Is Tilghman, MD dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Is parking easy in Tilghman, MD?

As of early 2026, 100% of users say parking is easy

Would people walk alone at night in Tilghman, MD?

As of early 2026, 100% of users say people would walk alone at night

Do kids play outside in Tilghman, MD?

As of early 2026, 100% of users say kids play outside

Are neighbors friendly in Tilghman, MD?

As of early 2026, 100% of users say neighbors are friendly

Do residents of Tilghman, MD plan to stay at least 5 years?

As of early 2026, 100% of users say they plan to stay for at least 5 years

Does Tilghman, MD show holiday spirit?

As of early 2026, 100% of users say there's holiday spirit

Are yards well-kept in Tilghman, MD?

As of early 2026, 100% of users say yards are well-kept

Is there wildlife in Tilghman, MD?

As of early 2026, 100% of users say there's wildlife

Is Tilghman, MD walkable to restaurants?

As of early 2026, 100% of users say it's walkable to restaurants

Are there community events in Tilghman, MD?

As of early 2026, 75% of users say there are community events

Is a car needed in Tilghman, MD?

As of early 2026, 67% of users say car is needed

Is Tilghman, MD walkable to grocery stores?

As of early 2026, 50% of users say it's walkable to grocery stores

What is 5427 Windward Dr estimated to be worth?

Trulia's estimated value for 5427 Windward Dr in Tilghman, MD is $498,900 .

What is the price history for 5427 Windward Dr?

5427 Windward Dr in Tilghman, MD last sold for $438,830 in August 2023.

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 5427 Windward Dr?

The closest schools to 5427 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 5427 Windward Dr?

The lot at 5427 Windward Dr in Tilghman, MD is about 0.52 acres (22,800 sq ft).

Does 5427 Windward Dr have a garage?

Yes, 5427 Windward Dr in Tilghman, MD has a garage.

OFF MARKET

$498,900

Trulia Estimate

Studio
4 Baths
2,289 sqft (on 0.52 acres)

5427 Windward Dr, Tilghman, MD 21671

Refinance Your Home

Currently Off Market - Sold Aug 9, 2023 for $438,830

Home Value

Trulia Estimate

$499K

Since last month

$5K (-0.9%)

Since last year

$30K (-5.7%)

Since last sale

$61K (+13.8%)

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 +3% in the last 10 years

Month	Estimated value
2026
August 2026	$500K
August 2026	$499K
July 2026	$504K
June 2026	$501K
May 2026	$512K
April 2026	$510K
March 2026	$514K
February 2026	$506K
January 2026	$515K
2025
December 2025	$512K
November 2025	$517K
October 2025	$511K
September 2025	$530K
August 2025	$530K
July 2025	$537K
June 2025	$539K
May 2025	$533K
April 2025	$532K
March 2025	$510K
February 2025	$490K
January 2025	$475K
2024
December 2024	$474K
November 2024	$472K
October 2024	$480K
September 2024	$483K

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	0.03	Single-Family Home	$375,000	12/10/25	3	2	1,512
5582 Trafalgar Cir, Tilghman, MD	0.29	Single-Family Home	$523,307	04/08/26	3	2.5	2,110
5379 Anchor Rd, Tilghman, MD	0.13	Single-Family Home	$510,000	12/05/25	2	2.5	1,232
5744 Johns Way, Tilghman, MD	0.60	Single-Family Home	$411,000	02/16/26	3	2.5	1,512
5489 Rude Ave, Tilghman, MD	0.52	Single-Family Home	$725,000	02/20/26	4	2.5	2,286
5654 Trafalgar Cir, Tilghman, MD	0.42	Single-Family Home	$455,000	08/21/26	3	2	1,710
5520 Leeward Ln, Tilghman, MD	0.15	Single-Family Home	$1,000,000	06/18/26	5	2.5	4,214
21424 Wharf Rd, Tilghman, MD	0.68	Single-Family Home	$349,000	11/04/25	2	1	1,464
5820 Tilghman Beach Dr, Tilghman, MD	0.73	Single-Family Home	$740,000	11/24/25	2	1	1,776
4940 Fairbank Rd, Tilghman, MD	0.97	Single-Family Home	$560,000	07/10/26	2	2	1,260

