44 Upland Dr, Garrison, NY 10524
OFF MARKET

$424,400

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 1,241 sqft (on 1.06 acres)

44 Upland Dr, Garrison, NY 10524

Est. Refi. Payment $3,053/mo*
Refinance Your Home
Currently Off Market - Sold Feb 20, 1998 for $158,000

Home Value

Trulia Estimate
$424K
Since last month
Increased$700 (+0.2%)
Since last year
Increased$20K (+5%)
Since last sale
Increased$269K (+170.1%)
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 +68% in the last 10 years
MonthEstimated value
2026
August 2026$427K
August 2026$424K
July 2026$426K
June 2026$430K
May 2026$416K
April 2026$400K
March 2026$395K
February 2026$375K
January 2026$377K
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
41 Winston Lane, Garrison, NY
0.41
Single-Family Home
$415,000
10/27/25
1
2
1,000
374 Sprout Brook Road, Garrison, NY
0.50
Single-Family Home
$265,000
03/05/26
2
1
807
157 Gallows Hill Rd, Garrison, NY
0.59
Single-Family Home
$138,000
03/06/26
3
2
1,080
27 Arden Drive, Garrison, NY
0.25
Single-Family Home
$602,500
06/26/26
3
2.5
1,378
122 Putnam Rd, Garrison, NY
0.62
Single-Family Home
$380,000
09/30/25
2
1.5
866
12 Valley Lane, Garrison, NY
0.57
Single-Family Home
$620,000
10/03/25
3
2
2,000
356 Sprout Brook Road, Garrison, NY
0.55
Single-Family Home
$415,000
08/31/26
2
2
928
58 Winston Lane, Garrison, NY
0.44
Single-Family Home
$813,500
09/12/25
2
2
2,254
440 Sprout Brook Road, Garrison, NY
0.80
Single-Family Home
$610,000
09/26/25
3
2
1,873
7 Ox Yoke Road, Garrison, NY
0.52
Single-Family Home
$459,000
02/05/26
3
3
2,788

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 Upland Drive, Garrison, NY 10524
0.09
$447,400
2
1
1,160
Off Market
45 Upland Drive, Garrison, NY 10524
0.09
$24,900
-
-
-
For Sale
17 Upland Drive, Garrison, NY 10524
0.21
$1,610,300
4
3.5
4,570
Off Market
27 Arden Drive, Garrison, NY 10524
0.25
$602,500
3
2.5
1,378
Recently Sold
100 Upland Drive, Garrison, NY 10524
0.30
$537,000
5
2
1,456
Recently Sold
13 Upland Drive, Garrison, NY 10524
0.28
$761,900
3
3
1,864
Off Market
9 Steuben Road, Garrison, NY 10524
0.39
$488,900
3
1
1,104
Off Market
57 Steuben Road, Garrison, NY 10524
0.39
$15,000
-
-
-
For Sale
41 Winston Lane, Garrison, NY 10524
0.41
$488,100
1
2
1,000
Off Market
6 Knox Lane, Garrison, NY 10524
0.43
$510,200
3
1.5
1,764
Off Market
32 Winston Lane, Garrison, NY 10524
0.42
$30,000
-
-
-
For Sale
58 Winston Lane, Garrison, NY 10524
0.44
$857,700
2
2
2,254
Off Market

Local Information

  • Map ViewExplore the area around 44 Upland Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1948
1.06 acre lot
1,241 sqft
$342/sqft

About this House

This single-family home is located at 44 Upland Dr, Garrison, NY. 44 Upland Dr is in Garrison, NY and in ZIP code 10524. This property has 2 bedrooms, 1 bathroom and approximately 1,241 sqft of floor space. This property has a lot size of 1.06 acres and was built in 1948.
44 Upland Dr, Garrison, NY 10524 is a 2 bedroom, 1 bathroom, 1,241 sqft single-family home built in 1948. It last sold for $158,000 on Feb 20, 1998. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $424,400, with a rent estimate of $3,775/month.

Home Details for 44 Upland Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Attic

Property Information

Year Built
Year Built: 1948
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Exterior Features

Exterior Home Features
Exterior: OtherFoundation Type: Crawl Raised

Community

Units in Building: 1

Lot Information

Lot Area: 1.06 acres

Price and Tax history

DateEventPrice
Feb 20, 1998
Source: N/A
Sold
$158,000

Market trends in Garrison

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
15
5MoM

Around this home

What Locals Say about Garrison

At least 26 Trulia users voted on each feature.

