86 Caldwell Rd, Bridgehampton, NY 11932
Property image
Property image
NOT ACTIVE

86 Caldwell Rd
Bridgehampton, NY 11932

  • 4 Beds
  • 3 Baths
  • 2,240 sqft (on 0.70 acres)

$2,332,700

Trulia Estimate
as of Aug 24, 2026

$2,332,700

Trulia Estimate
as of Aug 24, 2026
  • 4 Beds
  • 3 Baths
  • 2,240 sqft (on 0.70 acres)

Home Highlights

Property Type
Single-Family Home
Year Built
2005
Lot Size
0.7 acres
Living Area
2,240 sqft
Price/Sqft
$1,041
Parking
None

Local Information

  • Map ViewExplore the area around 86 Caldwell Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

At the end of a quiet cul-de-sac in the heart of Bridgehampton sits this cozy Cape perfect for all seasons. Beautifully landscaped and the house is charming with brand new updated interior with four bedrooms, three full baths, open kitchen living area, finished basement playroom and heated gunite salt water pool. Just north of Bridgehampton Village and only a few miles from ocean beaches and Sag Harbor this is a central location with easy access to all the Hamptons has to offer.
86 Caldwell Rd, Bridgehampton, NY 11932 is a 4 bedroom, 3 bathroom, 2,240 sqft single-family home built in 2005. It last sold for $495,000 on Apr 21, 2003 (8,150% above the $6,000 asking price). More recently, it was listed as a rental in January 2025 with an asking price of $4,500 per month. That rental listing was removed on December 5, 2025. It is currently off market. The Trulia Estimate is $2,332,700, with a rent estimate of $6,916/month.

Home Details for 86 Caldwell Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 2

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For Details

Exterior Features

Pool
Pool
Parking & Garage
Parking: None

Lot Information

Lot Area: 0.00 Acres

Comparable Sales for 86 Caldwell Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
41 Woodruff Ln, Bridgehampton, NY
0.35
Single-Family Home
$1,700,000
05/21/26
4
3
2,200 sqft
138 Sea Farm Ln, Bridgehampton, NY
0.53
Single-Family Home
$2,295,000
08/29/25
6
4
2,800 sqft
49 Birchwood Lane, Bridgehampton, NY
0.16
Single-Family Home
$4,950,000
01/13/26
6
7.5
6,000 sqft
49 Birchwood Ln, Bridgehampton, NY
0.16
Single-Family Home
$4,950,000
11/06/25
6
7.5
6,000 sqft
393 Brick Kiln Rd, Sag Harbor, NY
1.12
Single-Family Home
$1,400,000
05/26/26
4
3.5
5,000 sqft
136 Beckys Path, Bridgehampton, NY
0.70
Single-Family Home
$1,961,000
02/19/26
6
9
4,800 sqft
2148 Scuttle Hole Rd, Bridgehampton, NY
0.28
Single-Family Home
$7,000,000
04/13/26
7
7
8,200 sqft
3 Fair Hills Ln, Bridgehampton, NY
0.77
Single-Family Home
$6,880,000
12/01/25
6
6.5
5,769 sqft
30 Sagg Rd, Sagaponack, NY
1.15
Single-Family Home
$21,000
12/02/25
3
2
2,210 sqft
32 Meadow Ct, Water Mill, NY
1.31
Single-Family Home
$1,350,000
11/20/25
4
4.5
4,400 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

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
    Flag
  • 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

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Dec 5, 2025
Source: Zillow Rentals
ListingRemoved
$6,000
Sep 8, 2025
Source: Zillow Rentals
PriceChange
$6,000
Price increased by 33%
Sep 4, 2025
Source: Zillow Rentals
PriceChange
$4,500
Price decreased by 89%
Aug 1, 2025
Source: Zillow Rentals
PriceChange
$40,000
Price increased by 14%
Jul 1, 2025
Source: Zillow Rentals
PriceChange
$35,000
Price increased by 40%
This property is off market or not active on Trulia

Frequently asked questions about 86 Caldwell Rd

  • What is 86 Caldwell Rd estimated to be worth?
    Trulia's estimated value for 86 Caldwell Rd in Bridgehampton, NY is $2,332,700.
  • What is the price history for 86 Caldwell Rd?
    86 Caldwell Rd in Bridgehampton, NY last sold for $495,000 in April 2003.
  • Is Bridgehampton a buyer's or seller's market?
    Bridgehampton is currently a buyer's market, based on recent for-sale activity.
  • 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 recently sold homes in Bridgehampton, NY.
  • Does 86 Caldwell Rd have a pool?
    Yes, 86 Caldwell Rd in Bridgehampton, NY has a pool.
  • How big is the lot at 86 Caldwell Rd?
    The lot at 86 Caldwell Rd in Bridgehampton, NY is about 0.70 acres (30,492 sq ft).

Homes for rent near 86 Caldwell Rd

Skip to last item
Skip to first item

Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
Skip to last item
  • Results are loading
Skip to first item