Are yards well-kept in Bridgehampton, NY?

As of early 2026, 91% of users say yards are well-kept

Is a car needed in Bridgehampton, NY?

As of early 2026, 89% of users say car is needed

Do residents of Bridgehampton, NY plan to stay at least 5 years?

As of early 2026, 88% of users say they plan to stay for at least 5 years

Would people walk alone at night in Bridgehampton, NY?

As of early 2026, 84% of users say people would walk alone at night

Is parking easy in Bridgehampton, NY?

As of early 2026, 80% of users say parking is easy

Is Bridgehampton, NY dog-friendly?

As of early 2026, 73% of users say it's dog friendly

Is there wildlife in Bridgehampton, NY?

As of early 2026, 73% of users say there's wildlife

Does Bridgehampton, NY show holiday spirit?

As of early 2026, 71% of users say there's holiday spirit

Is Bridgehampton, NY walkable to restaurants?

As of early 2026, 65% of users say it's walkable to restaurants

Are there community events in Bridgehampton, NY?

As of early 2026, 64% of users say there are community events

Is Bridgehampton, NY quiet?

As of early 2026, 64% of users say it's quiet

Is Bridgehampton, NY walkable to grocery stores?

As of early 2026, 60% of users say it's walkable to grocery stores

Are neighbors friendly in Bridgehampton, NY?

As of early 2026, 57% of users say neighbors are friendly

Does Bridgehampton, NY have sidewalks?

As of early 2026, 42% of users say there are sidewalks

Do kids play outside in Bridgehampton, NY?

As of early 2026, 38% of users say kids play outside

Are the streets well-lit in Bridgehampton, NY?

As of early 2026, 35% of users say streets are well-lit

NOT ACTIVE

86 Caldwell Rd
Bridgehampton, NY 11932

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

$2,301,700

Trulia Estimate

as of May 25, 2026

Est. Refi. Payment $14,913/mo*

Refinance Your Home

$2,301,700

Trulia Estimate

as of May 25, 2026

Est. Refi. Payment $14,913/mo*

Refinance Your Home

4 Beds

3 Baths

2,240 sqft

(on 0.70 acres)

Local Information

-- mins to

Commute Destination

Description

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.

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

None

Outdoor

Pool

HOA

None

Price/Sqft

No Info

Listed

180+ days ago

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

Price History for 86 Caldwell Rd

Date	Price	Event	Source
12/05/2025	$6,000	ListingRemoved	Zillow Rentals

09/08/2025	$6,000	PriceChange	Zillow Rentals
Price Change $1,500 (33%)
09/04/2025	$4,500	PriceChange	Zillow Rentals
Price Change $35,500 (-89%)
08/01/2025	$40,000	PriceChange	Zillow Rentals
Price Change $5,000 (14%)
07/01/2025	$35,000	PriceChange	Zillow Rentals
Price Change $10,000 (40%)
02/13/2025	$25,000	PriceChange	Zillow Rentals
Price Change $20,500 (456%)
01/19/2025	$4,500	Listed For Rent	Zillow Rentals

12/31/2024	$40,000	ListingRemoved	Zillow Rentals

05/19/2023	$40,000	PriceChange	Zillow Rentals
Price Change $32,500 (433%)
05/01/2023	$7,500	PriceChange	Zillow Rentals
Price Change $3,000 (67%)
01/01/2023	$4,500	Listed For Rent	Zillow Rentals

01/01/2023		ListingRemoved	Zillow Rentals

12/09/2022	$4,500	PriceChange	Zillow Rentals
Price Change $25,500 (-85%)
03/08/2022	$30,000	PriceChange	Out East #91756
Price Change $25,500 (567%)
11/01/2021	$4,500	PriceChange	Out East #91756
Price Change $3,000 (-40%)
10/01/2021	$7,500	PriceChange	Out East #91756
Price Change $6,000 (-44%)
09/09/2021	$13,500	PriceChange	Out East #91756
Price Change $3,500 (35%)
08/21/2021	$10,000	Listed For Rent	Out East #91756

01/03/2021		ListingRemoved	Out East

10/09/2020	$10,000	Listed For Rent	Agent Provided

06/15/2020	$6,416	ListingRemoved	Agent Provided

06/14/2020	$6,416	Listed For Rent	Agent Provided

05/08/2020	$6,416	ListingRemoved	Agent Provided

01/23/2020	$6,416	Listed For Rent	Agent Provided

10/03/2019	$77,000	ListingRemoved	Agent Provided

04/21/2003	$495,000	Sold	N/A
Recording Date 04/21/2003 Contract Date 04/11/2003 County Transfer Tax N/A Total Transfer Tax $1,980
12/12/2002	$308,652	Sold	N/A
Recording Date 12/12/2002 Contract Date 11/04/2002 County Transfer Tax N/A Total Transfer Tax $1,236
05/02/2000	$11,000	Sold	N/A
Recording Date 05/02/2000 Contract Date 04/18/2000 County Transfer Tax N/A Total Transfer Tax $44

