66 Upper Shad Rd, Pound Ridge, NY 10576
Property image
Property image
OFF MARKET

$3,592,900

Trulia Estimate
  • 4 Beds
  • 5 Baths
  • 3,834 sqft (on 3.86 acres)

66 Upper Shad Rd, Pound Ridge, NY 10576

Est. Refi. Payment $22,755/mo*
Refinance Your Home
Currently Off Market - Sold Jul 1, 2015 for $2,550,000

Home Value

Trulia Estimate
$3.59M
Since last month
Increased$41K (+1.1%)
Since last year
Increased$334K (+10.2%)
Since last sale
Increased$1M (+41.1%)
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 +40% in the last 10 years
MonthEstimated value
2026
August 2026$3.6M
July 2026$3.56M
June 2026$3.51M
May 2026$3.37M
April 2026$3.31M
March 2026$3.34M
February 2026$3.23M
January 2026$3.22M
2025
2024
2023
2022
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
5 S Bedford Road, Pound Ridge, NY
0.39
Single-Family Home
$1,650,000
07/09/26
4
3.5
3,192
12 Hemlock Hill Road, Pound Ridge, NY
0.44
Single-Family Home
$1,510,000
10/24/25
3
3.5
3,261
137 Upper Shad Road, Pound Ridge, NY
0.73
Single-Family Home
$2,150,000
07/27/26
4
5.5
5,085
32 Pine Drive, Pound Ridge, NY
0.64
Single-Family Home
$1,390,000
09/04/25
4
3.5
5,020
99 High Ridge Road, Pound Ridge, NY
0.29
Single-Family Home
$1,175,000
09/03/25
2
3
2,485
3090 High Ridge Rd, Stamford, CT
0.98
Single-Family Home
$2,450,000
09/30/25
4
6
4,101
27 West Lane, Pound Ridge, NY
1.27
Single-Family Home
$1,650,000
12/16/25
4
3.5
3,950
27 West Lane, Pound Ridge, NY
1.28
Single-Family Home
$1,650,000
12/16/25
4
3.5
4,400
496 Trinity Pass Road, New Canaan, CT
0.80
Single-Family Home
$1,650,000
08/24/26
4
3.5
2,522
115 Mayapple Road, Stamford, CT
1.19
Single-Family Home
$1,725,000
01/06/26
4
4.5
3,770

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
39 Old Snake Hill Road, Pound Ridge, NY 10576
0.12
$3,500,000
5
5.5
4,718
For Sale
35 Old Snake Hill Road, Pound Ridge, NY 10576
0.15
$2,409,990
4
5.5
4,031
For Sale
47 Upper Shad Road, Pound Ridge, NY 10576
0.15
$1,023,900
3
3
2,398
Off Market
83 Upper Shad Rd, Pound Ridge, NY 10576
0.22
$1,453,000
3
3.5
3,467
Off Market
99 High Ridge Road, Pound Ridge, NY 10576
0.29
$1,271,600
2
3
2,485
Off Market
26 Hemlock Hill Road, Pound Ridge, NY 10576
0.39
$3,657,000
4
4.5
4,260
Off Market
5 S Bedford Road, Pound Ridge, NY 10576
0.39
$1,650,000
4
3.5
3,192
Recently Sold
12 Hemlock Hill Road, Pound Ridge, NY 10576
0.44
$1,623,900
3
3.5
3,261
Off Market
8 Hemlock Hill Road, Pound Ridge, NY 10576
0.48
$1,728,300
4
3
3,772
Off Market
15A High Ridge Road, Pound Ridge, NY 10576
0.45
$525,000
-
-
-
For Sale
8 Bayberry Way, Pound Ridge, NY 10576
0.50
$1,082,400
5
4
3,719
Off Market
106 Westchester Avenue, Pound Ridge, NY 10576
0.61
$1,430,500
3
3.5
2,854
Off Market

Local Information

  • Map ViewExplore the area around 66 Upper Shad Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1960
Lot Size
3.86 acres
Living Area
3,834 sqft
Price/Sqft
$937
Parking
Garage

About this House

Ultra sophisticated, waterfront, high quality home with wonderful views. Completely renovated and expanded with custom everything - cabinetry, millwork, kitchen, baths, waterworks fixtures, etc. Extraordinary property abuts Russell Nature Preserve for total privacy. Stone walls, spectacular gardens, cobblestoned drive, slate patio with outdoor fireplace & built-in bar and grill, ponds with docks for boating, fishing & ice skating, exceptional pool with infinity-edge spa, 3,000 s.f patio, full outdoor kitchen, shower, living & dining room. Top-of-the line Kitchen with white Calacatta marble, gorgeous baths, Marvin windows & doors, 6 zone central air & heat, full house Generac generator, copper gutters, sound system & reasonable taxes. A one-of-a-kind offering.
66 Upper Shad Rd, Pound Ridge, NY 10576 is a 4 bedroom, 5 bathroom, 3,834 sqft single-family home built in 1960. It last sold for $2,550,000 on Jul 1, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,592,900, with a rent estimate of $7,290/month.

