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20 Prospect Ave, Shelter Island Heights, NY, 11965

7beds
6baths
5,000sqft
$4,995,000
$999price/sqft
$35,187/moest. monthly cost
$1,407,480/yrincome needed

About This Home

Introducing Aquarelle at 20 Prospect Ave, an iconic piece of Shelter Island Heights history. Built in 1883, this distinguished home holds a cherished place among the original residences in this esteemed neighborhood, now classified as a national historic district. Once upon Prospect Avenue, once known as Divinity Hill, you'll find yourself transported to a time when Methodist ministers from New York flocked to this area in the late 1800s to worship at the Union Chapel in the Grove. These devout individuals constructed the houses along Divinity Hill, including 20 Prospect Ave. Originally, these homes did not have kitchens, as residents would either gather at the Chequit Inn for communal meals or have their meals delivered by donkey cart. One notable feature of this remarkable property is its expansive porch, which served as a sleeping porch during hot summer nights long before the invention of air conditioning. The architectural details evoke a sense of nostalgia, connecting you to the past while offering modern comforts. Named Aquarelle by its current owners, this home carries the essence of watercolor, paying homage to the owner's acclaimed career as a renowned watercolor artist. Every corner of this residence is imbued with creativity and inspiration. Additionally, the lower level offers a separate finished living space boasting abundant water views, kitchenette & bath, which can be utilized as a guest apartment or home office. Now, this historic gem stands as an extraordinary opportunity for the discerning buyer. Experience the rich heritage of Shelter Island Heights while shaping the future of this exceptional property. Embrace the chance to own a piece of history and create a masterpiece of your own.

Getting Around

32
WalkingCar-Dependent
0
TransitVery Limited Transit
22
BikeSomewhat Bikeable

Schools

6/10
Shelter Island SchoolGrades PK-121.6 mi

Construction

Type & Style

  • Home type: SingleFamily
  • Property subType: Single Family Residence

Interior

Basement

  • Basement: No

Bedrooms & Bathrooms

  • Bedrooms: 7
  • Bathrooms: 6
  • Full bathrooms: 6

Interior Area

  • Total structure area: 5,000
  • Total interior livable area: 5,000 sqft

Property

Features

  • Private pool: Yes
  • Has view: Yes
  • View description: Water
  • Has water view: Yes
  • Water view: Water
  • On waterfront: Yes
  • Waterfront features: Waterfront
  • Frontage type: Waterfront

Lot

  • Lot size: 1.20 Acres

Parking

  • Parking features: GarageDetached
  • Has garage: Yes

Climate Risk is Financial Risk

Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.

Biggest Threats for This Home

  • Coastal Flooding
    Coastal FloodingRelatively High
  • Hurricane
    HurricaneModerate
  • Inland Flooding
    Inland FloodingModerate
  • Winter Weather
    Winter WeatherModerate
  • Tsunami
    TsunamiInsufficient Data

How This Home’s Risks Compare

Coastal Flooding
Hurricane
Inland Flooding
Winter Weather
Tsunami

FEMA Declared Disasters in Suffolk County and New York

Flood
Severe Storm
Snowstorm
Straight Line Winds
Tropical Storm
Winter Storm

Understanding the Costs

Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.

Estimated Costs Today

MonthlyAnnual
Mortgage $25,257$303,084
Home Insurance *$2,361$28,332
Property Taxes $6,743$80,916
Electricity $826$9,915
Total$35,187$422,244
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$1,206,411/yr
40% on housing$1,055,610/yr
45% on housing$938,320/yr

New York FAIR Plan Programs

New York Property Insurance Underwriting Association

Covered
WildfireWildfire
HailHail
WindWind
Visit Website →
Current Policies
Residential: 20,669Commercial: 1,556
Total Premiums$32.27M
Total Exposure$7.63B

How Costs Could Change Over Time

Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.

Insurance Growth Rate5-year average: 4.6%
4.6%
0%30.0%
Electricity Growth Rate10-year average: 7.1%
7.1%
0%15.0%
Property Taxes Growth Rate2-year average: 1.0%
1.0%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$999This listing

vs Other Active Listings

Avg $/sqft

ZIP 11965$939
Suffolk County$724

vs Homes Sold Last Month

Median $/sqft

ZIP 11965$663
Suffolk County$412

Current Market Trends

Median Price Per Square Foot

The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.

Historicals for This Listing

Zestimate History ($/sqft)

No zestimate history available

Price History

DateEventPrice
2025-10-18Listed for sale$4,995,000
2025-08-05Pending sale$4,995,000
2025-02-13Price change$4,995,000
2024-06-11Listed for sale$5,450,000

For Sale by Agent

AgentHedgerow Exclusive Properties - Real Estate Sales Person
BrokerageHedgerow Exclusive Properties

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