. Built in 2003 and located on a sizable 8,058 sq ft lot in the highly sought-after Deep Creek South neighborhood of Chesapeake, this home offers both comfort and potential. Sale is subject to short sale

    Candice Myers BHHS RW Towne Realty

    2001 Kelsey Bay Ct, Chesapeake, VA 23323
  • /47

    $324,500

    • 3 Beds
    • 1.5 Baths
    • 1,724 Sq Ft

    1220 Boxwood Dr, Chesapeake, VA 23323

    Welcome to 1220 Boxwood Drive! This pristine property located in a quiet neighborhood in Chesapeake, right on the Elizabeth River is the perfect place to call this house, a home. 3 spacious bedrooms, with a beautifully updated full bathroom upstairs. The front living room boasts vaulted ceilings, with an elevated room to the left that could be used as a dining room or office space. Off the

    Emily Kennelly Thrive Realty

    1220 Boxwood Dr, Chesapeake, VA 23323
  • /21

    $375,000

    • 4 Beds
    • 2 Baths
    • 1,450 Sq Ft

    1057 Saint Julian Dr, Chesapeake, VA 23323

    This fully renovated gem nestled on a peaceful street! This stunning property offers modern amenities and classic charm, featuring two spacious full bathrooms and a convenient downstairs bedroom, perfect for guests. The updated interiors include a beautifully designed kitchen with new appliances, ensuring every meal feels like a special occasion. The full laundry room adds practicality to your

    Stephanie Hynes Redefy Real Estate

    1057 Saint Julian Dr, Chesapeake, VA 23323
  • /32

    $370,000

    • 3 Beds
    • 2 Baths
    • 1,164 Sq Ft

    2328 Skipjack Ln, Chesapeake, VA 23323

    Make this your first stop! Beautifully maintained gorgeous ranch! This home was completely renovated in 2020, upgrades include kitchen cabinets with granite, stainless steel appliances, granite bathroom vanities, lighting in the bathrooms and kitchen, tile in the bathrooms, laminate flooring in common areas, carpet in the bedrooms and plumbing fixtures throughout! Roof was replaced in 2021.

    Matthew Salway Iron Valley Real Estate Hampton Roads

    2328 Skipjack Ln, Chesapeake, VA 23323
  • /40

    $363,900

    • 4 Beds
    • 2 Baths
    • 2,456 Sq Ft

    2036 Maywood St, Chesapeake, VA 23323

    Make this your first stop! Amazing opportunity priced to sell. This Single Family Home is located in the Desired Deep Creek area of Chesapeake situated on nearly ½ Acre Lot! With over 2,400 Square Feet of Living Space this 4 Bedroom, 2 Full Bathroom Home has ample space to grow. This home boasts a Large Kitchen, Family Room, Detached 1 Car Garage and Updated Bathroom showers.! Roof installed

    Matthew Salway Iron Valley Real Estate Hampton Roads

    2036 Maywood St, Chesapeake, VA 23323
  • /41

    $430,000 Open Sat 10AM - 12PM

    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft

    300 Grain Way, Chesapeake, VA 23323

    Escape to your own slice of tranquility in this beautifully maintained 4-bedroom home, nestled in a quiet cul-de-sac. Recent upgrades ensure peace of mind, with a newer roof, recently new windows and HVAC, and most recently installed, an in line gas water heater. This home boasts modern touches, a tastefully updated kitchen and newer countertops. As a bonus, there is an attached powered

    Jennifer Saballos 1st Class Real Estate Coastal Breeze

    300 Grain Way, Chesapeake, VA 23323
  • /23

    $299,999

    • 3 Beds
    • 1 Bath
    • 1,025 Sq Ft

    3103 Hillburn Dr, Chesapeake, VA 23323

    Well maintained brick ranch. All appliances convey. HVAC was replaced in 2020. Newer laminate and bamboo flooring throughout the house. Back deck overlooking large fenced backyard. Detached one car garage. Do not miss out seeing this adorable home. Seller is motivated.

    Klisman Nguyen Iron Valley Real Estate Prestige

    3103 Hillburn Dr, Chesapeake, VA 23323
  • /2

    $430,000

    • 4 Beds
    • 3 Baths
    • 2,384 Sq Ft

    449 Sawyers Mill Crossing, Chesapeake, VA 23323

    This home is located on a corner lot in the sought after Sawyers Mill Community of Chesapeake and Grassfield School District. The home features 4 bedrooms, 3 full bathrooms, family room, dinning room, an additional multipurpose room down stairs for an office/guest room, 2 car garage and a fenced in backyard. New Roof in 2022. Price reflects the TLC this home needs in order to make it your own.

    Kim Stanley GreenTree Realty Inc.

