Moor your boat just a few hundred yards away at West Neck Bay and enjoy effortless waterfront living.Completely renovated inside and out in 2026, this stunning home features all-new Raymour & Flanigan furniture and furnishings throughout. Nestled in the beautiful, serene community of Harborview Acres — which offers deeded beach and mooring rights — this spacious 4-bedroom, 3-bath home sits on a lovely private half-acre lot.The property boasts a private, wooded backyard oasis complete with an in-ground pool, cabana, and bocce court — perfect for entertaining and relaxing. Inside, the home offers wonderful living spaces including a first-floor living room with a handsome stone fireplace and a second-floor bonus room featuring its own stone fireplace.A graceful U-shaped driveway provides plenty of off-street parking and leads to a single-car garage. The rear of the property backs directly onto acres of preserved wooded land, enhancing the peaceful setting and privacy.Located in a quiet neighborhood with close proximity to beaches, boating, and golf, this turnkey home offers the ideal blend of comfort, style, and coastal lifestyle.Ready for its next owner to enjoy!
For sale
$1,700,000
27 Terry Dr, Shelter Island, NY 11964
4beds
2,100sqft
Single Family Residence
Built in 1985
0.52 Acres Lot
$1,672,300 Zestimate®
$810/sqft
$-- HOA
What's special
In-ground poolPrivate wooded backyard oasisBocce courtPlenty of off-street parkingPrivate half-acre lotSingle-car garageGraceful u-shaped driveway
- 81 days |
- 482 |
- 6 |
Zillow last checked:
Listed by:
Daniel Gale Sotheby's International Realty 631-288-1050,
Neil Tevez - Associate Real Estate Broker 516-641-3326
Source: Out East,MLS#: 395969
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Cooling
- Central Air
Features
- Basement: Yes
- Has fireplace: Yes
Interior area
- Total structure area: 2,100
- Total interior livable area: 2,100 sqft
Property
Parking
- Parking features: GarageDetached
- Has garage: Yes
Features
- Stories: 2
- Has private pool: Yes
Lot
- Size: 0.52 Acres
Details
- Parcel number: 0700017000100058000
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Condition
- New construction: No
- Year built: 1985
Community & HOA
Location
- Region: Shelter Island
Financial & listing details
- Price per square foot: $810/sqft
- Tax assessed value: $1,339,000
- Date on market: 5/26/2026
- Lease term: Contact For Details
Estimated market value
$1,672,300
$1.59M - $1.76M
$7,854/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/26/2026 | Listed for sale | $1,700,000+70%$810/sqft |
Source: Out East #395969 Report a problem | ||
| 6/17/2024 | Listing removed | -- |
Source: Zillow Rentals Report a problem | ||
| 6/13/2024 | Listed for rent | $50,000$24/sqft |
Source: Zillow Rentals Report a problem | ||
| 6/28/2023 | Sold | $999,999-23.1%$476/sqft |
Source:  OneKey® MLS as distributed by MLS GRID #L3439725 Report a problem | ||
| 5/2/2023 | Pending sale | $1,300,000$619/sqft |
Source: OneKey® MLS as distributed by MLS GRID #3439725 Report a problem | ||
| 10/27/2022 | Listed for sale | $1,300,000+465.2%$619/sqft |
Source: OneKey® MLS as distributed by MLS GRID #3439725 Report a problem | ||
| 7/17/1996 | Sold | $230,000$110/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $1,339,000 +75% |
| 2024 | -- | $765,000 +10.4% |
| 2023 | -- | $693,000 |
| 2022 | -- | $693,000 |
| 2021 | -- | $693,000 +1% |
| 2020 | -- | $686,000 +0.4% |
| 2019 | -- | $683,000 +0.4% |
| 2018 | -- | $680,000 +1.6% |
| 2017 | $4,033 | $669,000 +1.5% |
| 2016 | -- | $659,000 +3.3% |
| 2015 | -- | $638,000 |
| 2014 | -- | $638,000 +2.9% |
| 2013 | -- | $620,000 -1% |
| 2012 | -- | $626,000 -4.6% |
| 2011 | -- | $656,000 |
| 2010 | -- | $656,000 -9.9% |
| 2009 | -- | $728,000 -1% |
| 2008 | -- | $735,300 +1% |
| 2007 | $3,719 +13.8% | $728,100 +49.7% |
| 2005 | $3,267 +5.9% | $486,400 +13.7% |
| 2004 | $3,084 +9.8% | $427,900 +12.8% |
| 2003 | $2,808 +6.8% | $379,500 +65% |
| 2002 | $2,629 | $230,000 |
| 2001 | -- | $230,000 |
| 2000 | $2,425 | $230,000 |
Find assessor info on the county website
Monthly payment
Climate risks
Neighborhood: 11964
Nearby schools
GreatSchools rating
- 8/10Shelter Island SchoolGrades: PK-12Distance: 1.7 mi
- $1,451,6004 bd2 ba2.6k sqft29 Terry Dr, Shelter Island, NY 11964Off Market
- $2,273,0005 bd3 ba3.7k sqft25 Terry Dr, Shelter Island, NY 11964Off Market
- $1,501,7003 bd3 ba1.8k sqft22 Terry Dr, Shelter Island, NY 11964Off Market
- $1,695,6003 bd2 ba2.6k sqft20 Terry Dr, Shelter Island, NY 11964Off Market
- $1,585,600-- bd-- ba-- sqft20 Terry Dr, Shelter Island, NY 11964Off Market
- $1,385,0003 bd2 ba1.7k sqft31 Terry Dr, Shelter Island, NY 11964Sold
- $395,100-- bd-- ba-- sqft23 Terry Dr, Shelter Island, NY 11964Off Market
- $1,995,1004 bd3 ba2.3k sqft12 Mimosa Pl, Shelter Island, NY 11964Off Market
A local agent can set up tours, give advice and negotiate with sellers.
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