Skip to last item

Results are loading

Skip to first item

Property Tax and Assessment

Year	2025
Tax
Assessment	$1,299,700

Home facts updated by county records

Comparable Sales for 86 Caldwell Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
103 Huntington Crossway, Bridgehampton, NY	0.18	Single-Family Home	$950,000	08/22/25	3	2	1,677
58 Hampton Court, Bridgehampton, NY	0.24	Single-Family Home	$1,800,000	06/24/25	5	2.5	1,520
138 Sea Farm Ln, Bridgehampton, NY	0.53	Single-Family Home	$2,295,000	08/29/25	6	4	2,800
4 Worchester, Bridgehampton, NY	0.73	Single-Family Home	$2,495,000	07/29/25	4	3.5	2,646
49 Birchwood Lane, Bridgehampton, NY	0.16	Single-Family Home	$4,950,000	01/13/26	6	7.5	6,000
49 Birchwood Ln, Bridgehampton, NY	0.16	Single-Family Home	$4,950,000	11/06/25	6	7.5	6,000
136 Beckys Path, Bridgehampton, NY	0.71	Single-Family Home	$1,961,000	02/19/26	6	9	4,800
196 Maple Ln, Bridgehampton, NY	1.33	Single-Family Home	$2,800,000	06/26/25	3	3	1,987
11 Sawasett Ave, Bridgehampton, NY	1.36	Single-Family Home	$3,025,000	07/23/25	4	4	2,384
3 Fair Hills Ln, Bridgehampton, NY	0.77	Single-Family Home	$6,880,000	12/01/25	6	6.5	5,769

Nearby homes

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

Skip to last item

FOR SALE
NEW - 2 DAYS AGO
0.49 ACRES
$5,495,000
7 bd
6.5 ba
4,100 sqft
21 Lily Pond Dr,
Sag Harbor, NY 11963
Listing by: Sotheby's International Realty
FOR SALE
$3,875,000
4 bd
3.5 ba
2,255 sqft
63 Chester Ave,
Bridgehampton, NY 11963
Listing by: Compass
FOR SALE
0.96 ACRES
$5,250,000
4 bd
4.5 ba
7,983 sqft
41 Edgewood Ave,
Bridgehampton, NY 11932
Listing by: Sotheby's International Realty
FOR SALE
1 ACRE
$4,399,999
4 bd
3.5 ba
5,000 sqft
397 Brick Kiln Rd,
Sag Harbor, NY 11963
Listing by: Compass
FOR SALE
1.01 ACRES
$2,850,000
3 bd
2 ba
2,210 sqft
30 Sagg Rd,
Sagaponack, NY 11962
Listing by: Brown Harris Stevens
FOR SALE
0.96 ACRES
$5,995,000
6 bd
6.5 ba
6,257 sqft
19 Barn Ln,
Bridgehampton, NY 11932
Listing by: Nest Seekers International
FOR SALE
NEW CONSTRUCTION
0.96 ACRES
$6,595,000
6 bd
7.5 ba
6,000 sqft
17 Barn Ln,
Bridgehampton, NY 11963
Listing by: Nest Seekers International
FOR SALE
0.33 ACRES
$2,495,000
4 bd
2 ba
1,287 sqft
14 Murray Pl,
Bridgehampton, NY 11932
Listing by: Compass
FOR SALE
0.29 ACRES
$2,484,000
6 bd
4 ba
4,000 sqft
768 Bridgehampton Sag Hbr,
Bridgehampton, NY 11932
Listing by: Saunders & Associates
FOR SALE
2.9 ACRES
$2,790,000
5 bd
4.5 ba
3,600 sqft
86 NW Path,
Sagaponack, NY 11962
Listing by: William Raveis Real Estate
FOR SALE
NEW CONSTRUCTION
0.92 ACRES
$7,499,000
6 bd
6 ba
6,836 sqft
481 Brick Kiln Rd,
Bridgehampton, NY 11932
Listing by: SERHANT.
FOR SALE
0.45 ACRES
$3,395,000
4 bd
4 ba
145 Sea Farm Ln,
Bridgehampton, NY 11932
Listing by: Saunders & Associates

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 86 Caldwell Rd.

