421 Willow Bend Dr, Chesapeake, VA 23323
OFF MARKET

$398,400

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 1,916 sqft (on 0.27 acres)

421 Willow Bend Dr, Chesapeake, VA 23323

Deep Creek West-Dismal Swamp
Est. Refi. Payment $2,517/mo*
Refinance Your Home

Home Value

Trulia Estimate
$398K
Since last month
Increased$2K (+0.4%)
Since last year
Increased$21K (+5.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +50% in the last 10 years
MonthEstimated value
2026
September 2026$399K
August 2026$398K
July 2026$397K
June 2026$397K
May 2026$397K
April 2026$395K
March 2026$395K
February 2026$391K
January 2026$389K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
400 Willow Bend Dr, Chesapeake, VA
0.08
Single-Family Home
$398,500
01/23/26
4
2.5
2,089
3101 Holly Ridge Dr, Chesapeake, VA
0.15
Single-Family Home
$425,000
11/18/25
4
2
1,860
500 Willow Bend Dr, Chesapeake, VA
0.14
Single-Family Home
$435,000
08/24/26
4
2
1,876
3205 Holly Ridge Dr, Chesapeake, VA
0.21
Single-Family Home
$455,000
09/11/26
4
2.5
2,214
3224 Mistletoe Way, Chesapeake, VA
0.26
Single-Family Home
$450,000
06/01/26
4
2.5
1,966
732 Willow Bend Dr, Chesapeake, VA
0.27
Single-Family Home
$434,900
06/15/26
4
2
2,000
548 Willow Bend Dr, Chesapeake, VA
0.33
Single-Family Home
$423,000
12/23/25
4
2
1,896
331 Appaloosa Trl, Chesapeake, VA
0.31
Single-Family Home
$475,000
07/10/26
4
2.5
2,148
304 Quail Meadow Dr, Chesapeake, VA
0.19
Single-Family Home
$325,000
07/10/26
3
2
1,430

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
400 Willow Bend Dr, Chesapeake, VA 23323
0.08
$398,500
4
2.5
2,089
Recently Sold
439 Willow Bend Dr, Chesapeake, VA 23323
0.10
$440,000
4
2
1,800
Recently Sold
500 Willow Bend Dr, Chesapeake, VA 23323
0.14
$435,000
4
2
1,876
Recently Sold
304 Quail Meadow Dr, Chesapeake, VA 23323
0.19
$325,000
3
2
1,430
Recently Sold
3101 Holly Ridge Dr, Chesapeake, VA 23323
0.15
$453,000
4
2
1,860
Off Market
502 Willow Bend Dr, Chesapeake, VA 23323
0.16
$430,000
4
2
1,778
Recently Sold
185 George Washington Hwy S, Chesapeake, VA 23323
0.24
$281,000
4
1
1,587
Recently Sold
749 Willow Bend Dr, Chesapeake, VA 23323
0.22
$445,000
4
2
2,026
Recently Sold
757 Willow Bend Dr, Chesapeake, VA 23323
0.23
$480,000
4
2
1,852
For Sale
753 Willow Bend Dr, Chesapeake, VA 23323
0.23
$399,900
4
2
2,053
For Sale
3205 Holly Ridge Dr, Chesapeake, VA 23323
0.21
$455,000
4
2.5
2,214
Recently Sold

Local Information

  • Map ViewExplore the area around 421 Willow Bend Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1987
0.27 acre lot
1,916 sqft
$208/sqft
1 Car Garage

About this House

What's unique:Oversized fenced backyardGranite countertopsLarge screened-in porch
Welcome to your new home! This spacious two-story residence is nestled in one of Chesapeake’s most sought-after neighborhoods. Offering 4 generously sized bedrooms, 2.5 bathrooms, a family room/den, dining room, and living room, this home provides the perfect blend of comfort and functionality.Step outside to a large screened-in porch overlooking an oversized fenced backyard on nearly 0.27 acres—ideal for relaxing or entertaining. Recent updates include: Granite countertops (2025), Flooring (2025) & 2023), HVAC system (2023), Water heater (2023).
421 Willow Bend Dr, Chesapeake, VA 23323 is a 4 bedroom, 3 bathroom, 1,916 sqft single-family home in Deep Creek West-Dismal Swamp, built in 1987. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $398,400, with a rent estimate of $2,938/month.
Last check for updates: about 24 hours ago
Listed by Kim Wilkins
RE/MAX Ultra, (757) 829-7200
Bought with: Melissa Mac Amazeen, Iron Valley Real Est. Prestige, (757) 432-4873
Source: REIN Inc., MLS#10602821

