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

$2,450,800

Trulia Estimate
as of Sep 3, 2026
  • 4 Beds
  • 2.5 Baths
  • 3,025 sqft (on 0.57 acres)
  • 4 Beds
  • 2.5 Baths
  • 3,025 sqft (on 0.57 acres)

65 Caldwell Rd, Bridgehampton, NY 11932

Home Highlights

Property Type
Single-Family Home
Year Built
2005
Lot Size
0.57 acres
Living Area
3,025 sqft
Price/Sqft
$810

Local Information

  • Map ViewExplore the area around 65 Caldwell Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Rental Registration #: P085334 This pristine beach house, conveniently located to Bridgehampton, Sag Harbor, beaches, wineries, horse country and farm stands boasts a large, open floor plan on the first floor, with pine floors, a wood-burning fireplace, bay windows in the dining area and beamed, vaulted ceilings in the kitchen, all of which give this charming rental a bright, airy feel. A spacious full master suite, complete with a large bathroom (separate soaking tub and shower) and walk-in closet is conveniently located on the first floor. On the second floor, there are two fantastic guest rooms, a stylish guest bathroom, and an open sleeping loft/office with vaulted ceilings. Enjoy grilling on the back deck immersed in nature, entertaining or reading a book beneath the pergola overlooking the gorgeous manicured landscape. There is an outdoor shower in the back yard and free-standing two-car garage affords ample storage for cars and toys.
65 Caldwell Rd, Bridgehampton, NY 11932 is a 4 bedroom, 3 bathroom, 3,025 sqft single-family home built in 2005. It last sold for $583,000 on Jun 9, 2004 (1,358% above the $40,000 asking price). More recently, it was listed as a rental in January 2026 with an asking price of $40,000 per month. That rental listing was removed on February 19, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,450,800, with a rent estimate of $7,690/month.

Home Details for 65 Caldwell Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 2
Heating & Cooling
Air ConditioningCooling System: Central Air

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: Detached Other, On Site

Lot Information

Lot Area: 0.00 Acres

Comparable Sales for 65 Caldwell Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
41 Woodruff Ln, Bridgehampton, NY
0.29
Single-Family Home
$1,700,000
05/21/26
4
3
2,200 sqft
49 Birchwood Lane, Bridgehampton, NY
0.11
Single-Family Home
$4,950,000
01/13/26
6
7.5
6,000 sqft
49 Birchwood Ln, Bridgehampton, NY
0.11
Single-Family Home
$4,950,000
11/06/25
6
7.5
6,000 sqft
136 Beckys Path, Bridgehampton, NY
0.68
Single-Family Home
$1,961,000
02/19/26
6
9
4,800 sqft
393 Brick Kiln Rd, Sag Harbor, NY
1.17
Single-Family Home
$1,400,000
05/26/26
4
3.5
5,000 sqft
2148 Scuttle Hole Rd, Bridgehampton, NY
0.33
Single-Family Home
$7,000,000
04/13/26
7
7
8,200 sqft
Address Not Disclosed, Sag Harbor, NY
1.22
Single-Family Home
$2,145,000
12/30/25
4
4
3,215 sqft
30 Sagg Rd, Sagaponack, NY
1.09
Single-Family Home
$21,000
12/02/25
3
2
2,210 sqft
3 Fair Hills Ln, Bridgehampton, NY
0.82
Single-Family Home
$6,880,000
12/01/25
6
6.5
5,769 sqft
32 Meadow Ct, Water Mill, NY
1.34
Single-Family Home
$1,350,000
11/20/25
4
4.5
4,400 sqft

Nearby homes

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Rental Market Trends in Bridgehampton

Last updated Sep 2026
Trulia Rent Estimate$7,690/mo
Average rent
$65K
$5KMoM
Available listings
138
View rental market trends in Bridgehampton, NY

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

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Feb 19, 2026
Source: Zillow Rentals
ListingRemoved
$40,000
Jan 8, 2026
Source: Zillow Rentals
Listed For Rent
$40,000
Jun 3, 2025
Source: Zillow Rentals
ListingRemoved
$31,666
Dec 10, 2024
Source: Zillow Rentals
Listed For Rent
$31,666
Sep 12, 2024
Source: Zillow Rentals
ListingRemoved
$25,000
This property is off market or not active on Trulia

Frequently asked questions about 65 Caldwell Rd

  • What is 65 Caldwell Rd estimated to be worth?
    Trulia's estimated value for 65 Caldwell Rd in Bridgehampton, NY is $2,450,800.
  • What is the price history for 65 Caldwell Rd?
    65 Caldwell Rd in Bridgehampton, NY last sold for $583,000 in June 2004.
  • 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 65 Caldwell Rd have air conditioning?
    Yes, 65 Caldwell Rd in Bridgehampton, NY has air conditioning.
  • Does 65 Caldwell Rd have a pool?
    Yes, 65 Caldwell Rd in Bridgehampton, NY has a pool.

Homes for rent near 65 Caldwell Rd

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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.
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