65 Caldwell Rd, Bridgehampton, NY 11932
NOT ACTIVE

65 Caldwell Rd
Bridgehampton, NY 11932

  • 4 Beds
  • 2.5 Baths
  • 3,025 sqft (on 0.57 acres)

$2,399,100

Trulia Estimate
as of Jun 18, 2026
Est. Refi. Payment $15,591/mo*
Refinance Your Home

$2,399,100

Trulia Estimate
as of Jun 18, 2026
Est. Refi. Payment $15,591/mo*
Refinance Your Home
4 Beds
2.5 Baths
3,025 sqft
(on 0.57 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
This property is off market or not active on Trulia

Home Highlights

Parking
No Info
Outdoor
Pool
A/C
Cooling only
HOA
None
Price/Sqft
No Info
Listed
160 days ago

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

Price History for 65 Caldwell Rd

DatePriceEventSource
02/19/2026$40,000ListingRemovedZillow Rentals
01/08/2026$40,000Listed For RentZillow Rentals
06/03/2025$31,666ListingRemovedZillow Rentals
12/10/2024$31,666Listed For RentZillow Rentals
09/12/2024$25,000ListingRemovedZillow Rentals
07/08/2024$25,000PriceChange
Zillow Rentals
07/01/2024$40,000PriceChange
Zillow Rentals
04/15/2024$31,666Listed For RentZillow Rentals
09/05/2023ListingRemovedZillow Rentals
06/26/2023$40,000Listed For RentZillow Rentals
06/27/2022ListingRemovedOut East
06/09/2022$35,000PriceChange
Out East #365401
04/24/2022$26,666Listed For RentOut East #365401
12/07/2020$1,690,000ListingRemovedAgent Provided
11/16/2020$1,690,000PendingAgent Provided
09/07/2020$1,690,000PriceChange
Agent Provided
07/25/2020$1,735,000PriceChange
Agent Provided
05/29/2020$1,825,000Listed For SaleAgent Provided
11/17/2019$1,839,500ListingRemovedAgent Provided
10/04/2019$1,839,500PriceChange
Agent Provided
09/27/2019$1,899,995PriceChange
Agent Provided
08/15/2019$1,895,000PriceChange
Agent Provided
05/13/2019$1,999,500Listed For SaleAgent Provided
06/09/2004$583,000Sold
N/A
05/02/2000$11,000Sold
N/A

Market trends in Bridgehampton

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
35
5MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$1,352,900
Home facts updated by county records

Homeowner tools

Estimated monthly rent$7,882/mo
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Homes for rent near 65 Caldwell Rd

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Comparable Sales for 65 Caldwell Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
103 Huntington Crossway, Bridgehampton, NY
0.16
Single-Family Home
$950,000
08/22/25
3
2
1,677
58 Hampton Court, Bridgehampton, NY
0.20
Single-Family Home
$1,800,000
06/24/25
5
2.5
1,520
138 Sea Farm Ln, Bridgehampton, NY
0.52
Single-Family Home
$2,295,000
08/29/25
6
4
2,800
4 Worchester, Bridgehampton, NY
0.67
Single-Family Home
$2,495,000
07/29/25
4
3.5
2,646
49 Birchwood Ln, Bridgehampton, NY
0.11
Single-Family Home
$4,950,000
11/06/25
6
7.5
6,000
49 Birchwood Lane, Bridgehampton, NY
0.11
Single-Family Home
$4,950,000
01/13/26
6
7.5
6,000
136 Beckys Path, Bridgehampton, NY
0.68
Single-Family Home
$1,961,000
02/19/26
6
9
4,800
Address Not Disclosed, Sag Harbor, NY
1.22
Single-Family Home
$2,145,000
10/23/25
4
4
3,215
196 Maple Ln, Bridgehampton, NY
1.30
Single-Family Home
$2,800,000
06/26/25
3
3
1,987
11 Sawasett Ave, Bridgehampton, NY
1.32
Single-Family Home
$3,025,000
07/23/25
4
4
2,384

Nearby homes

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Assigned Schools

These are the assigned schools for 65 Caldwell Rd.

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

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Homes for sale near 65 Caldwell Rd

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Off Market Homes Near 65 Caldwell Rd

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65 Caldwell Rd, Bridgehampton, NY 11932 is a 4 bedroom, 3 bathroom, 3,025 sqft single-family home built in 2005. This property is not currently available for sale. 65 Caldwell Rd was last sold on Jun 9, 2004 for $583,000 (1,358% higher than the asking price of $40,000). The current Trulia Estimate for 65 Caldwell Rd is $2,399,100.