85 Main Street, Chatham, MA 02633
Property image
Property image
OFF MARKET

85 Main Street
Chatham, MA 02633

  • 3 Beds
  • 3.5 Baths
  • 2,998 sqft (on 0.33 acres)

$4,007,200

Trulia Estimate
as of Aug 5, 2026
Est. Refi. Payment $22,671/mo*
Refinance Your Home

$4,007,200

Trulia Estimate
as of Aug 5, 2026
Est. Refi. Payment $22,671/mo*
Refinance Your Home
3 Beds
3.5 Baths
2,998 sqft
(on 0.33 acres)

Local Information

  • Map ViewExplore the area around 85 Main Street.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1820
Lot Size
0.33 acres
Living Area
2,998 sqft
Price/Sqft
$1,337
Parking
2 Car Garage

About this House

OFFERED FULLY FURNISHED INCLUDING ALL CONTENTS SO YOU CAN MOVE RIGHT IN! // Ideally situated in one of Chatham's most sought-after enclaves, just steps from iconic Lighthouse Beach, this exceptional home is rich in character and timeless charm. Beautifully maintained, it offers sun-filled, spacious interiors that transition seamlessly between formal elegance and casual comfort.The thoughtfully designed kitchen features a breakfast bar, dining area, and French doors that open to an exquisite outdoor oasis--complete with a stone patio, brand-new furnishings, and an expansive, manicured yard. The adjacent living room is bright and inviting, centered around a cozy fireplace, while a formal dining room and a welcoming family room--with a second fireplace and custom bar--offer perfect spaces for entertaining.The home includes three generously sized bedrooms, highlighted by a serene primary suite with a walk-in closet. Additional amenities include a two-car garage with a bonus room and full bath above, as well as an outdoor shower--an essential for beachside living. A rare opportunity.
85 Main Street, Chatham, MA 02633 is a 3 bedroom, 4 bathroom, 2,998 sqft single-family home built in 1820. It last sold for $4,000,000 on Oct 3, 2025 (9% below the $4,400,000 asking price). It is currently off market. The Trulia Estimate is $4,007,200, with a rent estimate of $5,926/month.

Home Details for 85 Main Street

Interior Features

Interior Details
Basement: Bulkhead Access,Interior Entry,FullNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Master Bathroom, Dining Room, Kitchen, Living RoomWet Bar
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2998 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Washer, Refrigerator, Gas Range, Gas Water HeaterDishwasherRefrigeratorWasher
Heating & Cooling
Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Has Heating Unspecified Type
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Door: French DoorsFlooring: Wood, Tile
Levels, Entrance, & Accessibility
Stories: 2Entry Location: First FloorFloors: Wood, Tile
View
Has a View

Exterior Features

Exterior Home Features
Roof: Pitched WoodPatio / Porch: PatioExterior: Outdoor Shower, GardenFoundation: BlockGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Garage Attached, Open
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 150

Property Information

Year Built
Year Built: 1820Year Renovated: 2005
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building
Construction Materials: Shingle SidingNot a New ConstructionNot Attached PropertyDoes Not Include Home Warranty
Property Information
Condition: Updated/Remodeled, ActualParcel Number: 16B76HA

Price & Status

Price
List Price: $4,400,000

Active Status

MLS Status: Closed

Location

Direction & Address
City: Chatham
School Information
Elementary School District: MonomoyJr High / Middle School District: MonomoyHigh School District: Monomoy

Building

Building Area
Building Area: 2998 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.33 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash

Miscellaneous

BasementMls Number: 22501580Water ViewWater View: Bay/HarborShowing Requirements: Appointment Required, Call Listing Agent
Last check for updates: about 9 hours ago
Listed by Chris Rhinesmith, (617) 967-0987
Compass Massachusetts, LLC
Bought with: Daneen Law, (508) 237-0977, Gibson Sotheby's International Realty
Source: CCIMLS, MLS#22501580

Price History for 85 Main Street

DatePriceEventSource
10/03/2025$4,000,000Sold
CCIMLS #22501580
09/09/2025$4,400,000PendingCCIMLS #22501580
08/20/2025$4,400,000PriceChange
CCIMLS #22501580
07/17/2025$4,600,000PriceChange
CCIMLS #22501580
05/19/2025$4,900,000PriceChange
CCIMLS #22501580
05/04/2025$5,200,000PriceChange
CCIMLS #22501580
04/11/2025$5,500,000Listed For SaleMLS PIN #73358712
07/16/2004$1,550,000Sold
N/A

