5 Highview Dr, Wainscott, NY 11975
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NOT ACTIVE

5 Highview Dr
Wainscott, NY 11975

  • 5 Beds
  • 6 Baths
  • 5,000 sqft (on 2.20 acres)

$3,734,400

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $24,519/mo*
Refinance Your Home

$3,734,400

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $24,519/mo*
Refinance Your Home
5 Beds
6 Baths
5,000 sqft
(on 2.20 acres)

Local Information

  • Map ViewExplore the area around 5 Highview Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Rental Registration #: 20-15 Rental Registration #: 18-321 Hilltop location features this incredible property in Wainscott. This newly renovated two-story, shingle style traditional home with 5,000
square feet of living space offers top quality finishes throughout and offers five bedrooms, five and one-half baths, a professional kitchen with a breakfast bar, a family room, a formal dining room, a living room, and two fireplaces. Outdoors enjoy the new heated pool with retractable cover, a hot tub, and spa, 1,800
square feet of new decking and beautiful new landscaping, along with a three-car garage.Spectacular property..
5 Highview Dr, Wainscott, NY 11975 is a 5 bedroom, 6 bathroom, 5,000 sqft single-family home built in 2003. More recently, it was listed as a rental in May 2021 with an asking price of $48,750 per month. That rental listing was removed on May 17, 2021. It is currently off market. The Trulia Estimate is $3,734,400, with a rent estimate of $8,000/month.
This property is off market or not active on Trulia

Home Highlights

Parking
No Info
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 5 Highview Dr

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Types of Rooms: Family Room
Appliances & Utilities
DryerRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa

Property Information

Year Built
Year Built: 2003
Property Type / Style
Property Type: Single Family Home

Exterior Features

Pool
Pool
Parking & Garage
Parking Spaces: 3Parking: None

Lot Information

Lot Area: 2.20 acres

Price History for 5 Highview Dr

DatePriceEventSource
05/17/2021ListingRemovedOut East
05/14/2021$48,750Listed For RentOut East #289174
05/03/2021ListingRemovedOut East
04/08/2021$48,750Listed For RentOut East #289174
02/28/2021ListingRemovedOut East
02/16/2021$48,750Listed For RentOut East #289174
09/25/2019$41,666ListingRemovedAgent Provided
07/24/2019$41,666Listed For RentAgent Provided
10/06/2018$75,000ListingRemovedAgent Provided
06/05/2018$75,000Listed For RentAgent Provided
10/12/2017$155,000ListingRemovedAgent Provided
09/21/2017$155,000Listed For RentAgent Provided
11/14/2016$3,995,000ListingRemovedAgent Provided
09/20/2015$3,995,000Listed For SaleAgent Provided

Market trends in East Hampton

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
214
7MoM
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Comparable Sales for 5 Highview Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
9 Deepview Ct, Wainscott, NY
0.22
Single-Family Home
$1,500,000
07/08/25
4
3
1,800
60 S Breeze Dr, Wainscott, NY
0.28
Single-Family Home
$2,151,000
03/24/26
4
3
2,458
5 Forest Xing, Sagaponack, NY
1.16
Single-Family Home
$4,350,000
03/03/26
5
5
5,000
5 Bark Ct, Wainscott, NY
0.27
Single-Family Home
$1,250,000
01/29/26
4
4.5
3,900
43 Red Fox Ln, East Hampton, NY
0.55
Single-Family Home
$1,854,000
08/04/25
3
2
2,400
790 Sagg Rd, Sagaponack, NY
1.42
Single-Family Home
$6,600,000
03/26/26
4
6
4,220
62 Whooping Hollow Rd, East Hampton, NY
1.08
Single-Family Home
$3,250,000
11/21/25
6
5.5
4,426
49 Cosdrew Ln, East Hampton, NY
1.20
Single-Family Home
$3,000,000
08/12/25
5
6
4,900
Address Not Disclosed, Sag Harbor, NY
1.38
Single-Family Home
$2,145,000
10/23/25
4
4
3,215
1258 Town Line Rd, Sagaponack, NY
1.43
Single-Family Home
$5,800,000
07/24/25
7
6.5
6,354

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 5 Highview Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about East Hampton

At least 168 Trulia users voted on each feature.

