26372 Westerly Road

Closed 8/29/25

Last Sold Price

$3,475,000

4 beds5 baths5,761 sqft$603/sqft

26372 Westerly Rd, Easton, MD 21601

Description

Your own private resort awaits you! This stunning 4-bedroom contemporary estate offers a beautifully landscaped parklike setting on a 7.26 acre point of land with 1,089 feet of frontage and private dock on Plaindealing Creek. This sophisticated home was designed by Alan Meyers, a celebrated Washington DC architect. The one level main house has 3 bedrooms, 2.5 baths and a 2-car garage. Your guests won’t want to leave the private 1-bedroom guest house with a full kitchen, 2 car garage and spacious...Your own private resort awaits you! This stunning 4-bedroom contemporary estate offers a beautifully landscaped parklike setting on a 7.26 acre point of land with 1,089 feet of frontage and private dock on Plaindealing Creek. This sophisticated home was designed by Alan Meyers, a celebrated Washington DC architect. The one level main house has 3 bedrooms, 2.5 baths and a 2-car garage. Your guests won’t want to leave the private 1-bedroom guest house with a full kitchen, 2 car garage and spacious living area that overlooks the water. The main residence offers highly crafted custom features including custom moldings, wood paneling, extensive built-ins and wide plank quartersawn white oak flooring. You will enjoy breathtaking panoramic water views from all rooms. The great room features a soaring cathedral ceiling, fireplace with custom limestone surround and hearth and a wall of glass overlooking the beautiful waterside pool and waterfront beyond. An outdoor entertaining deck features areas for lounging and dining and a 6-person hot tub. The kitchen adjoins the great room and features maple cabinetry, Corian counters and a bar counter. The kitchen opens to a glass-walled sun/breakfast room with a wood paneled vaulted ceiling. The family/media room features detailed maple paneling, extensive built-ins and a separate office. Not to be overlooked is the beautiful powder room that is a creative gem! The primary bedroom suite is a private haven featuring a built-in king-size bed that overlooks the waterfront, a sitting room and a luxurious spa-like bathroom that also enjoys a water view. The guest wing features 2 guest bedrooms with water views and 2 full bathrooms. There is a full-size laundry room, a separate pantry and more than ample closet space throughout the home. No detail has been spared in this beautifully conceived property. The home is well located in between Historic Easton and St. Michaels and their wonderful amenities, shopping and great restaurants. Please click on the movie camera icon to enjoy the virtual tour and floor plans that are keyed to the photos.

LISTING CLOSED: 08/29/2025 12:00 AM

Listed by Eugene M Smith • TTR Sotheby's International Realty
P: (410) 443-1571 gsmith@ttrsir.com

Property Details for 26372 Westerly Road

Status

Closed

MLS #

MDTA2009924

Days on Market

Taxes

$21,999 / year

HOA Fees

Condo/Co-op Fees

Property Type

Single Family

MLS Type

Residential / Fee Simple

Year Built

1988

Lot Size

7.26 AC / 316,246 SF

County

Talbot County

Tax ID Number

2102107015

Ownership

Fee Simple

Condo Coop Association

HOA

Structure Type

Detached

Style

Contemporary

Levels/Stories

Waterfront

Yes

Waterfront Features

Private Dock Site, Rip-Rap

Views

Water, Panoramic, Trees/Woods

Garage

Yes

Subdivision

WESTERLY

Subdivision

WESTERLY (TALBOT MD)

Legal Subdivision

Total Parking Spaces

Central Air

Yes

Basement

Above Grade Finished SQFT

5,761.00

Above Grade Fin SQFT Source

Assessor

Below Grade Finished SQFT

.00

Below Grade Fin SQFT Source

Assessor

Below Grade Unfinished SQFT

.00

Below Grade Unfin SQFT Source

Assessor

Total Below Grade SQFT

.00

Total Below Grade SQFT Source

Assessor

New Construction

Property Condition

Excellent

Get preapproved with Rocket Mortgage¹

Location

Listing Courtesy of TTR Sotheby's International Realty

Sold By TTR Sotheby's International Realty

Add your commute

Building Information for 26372 Westerly Road

Stories1Year Built1988Building Size-Lot Size7.26 AC / 316,246 SF

Payment Calculator

Get preapproved with
OriginPoint Mortgage or Rocket Mortgage¹

$19,496 per month

30 year fixed, 6.55% Interest

Principal and Interest

$17,663

Property Taxes

$1,833

HOA Dues

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Property Information for 26372 Westerly Road

Location

In City Limits: No
School District Name: TALBOT COUNTY PUBLIC SCHOOLS

School District County ID: 121138072466
SchoolDistrictSource: Listing Agent
County: TALBOT

