63 Chester Ave, Bridgehampton, NY 11963
Property image
Property image
PENDING

$3,875,000

  • 4 Beds
  • 3.5 Baths
  • 2,255 sqft

63 Chester Ave, Bridgehampton, NY 11963

Est. Mortgage $26,032/mo*
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Home Highlights

Single-Family Home
Built in 1952
$1,718/sqft

Local Information

  • Map ViewExplore the area around 63 Chester Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Relax, unwind, and enjoy effortless village living at this newly redesigned and fully renovated Cape Cod cottage on coveted Chester Street in Bridgehampton. Filled with natural light and thoughtfully updated throughout, the home offers a bright, airy layout with inviting living and dining spaces, an eat-in kitchen, and full-width sliders that open seamlessly to the outdoor entertaining areas.The sleek, open kitchen features custom cabinetry, a statement quartz countertop, Sub-Zero/Wolf appliances, a walk-in pantry, and refined finishes, creating a perfect setting for both everyday living and summer entertaining. The first floor includes a serene primary bedroom with an ensuite bath, an ensuite guest bedroom, a powder room, and a laundry space with built-in storage.Upstairs, two well-proportioned bedrooms share an updated bath, complemented by fresh interiors and a bonus deck offering village views and a sense of privacy.Outdoors, the property is designed for relaxed Hamptons living, featuring a heated pool, a generous stone patio, a lush lawn surrounded by mature greenery, alfresco dining, and a seating area for entertaining guests or family. Ideally located in the heart of Bridgehampton Village, the home is a short walk from Pierre's, Bobby Van's, boutiques, galleries, the train, the Jitney and all the best of village life.A charming, turnkey Bridgehampton retreat with style, comfort, and exceptional convenience.
Contact this Building
Property Website
Last check for updates: about 5 hours ago
Listing by: Compass
Jeremy Dunham - Associate Real Estate Broker, (631) 875-2475
Source: Out East, MLS#395633

Home Details for 63 Chester Ave

Interior Features

Interior Details
Basement: No
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2255 Square Feet
Heating & Cooling
Has CoolingAir Conditioning: Central AirNo Heating
Fireplace & Spa
No FireplaceNo Spa
Levels, Entrance, & Accessibility
Stories: 2
View
No View

Exterior Features

Exterior Home Features
Has a Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageParking: None
Pool
Pool: HeatedPool
Frontage
Not on Waterfront

Days on Market

Days on Market: 115

Property Information

Year Built
Year Built: 1952
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Not a New Construction

Price & Status

Price
List Price: $3,875,000Price Per Sqft: $1,718

Active Status

MLS Status: Pending

Location

Direction & Address
City: Bridgehampton

Agent Information

Listing Agent
Listing ID: 395633

Building

Building Area
Building Area: 2255 Square Feet

Lot Information

Lot Area: 10454.4 sqft

Miscellaneous

Mls Number: 395633Listing Url

Around this home

What Locals Say about Bridgehampton

At least 17 Trulia users voted on each feature.

  • 91 % Say yards are well-kept

  • 89 % Say car is needed

  • 88 % Say they plan to stay for at least 5 years

  • 84 % Say people would walk alone at night

  • 80 % Say parking is easy

  • 73 % Say it's dog friendly

  • 73 % Say there's wildlife

  • 71 % Say there's holiday spirit

  • 65 % Say it's walkable to restaurants

  • 64 % Say there are community events

  • 64 % Say it's quiet

  • 60 % Say it's walkable to grocery stores

  • 57 % Say neighbors are friendly

  • 42 % Say there are sidewalks

  • 38 % Say kids play outside

  • 35 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Randel M.
    "Ingerir here for three years and never had a problem. Everything is in close proximity from supermarkets to hardware you name it"
    0
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  • Dorettakgoldberg
    "combination of farms, beaches, private homes and upscale restaurants and shopping creates a unique and comfortable atmosphere"
    0
    Flag
  • Molly
    "Very quiet neighborhood. Walk to beach’s, kayaking 3 minutes away, grocery store 2 minutes away. Southampton school district. Walk to farm stand for your fresh organic vegetables and fruits."
    0
    Flag
  • mcaridi
    "live in the neighborhood , delightful "
    2
    Flag
  • Kathy J.
    "I bought a house here a couple of years ago and I find the area to be lovely and convenient. We wanted something within walking distance to town, yet country like in setting and this is it. It is near a pond and a very short distance by car to the Atlantic Ocean beach of Sagaponac."
    0
    Flag

