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

5423 Windward Dr
Tilghman, MD 21671

3 Beds
2.5 Baths
2,000 sqft (on 0.51 acres)

$387,600

Trulia Estimate

as of Jun 16, 2026

Est. Refi. Payment $2,211/mo*

Refinance Your Home

$387,600

Trulia Estimate

as of Jun 16, 2026

Est. Refi. Payment $2,211/mo*

Refinance Your Home

3 Beds

2.5 Baths

2,000 sqft

(on 0.51 acres)

Local Information

-- mins to

Commute Destination

Description

This single-family home is located at 5423 Windward Dr, Tilghman, MD. 5423 Windward Dr is in Tilghman, MD and in ZIP code 21671. This property has 3 bedrooms, 3 bathrooms and approximately 2,000 sqft of floor space. This property has a lot size of 0.51 acres and was built in 1973.

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

Garage

Outdoor

Porch

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 5423 Windward Dr

Interior Features
Interior Details BasementAtticNumber of Rooms: 3Types of Rooms: Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Sun RoomCeiling Fan
Heating & Cooling Heating: Other, OilAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility Stories: 2Floors: Hardwood
Appliances & Utilities DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: OtherPorch
Parking & Garage GarageParking Spaces: 8Parking: Garage Attached

Property Information
Year Built Year Built: 1973
Property Type / Style Property Type: Single Family HomeArchitecture: Split-level

Community
Units in Building: 1

Lot Information
Lot Area: 0.51 acres

Price History for 5423 Windward Dr

Date	Price	Event	Source
12/22/2005	$217,500	Sold	N/A
Recording Date 12/22/2005 County Transfer Tax N/A Total Transfer Tax N/A
09/16/2002	$172,000	Sold	N/A
Recording Date 09/16/2002 County Transfer Tax N/A Total Transfer Tax N/A

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	$226,500

Home facts updated by county records

Homeowner tools

Estimated monthly rent$2,539/mo

List your home for rent

Comparable Sales for 5423 Windward Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
5440 Anchor Rd, Tilghman, MD	0.05	Single-Family Home	$375,000	12/10/25	3	2	1,512
5582 Trafalgar Cir, Tilghman, MD	0.32	Single-Family Home	$523,307	04/08/26	3	2.5	2,110
5379 Anchor Rd, Tilghman, MD	0.10	Single-Family Home	$510,000	12/05/25	2	2.5	1,232
5744 Johns Way, Tilghman, MD	0.63	Single-Family Home	$411,000	02/16/26	3	2.5	1,512
21271 Phillips Rd, Tilghman, MD	0.68	Single-Family Home	$430,000	06/27/25	3	1.5	1,445
5489 Rude Ave, Tilghman, MD	0.52	Single-Family Home	$725,000	02/20/26	4	2.5	2,286
5772 Tilghman Island Rd, Tilghman, MD	0.68	Single-Family Home	$366,250	06/27/25	3	1.5	1,652
4869 Bar Neck Rd, Tilghman, MD	0.36	Single-Family Home	$209,143	12/16/25		2	1,070
21424 Wharf Rd, Tilghman, MD	0.71	Single-Family Home	$349,000	11/04/25	2	1	1,464
21503 Mission Rd, Tilghman, MD	1.14	Single-Family Home	$350,000	06/24/25	4	2	1,652

Nearby homes

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

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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
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
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
Est. $699,900
3 bd
2.5 ba
3,459 sqft
21379 Ferry Landing Rd,
Tilghman, MD 21671
TTR Sotheby's International Realty
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 5423 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 5423 Windward Dr

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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
0.3 ACRES
$499,888
3 bd
2 ba
1,710 sqft
5654 Trafalgar Cir,
Tilghman, MD 21671
Benson & Mangold, LLC
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
NEW CONSTRUCTION
$499,888
3 bd
2 ba
1,710 sqft
5654 Trafalgar Cir #3,
Tilghman, MD 21921
$475,000
3 bd
2.5 ba
2,072 sqft
5933 Tilghman Island 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
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
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
See more homes for sale in
Tilghman
Take a look

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Off Market Homes Near 5423 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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5423 Windward Dr, Tilghman, MD 21671 is a 3 bedroom, 3 bathroom, 2,000 sqft single-family home built in 1973. This property is not currently available for sale. 5423 Windward Dr was last sold on Dec 22, 2005 for $217,500. The current Trulia Estimate for 5423 Windward Dr is $387,600.

5423 Windward Dr
Tilghman, MD 21671

$387,600

$387,600

Local Information