Overview Property Details Payment Calculator Walkability

Add to favorites

Remove from favorites
Send to Friend
Watch changes on this property

139 Chappaquiddick Road, Edgartown MA 02539

Active

139 Chappaquiddick Road, Edgartown MA 02539

$10,750,000

Estimated $67,870/month Calculator

Single Family

7 Bedrooms

Baths

4855

Total Parking: 8 (1 Garage)

219,106 (5.03)

Built in 1938

Overlooking the active waters of the outer harbor and set just off the paved road, this remarkable waterfront estate occupies one of Chappaquiddick’s most spectacular stretches of beach, just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village. A rare and truly exceptional family compound, the property offers an extraordinary combination of scale, privacy, waterfront, and amenities. Expansive grounds unfold toward sweeping water views, with a gentle slope leading to a protected stretch of sandy beach and access to a 190-foot private dock with mooring. The stately main residence offers beautifully proportioned spaces updated with today’s comforts, with a thoughtful layout well suited to both intimate family living and multigenerational gatherings. The estate extends beyond the main residence to include 75 Landing Place, an additional waterfront parcel that seamlessly expands the property, offering beautiful vistas, greater privacy, and a sense of scale rarely found on Chappaquiddick. An additional three-acre parcel is also available, creating a singular opportunity to assemble a one-of-a-kind family compound of exceptional size and privacy, with the flexibility to shape the property for generations to come. Cherished by the same family for generations, this remarkable waterfront estate represents a rare opportunity to create something truly enduring—a private family retreat with the space, setting, and flexibility to become a legacy for generations to come.

This home has been viewed 6 times

Last Checked: October 14th, 2026 at 5:18am (Source: MLS PIN #73563263)

Garage Parking

Air Conditioning

Waterview

Waterfront

Lead Paint Free

General Information for 139 Chappaquiddick Road, Edgartown MA 02539

Listing ID73563263

Property TypeSingle Family / Detached

Price$10,750,000 ($2,214.21/SqFt)

StyleColonial

CityEdgartown

CountyDukes

MLS AreaChappaquiddick

Neighborhood(s)

Garage Parking1

ZoningR120

Year Built1938

Year Built SourcePublic Records

Year Built DetailsActual,Renovated Since

Interior Features for 139 Chappaquiddick Road, Edgartown MA 02539

Approximate Living Area Total4855

Living Area Includes BasementNo

Rooms17

Bedrooms7

Primary En Suite BathroomYes

BasementFull

Cooling1, Split

Fireplaces

Appliances

Flooring

Electric

Exterior Features for 139 Chappaquiddick Road, Edgartown MA 02539

Approximate Lot Size (Acres)5.03

Approximate Lot Size (Square Feet)219106

Total Parking8 (1 Garage)

Garage Parking1

WaterPrivate

SewerPrivate Sewer

Lot FeaturesGentle Sloping

Parking Features1

Exterior Features

Foundation Materials

Construction Materials

Road Frontage Type

Patio & Porch

Roof Material

Utility Connections

Water ViewsYes

Water Views FeaturesBay

Waterfront1

Waterfront FeaturesRiver

Pool Features

Horse Permitted0

Horse AmenitiesRiver

Disclosures for 139 Chappaquiddick Road, Edgartown MA 02539

Lead PaintNone

UFFI

Living Area Includes BasementNo

Living Area Disclosure

Building Area SourcePublic Records

Special Listing Conditions

ExclusionsWall Mounted Tv's-Brackets To Remain

Title 5A

Compensation Based On

Financial Information for 139 Chappaquiddick Road, Edgartown MA 02539

Association Fee

Association Fee Frequency

Association Fee Includes

Real Estate Tax19582

Tax Year2026

Assessed Value$7,895,941

Location Information for 139 Chappaquiddick Road, Edgartown MA 02539

Neighborhood(s)

MLS AreaChappaquiddick

Area Amenities

Contact Information for 139 Chappaquiddick Road, Edgartown MA 02539

Agent

Name: Katie Donahue & Rachel Serwa Group

Office

Name: Sandpiper Realty, Inc.

Phone: 508-627-3737

Team Members

Payment Calculator

, Interest

Property Taxes 1631.83

Principal & Interest 66238.08

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

Sandpiper Realty, Inc.

