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

5480 Windward Dr
Tilghman, MD 21671

4 Beds
3 Baths
1,936 sqft (on 0.71 acres)

$832,100

Trulia Estimate

as of Jul 4, 2026

Est. Refi. Payment $4,658/mo*

Refinance Your Home

$832,100

Trulia Estimate

as of Jul 4, 2026

Est. Refi. Payment $4,658/mo*

Refinance Your Home

4 Beds

3 Baths

1,936 sqft

(on 0.71 acres)

Local Information

Map ViewExplore the area around 5480 Windward Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

Waterfront, 100 feet shoreline, new pool grandfathered in to less than 100 feet to shore. Sit in pool and look at the magnificent bay! Dock. New pool bar.

5480 Windward Dr, Tilghman, MD 21671 is a 4 bedroom, 3 bathroom, 1,936 sqft single-family home built in 1973. It last sold for $595,000 on Jun 14, 2011. It is currently off market. The Trulia Estimate is $832,100, with a rent estimate of $3,178/month.

Home Highlights

Parking

Garage

Outdoor

Porch, Patio, Deck, Pool

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 5480 Windward Dr

Interior Features
Heating & Cooling Heating: Forced Air, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 1Floors: Hardwood
Interior Details Types of Rooms: Dining Room, Family Room, Master Bath, Office, Pantry, Sun RoomCeiling Fan
Appliances & Utilities Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa Fireplace
Windows, Doors, Floors & Walls Double Paned Windows
Security Security System

Exterior Features
Exterior Home Features Roof: CompositionDeckExterior: VinylFoundation Type: PiersLawnPatioPorch
Pool Pool
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached

Property Information
Year Built Year Built: 1973
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.71 acres

Additional Information
Intercom

Price History for 5480 Windward Dr

Date	Price	Event	Source
06/14/2011	$595,000	Sold	N/A
Recording Date 06/14/2011 County Transfer Tax N/A Total Transfer Tax N/A
04/29/2002	$315,000	Sold	N/A
Recording Date 04/29/2002 County Transfer Tax N/A Total Transfer Tax N/A
11/30/1998	$215,000	Sold	N/A
Recording Date 11/30/1998 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Tilghman

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

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Property Tax and Assessment

Year	2025
Tax
Assessment	$576,900

Home facts updated by county records

Comparable Sales for 5480 Windward Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
5582 Trafalgar Cir, Tilghman, MD	0.24	Single-Family Home	$523,307	04/08/26	3	2.5	2,110
5379 Anchor Rd, Tilghman, MD	0.22	Single-Family Home	$510,000	12/05/25	2	2.5	1,232
5520 Leeward Ln, Tilghman, MD	0.06	Single-Family Home	$1,000,000	06/18/26	5	2.5	4,214
5440 Anchor Rd, Tilghman, MD	0.11	Single-Family Home	$375,000	12/10/25	3	2	1,512
5489 Rude Ave, Tilghman, MD	0.56	Single-Family Home	$725,000	02/20/26	4	2.5	2,286
5744 Johns Way, Tilghman, MD	0.53	Single-Family Home	$411,000	02/16/26	3	2.5	1,512
5820 Tilghman Beach Dr, Tilghman, MD	0.65	Single-Family Home	$740,000	11/24/25	2	1	1,776
21424 Wharf Rd, Tilghman, MD	0.64	Single-Family Home	$349,000	11/04/25	2	1	1,464
6050 Sunset Ln, Tilghman, MD	1.09	Single-Family Home	$1,050,000	04/13/26	3	3	3,232
21368 Fairbank Cir, Tilghman, MD	1.18	Single-Family Home	$1,075,000	12/04/25	4	3	3,552

Nearby homes

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

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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
Leeward Ln,
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
SOLD
DEC 10, 2025
$375,000
3 bd
2 ba
1,512 sqft
5440 Anchor Rd,
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
SOLD
DEC 5, 2025
$510,000
2 bd
2.5 ba
1,232 sqft
5379 Anchor Rd,
Tilghman, MD 21671
Meredith Fine Properties
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. $699,800
3 bd
2.5 ba
3,459 sqft
21379 Ferry Landing Rd,
Tilghman, MD 21671
TTR Sotheby's International Realty
OFF MARKET
Est. $610,900
4 bd
2.5 ba
2,786 sqft
5636 Trafalgar Cir,
Tilghman, MD 21671
Monument Sotheby's International Realty
OFF MARKET
Ferry Landing Rd,
Tilghman, MD 21671
Long & Foster Real Estate, Inc.
FOR SALE
NEW CONSTRUCTION
QUICK MOVE-IN
$529,888
3 bd
2 ba
2,068 sqft
5648 Trafalgar Cir #4,
Tilghman, MD 21671
FOR SALE
NEW CONSTRUCTION
QUICK MOVE-IN
$489,888
3 bd
2 ba
1,710 sqft
5654 Trafalgar Cir #3,
Tilghman, MD 21921

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Additional Cost

Assigned Schools

These are the assigned schools for 5480 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 5480 Windward Dr

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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
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
$564,000
5 bd
3.5 ba
3,404 sqft
5559 Trafalgar Cir,
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
0.96 ACRES
$1,950,000
5 bd
4.5 ba
4,303 sqft
21485 Island Club Rd,
Tilghman, MD 21671
Benson & Mangold, LLC
$410,000
4 bd
2.5 ba
1,920 sqft
21406 Dogwood Cove 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
NEW CONSTRUCTION
$489,888
3 bd
2 ba
1,710 sqft
5654 Trafalgar Cir #3,
Tilghman, MD 21921
2.74 ACRES
$1,350,000
3 bd
2.5 ba
2,477 sqft
21441 Dogwood Cove Rd,
Tilghman, MD 21671
Chesapeake Bay Real Estate Plus, LLC
See more homes for sale in
Tilghman
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Off Market Homes Near 5480 Windward Dr

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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 16, 2026
$425,000
2 bd
1 ba
960 sqft
6343 Bozman Neavitt Rd,
Neavitt, MD 21652
Benson & Mangold, LLC
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 8, 2026
$523,307
3 bd
2.5 ba
2,110 sqft
5582 Trafalgar Cir,
Tilghman, MD 21671
Eastern Shore Real Estate, 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 5, 2025
$510,000
2 bd
2.5 ba
1,232 sqft
5379 Anchor Rd,
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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5480 Windward Dr
Tilghman, MD 21671

$832,100

$832,100

Local Information