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 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.
Resident
5y ago
"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
Resident
5y ago
"combination of farms, beaches, private homes and upscale restaurants and shopping creates a unique and comfortable atmosphere"
0
Flag
Molly
Resident
7y ago
"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
13y ago
"live in the neighborhood , delightful "
2
Flag
Kathy J.
15y ago
"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

Apartments for Rent

Skip to last item

Results are loading

Skip to first item

Explore by feature

APPLY INSTANTLY
0.29 ACRES
$45,000/mo
5 bd
3.5 ba
3,200 sqft
189 Lumber Ln,
Bridgehampton, NY 11963
Saunders & Associates
0.4 ACRES
$15,000/mo
2 bd
1 ba
660 sqft
1638 Bridgehampton Sag Harbor Tpke,
Sag Harbor, NY 11963
Compass
0.73 ACRES
$105,000/mo
5 bd
4.5 ba
3,525 sqft
312 Ocean Rd,
Bridgehampton, NY 11932
Brown Harris Stevens
$30,000/mo
2 bd
2.5 ba
2,000 sqft
876 Millstone Rd,
Water Mill, NY 11976
Douglas Elliman Real Estate
1.9 ACRES
$800,000/mo
8 bd
10.5 ba
10,093 sqft
678 Halsey Ln,
Water Mill, NY 11976
Bespoke Real Estate
0.59 ACRES
$55,000/mo
2 bd
3 ba
3,500 sqft
73 Newman Ave,
Bridgehampton, NY 11932
Douglas Elliman Real Estate
4.75 ACRES
$75,000/mo
7 bd
9 ba
7,900 sqft
2 Paumanok Rd,
Sag Harbor, NY 11963
Corcoran Group
2.7 ACRES
$100,000/mo
8 bd
7.5 ba
5,805 sqft
Address Not Disclosed,
Bridgehampton, NY 11932
Compass
1 ACRE
$225,000/mo
5 bd
7.5 ba
5,942 sqft
132 Ocean Rd,
Bridgehampton, NY 11932
Sotheby's International Realty
5.14 ACRES
$70,000/mo
10 bd
10 ba
7,250 sqft
375 Brick Kiln Rd,
Sag Harbor, NY 11963
Sotheby's International Realty
118 rentals with a garage in Bridgehampton, NY

Homes for sale near 86 Caldwell Rd

Skip to last item

NEW CONSTRUCTION
0.96 ACRES
$6,595,000
6 bd
7.5 ba
6,000 sqft
17 Barn Ln,
Bridgehampton, NY 11963
Listing by: Nest Seekers International
0.29 ACRES
$2,484,000
6 bd
4 ba
4,000 sqft
768 Bridgehampton Sag Hbr,
Bridgehampton, NY 11932
Listing by: Saunders & Associates
0.96 ACRES
$5,995,000
6 bd
6.5 ba
6,257 sqft
19 Barn Ln,
Bridgehampton, NY 11932
Listing by: Nest Seekers International
AUCTION
0.7 ACRES
Est. $2,035,500
3 bd
3 ba
2,128 sqft
112 Toppings Path,
Sag Harbor, NY 11963
0.45 ACRES
$3,395,000
4 bd
4 ba
145 Sea Farm Ln,
Bridgehampton, NY 11932
Listing by: Saunders & Associates
NEW CONSTRUCTION
0.88 ACRES
$3,399,000
4 bd
4 ba
2,800 sqft
630 Narrow Ln,
Sagaponack, NY 11962
Listing by: Corcoran Group
1.01 ACRES
$2,850,000
3 bd
2 ba
2,210 sqft
30 Sagg Rd,
Sagaponack, NY 11962
Listing by: Brown Harris Stevens
NOT ACTIVE
Est. $2,475,100
3 bd
2.5 ba
2,594 sqft
138 Beckys Path,
Bridgehampton, NY 11932
0.5 ACRES
$1,995,000
3 bd
2.5 ba
2,000 sqft
33 Laurel Ln,
Sag Harbor, NY 11963
Listing by: Corcoran Group
FOR SALE BY OWNER
1.1 ACRES
$3,975,000
4 bd
4 ba
2,800 sqft
5 Ranch Ct,
Sagaponack, NY 11962
See more homes for sale in
Bridgehampton
Take a look

