$1,250,000
4 Beds
3 Baths
1,936 sqft (on 0.71 acres)
5480 Windward Dr, Tilghman, MD 21671
Est. Mortgage $7,118/mo*
Get Pre-QualifiedHome Highlights
Property Type
Single-Family Home
Year Built
1973
Lot Size
0.71 acres
Price/Sqft
$646
Parking
1 Car Garage
HOA
$15/Monthly
Local Information
- Map ViewExplore the area around 5480 Windward Dr.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting front porch and foyer, where hardwood floors flow throughout the home. Recently renovated, the kitchen features white cabinetry, quartz countertops and large windows that fill the space with natural light while overlooking the front yard. The spacious living room is highlighted by a cathedral ceiling and opening to a year-round sunroom surrounded by walls of windows showcasing panoramic views of the Chesapeake Bay. The primary suite features a newly renovated bath with a tile and glass shower. Two guest bedrooms, an office and two additional beautifully renovated full baths occupy the opposite wing of the home, while the second level offers a fourth bedroom with skylights. Outside, you'll find everything needed to enjoy life on the water. The waterside pool with swim deck is complemented by a screened porch, expansive patio, covered seating area and a pool house/bar complete with air conditioning and electric. The private pier provides the perfect spot for fishing, crabbing, or simply taking in the spectacular sunsets, while the rip-rapped shoreline offers lasting shoreline protection. Additional improvements include an attached two-car garage, a storage shed with electric, and a new roof installed in 2025. Situated on high ground outside of the flood zone, this exceptional waterfront property offers direct access to some of the Chesapeake Bay's best fishing, boating, waterfront restaurants and the unforgettable Eastern Shore lifestyle.
Last check for updates: about 18 hours ago
Listing courtesy of Kimberly Crouch, (410) 829-7062
Benson & Mangold, LLC, (410) 745-0415
Source: Bright MLS, MLS#MDTA2014484
Also Listed on Bright MLS.
Home Details for 5480 Windward Dr
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Interior Details Number of Rooms: 12Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Primary Bathroom, Bathroom 2, Bathroom 3, Foyer, Kitchen, Living Room, Office, Sun Florida Room |
Beds & Baths Number of Bedrooms: 4Main Level Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3Number of Bathrooms (main level): 3 |
Dimensions and Layout Living Area: 1936 Square Feet |
Appliances & Utilities Appliances: Gas Water Heater, Water Heater |
Heating & Cooling Heating: Heat Pump,PropaneHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Heat Pump |
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace |
Levels, Entrance, & Accessibility Stories: 2Levels: TwoAccessibility: None |
View No View |
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Exterior Home Features Other Structures: Above Grade, Below GradeFoundation: Crawl SpaceHas a Private Pool |
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 1Parking: Storage,Garage Faces Front,Inside Entrance,Oversized,Driveway,Attached |
Pool Pool: Concrete, In Ground, PrivatePool |
Frontage WaterfrontWaterfront: BayOn Waterfront |
Water & Sewer Sewer: Public SewerWater Body: Chesapeake Bay |
Farm & Range Frontage Length: Water Frontage Ft: 110 |
Finished Area Finished Area (above surface): 1936 Square Feet |
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Days on Market: 52 |
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Year Built Year Built: 1973 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Contemporary |
Building Construction Materials: Vinyl SidingNot a New Construction |
Property Information Parcel Number: 2105187656 |
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Price List Price: $1,250,000Price Per Sqft: $646 |
Status Change & Dates Possession Timing: Close Of Escrow |
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MLS Status: ACTIVE |
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Direction & Address City: TILGHMANCommunity: Tilghman Island |
School Information Elementary School District: Talbot County Public SchoolsJr High / Middle School District: Talbot County Public SchoolsHigh School District: Talbot County Public Schools |
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Listing Agent Listing ID: MDTA2014484 |
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Building Area Building Area: 1936 Square Feet |
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Not Senior Community |
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Has an HOAHOA Fee: $185/Annually |
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Lot Area: 0.71 acres |
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Special Conditions: Standard |
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Listing Agreement Type: Exclusive Right To Sell |
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Business Information Ownership: Fee Simple |
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Mls Number: MDTA2014484Above Grade Unfinished Area: 1936 |
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Source Internet Automated Valuation Display: YSource Internet Consumer Comment: YSource Internet Entire Listing Display: YSource Internet Address Display: Y |
Around this home
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.
