99 Uncle Alberts Dr

$5,900,000
Price
2
Beds
1,850 Sq. Ft.
$3,189 / Sq. Ft.
1,850
Sq. Ft.
$3,189
per Sq. Ft.

Description

Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future 4-bedroom main house w/swimming pool, allowing you to envision the next chapter of luxury living on Cape...Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future 4-bedroom main house w/swimming pool, allowing you to envision the next chapter of luxury living on Cape Cod. Whether you're looking to enjoy the existing home w/separate post & beam garage w/power & water, or build your dream estate, the possibilities are truly remarkable. Additional to the expansive waterfront, this property boasts access to an adjacent cove down a winding 10-foot path. The current home features wood floors, a 2-car garage, office & generous outdoor living areas. An expansive deck provides the perfect vantage point to take in the ever-changing coastal scenery & sea breezes. Combining timeless Cape Cod charm with a vision for the future, 99 Uncle Alberts Dr is a one-of-a-kind offering on the waterfront, perfect for those seeking privacy & a truly iconic Chatham location.

Listing Agent

  1. Shane Masaschi

    Shane Masaschi

    Listing Agent

    Compass

Property Details for 99 Uncle Alberts Drive

Village
Chatham
School District
Monomoy
Waterfront Type
Lake/Pond
Waterview Type
Rivers
Waterfront
Yes
Waterview
Yes
FEMA 100 Yr Flood Plain
X
Town
Chatham
LISTING UPDATED: 11/23/2025 08:57 PM

Property Details for 99 Uncle Alberts Drive

StatusActive
MLS #22503829
Days on Market133
Taxes$1 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family / Single Family Residence
Year Built2004
Lot Size1.44 AC / 62,726 SF
CountyBarnstable County
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Virtual Tour

Building Information for 99 Uncle Alberts Drive

Stories2Year Built2004Building Size-Lot Size1.44 AC / 62,726 SF

Payment Calculator

$29,154 per month

30 year fixed, 6.28% Interest

Principal and Interest

$29,154

Property Taxes

$0

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 99 Uncle Alberts Drive

Summary
Location and General Information
  • Directions to Property: Rte 28 to Uncle Alberts Drive to end of cul-de-sac. Take right down private driveway. Appointment is required and no drive-bys please. Home is owner occupied.
  • Title Reference - Book: 33886
  • SqFt Source: Owner
  • Convenient To:Bike Path: Yes
  • Convenient To:Cape Cod Rail Trail: Yes
  • Convenient To:Conservation Area: Yes
  • Convenient To:Golf Course: Yes
  • Convenient To:In Town Location: Yes
  • Convenient To:Marina: Yes
  • Convenient To:Public Tennis: Yes
  • Convenient To:Shopping: Yes
  • Convenient To:Convenient to Water Body 1: Oyster Pond
  • Convenient To:Convenient to Water Body 2: Hardings Beach
  • Location Description:South of Route 28: Yes
  • Region: Lower Cape
  • County: Barnstable
  • City Postal ID: 02633
  • Street Number: 99
  • Water Body Name: Oyster Pond
  • MLSAreaMajor: Chatham
  • General Property Info:Water Body: Oyster Pond
Parking
  • Garage: Yes
  • Garage Description:Attached: Yes
  • Garage Description:Direct Entry: Yes
  • Garage Description:Under: Yes
  • Parking Description:Improved Driveway: Yes
  • Parking Description:Off-Street: Yes
  • Garage Spaces: 2.00
Taxes and HOA Information
  • Tax Year: 2025
  • Annual Assoc Fee: $0
  • Annual Taxes: $1
Property
Lot Information
  • Zoning: R
  • Tax ID: 12E-3-RC
  • Lot Size Source: Estimated
  • TopographyLot Desc:View: Yes
  • TopographyLot Desc:Easements: Yes
  • Land Use: 100 - Residential Property
  • Lot Size Square Feet: 62726
  • Sqft Total: 1850
  • Additional Finished Space: 1850
  • Lot Size Units: Acres
  • General Property Info:Leased Land: No
Property and Assessments
  • Total Assessment: $6
  • Land Assessments: $1
  • Building Assessments: $2
  • Other Assessments: $3
  • Renovated: No
  • Flood Ins Required: No
  • Lead Base Paint: No
  • Year Round: Yes
  • Landlord Pays:Hot Water: Yes
  • Year Built Desc:Actual: Yes
  • Property Type: Residential, Single Family Residence
  • Property Subtypes: Single Family Residence
  • Year Built Numeric: 2004
  • Construction Materials: Shingle
  • Property Type: Residential
Utilities
  • Fuel Type:Oil: Yes
  • Hot Water:Tank: Yes
  • Water:Town Water: Yes
  • Sewer:Septic Tank: Title V Grade Level
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Exterior Features: Private Yard, Garden
  • Private Dock: No
  • Private Dock Description: Electric
  • Foundation: Poured, Concrete Perimeter
  • Roof Description: Asphalt
  • Siding Description:Shingle: Yes
  • Private Pool YN: No
Interior Features
  • Basement Description:Finished: Yes
  • Basement Description:Full: Yes
  • Basement Description:Garage Access: Yes
  • Basement Description:Interior Access: Yes
  • Basement Description:Walk Out: Yes
  • Floors: Hardwood, Tile
  • Heating: Oil
  • Basement: Yes
  • Sep Living Qtrs Info: Beds: 0
  • Total Rooms: 7
  • Baths Total: 3
  • Baths Full: 2
  • Baths Half: 1
  • Bedrooms Total: 2
  • Total Floor Plans Count: 3
  • RoomsTotal: 7
  • Bathrooms Total (Decimal): 2.50
  • Bathrooms Total (Notational): 2.10
  • Heating: Yes
  • Stories: 2
  • General Property Info:Stories: 2
Rental
Rental Information
  • Owner Pays: Hot Water

