744 Willow Bend Dr, Chesapeake, VA 23323
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Property image
OFF MARKET

744 Willow Bend Dr
Chesapeake, VA 23323

Deep Creek West-Dismal Swamp
  • 3 Beds
  • 2 Baths
  • 1,532 sqft

$404,700

Trulia Estimate
as of Jul 19, 2026
Est. Refi. Payment $2,382/mo*

$404,700

Trulia Estimate
as of Jul 19, 2026
Est. Refi. Payment $2,382/mo*
3 Beds
2 Baths
1,532 sqft

Local Information

  • Map ViewExplore the area around 744 Willow Bend Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 744 Willow Bend Dr, Chesapeake, VA. 744 Willow Bend Dr is in the Deep Creek West-Dismal Swamp neighborhood in Chesapeake, VA and in ZIP code 23323. This property has 3 bedrooms, 2 bathrooms and approximately 1,532 sqft of floor space. This property has a lot size of 10236 sqft and was built in 1988.
744 Willow Bend Dr, Chesapeake, VA 23323 is a 3 bedroom, 2 bathroom, 1,532 sqft single-family home in Deep Creek West-Dismal Swamp, built in 1988. It last sold for $245,000 on Nov 8, 2016. More recently, it was listed as a rental in February 2023 with an asking price of $2,100 per month. That rental listing was removed on February 28, 2023. It is currently off market. The Trulia Estimate is $404,700, with a rent estimate of $2,409/month.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 744 Willow Bend Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet
Interior Details
Number of Rooms: 6Types of Rooms: Dining Room
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Vinyl, WoodFoundation Type: Other
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1988Year Updated: 2023
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 10236 sqft

Price History for 744 Willow Bend Dr

DatePriceEventSource
02/28/2023ListingRemovedZillow Rentals
02/21/2023$2,100Listed For RentZillow Rentals
11/08/2016$245,000Sold
N/A
09/22/2016$249,900Listed For SaleAgent Provided
04/28/2016$1,550ListingRemovedAgent Provided
03/16/2016$1,550Listed For RentAgent Provided
09/20/2014$1,550ListingRemovedAgent Provided
09/08/2014$1,550Listed For RentAgent Provided
10/11/2013$1,550ListingRemovedAgent Provided
08/30/2013$1,550Listed For RentAgent Provided
02/28/2013$1,550ListingRemovedAgent Provided
02/14/2013$1,550PriceChange
Agent Provided
01/26/2013$1,575PriceChange
Agent Provided
12/28/2012$1,600Listed For RentAgent Provided
06/09/2009$250,000Sold
N/A
05/03/2009$250,000PriceChange
Agent Provided
04/22/2009$259,900Listed For SaleAgent Provided
08/30/2007$255,000Sold
N/A
08/14/2002$134,000Sold
N/A

Market trends in Chesapeake

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$390K
$4.67K
MoM
Sale-to-List Price
100.0%
Price per sq ft
$216
$3
MoM
Available listings
930
19
MoM
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Property Tax and Assessment

Year2025
Tax$3,516
Assessment$348,100
Home facts updated by county records

Comparable Sales for 744 Willow Bend Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.11
Single-Family Home
$325,000
07/10/26
3
2
1,430
0.05
Single-Family Home
$434,900
06/15/26
4
2
2,000
0.23
Single-Family Home
$355,000
02/27/26
3
1
1,497
0.06
Single-Family Home
$415,000
07/23/25
4
2.5
1,969
0.25
Single-Family Home
$400,000
08/14/25
4
2
1,830
0.34
Single-Family Home
$395,000
09/15/25
4
2
1,658
0.14
Single-Family Home
$450,000
06/01/26
4
2.5
1,966
0.20
Single-Family Home
$398,500
01/23/26
4
2.5
2,089
0.35
Single-Family Home
$425,000
11/18/25
4
2
1,860
0.36
Single-Family Home
$420,000
02/27/26
4
2
1,740

Nearby homes

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Assigned Schools

These are the assigned schools for 744 Willow Bend Dr.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Neighborhood stats provided by third party data sources.

What Locals Say about Deep Creek West-Dismal Swamp

At least 69 Trulia users voted on each feature.
  • 93 % Say car is needed

  • 92 % Say parking is easy

  • 90 % Say it's dog friendly

  • 89 % Say yards are well-kept

  • 87 % Say kids play outside

  • 86 % Say there are sidewalks

  • 85 % Say it's quiet

  • 80 % Say streets are well-lit

  • 78 % Say people would walk alone at night

  • 78 % Say there's holiday spirit

  • 55 % Say neighbors are friendly

  • 52 % Say there's wildlife

  • 52 % Say they plan to stay for at least 5 years

  • 35 % Say there are community events

  • 27 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Annitabuenaventura
    "I love this neighborhood 🩷🩷🩷I live here for the last 5 years and it’s so nice, the people are always so nice and friendly! "
  • Casey Pillaca
    "Dog owners would love the sidewalks and the wide streets in deep creek. During Fourth of July this neighborhood get loud with fireworks "
  • Gabrielle Falu
    "There’s a lot of dogs in the neighborhood, so if you’re allergic this might not be the neighborhood for you"
  • Trulia User
    "Just use caution like you would any where else, but it feels pretty safe here. it's pretty nice around here"
  • Jamie G.
    "It’s a great place to walk your dogs! We do 3 miles a night and feel 100% safe every time. Lots of people walk their dogs after work."
  • Vaeloni W.
    "You will always meet or see someone walking dog(s) in this neighborhood. They also have a few pet parks among the area. "
  • Emily E.
    "Great feel. Lot sizes are small and houses are very close together. HOA forces people to keep their properties up which I like. "
  • Vaeloni W.
    "This is a pet friendly neighborhood. People are always out walking their dogs, your dog will feel right at home. "
  • Vaeloni W.
    "Family oriented and quiet neighborhood, You’ll feel welcomed for sure. Plus an easy commute to interstate. "
  • Chanita D.
    "Dog owners would love this neighborhood . Many of the neighbors have dogs everyone picks up behind their animals and the neighborhood is very clean "
  • Onepeople4all
    "I’ve lived in this neighborhood for 14 years, and the neighbors have continued to be friendly and it is a quiet and well kept community 💕."
  • Terfyparham
    "In the middle of everywhere. Country in the city. Safe, quite and convenient. Lived here for 10 years and love it."
  • Jymsteacher
    "The neighborhood is friendly and quiet. It feels very secluded but is close to the interstate, restaurants, and shopping."
  • Alfred H.
    "I live in this community and have fkr a while. I really like the Jones and community vibe here. Additionally while but close to goods and services I am with 5 miles drive to everything I need!"
  • Pw j.
    "The area is just rural enough... while not being too overwhelmingly 'country'. Good community of people willing to help each other and communicate amongst themselves. Quite an eclectic mix of housing styles make for interesting views and neighbors.. "
  • Lerche_family
    "I live in the Deep Creek section of Chesapeake and love the parks, rec. center and schools available. I have two children in Deep Creek Elem, both are in the gifted program and thriving. "
  • MerdineBoerger
    "This is an awesome area to bring up your family and not worry about the local crime. I love it here, "

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Homes for sale near 744 Willow Bend Dr

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Off Market Homes Near 744 Willow Bend Dr

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