Waterfront / Water Access

Water View: Yes
Water Access: Yes

Water Access Features: Private Access, Sail, Swimming Allowed, Fishing Allowed, Canoe/Kayak, Boat - Powered
Water Oriented: Yes
Navigable Water: Yes
Tidal Water: Yes
Water Body Name: PLAINDEALING CREEK
Water Body Type: Creek
Water Frontage In Feet: 1089.0
Riparian Rights Y/N: Yes
Docks Count: 1
Dock Type and Features: Pier (Perpendicular)
Dock/Slip Conveys Y/N: true
Dock/Slip Conveyance: Exclusive Use
Slips Count: 2
Boats Power Count: 1
Boats Nonpower Count: 1
Mean Low Water Feet: 4.00
Distance To Body Of Water: .00
Distance To Body Of Water Units: Blocks

Association / Community Info

Senior Community: No

Taxes and Assessment

Tax Year: 2024
Tax Assessed Value: $2,436,233

Year Assessed: 2024
County Tax: $21,999
Improvement Assessed Value: $894,700
City Town Tax: $0
Land Assessed Value: $1,292,600
Special Assessment Pymnt: Annually
Clean Green Assessed: No
Municipal Trash: No
Land Use Code: R
Agricultural Tax Due: No
Historic: No
Zoning: A2
Zoning Dscrp: Residential
Tax Lot: 5
School Tax: $0
Automatically Update Tax Values Y/N: Yes

Lease Information

Pets Allowed: Yes
Pet Restrictions: No Pet Restrictions

Rooms

Main

# Bedrooms Count Main Level: 3
# Bathrooms Count Main Level: 4

# Bathrooms Full Main Level: 3
# Bathrooms Half Main Level: 1

All Upper Levels

# Bedrooms Count All Upper Levels: 1
# Bathrooms Count All Upper Levels: 1

# Bathrooms Full All Upper Levels: 1
# Bathrooms Half All Upper Levels: 0

Upper Level 1

# Bedrooms Count Upper Level: 1
# Bathrooms Count Upper Level: 1

# Bathrooms Full Upper Level: 1
# Bathrooms Half Upper Level: 0

Upper Level 2

# Bedrooms Count Upper Level: 0
# Bathrooms Count Upper Level: 0

# Bathrooms Full Upper Level: 0
# Bathrooms Half Upper Level: 0

All Lower Levels

# Bedrooms All Lower Levels: 0
# Bathrooms All Lower Levels: 0

# Bathrooms Full All Lower Levels: 0
# Bathrooms Half All Lower Levels: 0

Lower Level 1

# Bathrooms Lower Level: 0
# Bathrooms Half Lower Level: 0

Lower Level 2

# Bedrooms Lower Level: 0
# Bathrooms Lower Level: 0

# Bathrooms Full Lower Level: 0
# Bathrooms Half Lower Level: 0

Rooms

Stories: Lower 1, Lower 2, Main, Upper 1, Upper 2

Building Info

Year Major Reno Remodel: 2008
Total Finished SQFT: 5,761.00

Total Finished SQFT Source: Assessor
Tax Total Finished SQFT: 5,761.00
Total SQFT: 5,761.00
Total SQFT Source: Assessor
Main Entrance Orientation: Southwest
Construction Materials: HardiPlank Type
Roof: Architectural Shingle
Ext Main Mid-res: http://bright-media02.prd.brightmls.com/bright/images/0000/8039/1938/1398/803919381398_512_384_WM_AIeyHKIzQMayd3wd.jpg
Wall and Ceiling Types: 9'+ Ceilings, Cathedral Ceilings, Paneled Walls, Vaulted Ceilings, Wood Ceilings
Flooring Type: Hardwood, Carpet
Foundation Details: Crawl Space
Room and Floor: Bedrooms-Main Level-1, Bedrooms-Main Level-2, Bedrooms-Main Level-3, Bathrooms Full-Main Level-1, Bathrooms Full-Main Level-2, Bathrooms Full-Main Level-3, Bathrooms Half-Main Level-1, Bedrooms-Upper Level 1-1, Bathrooms Full-Upper Level 1-1
# Bathrooms Full: 4
# Bathrooms Half: 1
Other Structure: Guest House, Shed

Lot / Land Information

Lot Size Source: Assessor
Lot Features: Partly Wooded, Adjoins - Open Space, Private, Landscaping

Location Type: Creek/Stream
Parcel ID: 5294339
Ground Rent Exists: No

Parking

Type Of Parking: Attached Garage
Num of Attached Garage Spaces: 4

Total Garage Spaces: 4
Garage Features: Garage Door Opener

Interior Features

Interior Features: Attic, Primary Bath(s), Built-Ins, Wood Floors, Floor Plan - Open, Breakfast Area, Ceiling Fan(s), Central Vacuum, Entry Level Bedroom, Kitchen - Gourmet, Pantry, Primary Bedroom - Bay Front, Recessed Lighting, Skylight(s), Walk-in Closet(s), WhirlPool/HotTub
Fireplace: Yes

