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

OFF MARKET

5396 Windward Dr
Tilghman, MD 21671

Studio
5 Baths
3,494 sqft (on 0.46 acres)

$1,104,900

Trulia Estimate

as of Aug 4, 2026

Est. Refi. Payment $6,369/mo*

Refinance Your Home

$1,104,900

Trulia Estimate

as of Aug 4, 2026

Est. Refi. Payment $6,369/mo*

Refinance Your Home

Studio

5 Baths

3,494 sqft

(on 0.46 acres)

Local Information

Map ViewExplore the area around 5396 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

2024

Lot Size

0.46 acres

Living Area

3,494 sqft

Price/Sqft

$316

Parking

Garage

About this House

This single-family home is located at 5396 Windward Dr, Tilghman, MD. 5396 Windward Dr is in Tilghman, MD and in ZIP code 21671. This property has 5 bathrooms and approximately 3,494 sqft of floor space. This property has a lot size of 0.46 acres and was built in 2024.

5396 Windward Dr, Tilghman, MD 21671 is a studio, 5 bathroom, 3,494 sqft single-family home built in 2024. It last sold for $237,500 on May 24, 2022. It is currently off market. The Trulia Estimate is $1,104,900, with a rent estimate of $4,399/month.

Home Details for 5396 Windward Dr

Interior Features
Heating & Cooling Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 2
Fireplace & Spa Fireplace

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

Property Information
Year Built Year Built: 2024
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 0.46 acres

Price History for 5396 Windward Dr

Date	Price	Event	Source
05/24/2022	$237,500	Sold	N/A
Recording Date 05/24/2022 Contract Date 05/20/2022 County Transfer Tax $24 Total Transfer Tax $36
06/30/2020	$165,000	Sold	N/A
Recording Date 06/30/2020 Contract Date 06/24/2020 County Transfer Tax $17 Total Transfer Tax $25

Market trends in Tilghman

Last updated June 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

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Property Tax and Assessment

Year	2025
Tax
Assessment	$933,400

Home facts updated by county records

Comparable Sales for 5396 Windward Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
5440 Anchor Rd, Tilghman, MD	0.12	Single-Family Home	$375,000	12/10/25	3	2	1,512
5379 Anchor Rd, Tilghman, MD	0.07	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
5520 Leeward Ln, Tilghman, MD	0.22	Single-Family Home	$1,000,000	06/18/26	5	2.5	4,214
5744 Johns Way, Tilghman, MD	0.68	Single-Family Home	$411,000	02/16/26	3	2.5	1,512
5489 Rude Ave, Tilghman, MD	0.58	Single-Family Home	$725,000	02/20/26	4	2.5	2,286
21424 Wharf Rd, Tilghman, MD	0.77	Single-Family Home	$349,000	11/04/25	2	1	1,464
21368 Fairbank Cir, Tilghman, MD	1.02	Single-Family Home	$1,075,000	12/04/25	4	3	3,552
6050 Sunset Ln, Tilghman, MD	1.25	Single-Family Home	$1,050,000	04/13/26	3	3	3,232
4940 Fairbank Rd, Tilghman, MD	0.89	Single-Family Home	$560,000	07/10/26	2	2	1,260

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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SOLD
DEC 5, 2025
$510,000
2 bd
2.5 ba
1,232 sqft
5379 Anchor Rd,
Tilghman, MD 21671
Meredith Fine Properties
SOLD
DEC 10, 2025
$375,000
3 bd
2 ba
1,512 sqft
5440 Anchor Rd,
Tilghman, MD 21671
Meredith Fine Properties
FOR SALE
0.71 ACRES
$1,250,000
4 bd
3 ba
1,936 sqft
5480 Windward Dr,
Tilghman, MD 21671
Benson & Mangold, LLC
SOLD
JUN 18, 2026
$1,000,000
5 bd
2.5 ba
4,214 sqft
5520 Leeward Ln,
Tilghman, MD 21671
Keller Williams Realty
OFF MARKET
Est. $342,800
3 bd
2 ba
1,120 sqft
21310 Landing Ln,
Tilghman, MD 21671
Benson & Mangold, LLC
OFF MARKET
Leeward Ln,
Tilghman, MD 21671
Meredith Fine Properties
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
FOR SALE
3D VIEW
$564,000
5 bd
3.5 ba
3,404 sqft
5559 Trafalgar Cir,
Tilghman, MD 21671
Meredith Fine Properties
OFF MARKET
Est. $695,100
3 bd
2.5 ba
3,459 sqft
21379 Ferry Landing Rd,
Tilghman, MD 21671
TTR Sotheby's International Realty
OFF MARKET
Lot 44 Ferry Landing Rd,
Tilghman, MD 21671
TTR Sotheby's International Realty
OFF MARKET
Ferry Landing Rd,
Tilghman, MD 21671
Thyme Real Estate Co LLC
OFF MARKET
Est. $608,200
4 bd
2.5 ba
2,786 sqft
5636 Trafalgar Cir,
Tilghman, MD 21671
Monument Sotheby's International Realty

