2 Windward Way, Dagsboro, DE 19939
OFF MARKET

$748,800

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 2,696 sqft (on 0.70 acres)

2 Windward Way, Dagsboro, DE 19939

Refinance Your Home
Currently Off Market - Sold Nov 15, 2017 for $375,000

Home Value

Trulia Estimate
$749K
Since last month
Increased$1K (+0.2%)
Since last year
Increased$107K (+16.6%)
Since last sale
Increased$376K (+100.2%)
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 +121% in the last 10 years
MonthEstimated value
2026
August 2026$751K
August 2026$750K
July 2026$749K
June 2026$757K
May 2026$753K
April 2026$765K
March 2026$636K
February 2026$643K
January 2026$633K
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
30106 Pelican Beach Cir, Dagsboro, DE
0.12
Single-Family Home
$465,000
02/27/26
3
2.5
2,617
30131 Shipwatch Cir, Dagsboro, DE
0.20
Single-Family Home
$575,000
08/31/26
4
2.5
2,600
34858 Tenleys Trl, Dagsboro, DE
0.04
Single-Family Home
$641,290
08/24/26
3
3
2,874
34833 Seagrass Plantation Ln, Dagsboro, DE
0.21
Single-Family Home
$500,000
04/16/26
4
3
2,100
34899 Preserve Ln, Dagsboro, DE
0.11
Single-Family Home
$465,000
10/23/25
3
2.5
2,111
606 Saint Andrews Ct, Dagsboro, DE
0.59
Single-Family Home
$395,000
12/05/25
5
3.5
2,518
30213 Back Bay Dr, Dagsboro, DE
0.29
Single-Family Home
$575,000
07/29/26
4
2.5
2,256
608 Saint Andrews Ct, Dagsboro, DE
0.60
Single-Family Home
$475,000
09/18/25
4
3
3,000
29562 Turnberry Dr, Dagsboro, DE
0.42
Single-Family Home
$480,000
10/14/25
4
2.5
2,316
30437 Holts Landing Rd, Dagsboro, DE
0.47
Single-Family Home
$450,000
02/27/26
3
2.5
1,712

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
34856 Tenleys Trl, Dagsboro, DE 19939
0.03
$570,000
3
3
2,569
Recently Sold
34858 Tenleys Trl, Dagsboro, DE 19939
0.04
$641,290
3
3
2,874
Recently Sold
34869 Tenleys Trl, Dagsboro, DE 19939
0.04
$699,990
4
2.5
2,874
For Sale
34855 Tenleys Trl, Dagsboro, DE 19939
0.08
$899,990
3
3.5
2,535
For Sale
30106 Pelican Beach Cir, Dagsboro, DE 19939
0.12
$465,000
3
2.5
2,617
Recently Sold
34899 Preserve Ln, Dagsboro, DE 19939
0.11
$463,800
3
2.5
2,111
Off Market
34865 Tenleys Trl, Dagsboro, DE 19939
0.11
$694,040
3
3.5
2,561
Recently Sold
34856 Tenleys Trails, Dagsboro, DE 19939
0.11
$711,700
3
3
2,569
Off Market
34866 Tenleys Trl, Dagsboro, DE 19939
0.10
$499,999
3
2
1,563
For Sale
New Haven, Dagsboro, DE 19939
0.13
$499,990+
3
2
1,419
-
Raleigh, Dagsboro, DE 19939
0.13
$547,990+
3
2
1,648
-
Annapolis, Dagsboro, DE 19939
0.13
$617,990+
3
2.5
2,475
-

Local Information

  • Map ViewExplore the area around 2 Windward Way.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1998
0.7 acre lot
2,696 sqft
$278/sqft
Garage

About this House

This single-family home is located at 2 Windward Way, Dagsboro, DE. 2 Windward Way is in Dagsboro, DE and in ZIP code 19939. This property has 4 bedrooms, 4 bathrooms and approximately 2,696 sqft of floor space. This property has a lot size of 0.70 acres and was built in 1998.
2 Windward Way, Dagsboro, DE 19939 is a 4 bedroom, 4 bathroom, 2,696 sqft single-family home built in 1998. It last sold for $375,000 on Nov 15, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $748,800, with a rent estimate of $3,312/month.