Home Details for 421 Willow Bend Dr

Interior Features

Interior Details
Basement: Crawl SpaceNumber of Rooms: 8
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1916 Square Feet
Appliances & Utilities
Appliances: Dishwasher, ENERGY STAR Qualified Appliances, Electric Range, Refrigerator, Electric Water HeaterDishwasherLaundry: Dryer Hookup,Washer HookupRefrigerator
Heating & Cooling
Heating: Heat PumpHas CoolingAir Conditioning: Heat PumpHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Wood BurningHas a Fireplace
Windows, Doors, Floors & Walls
Flooring: Carpet, Ceramic Tile, Vinyl
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Ceramic Tile, Vinyl
View
No View

Exterior Features

Exterior Home Features
Roof: Asphalt ShinglePatio / Porch: Deck, Screened PorchFencing: Back Yard, Privacy, Wood, Fenced
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 1Parking: Garage Att 1 Car,Oversized,Driveway
Pool
Pool: None
Frontage
Waterfront: Not WaterfrontNot on Waterfront
Water & Sewer
Sewer: City/County
Farm & Range
Not Allowed to Raise Horses

Property Information

Year Built
Year Built: 1987
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Traditional,Transitional
Building
Construction Materials: Vinyl SidingNot a New ConstructionNot Attached Property

Price & Status

Price
List Price: $385,000
Status Change & Dates
Off Market Date: Fri Oct 03 2025Possession Timing: Settlement

Active Status

MLS Status: Sold

Location

Direction & Address
City: ChesapeakeCommunity: Mill Creek
School Information
Elementary School: Deep Creek Central ElementaryJr High / Middle School: Deep Creek MiddleHigh School: Deep Creek

HOA

No HOA

Lot Information

Lot Area: 0.27 acres

Offer

Contingencies: Non Contingent

Miscellaneous

Mls Number: 10602821Attic: Scuttle

Price and Tax history

YearProperty taxTax assessment
2025
$3,716
$367,900
Home facts updated by county records

Market trends in Chesapeake

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$420K
$6.67KMoM
Sale-to-List Price
100.0%
Price per sq ft
$221
$2MoM
Available listings
986
12MoM

Around this home

Neighborhood Overview

Deep Creek West-Dismal Swamp
See Local Highlights
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! "
    0
    Flag
  • 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 "
    0
    Flag
  • Gabrielle Falu
    "There’s a lot of dogs in the neighborhood, so if you’re allergic this might not be the neighborhood for you"
    0
    Flag
  • Trulia User
    "Just use caution like you would any where else, but it feels pretty safe here. it's pretty nice around here"
    0
    Flag
  • 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."
    2
    Flag
  • 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. "
    1
    Flag
  • 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. "
    1
    Flag
  • Vaeloni W.
    "This is a pet friendly neighborhood. People are always out walking their dogs, your dog will feel right at home. "
    0
    Flag
  • Vaeloni W.
    "Family oriented and quiet neighborhood, You’ll feel welcomed for sure. Plus an easy commute to interstate. "
    0
    Flag
  • 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 "
    0
    Flag
  • 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 💕."
    5
    Flag
  • Terfyparham
    "In the middle of everywhere. Country in the city. Safe, quite and convenient. Lived here for 10 years and love it."
    2
    Flag
  • Jymsteacher
    "The neighborhood is friendly and quiet. It feels very secluded but is close to the interstate, restaurants, and shopping."
    0
    Flag
  • 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!"
    0
    Flag
  • 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.. "
    6
    Flag
  • 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. "
    2
    Flag
  • MerdineBoerger
    "This is an awesome area to bring up your family and not worry about the local crime. I love it here, "
    1
    Flag

LGBTQ Local Legal Protections

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent. © 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW. REIN updates its listings on a daily basis. Data last updated: 2026-09-24 13:09:33 PDT
Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.
This application does not include information on all of the properties available for sale at this time.
Some or all of the listings (or Listing Data) represented in this application have been enhanced with information not provided by REIN. Such enhancements may include information obtained from Zillow Inc. and other third-party or publicly available sources and are not part of the Listing Data provided by REIN.

Frequently asked questions about 421 Willow Bend Dr

  • What is 421 Willow Bend Dr estimated to be worth?
    Trulia's estimated value for 421 Willow Bend Dr in Chesapeake, VA is $398,400.
  • Is Chesapeake a buyer's or seller's market?
    Chesapeake is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Chesapeake?
    The median sale price in Chesapeake is $420K. That is up $6.67K from the prior month.
  • What do residents say about the Deep Creek West-Dismal Swamp neighborhood?
    Residents describe the Deep Creek West-Dismal Swamp neighborhood in Chesapeake, VA as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Deep Creek West-Dismal Swamp, Chesapeake.
  • Does 421 Willow Bend Dr have air conditioning?
    Yes, 421 Willow Bend Dr in Chesapeake, VA has air conditioning.
  • Does 421 Willow Bend Dr have laundry facilities?
    Yes, 421 Willow Bend Dr in Chesapeake, VA has laundry facilities.

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