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	0.03	$375,000	3	2	1,512	Recently Sold
5379 Anchor Rd, Tilghman, MD 21671	0.13	$510,000	2	2.5	1,232	Recently Sold
5480 Windward Dr, Tilghman, MD 21671	0.10	$1,250,000	4	3	1,936	For Sale
21310 Landing Ln, Tilghman, MD 21671	0.13	$340,200	3	2	1,120	Off Market
5520 Leeward Ln, Tilghman, MD 21671	0.15	$1,000,000	5	2.5	4,214	Recently Sold
Leeward Ln, Tilghman, MD 21671	0.23	-	-	-	-	Off Market
5582 Trafalgar Cir, Tilghman, MD 21671	0.29	$523,307	3	2.5	2,110	Recently Sold
5559 Trafalgar Cir, Tilghman, MD 21671	0.32	$550,000	5	3.5	3,404	For Sale
21379 Ferry Landing Rd, Tilghman, MD 21671	0.33	$687,000	3	2.5	3,459	Off Market
Lot 44 Ferry Landing Rd, Tilghman, MD 21671	0.37	-	-	-	-	Off Market
Ferry Landing Rd, Tilghman, MD 21671	0.38	-	-	-	-	Off Market
5636 Trafalgar Cir, Tilghman, MD 21671	0.41	$598,600	4	2.5	2,786	Off Market

Local Information

Map ViewExplore the area around 5427 Windward Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 2023

0.52 acre lot

2,289 sqft

$218/sqft

Garage

About this House

This single-family home is located at 5427 Windward Dr, Tilghman, MD. 5427 Windward Dr is in Tilghman, MD and in ZIP code 21671. This property has 4 bathrooms and approximately 2,289 sqft of floor space. This property has a lot size of 0.52 acres and was built in 2023.

5427 Windward Dr, Tilghman, MD 21671 is a studio, 4 bathroom, 2,289 sqft single-family home built in 2023. It last sold for $438,830 on Aug 9, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $498,900, with a rent estimate of $3,544/month.

Home Details for 5427 Windward Dr

Interior Features
Heating & Cooling Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 1.5
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: Other
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 2023
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 0.52 acres

Price and Tax history

Date	Event	Price
Aug 9, 2023 Source: N/A	Sold	$438,830
Mar 30, 2022 Source: N/A	Sold	$62,000
Aug 31, 2012 Source: N/A	Sold	$120,000
Jun 27, 2005 Source: N/A	Sold	$115,000
Aug 11, 1998 Source: N/A	Sold	$27,500

Year	Property tax	Tax assessment
2025	$4,133	$451,600

Additional Cost

Market trends in Tilghman

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

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Price per sq ft

—

Available listings

3MoM

Around this home

Tilghman Elementary School
PK-5
Public
93 Students
Talbot County Public Schools
2/10
GreatSchools Rating
Parent Rating Average
Tilghman Elementary School packs big school resources in a small package. The school has excellent and dedicated teaching staff augmented by strong community volunteer program that assists in areas such as tutoring, music and art. The teacher to student ratio is excellent so the strengths and weaknesses of each child are well known and the test scores, which are well above state average, reflect it. A real gem in the public school system.
Parent Review
5y ago
3 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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 5427 Windward Dr

What is 5427 Windward Dr estimated to be worth?
Trulia's estimated value for 5427 Windward Dr in Tilghman, MD is $498,900.
What is the price history for 5427 Windward Dr?
5427 Windward Dr in Tilghman, MD last sold for $438,830 in August 2023.
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 5427 Windward Dr?
The closest schools to 5427 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 5427 Windward Dr?
The lot at 5427 Windward Dr in Tilghman, MD is about 0.52 acres (22,800 sq ft).
Does 5427 Windward Dr have a garage?
Yes, 5427 Windward Dr in Tilghman, MD has a garage.