Home Details for 66 Upper Shad Rd

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1960Year Updated: 1973
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Wood
Pool
Pool
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 3.86 acres

Price and Tax history

DateEventPrice
Jul 1, 2015
Source: OneKey® MLS as distributed by MLS GRID #H4507404
Sold
$2,550,000
Apr 22, 2015
Source: Agent Provided
Listed For Sale
$2,095,000

Market trends in Pound Ridge

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
23
8MoM

Around this home

What Locals Say about Pound Ridge

At least 25 Trulia users voted on each feature.

  • 97 % Say it's quiet

  • 94 % Say parking is easy

  • 91 % Say yards are well-kept

  • 89 % Say car is needed

  • 88 % Say it's dog friendly

  • 88 % Say there's wildlife

  • 77 % Say they plan to stay for at least 5 years

  • 73 % Say people would walk alone at night

  • 66 % Say there's holiday spirit

  • 59 % Say neighbors are friendly

  • 57 % Say there are community events

  • 44 % Say kids play outside

  • 38 % Say it's walkable to restaurants

  • 22 % Say it's walkable to grocery stores

  • 21 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Keren Richter
    "It’s a car based area. If you take the train, you have to drive to the station in another town (Mt Kisco or Bedford Hills)"
    0
    Flag
  • Thomasbuczkowski
    "Space and privacy are great for dogs. Many people place invisible fences so pets can roam but stay inside boundaries."
    0
    Flag
  • Kevin B.
    "Beautiful place to live especially with a young family. Lots of privacy and small town feel. A little slice of heaven. "
    2
    Flag
  • John E.
    "Amazing town. Unpretentious, friendly with people who deeply care about the town. Also, the road maintenance is second to none. Major windstorm,no problem cleanedsday. "
    0
    Flag
  • John E.
    "Pound Ridge is amazing, but Is spread out, so be prepared to drive Your kids. Great schools and very, very safe!"
    0
    Flag
  • Maritza
    "nature, peaceful, quite, people are friendly and courteous, just beautiful small town yet close to nyc"
    2
    Flag
  • Maritza
    "check the schools and amenities, it’s a quiet town and simple lifestyle, nature is beautiful, close other great towns "
    0
    Flag
  • Asia L.
    "There are tons of family activities and events for all. Cute restaurants, parks, hiking trails and stunning views. Pound Ridge is an exclusive town, breathtaking."
    0
    Flag
  • pschantz
    "Pound Ridge has a very rural feel, despite being only 45 miles from Manhattan and 12 miles from Stamford. If you enjoy country living but want to be near major urban areas, this is definitely your spot."
    0
    Flag
  • pschantz
    "Lovely area if you like country living and privacy with a 50 minute drive to Midtown Manhattan."
    0
    Flag
  • Italianews
    "I love living here. It has that small town atmosphere, yet you're 20 minutes from downtown Stamford and less than an hour from NYC"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 66 Upper Shad Rd

  • What is 66 Upper Shad Rd estimated to be worth?
    Trulia's estimated value for 66 Upper Shad Rd in Pound Ridge, NY is $3,592,900.
  • What is the price history for 66 Upper Shad Rd?
    66 Upper Shad Rd in Pound Ridge, NY last sold for $2,550,000 in July 2015.
  • Is Pound Ridge a buyer's or seller's market?
    Pound Ridge is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Pound Ridge?
    Residents describe Pound Ridge, NY as quiet, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Pound Ridge, NY.
  • Does 66 Upper Shad Rd have air conditioning?
    Yes, 66 Upper Shad Rd in Pound Ridge, NY has air conditioning.
  • Does 66 Upper Shad Rd have a pool?
    Yes, 66 Upper Shad Rd in Pound Ridge, NY has a pool.

Explore by feature - Air Conditioning

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Off Market Homes Near 66 Upper Shad Rd

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