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69 Hillside Dr , Sag Harbor, NY 11963

$1,599,000

5
beds
5 full · 2 half
baths
3,843
sqft
1954
year built

Approved to be built for 3,843 square feet new residential single-family home in Sag Harbor Village Suffolk County Department of Health for septic system and Sag Harbor Village Architectural Review Board approved plans. Designed by renowned Hamptons architect Peter Cook, 69 Hillside Drive has an enviable location and inspired design ready to deliver the best of luxury living in the Hamptons. Just moments from Main Street and with a short walking distance to private Nineveh Beach access, this prime property offers both convenience and coastal charm with a chic contemporary style home boasting 3,843 +/- sq. ft. (including the fully finished lower level), 5 bedrooms, 5 full baths and 2 half baths, 10'x'20 in ground pool and pool house. Enter an elegant open-concept floor plan with large windows that beam light from the rear grounds. The main level includes a large eat-in kitchen, dedicated dining space, large great room, and first-floor ensuite jr. primary. Ready for entertaining and everyday luxury living. Upstairs find 3 well-appointed bedrooms, each ensuite with large closets. The primary suite is exceptional with an oversized patio, ultra-luxe bath, and fireplace. The lower level is bright and open with two egress points, adding a large playroom area, home gym, ensuite bedroom, a full bath and ample storage. Exterior spaces are equally elegant with sunny pool, pool house, outdoor shower, sunken courtyard, outdoor kitchen and ample dining and lounging space. This enviable location in Sag Harbor delivers the best of the Hamptons lifestyle with nearby marinas, golf, equestrian, private beach access and moments from the boutique shops and dining found in the Village.

Highlights

  • Residential
  • Single Family Residence
  • Built in 1954
  • 0.23 Acre Lot
  • 2 days on Market

  • Bedrooms
    5
  • Bathrooms
    5 full · 2 half
  • Year Built
    1954
  • Architectural Style
    Ranch
  • Construction Materials
    Frame
  • Parking Features
    Driveway, Garage Door Opener, Off Street
  • Living Area
    3843.0
  • Interior Features
    Natural Woodwork
  • Appliances
    Dryer, Dishwasher, Refrigerator, Washer, Oven, Stainless Steel Appliance(s)
  • Flooring
    Wood
  • Pool Features
    In Ground, Private
  • Cooling
    Central Air
  • Heating
    Forced Air, Propane
  • Basement
    Full

  • Acres
    0.23
  • Water Front Features
    Waterfront Access
  • View
    Trees/Woods, Water
  • Utilities
    Electricity Connected, Sewer Connected
  • Water
    Public

  • County
    Suffolk
  • City
    Sag Harbor
  • Zip Code
    11963
  • High School
    Pierson Middle/High School
  • Middle School
    Pierson Middle/High School
  • Elementary School
    Sag Harbor Elementary School

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Frequently Asked Questions

How do I schedule a tour of 69 Hillside Dr?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 69 Hillside Dr.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 69 Hillside Dr?

Click Ask a Question to talk with our team. You already know it is a 5 bed, 5 bath, listed for $1,599,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Sag Harbor, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 69 Hillside Dr?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 69 Hillside Dr at around $9,480. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 69 Hillside Dr?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Suffolk County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 69 Hillside Dr?

In most cases, yes. Whether 69 Hillside Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Sag Harbor's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 69 Hillside Dr?

We can handle that for you. Our preferred local agent specializes in residentials in Sag Harbor and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $1,599,000 with 3,843 sqft of space—that comes out to approximately $416 per square foot.

How long has this property been on the market?

69 Hillside Dr was listed on November 06, 2026, which means it's been on the market for 2 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1954, making it approximately 72 years old.

What is the lot size of this property?

69 Hillside Dr sits on a 0.23-acre lot, which is 10,019 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Sag Harbor Elementary School
  • Middle: Pierson Middle/High School
  • High: Pierson Middle/High School

Want to see how these schools compare? Check out our Suffolk County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 69 Hillside Dr?

The most recent public record shows annual property taxes for 69 Hillside Dr were approximately $4,570. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 69 Hillside Dr still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, OneKey MLS. All rights reserved.

Last Updated: November 08, 2026 at 09:04PM | Source: OneKey MLS | MLS#: 1071383