Market trends in Tilghman
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
17
3MoM
Home Value
Trulia Estimate
$1.17MSince last month
Decreased$27K (-2.3%)Since last year
Increased$305K (+35.2%)Since last sale
Increased$576K (+96.8%)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 +109% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| August 2026 | $1.17M |
| July 2026 | $1.2M |
| June 2026 | $832K |
| May 2026 | $839K |
| April 2026 | $817K |
| March 2026 | $830K |
| February 2026 | $821K |
| January 2026 | $832K |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
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 |
|---|---|---|---|---|---|---|---|
0.24 | Single-Family Home | $523,307 | 04/08/26 | 3 | 2.5 | 2,110 | |
0.22 | Single-Family Home | $510,000 | 12/05/25 | 2 | 2.5 | 1,232 | |
0.06 | Single-Family Home | $1,000,000 | 06/18/26 | 5 | 2.5 | 4,214 | |
0.11 | Single-Family Home | $375,000 | 12/10/25 | 3 | 2 | 1,512 | |
0.56 | Single-Family Home | $725,000 | 02/20/26 | 4 | 2.5 | 2,286 | |
0.53 | Single-Family Home | $411,000 | 02/16/26 | 3 | 2.5 | 1,512 | |
0.37 | Single-Family Home | $455,000 | 08/21/26 | 3 | 2 | 1,710 | |
0.65 | Single-Family Home | $740,000 | 11/24/25 | 2 | 1 | 1,776 | |
1.05 | Single-Family Home | $560,000 | 07/10/26 | 2 | 2 | 1,260 | |
0.64 | Single-Family Home | $349,000 | 11/04/25 | 2 | 1 | 1,464 |
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 |
|---|---|---|---|---|---|---|
0.06 | $1,000,000 | 5 | 2.5 | 4,214 | Recently Sold | |
0.14 | - | - | - | - | Off Market | |
0.13 | $340,200 | 3 | 2 | 1,120 | Off Market | |
0.11 | $375,000 | 3 | 2 | 1,512 | Recently Sold | |
0.24 | $523,307 | 3 | 2.5 | 2,110 | Recently Sold | |
0.22 | $510,000 | 2 | 2.5 | 1,232 | Recently Sold | |
0.28 | $550,000 | 5 | 3.5 | 3,404 | For Sale | |
0.33 | $687,000 | 3 | 2.5 | 3,459 | Off Market | |
0.35 | $598,600 | 4 | 2.5 | 2,786 | Off Market | |
0.36 | $529,888 | 3 | 2 | 2,068 | For Sale | |
0.36 | - | 3 | 2 | 1,710 | Off Market |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Jul 13, 2026 Source: Bright MLS #MDTA2014484 | Listed For Sale | $1,250,000 |
Jun 14, 2011 Source: N/A | Sold | $595,000 |
Apr 29, 2002 Source: N/A | Sold | $315,000 |
Nov 30, 1998 Source: N/A | Sold | $215,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $5,280 | $576,900 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Kimberly Crouch, Benson & Mangold, LLC, (410) 745-0415
Agent Phone: (410) 829-7062
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement.
Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale.
Property information displayed is deemed reliable but is not guaranteed.
Copyright 2026 Bright MLS, Inc. Click here for more information
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Frequently asked questions about 5480 Windward Dr
- What is the estimated monthly payment for 5480 Windward Dr?Based on a $1,250,000 list price with 20% down at today's rates, the estimated monthly payment for 5480 Windward Dr in Tilghman, MD is approximately $7,348 (about $6,585 principal & interest, $688 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What are the closest schools to 5480 Windward Dr?The closest schools to 5480 Windward Dr in Tilghman, MD are St. Michaels Middle/High School (rated 6/10), Tilghman Elementary School (Pre-K, rated 2/10).
- What is 5480 Windward Dr estimated to be worth?Trulia's estimated value for 5480 Windward Dr in Tilghman, MD is $1,168,100.
- Does 5480 Windward Dr have air conditioning?Yes, 5480 Windward Dr in Tilghman, MD has air conditioning.
- Does 5480 Windward Dr have a pool?Yes, 5480 Windward Dr in Tilghman, MD has a pool.
- How big is the lot at 5480 Windward Dr?The lot at 5480 Windward Dr in Tilghman, MD is about 0.71 acres (31,065 sq ft).
5480 Windward Dr, Tilghman, MD 21671 is a 4 bedroom, 3 bathroom, 1,936 sqft single-family home built in 1973. This property is currently available for sale and was listed by Bright MLS on Jul 13, 2026. The MLS # for this home is MLS# MDTA2014484.