Home Details for 2 Windward Way

Interior Features

Interior Details
BasementNumber of Rooms: 6Types of Rooms: Dining RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, Heat Pump, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Laminate, Linoleum Vinyl
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: Asphalt, OtherExterior: VinylFoundation Type: Masonry
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1998
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.70 acres

Price and Tax history

DateEventPrice
Nov 15, 2017
Source: N/A
Sold
$375,000
Aug 22, 2017
Source: Agent Provided
Listed For Sale
$378,900

Market trends in Dagsboro

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
53
8MoM

Around this home

What Locals Say about Dagsboro

At least 20 Trulia users voted on each feature.

  • 81 % Say people would walk alone at night

  • 79 % Say it's quiet

  • 79 % Say there's holiday spirit

  • 75 % Say car is needed

  • 74 % Say parking is easy

  • 72 % Say it's dog friendly

  • 68 % Say yards are well-kept

  • 68 % Say they plan to stay for at least 5 years

  • 56 % Say neighbors are friendly

  • 54 % Say kids play outside

  • 50 % Say there are sidewalks

  • 46 % Say streets are well-lit

  • 43 % Say there's wildlife

  • 36 % Say there are community events

  • 21 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Mlsax
    "I have lived in Dagsboro at Seagrass Plantation for 3 years and love it as neighbors help each other. We take pride in our neighborhood as many volunteers clean, plant flowers and decorate for holidays. The neighborhood is safe, many people walk their dogs, and bicycle. "
    0
    Flag
  • Mlsax
    "The association has several activities. The neighborhood beach is a great place to see Fourth of July fireworks. The Indian river and the blackwater tributaries are fun to Kayak. It’s a great biking and dog walking community. "
    0
    Flag
  • Christopher H.
    "Lots of Back roads and corn fields. Everything is approximately a thirty to forty five minute drive. "
    4
    Flag
  • Jess M.
    "I have lived in this neighborhood for almost 3 yrs now. Everyone is very friendly. We all look out for each other. It’s an absolutely perfect place to retire. Or some use it as a little getaway from the hustle and bustle of life. My sister refers to it has her happy place. In the summer there is a lot of fun or relaxing things to do. Such as boating,fishing, crabbing, going to the beach, going to state or national parks to see the wild horses on the beach, etc.. I could go on for days. However in the winter it tends to be harder to find things to do. "
    7
    Flag
  • Holly S
    "Friendly community - well lit, feels safe. Have had no issues with any noise situations. HOA seems to take care of issues before they are issues (Ex:Trash Disposal/parking,etc)."
    0
    Flag
  • Ppickles39
    "I met more neighbors here after 1 year than I ever did at my previous home of 15 years. Neighbors are just so friendly & quiet. All the yards are pristine. So glad we found this neighborhood "
    3
    Flag
  • Robinrmurchie
    "parades where everyoene meets on main street. Businesses hand out flyers and greet you. the decoration in the park is comforting and beautifully done. "
    3
    Flag
  • Visiter
    "Beautiful, peaceful, friendly, safe, and well maintained area. On the Indian River, which leads to the ocean, complete with boat launch, docks & slips. Excellent location for boating, crabbing, clamming & duck feeding. Just a short drive to the beach. Great for those who like to visit the beach, without living right in the midst of the crowds and nightlife. Neighbors are very friendly, pleasant, welcoming and helpful. A great place for walks by the water, with no through traffic. Loved sitting out on the deck, enjoying the view of the water. Gorgeous sunsets! And lots of birds. :)"
    0
    Flag
  • Martyslures
    "Bay colony has there own marina. If you love boating and fishing and swimming -this is the place for you! We have our own pool-hot tub and tennis court. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 2 Windward Way

  • What is 2 Windward Way estimated to be worth?
    Trulia's estimated value for 2 Windward Way in Dagsboro, DE is $748,800.
  • What is the price history for 2 Windward Way?
    2 Windward Way in Dagsboro, DE last sold for $375,000 in November 2017.
  • Is Dagsboro a buyer's or seller's market?
    Dagsboro is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Dagsboro?
    Residents describe Dagsboro, DE as quiet, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Dagsboro, DE.
  • Does 2 Windward Way have air conditioning?
    Yes, 2 Windward Way in Dagsboro, DE has air conditioning.
  • Does 2 Windward Way have laundry facilities?
    Yes, 2 Windward Way in Dagsboro, DE has in-unit laundry.

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