  • 90 % Say yards are well-kept

  • 86 % Say it's dog friendly

  • 85 % Say car is needed

  • 80 % Say parking is easy

  • 79 % Say there's wildlife

  • 77 % Say people would walk alone at night

  • 76 % Say it's quiet

  • 72 % Say they plan to stay for at least 5 years

  • 66 % Say there's holiday spirit

  • 63 % Say neighbors are friendly

  • 54 % Say kids play outside

  • 43 % Say there are community events

  • 38 % Say it's walkable to restaurants

  • 38 % Say it's walkable to grocery stores

  • 33 % Say there are sidewalks

  • 28 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Jeff Coe
    "Running on the beach… before 9AM or after 6PM in summer. There are plenty of dog owners in the neighborhood to befriend. There are also a good number of dog groomers in the area if that is needed for your dog. "
    0
    Flag
  • Ralph
    "People are always walking their dogs and are friendly. Dogs are welcome and part of the community. There is a very large dog park less than a mile away"
    0
    Flag
  • Ralph
    "Dogs are welcome and visible walking everywhere. There’s a 21 acre dog park. There’s nothing not to like for dogs."
    0
    Flag
  • 2t5vmtgngs
    "I’m not a parent so I don’t really know. I would say the kids are safe to play on the side streets, just keep them off the main roads and they can have a nice independent fun childhood. "
    0
    Flag
  • Ashley Alarcon
    "I love the East Hampton it’s truly a beautiful town and well worth its visit time and loving here too, comes with lots of joy and community love."
    0
    Flag
  • Trulia User
    "Great place altogether, very comfortable and relaxed. "
    0
    Flag
  • Trulia User
    "Lush by water, quiet, mature trees and vegetation, minimal light pollution, near town but feels very remote"
    1
    Flag
  • Trulia User
    "You would definitely need a car to get around the Hamptons. But if you are traveling to NYC from the Hamptons there’s the Hampton Jitney bus you can take. "
    2
    Flag
  • Trulia User
    "I have lived in this neighborhood more than 20 years and enjoy the central location—close to Village, beaches and shopping."
    2
    Flag
  • Trulia User
    "I see people walking around with their pets all the time running right on my corner is the school Cars always slows down neighborhood is very friendly "
    0
    Flag
  • Danielle
    "No street lights so no walking or riding at night. Very little or no real frond to speak of around here. There were car break ins last spring and summer but other wise it’s always been pretty quiet. "
    0
    Flag
  • Danielle
    "There are no street lights so it’s not safe to walk or ride at night. It’s fairly safe as far as crimes goes. Over the past year there had been car break ins but no home burglaries. "
    0
    Flag
  • Danielle
    "Certain roads are good for walking dogs but not Long Lane and Cedar. There are no sidewalks and the traffic is heavy. There are plenty of spots to drive your dog to for a good leash walk. "
    1
    Flag
  • Danielle D.
    "I’ve lived here for over 25 years. It’s a unique area. I’m on Long Lane it’s mostly agricultural and commercial. The traffic can be heavy at certain times of the year due to the high school and the commercial nurseries. But the trade off is worth it. I love it because it’s still feels rural. I have learned to live with the dust and diesels because it’s so close to town but isn’t overly suburbanized. You have to still have some grit to live here. "
    4
    Flag
  • Trulia User
    "Lots of traffic and no room for cyclists or walkers Lots of Traffic in town too much I don’t have anything else to say "
    1
    Flag
  • Trulia User
    "Great place to live. We enjoy all that springs has to offer. The beaches, shops and neighbors are terrific "
    0
    Flag
  • Trulia User
    "There is lot of families but there isn’t parks or entertainment places for people to go with their kids "
    0
    Flag
  • Mk T.
    "In this area is good for the live quite and sweet no people destroy everybody clean the yard and is beautiful place no garbage in the road the cars no going fast and everyone respect "
    5
    Flag
  • Jeremy D.
    "Great location. Wonderful neighbors. Far enough out of town it feels country. Bay beaches everywhere. "
    0
    Flag
  • Leonora.loeb
    "Safe and friendly! Parks, beaches, day camps, horseback riding, and even a frequently used skate park are great places for kids in the area"
    0
    Flag
  • Georgie
    "Everyone is very polite and friendly, and so are their dogs. Lots of older couples, families and kids. "
    0
    Flag
  • Hansbald
    "Many people walk their dogs on our quiet streets. Short drive to the beach where the dogs can run free at certain times."
    0
    Flag
  • Julie H.
    "Very nice surroundings. I’ve lived here my whole life. Best place to be all year round. Very nice people who live here. "
    11
    Flag
  • Julio A.
    "What makes my neighborhood unique is how people really help out,like people come and pick up the trash which is a problem how we are littering, but they pick it up. How your neighborhood is so hype which is great so you can have fun and more."
    9
    Flag
  • Noah S.
    "We love the chill vibes around here. This is a neighborhood that surpasses any neighborhood in Miami, Los Angeles, Puerto Banus, Thailand and etc. The view and the quality is surreal. It feels like you’re stuck in 1960’s with a modern touch."
    3
    Flag
  • Denisgcarr
    "You must have a car to get anywhere. Traffic is usually very light. Public transportation is limited to a sporadic bus schedule. "
    0
    Flag
  • Geovadj
    "drive carefylly because wild life are around, like deers. and many people usully ride bikes and run avery day."
    0
    Flag
  • Crozierk1775
    "It’s a very safe environment with a lot of character and history. There are plenty of parks and sporting areas for extra curricular activities. "
    0
    Flag
  • Francis Z.
    "We personally use our vehicles to get to where we need to go. There is public transportation available should we need it. "
    0
    Flag
  • Bermeojose
    "The thing that makes my neighborhood unique is that it’s not loud and the street are clean and that helps me because I live right next to the street ."
    6
    Flag
  • John Kernell
    "Quiet neighborhood close to the harbor and world class beaches. Great restaurants with harbor views nearby. 15 acre enclosed dog park might be worlds best."
    1
    Flag
  • Cindy C.
    "I have been living out here for 3 months and have not been able to find anything to do in the area. School district is really great though!"
    0
    Flag
  • Monica27avila
    "I like my neighbors every one is so kind is quite place no too much traffic is perfect I live here for 14 years "
    3
    Flag
  • Sarahfkinn
    "Must have a car or take taxis. There is limited public transit that does not service the neighborhood. "
    3
    Flag
  • Koc0516
    "Great location to live in I can avoid the slow main roads and get most places on the back roads, which in season can save hours "
    0
    Flag

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Homes for sale near 5 Highview Dr

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Off Market Homes Near 5 Highview Dr

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