5420 Windward Dr, Tilghman, MD 21671
Large Master
Stainless-solid wood cabinet
OFF MARKET

$869,800

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,352 sqft (on 0.46 acres)

5420 Windward Dr, Tilghman, MD 21671

Refinance Your Home
Currently Off Market - Sold Feb 3, 2021 for $725,000

Home Value

Trulia Estimate
$870K
Since last month
Decreased$11K (-1.3%)
Since last year
Decreased$20K (-2.3%)
Since last sale
Increased$145K (+20%)
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 +62% in the last 10 years
MonthEstimated value
2026
August 2026$870K
August 2026$869K
July 2026$881K
June 2026$894K
May 2026$899K
April 2026$885K
March 2026$889K
February 2026$877K
January 2026$884K
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
5440 Anchor Rd, Tilghman, MD
0.08
Single-Family Home
$375,000
12/10/25
3
2
1,512
5582 Trafalgar Cir, Tilghman, MD
0.32
Single-Family Home
$523,307
04/08/26
3
2.5
2,110
5489 Rude Ave, Tilghman, MD
0.56
Single-Family Home
$725,000
02/20/26
4
2.5
2,286
5379 Anchor Rd, Tilghman, MD
0.12
Single-Family Home
$510,000
12/05/25
2
2.5
1,232
5520 Leeward Ln, Tilghman, MD
0.16
Single-Family Home
$1,000,000
06/18/26
5
2.5
4,214
5654 Trafalgar Cir, Tilghman, MD
0.45
Single-Family Home
$455,000
08/21/26
3
2
1,710
5744 Johns Way, Tilghman, MD
0.62
Single-Family Home
$411,000
02/16/26
3
2.5
1,512
21368 Fairbank Cir, Tilghman, MD
1.08
Single-Family Home
$1,075,000
12/04/25
4
3
3,552
5820 Tilghman Beach Dr, Tilghman, MD
0.75
Single-Family Home
$740,000
11/24/25
2
1
1,776
6050 Sunset Ln, Tilghman, MD
1.18
Single-Family Home
$1,050,000
04/13/26
3
3
3,232

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
5440 Anchor Rd, Tilghman, MD 21671
0.08
$375,000
3
2
1,512
Recently Sold
5480 Windward Dr, Tilghman, MD 21671
0.10
$1,250,000
4
3
1,936
For Sale
5379 Anchor Rd, Tilghman, MD 21671
0.12
$510,000
2
2.5
1,232
Recently Sold
5520 Leeward Ln, Tilghman, MD 21671
0.16
$1,000,000
5
2.5
4,214
Recently Sold
21310 Landing Ln, Tilghman, MD 21671
0.17
$340,200
3
2
1,120
Off Market
Leeward Ln, Tilghman, MD 21671
0.24
-
-
-
-
Off Market
5582 Trafalgar Cir, Tilghman, MD 21671
0.32
$523,307
3
2.5
2,110
Recently Sold
5559 Trafalgar Cir, Tilghman, MD 21671
0.36
$550,000
5
3.5
3,404
For Sale
21379 Ferry Landing Rd, Tilghman, MD 21671
0.37
$687,000
3
2.5
3,459
Off Market
Lot 44 Ferry Landing Rd, Tilghman, MD 21671
0.41
-
-
-
-
Off Market
Ferry Landing Rd, Tilghman, MD 21671
0.43
-
-
-
-
Off Market
5636 Trafalgar Cir, Tilghman, MD 21671
0.44
$598,600
4
2.5
2,786
Off Market

Local Information

  • Map ViewExplore the area around 5420 Windward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2009
0.46 acre lot
2,352 sqft
$370/sqft
Garage

About this House

This single-family home is located at 5420 Windward Dr, Tilghman, MD. 5420 Windward Dr is in Tilghman, MD and in ZIP code 21671. This property has 4 bedrooms, 3 bathrooms and approximately 2,352 sqft of floor space. This property has a lot size of 0.46 acres and was built in 2009.
5420 Windward Dr, Tilghman, MD 21671 is a 4 bedroom, 3 bathroom, 2,352 sqft single-family home built in 2009. It last sold for $725,000 on Feb 3, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $869,800, with a rent estimate of $3,155/month.

Home Details for 5420 Windward Dr

Interior Features

Interior Details
BasementTypes of Rooms: Walk In Closet, Dining RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, Heat PumpAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: OtherFoundation Type: PiersSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2009
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price and Tax history

DateEventPrice
Feb 3, 2021
Source: N/A
Sold
$725,000
Nov 20, 2020
Source: Agent Provided
Pending
$750,000
Oct 24, 2020
Source: Agent Provided
Listed For Sale
$750,000
Nov 16, 2011
Source: N/A
Sold
$667,000
Jun 6, 2002
Source: N/A
Sold
$337,500

Market trends in Tilghman

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
15
2MoM

Around this home

What Locals Say about Tilghman

At least 1 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 100 % Say parking is easy

  • 100 % Say people would walk alone at night

  • 100 % Say kids play outside

  • 100 % Say neighbors are friendly

  • 100 % Say they plan to stay for at least 5 years

  • 100 % Say there's holiday spirit

  • 100 % Say yards are well-kept

  • 100 % Say there's wildlife

  • 100 % Say it's walkable to restaurants

  • 75 % Say there are community events

  • 67 % Say car is needed

  • 50 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Frequently asked questions about 5420 Windward Dr

  • What is 5420 Windward Dr estimated to be worth?
    Trulia's estimated value for 5420 Windward Dr in Tilghman, MD is $869,800.
  • What is the price history for 5420 Windward Dr?
    5420 Windward Dr in Tilghman, MD last sold for $725,000 in February 2021.
  • Is Tilghman a buyer's or seller's market?
    Tilghman is currently a buyer's market, based on recent for-sale activity.
  • What are the closest schools to 5420 Windward Dr?
    The closest schools to 5420 Windward Dr in Tilghman, MD are St. Michaels Middle/High School (rated 6/10), Tilghman Elementary School (Pre-K, rated 2/10).
  • Does 5420 Windward Dr have air conditioning?
    Yes, 5420 Windward Dr in Tilghman, MD has air conditioning.
  • Does 5420 Windward Dr have laundry facilities?
    Yes, 5420 Windward Dr in Tilghman, MD has in-unit laundry.

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