Katie Donahue & Rachel Serwa Group

Agent Phone

Office Phone

(508) 627-3737

Text Agent Call Agent Call Office

Array
(
    [acres] => Approx. 5.03 acres (219,106 SqFt)
    [add_date] => 2026-09-15 04:53:35
    [address] => Chappaquiddick Road
    [agent] => Array
        (
            [address] => 
            [city] => 
            [id] => TM362163
            [name] => Katie Donahue & Rachel Serwa Group
            [national_association] => 
            [office] => AN9490
            [state] => 
            [zip] => 
        )

[apod_available] => Array
        (
        )

[appliances] => Array
        (
        )

[approx_living_area_total] => 4855
    [approx_lot_size_acres] => 5.03
    [approx_lot_size_sqft] => 219106
    [assessed_value] => $7,895,941
    [association] => 
    [association_fee] => Array
        (
        )

[association_fee_frequency] => Array
        (
        )

[association_fee_includes] => Array
        (
        )

[association_required] => Array
        (
        )

[available_date] => 
    [available_now] => 0
    [basement] => Array
        (
            [0] => Full
        )

[bathrooms] => 
    [bedrooms] => 7
    [building_amenities] => Array
        (
        )

[building_area_source] => Array
        (
            [0] => Public Records
        )

[building_management] => Array
        (
        )

[building_debug] => 
    [building_id] => 
    [building_parent] => 0
    [building_name] => 
    [building_name_from_address] => 
    [building_url] => 
    [buyer_agent_compensation] => 
    [buyer_agent_id] => 
    [buyer_office_id] => 
    [c_style] => Array
        (
            [0] => Detached
        )

[c_type] => Array
        (
            [0] => Single Family
        )

[cap_rate] => 
    [city] => Edgartown
    [community_features] => Array
        (
        )

[compensation_based_on] => Array
        (
        )

[complex_complete] => Array
        (
        )

[construction_materials] => Array
        (
        )

[construction_status] => 
    [cooling] => Array
        (
            [0] => 1
            [1] => Split
        )

[cooperating_agent_commission] => Array
        (
        )

[county] => Dukes
    [cultivation_acres] => 
    [date_available_note] => 
    [deposit_amount] => Array
        (
        )

[deposit_required] => Array
        (
        )

[deqe] => 
    [description] => Overlooking the active waters of the outer harbor and set just off the paved road, this remarkable waterfront estate occupies one of Chappaquiddick’s most spectacular stretches of beach, just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village. A rare and truly exceptional family compound, the property offers an extraordinary combination of scale, privacy, waterfront, and amenities. Expansive grounds unfold toward sweeping water views, with a gentle slope leading to a protected stretch of sandy beach and access to a 190-foot private dock with mooring. The stately main residence offers beautifully proportioned spaces updated with today’s comforts, with a thoughtful layout well suited to both intimate family living and multigenerational gatherings. The estate extends beyond the main residence to include 75 Landing Place, an additional waterfront parcel that seamlessly expands the property, offering beautiful vistas, greater privacy, and a sense of scale rarely found on Chappaquiddick. An additional three-acre parcel is also available, creating a singular opportunity to assemble a one-of-a-kind family compound of exceptional size and privacy, with the flexibility to shape the property for generations to come. Cherished by the same family for generations, this remarkable waterfront estate represents a rare opportunity to create something truly enduring—a private family retreat with the space, setting, and flexibility to become a legacy for generations to come.
    [disclosures] => 
    [documents_available] => Array
        (
        )

[electric] => Array
        (
        )

[electric_expense] => Array
        (
        )

[elementary_school] => 
    [en_suite_bath] => Array
        (
            [0] => Yes
        )

[energy_features] => 
    [entry_level] => Array
        (
        )

[estimated_monthly_payment] => 
    [exclusions] => Array
        (
            [0] => Wall Mounted Tv's-Brackets To Remain
        )

[exterior_features] => Array
        (
        )

[facilitator_compensation] => 
    [fee_paid_by_tennant] => 
    [financial_data_source] => Array
        (
        )

[fireplaces] => Array
        (
        )

[first_month_required] => Array
        (
        )

[floor_number] => 0
    [flooring] => Array
        (
        )

[for_sale_by_owner] => 
    [foundation_area] => 
    [foundation_materials] => Array
        (
        )

[frontage_length] => 
    [full_baths] => 
    [garage_parking] => 1
    [gas] => Array
        (
        )

[gas_expense] => Array
        (
        )

[gross_income] => Array
        (
        )

[half_baths] => 
    [handicap_access] => 
    [heating] => 
    [heating_expense] => Array
        (
        )

[high_school] => 
    [horse_features] => Array
        (
            [0] => River
        )

[horse_permitted] => 0
    [hot_water] => Array
        (
        )

[id] => 
    [insurance_expense] => Array
        (
        )

[insurance_required] => Array
        (
        )

[interior_features] => Array
        (
        )

[last_month_required] => Array
        (
        )

[last_sync_date] => 2026-10-14 05:18:35
    [laundry_features] => Array
        (
        )

[lead_paint] => Array
        (
            [0] => None
        )

[lease_term] => Array
        (
        )

[levels_in_unit] => 
    [living_area] => 
    [living_area_disclosure] => Array
        (
        )

[living_area_includes_basement] => Array
        (
            [0] => No
        )

[lot_features] => Array
        (
            [0] => Gentle Sloping
        )

[management_expense] => Array
        (
        )

[middle_school] => 
    [miscellaneuos_expense] => Array
        (
        )