Fireplaces Count: 2
Fireplace Features: Wood, Gas/Propane
Appliances: Built-In Microwave, Built-In Range, Central Vacuum, Dishwasher, Dryer, Extra Refrigerator/Freezer, Washer, Refrigerator
Accessibility Features: None
Security Features: Security System
Window Features: Palladian, Screens
Laundry Type: Main Floor
Virtual Tour URL Unbranded: https://links.us1.defend.egress.com/Warning?crId=684387e25a0b77339678f47c&Domain=ttrsir.com&Threat=eNpzrShJLcpLzAEADmkDRA%3D%3D&Lang=en&Base64Url=eNrLKCkpKLbS1y_JKCrVLclI1c1JzSvWzSwrTdMry0wt1ysoyi9ILSqp1DcyNjY2MDC3z0ypsDUEACI4EuI%3D&@OriginalLink=thru-the-lens-ivuf.view.property

Exterior Features

Exterior Features: Extensive Hardscape, Flood Lights, Exterior Lighting, Hot Tub
Outdoor Living Structures: Deck(s)

Pool: Yes - Personal
Personal Pool Features: Saltwater, Gunite

Utilities

Utilities: Propane, Cable TV Available
Heating: Yes

Cooling Type: Central A/C, Zoned
Cooling Fuel: Electric
Heating Type: Heat Pump - Oil BackUp
Heating Fuel: Electric, Oil
Hot Water: Electric
Water Source: Well
Sewer Septic: On Site Septic
Internet Services: Fiber Optic

Confidential Data

Listing Office

List Agent AOR: Mid-Shore Board of REALTORS
List Agent URL: www.stmichaelsrealtor.net

Property History for 26372 Westerly Road

Date	Event & Source	Price	Appreciation
Sep 26, 2025	Closed (Public Record) Public Record #1917476816	$3,475,000	+3.9% / yr
Aug 29, 2025	Closed BRIGHT #MDTA2009924	$3,475,000	—
Jun 28, 2025	Pending BRIGHT #MDTA2009924		—
Jun 28, 2025	Active Under Contract BRIGHT #MDTA2009924		—
Jun 8, 2025	Listed (Active) BRIGHT #MDTA2009924		—
Jun 2, 2025	Temp Off Market BRIGHT #MDTA2009924		—
Jun 2, 2025	Listed (Active) BRIGHT #MDTA2009924	$3,795,000	—
Dec 27, 2013	Closed (Public Record) Public Record #392953679	$2,225,000	—
Dec 27, 2013	Closed BRIGHT #1003468882	$2,225,000	—
Nov 21, 2013	Pending BRIGHT #1003468882		—
Apr 22, 2013	Listed (Active) BRIGHT #1003468882	$2,750,000	—
Aug 15, 1996	Closed BRIGHT #MDTA117258	$855,000	—
May 12, 1996	Pending BRIGHT #MDTA117258		—
Apr 30, 1996	Listed (Active) BRIGHT #MDTA117258	$887,000	—

Date	Event & Source	Price
09/26/2025	Closed (Public Record) Public Record #1917476816	$3,475,000 +3.9% / yr
08/29/2025	Closed BRIGHT #MDTA2009924	$3,475,000
06/28/2025	Pending BRIGHT #MDTA2009924	—
06/28/2025	Active Under Contract BRIGHT #MDTA2009924	—
06/08/2025	Listed (Active) BRIGHT #MDTA2009924	—
06/02/2025	Temp Off Market BRIGHT #MDTA2009924	—
06/02/2025	Listed (Active) BRIGHT #MDTA2009924	$3,795,000
12/27/2013	Closed (Public Record) Public Record #392953679	$2,225,000
12/27/2013	Closed BRIGHT #1003468882	$2,225,000
11/21/2013	Pending BRIGHT #1003468882	—
04/22/2013	Listed (Active) BRIGHT #1003468882	$2,750,000
08/15/1996	Closed BRIGHT #MDTA117258	$855,000
05/12/1996	Pending BRIGHT #MDTA117258	—
04/30/1996	Listed (Active) BRIGHT #MDTA117258	$887,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 26372 Westerly Road

Taxable ValueLand$1,357,200Additions$1,203,500Total$2,560,700

Tax Record2023$19,775 ($1,648 / month)

Home Facts

Beds0Baths4.5Total Finished SqFt4,161 SqFtAbove Grade Finished SqFt4,161 SqFtStories1Lot Size316,246 SqFtStyleSingle Family ResidenceYear Built1988ZoningA2CountyTALBOTAPN02-107015Fireplace TypeHas Fireplace

Schools near 26372 Westerly Road

This home is within Talbot County Public Schools.