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Additional Cost

Assigned Schools

These are the assigned schools for 5396 Windward Dr.

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

Apartments for Rent

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Homes for sale near 5396 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
$564,000
5 bd
3.5 ba
3,404 sqft
5559 Trafalgar Cir,
Tilghman, MD 21671
Meredith Fine Properties
0.96 ACRES
$1,950,000
5 bd
4.5 ba
4,303 sqft
21485 Island Club Rd,
Tilghman, MD 21671
Benson & Mangold, LLC
1.48 ACRES
$1,995,000
5 bd
3.5 ba
3,906 sqft
5698 Leeward Ln,
Tilghman, MD 21671
Benson & Mangold, LLC
NEW CONSTRUCTION
0.3 ACRES
$529,888
3 bd
2 ba
2,068 sqft
5648 Trafalgar Cir,
Tilghman, MD 21671
Benson & Mangold, LLC
NEW CONSTRUCTION
0.3 ACRES
$489,888
3 bd
2 ba
1,710 sqft
5654 Trafalgar Cir,
Tilghman, MD 21671
Benson & Mangold, LLC
0.91 ACRES
$950,000
4 bd
3 ba
2,850 sqft
4938 Fairbank Rd,
Tilghman, MD 21671
Meredith Fine Properties
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
NEW CONSTRUCTION
0.77 ACRES
$2,475,000
7 bd
5.5 ba
4,151 sqft
21642 Chicken Point Rd,
Tilghman, MD 21671
Chesapeake Bay Real Estate Plus, LLC
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Tilghman
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Off Market Homes Near 5396 Windward Dr

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SOLD
JUL 27, 2026
$1,250,000
4 bd
2.5 ba
3,037 sqft
21408 Broad Cove Ln,
Tilghman, MD 21671
Compass
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
JUN 25, 2026
$1,250,000
Black walnut point Rd,
Tilghman, MD 21671
SOLD
JUN 18, 2026
$1,000,000
5 bd
2.5 ba
4,214 sqft
5520 Leeward Ln,
Tilghman, MD 21671
Keller Williams Realty
SOLD
APR 13, 2026
$1,050,000
3 bd
3 ba
3,232 sqft
6050 Sunset Ln,
Tilghman, MD 21671
Chesapeake Bay Real Estate Plus, LLC
SOLD
APR 1, 2026
$983,000
2 bd
2 ba
1,383 sqft
6271 Neavitt Manor Rd,
Neavitt, MD 21652
Benson & Mangold, LLC
SOLD
FEB 25, 2026
$799,000
4 bd
2 ba
1,724 sqft
22769 Almost Neavitt Rd,
Bozman, MD 21612
Long & Foster Real Estate, Inc.
SOLD
FEB 20, 2026
$725,000
4 bd
2.5 ba
2,286 sqft
5489 Rude Ave,
Tilghman, MD 21671
Meredith Fine Properties
SOLD
DEC 4, 2025
$1,075,000
4 bd
3 ba
3,552 sqft
21368 Fairbank Cir,
Tilghman, MD 21671
Benson & Mangold, LLC
SOLD
NOV 24, 2025
$740,000
2 bd
1 ba
1,776 sqft
5820 Tilghman Beach Dr,
Tilghman, MD 21671
Meredith Fine Properties
See more homes for sale in
Tilghman
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5396 Windward Dr
Tilghman, MD 21671

$1,104,900

$1,104,900