Skip to first item

Off Market Homes Near 86 Caldwell Rd

Skip to last item

SOLD
MAY 22, 2026
$1,680,000
4 bd
2 ba
1,783 sqft
961 Brick Kiln Road,
Sag Harbor, NY 11963
Douglas Elliman Real Estate
SOLD
MAY 21, 2026
$1,540,000
3 bd
2 ba
1,800 sqft
30 Huckleberry Lane,
East Hampton, NY 11937
Brown Harris Stevens Hamptons
SOLD
MAY 4, 2026
$1,825,000
3 bd
2.5 ba
1,800 sqft
32 Farmstead Ln,
Water Mill, NY 11976
SOLD
MAY 4, 2026
$3,425,000
4 bd
4.5 ba
2,801 sqft
1 Spruce Court,
Water Mill, NY 11976
Sothebys Int'l Realty Hamptons
SOLD
APR 28, 2026
$1,250,000
3 bd
2 ba
1,268 sqft
4528 Noyac Road,
Sag Harbor, NY 11963
Douglas Elliman Real Estate
SOLD
APR 21, 2026
$1,995,000
3 bd
2 ba
1,800 sqft
28 Ridge Rd,
Wainscott, NY 11975
Brown Harris Stevens Hamptons
SOLD
APR 14, 2026
$1,375,000
3 bd
2 ba
1,300 sqft
31 Bayberry Lane,
Sag Harbor, NY 11963
Brown Harris Stevens Hamptons
SOLD
APR 14, 2026
$3,250,000
5 bd
3.5 ba
5,000 sqft
1224 Brick Kiln Rd,
Sag Harbor, NY 11963
SOLD
APR 13, 2026
$1,901,000
2 bd
2.5 ba
1,852 sqft
2803 Noyac Road,
Sag Harbor, NY 11963
Douglas Elliman Real Estate
SOLD
MAR 24, 2026
$2,151,000
4 bd
3 ba
2,458 sqft
60 S Breeze Dr,
Wainscott, NY 11975
See more homes for sale in
Bridgehampton
Take a look

Skip to first item

Homes for rent near 86 Caldwell Rd

Skip to last item

APPLY INSTANTLY
0.29 ACRES
$45,000/mo
5 bd
3.5 ba
3,200 sqft
189 Lumber Ln,
Bridgehampton, NY 11963
Saunders & Associates
NEW - 1 DAY AGO
1.4 ACRES
$60,000/mo
4 bd
3 ba
2,900 sqft
151 Kellis Pond Ln,
Bridgehampton, NY 11932
Corcoran Group
NEW - 1 DAY AGO
0.26 ACRES
$33,000/mo
3 bd
3 ba
1,500 sqft
43 Bluff Point Rd,
Sag Harbor, NY 11963
Corcoran Group
NEW - 1 DAY AGO
1.5 ACRES
$75,000/mo
4 bd
3 ba
3,000 sqft
Address Not Disclosed,
Sagaponack, NY 11962
Nest Seekers International
NEW - 1 DAY AGO
0.43 ACRES
$30,000/mo
5 bd
3 ba
3,200 sqft
16 Whalers Walk,
Sag Harbor, NY 11963
Douglas Elliman Real Estate
NEW - 2 DAYS AGO
$10,000/mo
2 bd
1 ba
950 sqft
4019 Noyack Rd,
Sag Harbor, NY 11963
Douglas Elliman Real Estate
5.4 ACRES
$66,666/mo
4 bd
5.5 ba
5,500 sqft
1172 Brick Kiln Rd,
Sag Harbor, NY 11963
Compass
0.26 ACRES
$31,666/mo
4 bd
3.5 ba
3,358 sqft
16 Lincoln St,
Sag Harbor, NY 11963
Douglas Elliman Real Estate
0.4 ACRES
$15,000/mo
2 bd
1 ba
660 sqft
1638 Bridgehampton Sag Harbor Tpke,
Sag Harbor, NY 11963
Compass
$35,000/mo
3 bd
2 ba
1981 Montauk Hwy,
Bridgehampton, NY 11932
Signature Premier Properties
See more homes for rent in
Bridgehampton
Take a look

Skip to first item

86 Caldwell Rd, Bridgehampton, NY 11932 is a 4 bedroom, 3 bathroom, 2,240 sqft single-family home built in 2005. This property is not currently available for sale. 86 Caldwell Rd was last sold on Apr 21, 2003 for $495,000 (8,150% higher than the asking price of $6,000). The current Trulia Estimate for 86 Caldwell Rd is $2,301,700.

86 Caldwell Rd
Bridgehampton, NY 11932

$2,301,700

$2,301,700

Local Information