[mls_area] => Chappaquiddick
    [mls_id] => 73563263
    [neighborhoods] => 
    [net_income_calc] => -19582
    [net_operating_income] => Array
        (
        )

[number_of_lots] => Array
        (
        )

[number_of_units] => 
    [office] => Array
        (
            [id] => AN9490
            [name] => Sandpiper Realty, Inc.
            [phone] => 508-627-3737
        )

[operating_expense] => Array
        (
        )

[optional_fee_includes] => Array
        (
        )

[optional_price] => 0
    [outdoor_space_available] => Array
        (
        )

[owner_occupancy_source] => 
    [parking_features] => Array
        (
            [0] => 1
        )

[pasture_area] => 
    [patio_and_porch] => Array
        (
        )

[perc_test] => Array
        (
        )

[perc_test_date] => 
    [pet_policy] => Array
        (
            [0] => Allowed
        )

[phone] => 
    [pool_features] => Array
        (
        )

[price] => 10750000
    [price_per_sqft] => 2214.21
    [price_per_unit] => 10750000
    [private_pool] => 
    [property_sub_type] => Array
        (
            [0] => Single Family Residence
        )

[real_estate_tax] => 19582
    [references_required] => Array
        (
        )

[rent_includes] => Array
        (
        )

[repair_maintenance_expense] => Array
        (
        )

[road_frontage_type] => Array
        (
        )

[roof_material] => Array
        (
        )

[rooms] => 17
    [schools] => 
    [senior_community] => 
    [sewer] => Array
        (
            [0] => Private Sewer
        )

[sewer_expense] => Array
        (
        )

[short_sale] => Array
        (
        )

[special_listing_conditions] => Array
        (
        )

[state] => Massachusetts
    [state_code] => MA
    [status] => Array
        (
            [0] => Active
        )

[street_number] => 139
    [structure_type] => Array
        (
        )

[style] => Array
        (
            [0] => Colonial
        )

[subagent_compensation] => 
    [tag_accessible_features] => 
    [tag_air_conditioning] => 1
    [tag_association_pool] => 
    [tag_beach_access] => 
    [tag_beach_front] => 
    [tag_elevator] => 
    [tag_equestrian] => 
    [tag_garage_parking] => 1
    [tag_generator] => 
    [tag_green_features] => 
    [tag_laundry] => 
    [tag_lead_paint_free] => 1
    [tag_loft] => 
    [tag_pet_friendly] => 
    [tag_pre_construction] => 
    [tag_private_outdoor_space] => 
    [tag_private_pool] => 
    [tag_professional_management] => 
    [tag_recently_renovated] => 
    [tag_senior_community] => 
    [tag_townhouse] => 
    [tag_waterfront] => 1
    [tag_waterview] => 1
    [tax_year] => 2026
    [team] => TM362163
    [team_agents] => Array
        (
            [TM362163] => Array
                (
                    [agent_mls_id] => TM362163
                    [full_name] => Katie Donahue & Rachel Serwa Group
                    [address] => 
                    [city] => 
                    [state] => 
                    [postal_code] => 
                    [national_association_id] => 
                    [office_mls_id] => AN9490
                )

)

[terms] => Array
        (
        )

[timber_acres] => 
    [title_5] => A
    [total_gross_expense] => 19582
    [total_gross_income] => 0
    [total_parking] => 8 (1 Garage)
    [trash_expense] => Array
        (
        )

[travel_routes] => 
    [uffi] => Array
        (
        )

[unit_1_bathrooms] => 
    [unit_1_bedrooms] => 
    [unit_1_floor] => 
    [unit_1_lease] => Array
        (
        )

[unit_1_levels] => 
    [unit_1_rent] => Array
        (
        )

[unit_2_bathrooms] => 
    [unit_2_bedrooms] => 
    [unit_2_floor] => 
    [unit_2_lease] => Array
        (
        )

[unit_2_levels] => 
    [unit_2_rent] => Array
        (
        )

[unit_3_bathrooms] => 
    [unit_3_bedrooms] => 
    [unit_3_floor] => 
    [unit_3_lease] => Array
        (
        )

[unit_3_levels] => 
    [unit_3_rent] => Array
        (
        )

[unit_4_bathrooms] => 
    [unit_4_bedrooms] => 
    [unit_4_floor] => 
    [unit_4_lease] => Array
        (
        )

[unit_4_levels] => 
    [unit_4_rent] => Array
        (
        )

[unit_level] => 
    [unit_number] => 
    [units_owner_occupied] => 
    [unparsed] => 139 Chappaquiddick Road, Edgartown MA 02539
    [utilities] => Array
        (
        )

[view] => Array
        (
        )

[water] => Array
        (
            [0] => Private
        )

[water_expense] => Array
        (
        )

[water_views] => Array
        (
            [0] => Yes
        )

[water_views_features] => Array
        (
            [0] => Bay
        )

[waterfront] => 1
    [waterfront_features] => Array
        (
            [0] => River
        )

[raw] => 
)

EXIT

34 More Photos