Rating	School	Type	Grades	Distance
5/10	St. Michaels Elementary School	Public - Serves this home	PK to 5	4.5 mi
5/10	St. Michaels Middle/High School	Public - Serves this home	6 to 12	4.5 mi
5/10	Easton High School	Public - Serves this home	9 to 12	5.5 mi


Rating	School	Distance
5/10	St. Michaels Elementary School PublicPK to 5 Serves this home	4.5 mi
5/10	St. Michaels Middle/High School Public6 to 12 Serves this home	4.5 mi
5/10	Easton High School Public9 to 12 Serves this home	5.5 mi

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

New listings in 21601

$989,000 | 204 Brookletts Avenue, Easton, MD 21601

1/71

New

$989,000

3
Bedrooms: 3
Bathrooms: 2,469
Square Feet: 0.18
Acres

204 Brookletts Avenue, Easton, MD 21601

1/40

$1,150,000

3
Bedrooms: 3
Bathrooms: 4,453
Square Feet: 0.25
Acres

7040 Schoolhouse Lane, Easton, MD 21601

$865,000

5
Bedrooms: 3
Bathrooms: 4,051
Square Feet: 2
Acres

30595 Kingston Road, Easton, MD 21601

Coming SoonOpen: 9/11 05:00PM - 08:00PM

$525,000

3
Bedrooms: 3
Bathrooms: 2,729
Square Feet: 0.27
Acres

29796 Lyons Drive, Easton, MD 21601

Coming Soon

$365,000

3
Bedrooms: 2
Bathrooms: 1,820
Square Feet: 0.24
Acres

29266 Pin Oak Way, Easton, MD 21601

$350,000

4
Bedrooms: 1
Bathrooms: 1,248
Square Feet: 0.15
Acres

605 August Street, Easton, MD 21601

$429,990 | 635 Elizabeth Street, Easton, MD 21601

1/57

Active Under Contract

$429,990

3
Bedrooms: 2
Bathrooms: 1,582
Square Feet: 0.22
Acres

635 Elizabeth Street, Easton, MD 21601

1/47

$2,495,000

3
Bedrooms: 3
Bathrooms: 2,986
Square Feet: 3.3
Acres

27476 Travelers Rest Court, Easton, MD 21601

Listed By Coldwell Banker Realty

$415,000

4
Bedrooms: 3
Bathrooms: 2,671
Square Feet: 0.11
Acres

29141 Superior Circle, Easton, MD 21601

Nearby home values

Address	Sold price	Beds	Baths	Sqft	Lot (Sqft)
This home: 26372 Westerly Road, Easton, MD 21601	$3,475,000	4	5	5,761	316,246
26366 Westerly Road, Easton, MD 21601	$2,000,000	4	4	4,770	202,990
6690 Hopkins Neck Road, Easton, MD 21601	$705,000	4	3	3,575	157,034
26362 Westerly Road, Easton, MD 21601	$2,400,000	4	5	3,272	185,130
26330 Westerly Road, Easton, MD 21601	$1,000,000	3	3	2,392	183,823
6420 Hopkins Neck Road, Easton, MD 21601	$650,000	4	4	–	94,090
6694 Hopkins Neck Road, Easton, MD 21601	$2,775,000	4	4	5,690	923,472
6416 Hopkins Neck Road, Easton, MD 21601	$1,700,000	–	3.5	3,367	720,918
6625 Schoolhouse Lane, Royal Oak, MD 21662	–	–	3	3,461	1,195,635
6695 Schoolhouse Lane, Royal Oak, MD 21662	–	–	4	2,782	396,832
6768 Hopkins Neck Road, Easton, MD 21601	$420,000	–	4	3,610	1,078,284
6744 Hopkins Neck Road, Easton, MD 21601	–	–	3	2,811	227,819
6398 Hopkins Neck Road, Easton, MD 21601	$4,200,000	5	8	8,453	231,652
6821 Schoolhouse Lane, Royal Oak, MD 21662	–	–	7	6,111	2,966,349
6645 Schoolhouse Lane, Royal Oak, MD 21662	–	–	3	3,220	648,608
26326 Heronwood Road, Easton, MD 21601	$2,451,000	4	5	4,371	220,414

Explore Nearby Homes

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of TTR Sotheby's International Realty

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 08/29/2025 01:44 PM

Know your buying power with a preapproval and custom rate in minutes

Explore Nearby Homes

Homes in Nearby 21601 Neighborhoods

Homes in Nearby 21601 Cities

Homes in Nearby 21601 Zip Codes