    449 Sawyers Mill Crossing, Chesapeake, VA 23323
  • /25

    $314,999

    • 3 Beds
    • 2 Baths
    • 1,118 Sq Ft

    1105 Sir Gawaine Dr, Chesapeake, VA 23323

    Welcome home to this charming 3 bedroom, 2 bath ranch-style home located in the heart of Chesapeake! Featuring an open- concept kitchen perfect for entertaining, this home offers a functional layout ideal for families or first-time buyers. Enjoy a generously sized backyard --- great for pets, gardening or summer BBQs. Located in a quiet neighborhood with easy access to shopping, schools and

    Caitlin Dress COVA Home Realty

    1105 Sir Gawaine Dr, Chesapeake, VA 23323
  • /39

    $389,000

    • 4 Beds
    • 1.5 Baths
    • 1,425 Sq Ft

    3234 Troy Ln, Chesapeake, VA 23323

    Welcome to Strawberry Acres! This 4-bedroom home offers a great location and plenty of updates. Inside, you’ll find fresh paint throughout, a new HVAC system, and a mini split added to the room over the garage for extra comfort. The exterior features a huge fully fenced backyard, perfect for gatherings, pets, or play. There’s also a brand-new shed for storage. Parking is no issue with an attached

    Matthew Spencer Rock Steady Group

    3234 Troy Ln, Chesapeake, VA 23323
  • /49

    $799,900 Open Sat 1PM - 4PM

    • 5 Beds
    • 3 Baths
    • 3,941 Sq Ft

    712 Greenwing Dr, Chesapeake, VA 23323

    Deep Water in Chesapeake! This absolutely stunning home has been upgraded from top to bottom. Exterior features include a brand new roof (2025) with lifetime warranty, new siding and trim (2022) with lifetime warranty, new triple-pane windows (2022) with lifetime warranty, new gutters (2022), new well pump (2025), inground sprinkler system, and a completely rebuilt front porch (2024). Inside

    Melissa Humpert RE/MAX Alliance

    712 Greenwing Dr, Chesapeake, VA 23323
  • /30

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 2,998 Sq Ft

    1463 Rivers Edge Trace, Chesapeake, VA 23323

    Come and see this beautifully maintained brick home on the end of a cul-de-sac. This corner lot sits on OVER 4 ACRES of land and still features a fenced in backyard and enormous deck. This home comes freshly updated with new carpet throughout the entire second floor and new LVP in the main living spaces. Call today for your private showing!

    joshua barras Own Real Estate LLC

    1463 Rivers Edge Trace, Chesapeake, VA 23323
  • /50

    $648,500

    • 5 Beds
    • 3 Baths
    • 2,600 Sq Ft

    1860 Millville Rd, Chesapeake, VA 23323

    Welcome to this exceptional 5-bedroom, 3-bath custom-built home in the sought-after Grassfield area of Chesapeake! Situated on a nearly half-acre lot (.49 acres), this property features a long concrete driveway. Inside, you’ll find granite countertops throughout, luxury vinyl plank flooring on the first floor, and all stainless-steel appliances in a modern, open kitchen. The beaded vinyl siding

    Porter Young Wainwright Real Estate

    1860 Millville Rd, Chesapeake, VA 23323
  • /37

    $329,000

    • 3 Beds
    • 1.5 Baths
    • 1,456 Sq Ft

    917 Page Ct, Chesapeake, VA 23323

    Welcome to your retreat! This beautifully maintained 3-bedroom brick ranch offers comfort, charm, and thoughtful updates. The kitchen features granite countertops, matching stainless steel appliances, and freshly painted cabinets. A cozy den with fireplace is ideal for a home office, playroom, or hobby space. Inside, enjoy newly painted rooms, updated ceiling fans and lighting, and a stylish

    Alisia Minott NextHome Mission to Serve

    917 Page Ct, Chesapeake, VA 23323
  • /42

    $609,900

    • 4 Beds
    • 2.5 Baths
    • 3,050 Sq Ft

    1853 Rockwood Dr, Chesapeake, VA 23323

    Situated in the sought-after Grassfield school district and just minutes from the expressway, shopping, and dining, this home truly has it all. Step into this beautifully maintained home where rich hardwood floors and natural light create a warm, inviting atmosphere. The gourmet chef’s kitchen is equipped with stainless steel appliances, 42-inch cabinets, quartz countertops, two pantries, and a

    Steve Marable Iron Valley Real Estate Hampton Roads

    1853 Rockwood Dr, Chesapeake, VA 23323
  • /34

    $419,000

    • 4 Beds
    • 3.5 Baths
    • 1,836 Sq Ft

    708 Glen Oak Crossing, Chesapeake, VA 23323

    Discover this 4-bedroom, 3.5-bath lakefront home in sought-after Woodlake Forest. Enjoy peaceful water views, a private pool, and a layout great for everyday living or entertaining. Granite countertops & kitchen sink (2014) Bathtub & toilets (2015)Pool & gutters (2016) Water heater (2018) Kitchen backsplash (2020) New windows (2023) Deck railing (2024) fence & guest-room HVAC (2025)The

    Dakota Bush LPT Realty LLC

    708 Glen Oak Crossing, Chesapeake, VA 23323
  • /34

    $565,000

    • 5 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    1857 Shipyard Rd, Chesapeake, VA 23323

