255 Sailcloth Way, Chester, MD 21619 - Photo 1

1/1

$898,000

Sold
Closed
Single Family
4 Beds
4 Full Baths
3,450 Sq. Ft.
6 Car Garage

1/1

Property Description

Welcome to 255 Sailcloth Way in Chester's premier 55+ community-K. Hovnanian's Four Seasons at Kent Island. This upgraded Santorini model is perfectly situated on a cul-de-sac premium lot and features 4 bedrooms, 4 full baths, and double primary suites-ideal for multigenerational living or hosting guests in comfort. Enjoy high-end finishes throughout, including LVP flooring, a chef's kitchen with upgraded cabinetry and gas cooking, luxury baths with roll-in showers, a loft, and a rare sky basement for added storage space. . You will fall in love with open concept kitchen and family room. The 12 foot island will surely be the focal point and heart of the home perfect for prep or serving gatherings. The walk in pantry and beverage station add a touch of luxury to the already well appointed kitchen. The wall of windows that frames the family room includes a slider out to your private screened in porch with recessed lighting and two ceiling fans - perfect for enjoying your morning coffee or a crab feast. The upgraded loft is ideal for guests or in home caretaker with private living space, a full bath and bedroom with a walk in closet. This home is classy, stylish and luxurious all while offering maintenance free living. The time is now to enjoy the Resort-style amenities, stunning design, and unbeatable location-this one checks every box!

Full Property Details

Full Property Details for 255 Sailcloth Way

General

Sold For: $898,000
HOA FEE: $305/month
Taxes: $6,424 (2024)
Status: Closed
Type: Single Family
Source: BrightMLSMidAtlantic
MLS ID: MDQA2013944
Added to Site: 183 day(s) ago

Rooms

Bathrooms

Total Bathrooms: 4
Full Bathrooms: 4
Upper Floor Baths: 1
Upper - Full Baths: 1
Main Floor Baths: 3
Main - Full Baths: 3

Bedrooms

Total Bedrooms: 4
Bedrooms Upper: 1
Bedrooms Main & Up: 3

Additional Information

Shared Pool: Yes
Pool: Yes

Parking

Garage: Yes
Garage Spaces: 6
Total Spaces: 6
Parking Type: Attached Garage, Detached Garage
Garage Description: Garage - Side Entry, Garage Door Opener, Additional Storage Area, Inside Access

Location

County: Queen Annes
Development Name: Four Seasons At Kent Island
Subdivision: Four Seasons At Kent Island
Driving Directions: Enter Four Seasons community, turn left onto Sailcloth, follow to the cul de sac, last house on the left.

School Information

School District: Queen Anne's County Public Schools

Community

Association: Yes
Adult Community: Yes

Heating & Cooling

Central air: Yes
Cooling Type: Central A/C, Ceiling Fan(s)
Cooling Fuel: Electric
Heating Type: Heat Pump(s)
Heating Fuel: Propane - Leased
Water Heater: Instant Hot Water, Propane

Utilities

Sewer: Public Sewer
Water: Public
Utility Description: Propane - Community

Structural Information

Architectural Info: Coastal, Contemporary, Craftsman
Architectural Style: Coastal, Contemporary, Craftsman
Structure Type: Detached
Construction: HardiPlank Type
Foundation: Slab
Roof: Architectural Shingle
Stories/Levels: 0
Stories Description: Main, Upper 1
Square Feet: 3,450
Sq. Ft. Source: Estimated
Living Area: 3,450 Sq. Ft.
Year Built: 2021
Year Built Source: Assessor

Lot Features

Lot Size (Acres): 0.17
Lot Size (Sq. Ft.): 7,523
Lot Size Source: Assessor
Zoning: SMPD

Financial Considerations

Price Per Sq. Ft.: $275.36
Association Fee: $305
Assoc Fee Freq.: Monthly
Assessment Year: 2025
County Tax: $6,424
County Tax Freq: Annually
Tax w/Assessment: $714,067
Tax Amount: $6,424
Tax Year: 2024
Terms: Standard Sale
Tax Total Finished Sq. Ft.: 3057

Disclosures and Reports

Ownership: Fee Simple
Lot Number: 197

Listed by Keller Williams Flagship, Kathleen Higginbotham
Sold by Unrepresented Buyer Office, Unrepresented Buyer

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Listing agent

— 255 Sailcloth Way —

Kathleen Higginbotham

Keller Williams Flagship

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Schools

Schools serving 255 Sailcloth Way

School District:Queen Annes County Public Schools

Name	Grades	Distance
Bayside Elementary School, Stevensville, MD 301 Church Street, Stevensville, MD 21666	3-5	0.9 mi
Kent Island Elementary School 110 Elementary Way, Stevensville, MD 21666	PK-2	1 mi
Stevensville Middle School 610 Main Street, Stevensville, MD 21666	6-8	1 mi
Kent Island High School 900 Love Point Road, Stevensville, MD 21666	9-12	1.2 mi

Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 255 Sailcloth Way

Date

Details

Price

Change

Source

10/01/2025

Sold

$898,000

-5.47%

MLS

7/18/2025

Listed

$950,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

932 Kimberly Way, Stevensville, MD 21666 - Photo 1

Just Listed

$465,000

Open House

932 Kimberly Way Stevensville, MD 21666

Single Family
Active
Updated 2 days ago

3
Beds
3
Total Baths
1,419
Sq. Ft.

Listed by Redfin Corp, Barbara A McCaffrey

301 John Kallis Ln, Stevensville, MD 21666 - Photo 1

Just Listed

$1,995,000

301 John Kallis Ln Stevensville, MD 21666

Single Family
Active
Updated 21 hours ago

3
Beds
3
Total Baths
3,216
Sq. Ft.

Listed by TTR Sotheby's International Realty, Bradley R Kappel

5 Mariners Way, Stevensville, MD 21666 - Photo 1

Just Listed

$255,000

Open House

5 Mariners Way #2 Stevensville, MD 21666

Townhouse
Active
Updated 8 hours ago

2
Beds
2
Total Baths
968
Sq. Ft.

Listed by Long & Foster Real Estate, Inc., Deborah A Shiley

117 Web Foot Ln, Stevensville, MD 21666 - Photo 1

Just Listed

$650,000

Open House

117 Web Foot Ln Stevensville, MD 21666

Single Family
Active
Updated 1 day ago

4
Beds
3
Total Baths
2,553
Sq. Ft.

Listed by Long & Foster Real Estate, Inc., Violeta I Aguirre

1000 Chesapeake Dr, Stevensville, MD 21666 - Photo 1

Price Reduced

-$11,000 (-1.47%)

$739,000

1000 Chesapeake Dr Stevensville, MD 21666

Single Family
Active
Updated 3 days ago

5
Beds
3
Total Baths
3,864
Sq. Ft.

Listed by The DD McCracken Home Team (410) 224-2200

101 Beachside Dr, Stevensville, MD 21666 - Photo 1

101 Beachside Dr Stevensville, MD 21666

Single Family
Active
Updated 3 days ago

5
Beds
4
Total Baths
2,600
Sq. Ft.

Listed by Coastal Realty Maryland, Candice Friday

325 Larch Pl, Stevensville, MD 21666 - Photo 1

325 Larch Pl Stevensville, MD 21666

Single Family
Active
Updated 3 days ago

4
Beds
3
Total Baths
2,232
Sq. Ft.

Listed by Chesapeake Real Estate Associates, LLC, Martine H McGinty

241 Jessica Lynn Ave, Stevensville, MD 21666 - Photo 1

241 Jessica Lynn Ave Stevensville, MD 21666

Townhouse
Active
Updated 1 day ago

4
Beds
4
Total Baths

Listed by Keller Williams Flagship, George 112,540 Bailey

194 Sailcloth Way, Chester, MD 21619 - Photo 1

Sold

$790,000

194 Sailcloth Way Chester, MD 21619

Single Family
Closed

3
Beds
3
Total Baths
2,453
Sq. Ft.

Listed by Ross Hunsberger
Sold by Real Broker, LLC, Veronica M Lawson

235 Bayberry Dr, Chester, MD 21619 - Photo 1

Sold

$910,000

235 Bayberry Dr Chester, MD 21619

Single Family
Closed

3
Beds
4
Total Baths
3,514
Sq. Ft.

Listed by RE/MAX Executive, Ralph S. Kennedy and RE/MAX Executive, Jennifer Anne Thomas
Sold by RE/MAX Executive, Jennifer Anne Thomas

223 Broadwater Dr, Chester, MD 21619 - Photo 1

Sold

$837,000

223 Broadwater Dr Chester, MD 21619

Single Family
Closed

3
Beds
3
Total Baths
2,745
Sq. Ft.

Listed by RE/MAX Executive, Ralph S. Kennedy
Sold by Greater Annapolis Realty, Joseph E Fagiolo

130 Sunrise Ct, Chester, MD 21619 - Photo 1

Sold

$935,000

130 Sunrise Ct Chester, MD 21619

Single Family
Closed

3
Beds
4
Total Baths
3,494
Sq. Ft.

Listed by Engel & Volkers Annapolis, Meghan Richardson and Engel & Volkers Annapolis, Tonia M Falkowski
Sold by RE/MAX Executive, Jennifer Anne Thomas

255 Sailcloth Way, Chester, MD 21619 (MLS# MDQA2013944) is a Single Family property that was sold at $898,000 on October 01, 2025. Want to learn more about 255 Sailcloth Way? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.

255 Sailcloth Way Chester, MD 21619