5401 Windward Dr, Tilghman, MD 21671
OFF MARKET

$360,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,248 sqft (on 0.45 acres)

5401 Windward Dr, Tilghman, MD 21671

Est. Refi. Payment $2,103/mo*
Refinance Your Home
Currently Off Market - Sold Dec 11, 2018 for $225,000

Home Value

Trulia Estimate
$361K
Since last month
Decreased$2K (-0.6%)
Since last year
Increased$700 (+0.2%)
Since last sale
Increased$136K (+60.4%)
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 +90% in the last 10 years
MonthEstimated value
2026
August 2026$361K
August 2026$360K
July 2026$363K
June 2026$364K
May 2026$369K
April 2026$363K
March 2026$363K
February 2026$355K
January 2026$353K
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
0.10
Single-Family Home
$375,000
12/10/25
3
2
1,512
5379 Anchor Rd, Tilghman, MD
0.05
Single-Family Home
$510,000
12/05/25
2
2.5
1,232
5582 Trafalgar Cir, Tilghman, MD
0.38
Single-Family Home
$523,307
04/08/26
3
2.5
2,110
5654 Trafalgar Cir, Tilghman, MD
0.50
Single-Family Home
$455,000
08/21/26
3
2
1,710
5744 Johns Way, Tilghman, MD
0.68
Single-Family Home
$411,000
02/16/26
3
2.5
1,512
21424 Wharf Rd, Tilghman, MD
0.76
Single-Family Home
$349,000
11/04/25
2
1
1,464
5489 Rude Ave, Tilghman, MD
0.54
Single-Family Home
$725,000
02/20/26
4
2.5
2,286
4940 Fairbank Rd, Tilghman, MD
0.88
Single-Family Home
$560,000
07/10/26
2
2
1,260
5520 Leeward Ln, Tilghman, MD
0.23
Single-Family Home
$1,000,000
06/18/26
5
2.5
4,214
4869 Bar Neck Rd, Tilghman, MD
1.25
Single-Family Home
$162,000
07/01/26
2
2
1,070

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
5379 Anchor Rd, Tilghman, MD 21671
0.05
$510,000
2
2.5
1,232
Recently Sold
5440 Anchor Rd, Tilghman, MD 21671
0.10
$375,000
3
2
1,512
Recently Sold
5480 Windward Dr, Tilghman, MD 21671
0.17
$1,250,000
4
3
1,936
For Sale
21310 Landing Ln, Tilghman, MD 21671
0.21
$340,200
3
2
1,120
Off Market
5520 Leeward Ln, Tilghman, MD 21671
0.23
$1,000,000
5
2.5
4,214
Recently Sold
Leeward Ln, Tilghman, MD 21671
0.31
-
-
-
-
Off Market
5582 Trafalgar Cir, Tilghman, MD 21671
0.38
$523,307
3
2.5
2,110
Recently Sold
21379 Ferry Landing Rd, Tilghman, MD 21671
0.40
$687,000
3
2.5
3,459
Off Market
5559 Trafalgar Cir, Tilghman, MD 21671
0.40
$550,000
5
3.5
3,404
For Sale
Lot 44 Ferry Landing Rd, Tilghman, MD 21671
0.43
-
-
-
-
Off Market
Ferry Landing Rd, Tilghman, MD 21671
0.45
-
-
-
-
Off Market
5636 Trafalgar Cir, Tilghman, MD 21671
0.49
$598,600
4
2.5
2,786
Off Market

Local Information

  • Map ViewExplore the area around 5401 Windward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1994
Lot Size
0.45 acres
Living Area
1,248 sqft
Price/Sqft
$289

About this House

This lovely rancher overlooks the waters of the Chesapeake Bay. Perfectly sited across from the community waterfront lot this home takes full advantage of the westerly sunset views. The home offers an open floor plan & was recently upgraded w/new lam. wood floors, counter tops & fresh paint. Master BA is complete w/shower & large soaking tub. Shed/workshop. Less then 1 mile to public boat landing.
5401 Windward Dr, Tilghman, MD 21671 is a 3 bedroom, 2 bathroom, 1,248 sqft single-family home built in 1994. It last sold for $225,000 on Dec 11, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $360,800, with a rent estimate of $2,004/month.

Home Details for 5401 Windward Dr

Interior Features

Heating & Cooling
Heating: Baseboard, ElectricHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
Dishwasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Vinyl

Property Information

Year Built
Year Built: 1994
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.45 acres

Price and Tax history

DateEventPrice
Dec 11, 2018
Source: N/A
Sold
$225,000
Aug 13, 2018
Source: Agent Provided
Pending
$250,000
Jan 19, 2018
Source: Agent Provided
PriceChange
$250,000
Price decreased by 7%
Apr 14, 2017
Source: Agent Provided
Listed For Sale
$269,500

Market trends in Tilghman

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
17
3MoM

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 5401 Windward Dr

  • What is 5401 Windward Dr estimated to be worth?
    Trulia's estimated value for 5401 Windward Dr in Tilghman, MD is $360,800.
  • What is the price history for 5401 Windward Dr?
    5401 Windward Dr in Tilghman, MD last sold for $225,000 in December 2018.
  • 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 5401 Windward Dr?
    The closest schools to 5401 Windward Dr in Tilghman, MD are St. Michaels Middle/High School (rated 6/10), Tilghman Elementary School (Pre-K, rated 2/10).
  • How big is the lot at 5401 Windward Dr?
    The lot at 5401 Windward Dr in Tilghman, MD is about 0.45 acres (19,501 sq ft).

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