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440 Grand Island Dr Barnstable — Photo 1 of 42

440 Grand Island Dr Barnstable — Photo 1 of 42

Recent Drop: $500,000

$7,750,000
$7,250,000

$7,250,000

Investment Analysis — 440 Grand Island Dr

Barnstable, MA 02655 — Oyster Harbors

Based on HUD Small Area Fair Market Rent for Barnstable Town, MA MSA, a 7-bedroom in 02655 carries an estimated $3,650/mo in gross rent — about a -1.13% cap rate and $-81,623/yr in estimated NOI at the $7,250,000 list price. Adjust every assumption in the calculator below.

View Standard Listing

Beds

7

Baths

10

SqFt

11,546

Style

Single Family

Built

2013

Privately sited within the prestigious Oyster Harbors golf enclave, this extraordinary estate is a masterclass in architectural sophistication and resort-style living. Encompassing a 10,000-square-foot main residence, a stunning two-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. A gracious covered front porch welcomes you into a dramatic foyer, setting the tone for the refined interiors that follow. The main living spaces unfold in a thoughtfully designed layout that flows from formal living and family rooms to an elegant dining area with each space inviting connection, comfort, and celebration. At the heart of the home, the chef's kitchen is both striking and functional, anchored by dual oversized islands clad in premium granite, and accompanied by a fireside sitting room that beckons lingering conversation. Adjacent, the spectacular sunroom redefines indoor-outdoor living with a custom crafted bar and casual seating area at one end and a full second kitchen with custom built-in grill and dining area at the other, all enclosed by retractable screens for effortless seasonal enjoyment. Tucked away on the main level, the primary suite offers a private sanctuary, with its own fireplace, luxurious spa-like bath, and refined home office. The comfort and sophistication continue on the second level with four generously proportioned en-suite bedrooms and an inviting sitting room. Designed for comfort and connection, the finished lower level offers a wine cellar, media room, game room, and fitness space. This lavish interior flows effortlessly to an equally impressive exterior, where lush landscaping surrounds a resort-style pool framed by expansive lounging areas-perfect for everything from quiet afternoons to grand entertaining. Completing this offering is a beautiful two-bedroom guest house providing privacy and comfort for visiting guests. Set within a prestigious gated enclave with coveted beach and dock rights, this remarkable estate is the perfect fusion of architectural sophistication and everyday warmth - an extraordinary offering in one of Cape Cod's most prestigious settings. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

Estimates — not financial advice

These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.

Property Details

Financials

Original Price$8,000,000
Annual Taxes$59,471
HOA Fee$4620

Parking

Garage3
Off-Street9

Interior Specifications

Total Rooms16
Fireplaces7
FlooringWood, Tile, Carpet, Marble, Flooring - Wood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet
BasementFull, Finished, Interior Entry

Climate & Utilities

HeatingCentral, Oil, Fireplace(s), Fireplace
CoolingCentral Air
WaterPublic
SewerPrivate Sewer

Building & Exterior

Construction--
RoofWood
FoundationConcrete Perimeter
ZoningRF

Property & Lot

Acres1.1
SqFt Lot47,916
Lot FeaturesCleared, Level

Amenities & Appliances

Range • Oven • Dishwasher • Microwave • Indoor Grill • Refrigerator • Washer • Dryer • Wine Refrigerator • Range Hood • Plumbed For Ice Maker

Neighborhood

Shopping • Golf • Conservation Area • House of Worship • Marina • Private School

Geography

Floorplan Breakdown

Structural Layout

Second
Bedroom 2Bedroom 3Bedroom 4Bedroom 5
First
Living RoomDining RoomKitchenOfficeFamily RoomPrimary Bedroom
Living Room
Lvl First

Cathedral Ceiling(s), Flooring - Wood, French Doors, Recessed Lighting

Dining Room
Lvl First

Coffered Ceiling(s), Closet/Cabinets - Custom Built, Flooring - Wood, Recessed Lighting

Kitchen
Lvl First

Flooring - Wood, Pantry, Countertops - Upgraded, Kitchen Island, Breakfast Bar / Nook, Second Dishwasher

Office
Lvl First

Fireplace, Ceiling - Cathedral, Flooring - Wood

Family Room
Lvl First

Flooring - Wood, French Doors, Exterior Access

Primary Bedroom
Lvl First

Bathroom - Full, Walk-In Closet(s), Flooring - Wall to Wall Carpet, French Doors, Double Vanity, Exterior Access

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second

Bathroom - Full, Closet, Flooring - Wood, Recessed Lighting

Bedroom 4
Lvl Second

Bathroom - Full, Closet, Flooring - Wall to Wall Carpet

Bedroom 5
Lvl Second

Bathroom - Full, Closet, Flooring - Wall to Wall Carpet

Property History

Price Drop
$7,250,000

Was $7,750,000

Sep 1, 2026

MLS® 73383981

Price Drop
$7,750,000

Was $8,000,000

Sep 5, 2025

MLS® 73383981

Listed
$8,000,000

Jun 2, 2025

MLS® 73383981

Listing Provided By

Listing Agent: Robert Kinlin

Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties

MLS® Number: 73383981