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

5401 Windward Dr
Tilghman, MD 21671

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

$367,000

Trulia Estimate

as of Jun 16, 2026

Est. Refi. Payment $2,098/mo*

Refinance Your Home

$367,000

Trulia Estimate

as of Jun 16, 2026

Est. Refi. Payment $2,098/mo*

Refinance Your Home

3 Beds

2 Baths

1,248 sqft

(on 0.45 acres)

Local Information

-- mins to

Commute Destination

Description

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.

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

No Info

Outdoor

Deck

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

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 History for 5401 Windward Dr

Date	Price	Event	Source
12/11/2018	$225,000	Sold	N/A
Recording Date 12/11/2018 Contract Date 09/24/2018 County Transfer Tax $23 Total Transfer Tax $34
08/13/2018	$250,000	Pending	Agent Provided

01/19/2018	$250,000	PriceChange	Agent Provided
Price Change $19,500 (-7%)
04/14/2017	$269,500	Listed For Sale	Agent Provided

Market trends in Tilghman

Last updated May 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	$240,600

Home facts updated by county records

Homeowner tools

Estimated monthly rent$2,039/mo

List your home for rent

Comparable Sales for 5401 Windward Dr

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
21271 Phillips Rd, Tilghman, MD	0.73	Single-Family Home	$430,000	06/27/25	3	1.5	1,445
4869 Bar Neck Rd, Tilghman, MD	0.34	Single-Family Home	$209,143	12/16/25		2	1,070
5744 Johns Way, Tilghman, MD	0.68	Single-Family Home	$411,000	02/16/26	3	2.5	1,512
5772 Tilghman Island Rd, Tilghman, MD	0.74	Single-Family Home	$366,250	06/27/25	3	1.5	1,652
21424 Wharf Rd, Tilghman, MD	0.76	Single-Family Home	$349,000	11/04/25	2	1	1,464
4897 Black Walnut Point Rd, Tilghman, MD	0.94	Single-Family Home	$547,000	06/20/25	3	2	1,056
5489 Rude Ave, Tilghman, MD	0.54	Single-Family Home	$725,000	02/20/26	4	2.5	2,286

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
OFF MARKET
Est. $343,900
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
OFF MARKET
Est. $699,900
3 bd
2.5 ba
3,459 sqft
21379 Ferry Landing Rd,
Tilghman, MD 21671
TTR Sotheby's International Realty
FOR SALE
OPEN SAT, 11-1PM
3D VIEW
$564,000
5 bd
3.5 ba
3,404 sqft
5559 Trafalgar Cir,
Tilghman, MD 21671
Meredith Fine Properties
OFF MARKET
Ferry Landing Rd,
Tilghman, MD 21671
Long & Foster Real Estate, Inc.
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. $614,300
4 bd
2.5 ba
2,786 sqft
5636 Trafalgar Cir,
Tilghman, MD 21671
Monument Sotheby's International Realty
FOR SALE
NEW CONSTRUCTION
QUICK MOVE-IN
$544,888
3 bd
2 ba
2,068 sqft
5648 Trafalgar Cir #4,
Tilghman, MD 21671

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Additional Cost

Assigned Schools

These are the assigned schools for 5401 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 5401 Windward Dr

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NEW CONSTRUCTION
0.3 ACRES
$499,888
3 bd
2 ba
1,710 sqft
5654 Trafalgar Cir,
Tilghman, MD 21671
Benson & Mangold, LLC
NEW CONSTRUCTION
0.3 ACRES
$544,888
3 bd
2 ba
2,068 sqft
5648 Trafalgar Cir,
Tilghman, MD 21671
Benson & Mangold, LLC
NEW CONSTRUCTION
$499,888
3 bd
2 ba
1,710 sqft
5654 Trafalgar Cir #3,
Tilghman, MD 21921
0.58 ACRES
$1,150,000
4 bd
2.5 ba
3,040 sqft
21477 Island Club Rd,
Tilghman, MD 21671
TTR Sotheby's International Realty
OPEN SAT, 11-1PM
$564,000
5 bd
3.5 ba
3,404 sqft
5559 Trafalgar Cir,
Tilghman, MD 21671
Meredith Fine Properties
NEW CONSTRUCTION
$544,888
3 bd
2 ba
2,068 sqft
5648 Trafalgar Cir #4,
Tilghman, MD 21671
$475,000
3 bd
2.5 ba
2,072 sqft
5933 Tilghman Island Rd,
Tilghman, MD 21671
Meredith Fine Properties
0.81 ACRES
$870,000
3 bd
2 ba
1,314 sqft
21560 Chicken Point Rd,
Tilghman, MD 21671
Chesapeake Bay Real Estate Plus, LLC
NEW
COMING SOON 7/1
0.91 ACRES
$895,000
4 bd
3 ba
2,850 sqft
4938 Fairbank Rd,
Tilghman, MD 21671
Meredith Fine Properties
1.48 ACRES
$1,995,000
5 bd
3.5 ba
3,906 sqft
5698 Leeward Ln,
Tilghman, MD 21671
Benson & Mangold, LLC
See more homes for sale in
Tilghman
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Off Market Homes Near 5401 Windward Dr

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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
SOLD
FEB 20, 2026
$350,000
2 bd
1 ba
864 sqft
6135 Summit St,
Tilghman, MD 21671
Meredith Fine Properties
SOLD
FEB 16, 2026
$411,000
3 bd
2.5 ba
1,512 sqft
5744 Johns Way,
Tilghman, MD 21671
Tilghman Island Realty Inc
SOLD
JAN 8, 2026
$300,000
2 bd
1 ba
1,080 sqft
5909 Tilghman Island Rd,
Tilghman, MD 21671
SOLD
DEC 16, 2025
$209,143
2 ba
1,070 sqft
4869 Bar Neck Rd,
Tilghman, MD 21671
SOLD
DEC 10, 2025
$375,000
3 bd
2 ba
1,512 sqft
5440 Anchor Rd,
Tilghman, MD 21671
Meredith Fine Properties
SOLD
DEC 5, 2025
$510,000
2 bd
2.5 ba
1,232 sqft
5379 Anchor Rd,
Tilghman, MD 21671
Meredith Fine Properties
See more homes for sale in
Tilghman
Take a look

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5401 Windward Dr, Tilghman, MD 21671 is a 3 bedroom, 2 bathroom, 1,248 sqft single-family home built in 1994. This property is not currently available for sale. 5401 Windward Dr was last sold on Dec 11, 2018 for $225,000. The current Trulia Estimate for 5401 Windward Dr is $367,000.

5401 Windward Dr
Tilghman, MD 21671

$367,000

$367,000

Local Information