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55 Winterset Drive, Chatham, MA 02633

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For Sale

$2,495,000

4 beds • 3 baths • 1 half baths • 4,072 sqft

Estimated Payment

$      /mo. †

APR for 30 years

Change Loan Terms

  • Single Family Detached
    Property type

  • $612.72
    Price per square foot

  • Over 50 Years Old
    Age

  • Fireplace
    Fireplace

Explore this Property

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & 2 walk-in closets, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. May be sold furnished.
MLS# 22502257

Courtesy Of Bayview Real Estate Trust

(508) 362-8543

Property Features

  • Age
    Over 50 Years Old
  • Amenities
    Deck, Porch, Patio, Garden, Cable Ready
  • Appliances
    Dishwasher, Dryer, Microwave, Range, Range - Gas, Refrigerator, Washer
  • Architecture Style
    Other
  • Fireplace
    Fireplace
  • Floor Covering
    Carpet, Hardwood, Tile
  • Lot Size
    1.94 Acres
  • Roof Type
    Asphalt

Map and Directions

Directions to 55 Winterset Drive, Chatham, MA 02633

Home seller CENTURY 21 Tassinari & Associates, Inc

Get to know the neighborhood. A local affiliated CENTURY 21 office will help you set up tours, give advice, and negotiate with sellers.

CENTURY 21 Tassinari & Associates, Inc

(508) 747-1258
Learn More About Us

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Monthly Payment Breakdown

  • Principle and Interest
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  • Hazard Insurance
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Calculators provided for estimating purposes only. Consult with your lender to determine precise payment requirements.

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Copyright © 2025 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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This information is provided for general informational purposes only and should not be relied on in making any home-buying decisions. School information does not guarantee enrollment. Contact a local real estate professional or the school district(s) for current information on schools. This information is not intended for use in determining a person's eligibility to attend a school or to use or benefit from other city, town or local services.

† Based on a 30-year fixed rate of 3.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Interest rates are also subject to credit and property approval based on secondary market guidelines. The rates shown are based on average rates for our best qualified customers. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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