Market trends in Bridgehampton

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
27
6MoM

Home Value

Trulia Estimate
$3.59M
Since last month
Decreased$34K (-0.9%)
Since last year
Increased$1M (+52.3%)
Since last sale
Increased$2M (+140.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +146% in the last 10 years
MonthEstimated value
2026
August 2026$3.6M
August 2026$3.59M
July 2026$3.63M
June 2026$3.68M
May 2026$3.83M
April 2026$2.31M
March 2026$2.47M
February 2026$2.35M
January 2026$2.17M
2025
2024
2023
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
96 Audubon Avenue, Bridgehampton, NY
0.68
Single-Family Home
$4,450,000
12/11/25
3
3
2,400
107 Edgewood Avenue, Bridgehampton, NY
0.54
Single-Family Home
$5,100,000
12/02/25
5
5
4,276
6 Cody Way, Bridgehampton, NY
0.21
Single-Family Home
$10,018,000
05/15/26
8
9
9,500
85 Pheasant Dr, Bridgehampton, NY
0.63
Single-Family Home
$9,995,000
09/18/25
7
9
7,693
488 Lumber Ln, Bridgehampton, NY
0.74
Single-Family Home
$4,500,000
12/31/25
3
3
3,500
36 Chase Ct, Bridgehampton, NY
0.93
Single-Family Home
$7,300,000
11/05/25
6
7.5
8,200

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
74 Chester Ave, Bridgehampton, NY 11932
0.04
$5,592,400
6
5.5
5,450
Off Market
37 Chester Ave, Bridgehampton, NY 11932
0.05
$3,450,400
3
2
1,722
Off Market
237 Maple Ln, Bridgehampton, NY 11932
0.07
$3,995,000
5
4
2,989
For Sale
72 Lumber Ln, Bridgehampton, NY 11932
0.08
$5,822,500
4
3.5
4,888
Off Market
27 Halsey St, Bridgehampton, NY 11932
0.10
$3,774,500
4
3
2,300
Off Market
119 Lumber Ln, Bridgehampton, NY 11963
0.11
$3,995,000
4
2
2,100
For Sale
32 Halsey St, Bridgehampton, NY 11932
0.12
$3,133,400
3
2
1,600
Off Market
91 Lumber Ln, Bridgehampton, NY 11932
0.12
$3,667,600
4
3
2,616
Off Market
690 Bridgehampton Sag, Bridgehampton, NY 11932
0.11
$5,672,100
5
6
6,700
Off Market
690 Bridgehampton Sh Harbor, Bridgehampton, NY 11932
0.11
$4,829,400
5
6.5
-
Off Market
76 Audubon Ave, Bridgehampton, NY 11932
0.13
$6,271,700
5
3.5
3,523
Off Market
39 Lumber Lane, Bridgehampton, NY 11932
0.16
$4,249,100
2
5
-
Off Market

Price and Tax history

DateEventPrice
May 29, 2026
Source: Out East #395633
Pending
$3,875,000
May 16, 2026
Source: Out East #395633
Listed For Sale
$3,875,000
Jun 1, 2022
Source: Out East
ListingRemoved
May 2, 2022
Source: Out East #359123
Listed For Rent
$22,000
Feb 10, 2022
Source: Out East
ListingRemoved

LGBTQ Local Legal Protections

Jeremy Dunham - Associate Real Estate Broker, Compass
Agent Phone: (631) 875-2475

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Frequently asked questions about 63 Chester Ave

  • What is the estimated monthly payment for 63 Chester Ave?
    Based on a $3,875,000 list price with 20% down at today's rates, the estimated monthly payment for 63 Chester Ave in Bridgehampton, NY is approximately $26,619 (about $20,570 principal & interest, $5,974 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Bridgehampton?
    Residents describe Bridgehampton, NY as well-kept, established, and easy to park in. Most residents say you need a car. See homes for sale in Bridgehampton, NY.
  • What are the closest schools to 63 Chester Ave?
    The closest schools to 63 Chester Ave in Bridgehampton, NY are Bridgehampton School (K-12, rated 3/10).
  • What is 63 Chester Ave estimated to be worth?
    Trulia's estimated value for 63 Chester Ave in Bridgehampton, NY is $3,591,600.
  • Does 63 Chester Ave have air conditioning?
    Yes, 63 Chester Ave in Bridgehampton, NY has air conditioning.
  • Does 63 Chester Ave have a pool?
    Yes, 63 Chester Ave in Bridgehampton, NY has a pool.
63 Chester Ave, Bridgehampton, NY 11963 is a 4 bedroom, 4 bathroom, 2,255 sqft single-family home built in 1952. This property is currently available for sale and was listed by Out East on May 18, 2026. The MLS # for this home is MLS# 395633.