    Prepare to fall in love with this beautiful home in Windrose Farms. Lovely open floor plan with spacious family room and formal dining room. Eat-in-kitchen with stainless steel appliances, island and large pantry. Generous sized master suite with dual sinks, garden tub and shower. Large finished room above garage. Nice sized corner lot with side entry garage and front porch! Grassfield High

    Ron Sawyer RE/MAX Prime

    1857 Shipyard Rd, Chesapeake, VA 23323
  • /25

    $379,000

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

    1444 Culpepper Ave, Chesapeake, VA 23323

    Pictures don't do this justice. Old Ranch turned into 2025 Open Floor plan just like TV. All new appliances & hot water heater. New Roof, Windows and siding. All new inside, doors, floors and ceiling fans & lights. Bathrooms New too. Kitchen, Kitchen, Kitchen. Cabinets to ceilings, Central island for entertaining huge great room. Did you need that "extra room" converted garage will suffice.

    Jay Kotchka BHHS RW Towne Realty

    1444 Culpepper Ave, Chesapeake, VA 23323
  • /34

    $449,900

    • 4 Beds
    • 3 Baths
    • 1,850 Sq Ft

    2416 Broadnax Cir, Chesapeake, VA 23323

    Welcome to this beautifully maintained 4 bedroom, 3 bath ranch-style home in sought-after Deep Creek. This home features numerous upgrades throughout, offering both style and functionality. Enjoy single-level living with the added bonus of a spacious finished room over the garage— for a guest suite, home office, or playroom. The fully fenced backyard provides privacy and a great space for

    Ken Capps World Class Realty

    2416 Broadnax Cir, Chesapeake, VA 23323
  • /50

    $615,000

    • 4 Beds
    • 2.5 Baths
    • 2,849 Sq Ft

    2000 Kelsey Bay Ct, Chesapeake, VA 23323

    Welcome to the Mill Creek Harbor neighborhood! This MOVE-IN ready home is located in the highly sought-after Grassfield section of Chesapeake, zoned for Grassfield schools. This nice sized corner lot is in a cul-de-sac with a beautifully maintained landscape offering a welcoming curb appeal. As you step inside, this home immediately shows off its' nice sized square footage with high ceilings and

    Richard Febus Next Chapter VA Realty Inc

    2000 Kelsey Bay Ct, Chesapeake, VA 23323
  • /2

    $365,000

    • 4 Beds
    • 2 Baths
    • 1,973 Sq Ft

    601 Wooddale Ct, Chesapeake, VA 23323

    Jordan L. Williams Keller Williams Coastal Virginia Chesapeake

    601 Wooddale Ct, Chesapeake, VA 23323
  • /13

    $533,750 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    2821 Margaret Booker Dr, Chesapeake, VA 23323

    Gorgeous new (ready to move in) new construction by local builder with more than 5000 units built. Granite/LVP/Luxury tiled shower/WIC's/open floorplan/2-car garage/covered porch/SS fridge-range-microwave-dishwasher/garage door opener...all included. Walk to schools all the way from 1st grade to 12th grade graduation within three blocks! 2 blocks from recreation center w/tennis courts/BBall, gym,

    Jimmy Reece The Real Estate Group

    2821 Margaret Booker Dr, Chesapeake, VA 23323
  • /45

    $669,900 New Construction

    • 5 Beds
    • 3 Baths
    • 2,350 Sq Ft

    2116 Cedar Rd, Chesapeake, VA 23323

    Rare find on Cedar Road! This 5-bedroom, 3-bath home offers over 2,300 sq ft on 2.5 acres with a wooded backyard for a true mini wilderness escape. Features include LVP flooring, first-floor bedroom with full bath, quartz counters, tile backsplash, pendant lighting, and a two-car garage. The primary suite boasts a garden tub and tile shower. Modern finishes and private acreage—this home will not

    Marcus Anderson Iron Valley Real Estate Norfolk

    2116 Cedar Rd, Chesapeake, VA 23323
  • /34

    $324,700

    • 4 Beds
    • 2 Baths
    • 2,222 Sq Ft

    3201 Jean Ct, Chesapeake, VA 23323

    Charming 4 bedroom 2 bath brick ranch . This 2,222-sqft home sits on over a half acre corner lot. Home offers office, dining and living room, large family room, large screened in deck and so much more . Come see take a look!

    Katrina Ellis CENTURY 21 Nachman Realty

    3201 Jean Ct, Chesapeake, VA 23323

Home Trends in Deep Creek-Portsmouth, VA

Housing Trends

Median Sale Price
$385,000
Median Single Family Sale Price
$383,000
Median Townhouse Sale Price
$418,000
Average Price Per Sq Ft
$217
Number of Homes for Sale
54
Last 12 months Home Sales
435
Months of Supply
1.50
Median List Price
$389,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
18%
How to Buy a Home How to Finance a Home How to Sell a Home