Apartments for Rent

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Off Market Homes Near 5427 Windward Dr

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SOLD
SEP 2, 2026
$345,000
3 bd
1 ba
1,144 sqft
21527 Chicken Point Rd,
Tilghman, MD 21671
Meredith Fine Properties
SOLD
AUG 21, 2026
$265,000
3 bd
1 ba
996 sqft
21530 Coopertown Rd,
Tilghman, MD 21671
Benson & Mangold, LLC
SOLD
AUG 21, 2026
$455,000
3 bd
2 ba
1,710 sqft
5654 Trafalgar Cir,
Tilghman, MD 21671
Benson & Mangold, LLC
SOLD
AUG 13, 2026
$729,000
3 bd
2.5 ba
2,840 sqft
6660 Reeses Pride Rd,
Sherwood, MD 21665
Meredith Fine Properties
SOLD
JUL 10, 2026
$560,000
2 bd
2 ba
1,260 sqft
4940 Fairbank Rd,
Tilghman, MD 21671
TTR Sotheby's International Realty
SOLD
MAY 29, 2026
$400,000
9 bd
2.5 ba
5,389 sqft
21486 Mission Rd,
Tilghman, MD 21671
TTR Sotheby's International Realty
SOLD
MAY 20, 2026
$275,000
3 bd
1 ba
1,224 sqft
21749 Camper Cir,
Tilghman, MD 21671
Meredith Fine Properties
SOLD
APR 16, 2026
$425,000
2 bd
1 ba
960 sqft
6343 Bozman Neavitt Rd,
Neavitt, MD 21652
Benson & Mangold, LLC
SOLD
APR 8, 2026
$523,307
3 bd
2.5 ba
2,110 sqft
5582 Trafalgar Cir,
Tilghman, MD 21671
Eastern Shore Real Estate, LLC
SOLD
MAR 20, 2026
$350,000
1 ba
672 sqft
21558 Bar Neck Cove Rd,
Tilghman, MD 21671
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Homes for sale near 5427 Windward Dr

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0.71 ACRES
$1,250,000
4 bd
3 ba
1,936 sqft
5480 Windward Dr,
Tilghman, MD 21671
Benson & Mangold, LLC
$550,000
5 bd
3.5 ba
3,404 sqft
5559 Trafalgar Cir,
Tilghman, MD 21671
Meredith Fine Properties
NEW CONSTRUCTION
0.3 ACRES
$529,888
3 bd
2 ba
2,068 sqft
5648 Trafalgar Cir,
Tilghman, MD 21671
Benson & Mangold, LLC
0.58 ACRES
$985,000
4 bd
2.5 ba
3,040 sqft
21477 Island Club Rd,
Tilghman, MD 21671
TTR Sotheby's International Realty
1.48 ACRES
$1,945,000
5 bd
3.5 ba
3,906 sqft
5698 Leeward Ln,
Tilghman, MD 21671
Benson & Mangold, LLC
0.96 ACRES
$1,950,000
5 bd
4.5 ba
4,303 sqft
21485 Island Club Rd,
Tilghman, MD 21671
Benson & Mangold, LLC
NEW CONSTRUCTION
$529,888
3 bd
2 ba
2,068 sqft
5648 Trafalgar Cir #4,
Tilghman, MD 21671
$410,000
4 bd
2.5 ba
1,920 sqft
21406 Dogwood Cove Rd,
Tilghman, MD 21671
Meredith Fine Properties
2.74 ACRES
$1,200,000
3 bd
2.5 ba
2,477 sqft
21441 Dogwood Cove Rd,
Tilghman, MD 21671
Chesapeake Bay Real Estate Plus, LLC
0.91 ACRES
$925,000
4 bd
3 ba
2,850 sqft
4938 Fairbank Rd,
Tilghman, MD 21671
Meredith Fine Properties
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