Property History for 99 Uncle Alberts Drive

DateEvent & SourcePriceAppreciation
Aug 18, 2025

Listed (Active)

MLS PIN #73419421

$5,900,000—
Aug 7, 2025

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22503829

$5,900,000—
Oct 31, 2024

Expired

MLS PIN #73208512

$5,495,000—
Oct 31, 2024

Expired

Cape Cod & Islands Multiple Listing Service #22400763

$5,495,000—
Mar 1, 2024

Listed (Active)

MLS PIN #73208512

$5,495,000—
Mar 1, 2024

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22400763

$5,495,000—
Nov 6, 2023

Expired

MLS PIN #73110440

$7,500,000—
Nov 6, 2023

Expired

Cape Cod & Islands Multiple Listing Service #22301766

$7,500,000—
May 11, 2023

Listed (Active)

MLS PIN #73110440

$9,995,000—
May 5, 2023

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22301766

$9,995,000—
Dec 19, 2022

Expired

Cape Cod & Islands Multiple Listing Service #22204168

$9,995,000—
Aug 7, 2022

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22204168

$9,995,000—
Dec 31, 2017

Expired

Cape Cod & Islands Multiple Listing Service #21714316

$4,500,000—
Jul 29, 2017

Listed (Active)

Cape Cod & Islands Multiple Listing Service #21714316

$4,500,000—
DateEvent & SourcePrice
08/18/2025

Listed (Active)

MLS PIN #73419421

$5,900,000
08/07/2025

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22503829

$5,900,000
10/31/2024

Expired

MLS PIN #73208512

$5,495,000
10/31/2024

Expired

Cape Cod & Islands Multiple Listing Service #22400763

$5,495,000
03/01/2024

Listed (Active)

MLS PIN #73208512

$5,495,000
03/01/2024

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22400763

$5,495,000
11/06/2023

Expired

MLS PIN #73110440

$7,500,000
11/06/2023

Expired

Cape Cod & Islands Multiple Listing Service #22301766

$7,500,000
05/11/2023

Listed (Active)

MLS PIN #73110440

$9,995,000
05/05/2023

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22301766

$9,995,000
12/19/2022

Expired

Cape Cod & Islands Multiple Listing Service #22204168

$9,995,000
08/07/2022

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22204168

$9,995,000
12/31/2017

Expired

Cape Cod & Islands Multiple Listing Service #21714316

$4,500,000
07/29/2017

Listed (Active)

Cape Cod & Islands Multiple Listing Service #21714316

$4,500,000

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

Public Records for 99 Uncle Alberts Drive

Taxable ValueLand-Additions-Total-
Tax Record2015$7,110 ($592 / month)
Home Facts
Beds2Baths2Total Finished SqFt1,776 SqFtAbove Grade Finished SqFt1,776 SqFtStories2Lot Size72,963 SqFtStyleMiscellaneous ResidentialYear Built2004Year Renovated2006ZoningR20CountyBARNSTABLEAPNM:12E B:003A L:B2

Schools near 99 Uncle Alberts Drive

This home is within Monomoy Regional School District.
Rating
School
Type
Grades
Distance
Public - PK to 4
Public - K to 4
Public - 5 to 7
Public - 8 to 12
Rating
School
Distance
Harwich Elementary School
PublicPK to 4

Chatham Elementary School
PublicK to 4

Monomoy Regional Middle School
Public5 to 7

Monomoy Regional High School
Public8 to 12

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.

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99 Uncle Alberts Drive is a single family home for sale in Chatham, MA 02633. This property was listed for sale on August 7, 2025 by Compass, it's currently listed at $5,900,000. This listing's school district is Monomoy Regional School District. Nearby schools include Harwich Elementary School, Chatham Elementary School and Monomoy Regional Middle School. 99 Uncle Alberts Drive is a 2-bed, 3-bath, 1,850 sqft single family home built in 2004.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

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 Compass includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. Neither the listing firm nor Compass shall be responsible for any typographical errors, misinformation, or 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 2025 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.