55 Winterset Drive, Chatham, MA 02633

Chatham
Local realty services provided by:Better Homes and Gardens Real Estate The Shanahan Group
55 Winterset Drive,Chatham, MA 02633
$2,295,000
  • 4 Beds
  • 4 Baths
  • 4,072 sq. ft.
  • Single family
  • Active
Listed by: janet stuart
Office: coldwell banker realty
MLS#:22603375
Source:CAPECOD

Price summary

  • Price:$2,295,000
  • Price per sq. ft.:$563.61
  • Monthly HOA dues:$6.25

About this home

Welcome to this exceptional Great Hill Estates retreat, set on 1.8 private acres with deeded rights to Lover's Lake for kayaking, swimming, and canoeing just a short stroll away. Elevated above a scenic corner lot, this 4-bedroom, 3.5-bath home offers peaceful natural surroundings and room to relax both inside and out.A sought-after first-floor primary suite features an ensuite bath and laundry, providing convenient single-level living. The heart of the home is a spacious kitchen with a large island, dining area, and adjacent family room with vaulted beamed ceilings and a wood-burning fireplace. A separate living room with a gas fireplace opens to a wraparound deck, perfect for outdoor dining, entertaining, or simply enjoying the views. Upstairs, two spacious bedrooms share a full bath, including one with a fireplace and sitting area that offers a private retreat-like feel. The walk-out lower level features a fourth bedroom, full bath, second laundry area, and direct access to a...

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Home facts

  • Year built:1970
  • Subdivision & Development:Great Hills
  • Listing ID #:22603375
  • Added:114 day(s) ago
  • Updated:November 04, 2026 at 10:59 PM

Rooms and interior

  • Bedrooms:4
  • Total bathrooms:4
  • Rooms Total:8
  • Basement Description:Finished, Full, Garage Access, Interior Access, Walk-Out Access
  • Living area:4,072 sq. ft.

Heating and cooling

  • Cooling:Central Air

Structure and exterior

  • Year built:1970
  • Building area:4,072 sq. ft.
  • Lot area:1.94 Acres
  • Lot Features:Corner Lot
  • Construction Materials:Shingle Siding

Finances and disclosures

  • Price:$2,295,000
  • Price per sq. ft.:$563.61
  • Tax amount:$5,655

Features and amenities

  • Amenities:Central Vacuum, Recessed Lighting

Parking

  • Parking description:Direct Access, Garage Door Opener, Off Street, Paved
  • Garage spaces:2
MLS LogoDisclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Coldwell Banker Realty include the name of the listing broker. Neither the listing company nor Better Homes and Gardens Real Estate The Shanahan Group shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

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