Market trends in Chatham

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
75
2MoM
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Property Tax and Assessment

Year2025
Tax$11,257
Assessment$3,244,100
Home facts updated by county records

Comparable Sales for 85 Main Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
32 Sunset Lane, Chatham, MA
0.28
Single-Family Home
$1,622,500
03/09/26
3
2
1,626
51 Shattuck Place, Chatham, MA
0.60
Single-Family Home
$2,610,000
10/02/25
3
2.5
2,133
150 Main Street, Chatham, MA
0.15
Single-Family Home
$6,000,000
04/14/26
7
2.5
2,552
213 Main Street, Chatham, MA
0.23
Single-Family Home
$1,800,000
07/31/26
4
2
1,236
404 Stage Harbor Road, Chatham, MA
0.90
Single-Family Home
$3,020,000
01/15/26
4
3.5
2,905
169 Shore Road, Chatham, MA
0.62
Single-Family Home
$7,790,000
09/24/25
4
4.5
4,020
8 Kingsbury Way, Chatham, MA
0.83
Single-Family Home
$2,199,900
04/29/26
3
2.5
1,651
24 Shattuck Pl, Chatham, MA
0.66
Single-Family Home
$1,785,000
11/24/25
4
2.5
1,514
85 Cedar Street, Chatham, MA
0.92
Single-Family Home
$4,050,000
07/13/26
5
3.5
3,080

Nearby homes

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Assigned Schools

These are the assigned schools for 85 Main Street.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Chatham

At least 40 Trulia users voted on each feature.

  • 88 % Say there's wildlife

  • 87 % Say parking is easy

  • 83 % Say there's holiday spirit

  • 83 % Say yards are well-kept

  • 83 % Say it's dog friendly

  • 82 % Say people would walk alone at night

  • 82 % Say car is needed

  • 73 % Say it's quiet

  • 71 % Say they plan to stay for at least 5 years

  • 59 % Say neighbors are friendly

  • 48 % Say it's walkable to restaurants

  • 47 % Say kids play outside

  • 38 % Say there are community events

  • 33 % Say there are sidewalks

  • 21 % Say streets are well-lit

  • 20 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Snbrinc
    "I’m 4th generation living in this neighborhood. Very special highly desirable place. Proud to be a native. "
    1
    Flag
  • Lilsweeti56
    "Lots of farms. Stop and shop is also close by along with cvs and some banks. Close by to highway. Most people are friendly"
    1
    Flag
  • Virginia S.
    "It’s beautiful, near stores, beach, highways. Quiet and neighbors mind their own business. Lake at end of our street."
    0
    Flag
  • Pmil
    "They would like that most people keep their dog on a leash. They would not like the coyotes in winter"
    1
    Flag
  • Mil
    "Most dogs are on leashes, and in some areas they have doggie poop bags, they have a lot of green. Peomost people pick up after their pets. In winter be careful, foxes and coyotes, deer and wild turkeys are found"
    2
    Flag
  • George G.
    "Easy because it is a small place in the Cape Cod and I love it here because it is also a older community "
    0
    Flag
  • Tuscansun83
    "It's such a peaceful place Chatham is one of the best towns to live in year round or part time it's just beautiful"
    0
    Flag
  • jandesmar
    "I love that it is so close to the boat landing that we can walk to it and watch the activity with our grandchildren. We can also walk to the beach which is a mile away to swim and watch the sunsets,"
    0
    Flag
  • Nancy P.
    "Safe small town with beautiful beaches and a strong sense of community. I love living here. Great place to grow up and raise children "
    1
    Flag
  • Jack D. B.
    "I grew up nearby and can attest to what a great location this is - an easy walk to town, yet just far enough from the peak summer hustle and bustle. "
    0
    Flag
  • mwff1
    "Wonderful, convenient, yet very private area! Conservation and park areas prevalent nearby"
    0
    Flag

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Apartments for Rent

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Homes for sale near 85 Main Street

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Off Market Homes Near 85 Main Street

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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 CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. 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. This site was last updated 2022-04-05 08:58:10 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2022© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.