  • 97 % Say car is needed

  • 91 % Say yards are well-kept

  • 86 % Say there's wildlife

  • 77 % Say it's quiet

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

  • 77 % Say it's dog friendly

  • 75 % Say there's holiday spirit

  • 75 % Say people would walk alone at night

  • 72 % Say parking is easy

  • 60 % Say neighbors are friendly

  • 54 % Say there are community events

  • 50 % Say kids play outside

  • 17 % Say it's walkable to grocery stores

  • 11 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Safe to walk on the roads"
    0
    Flag
  • Brettwas
    "Farmers market, the famous Halloween parade, barn parties, plays at the depot theater, Shakespeare festival "
    0
    Flag
  • Brettwas
    "Exceptionally rural. The town is literally mostly parkland. There are two main arteries that run north and south (9 & 9D) and the vast majority of local road off of them are v low traffic. "
    0
    Flag
  • Ian Brier
    "This is a woodsy area with plenty of room for dogs to run around and get exercise. There are many trails."
    0
    Flag
  • Alexandra A.
    "Safe place to live, streets are clean, quite and nice. Neighbors mind their own business. I love everything about it."
    0
    Flag
  • Ian B.
    "It has environmental beauty while still being within commuting proximity to a major city. Life here is seasonal and connected to nature."
    0
    Flag
  • Jenn L.
    "Easy commute by car, one and a half hours to midtown. Trains are about the same to grand central. We prefer the palisades pkwy route even though you cross the river...it’s prettier and the same amount of time. Traffic/rush hour can change these times dramatically. Coming from the city late at night can be a real drag, though."
    0
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  • Jenn L.
    "country living, modern people. best of both worlds. dirt roads, parades, community events, arts , politics, beauty. "
    0
    Flag
  • GeoG
    "Events at the Depot performance space, Cold Spring Film Society - summer movies by the river, Farmers Market "
    0
    Flag
  • ladygarrison
    "Could not imagine a more ideal community in which to live. We look out for one another. There are plenty of arts and culture. Our Main Street is free of corporate shops with each business independently owned. "
    0
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  • Kathleen K.
    "Most properties are large enough to let the dog go, smaller lots have fewer options and have to pick up. Nice scenery but no sidewalks here."
    0
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  • Eugenia Y.
    "Outdoor movies and Shakespeare festival during the summers. Hiking trails accessible from our backyard. "
    0
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  • perry
    "A nature lovers paradise! Great schools."
    0
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  • Kathleen K.
    "Living in Historic Continental Village, I can enjoy the country feeling of the past with the town maintained dirt roads, the private lake community with swimming, tennis, basketball, fishing, boating, community events. An hour from NYC, excellent Westchester Lakeland School District. Convenient to shopping, the Hudson River and attractions."
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  • Kathleen K.
    "I'm feel happy to have discovered the Continental Village section of Garrison more than 33 years ago. I raised my family here, the children went to the Lakeland School District and have been very successful adults thanks to the education they received here. The added bonus of having the lake with tennis, basketball, opportunities for non motor boat fun and community events make this a very special plance to live"
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  • Peter D.
    "Have lived here over two years. Road noise is excessive (trucks braking with engines, un-muffled cycles), mostly because noise ordinances are not enforced. Train noise (whistles and rumble) due to unguarded crossing on commuter rail. Helicopters flying between West Point and who-knows-where flying low. Supermarket is 7.5 miles away. Decent restaurants are few and many miles away. This is not the country and not the city. Too bad."
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  • Kathleen K.
    "We've enjoyed living here more than 32 years. We've endeavor end to add to the house as our family grew, now housing 4 generations from 6-95. We've loved living close enough to commute to NYC and yet raise chickens, grow organic vegetables, send our children and now Grand daughter to wonderful Lakeland School District. Our property fronts one of the oldest roads in the country, The Old Albany Post Road. Plenty of history to enjoy, as well as recreation at our nearby private lake. Our sandy beached lake has lifeguards to tach the children to swim, a clubhouse for community or private events, a tennis and basketball court, playground and you can boat with your canoe, kayak or rowboat. The Historic Town of Cold Spring is just minutes away for antique shopping or fine dining and the US Military Academy at West Point is right across the River. "
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  • perry
    "An amazing community with all the comforts of a small town, but the amenities of a great city. Hiking, nature, great restaurants and schools, theater, all on the Hudson river and just an hour beautiful train ride to NYC! It's paradise."
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LGBTQ Local Legal Protections

Frequently asked questions about 44 Upland Dr

  • What is 44 Upland Dr estimated to be worth?
    Trulia's estimated value for 44 Upland Dr in Garrison, NY is $424,400.
  • What is the price history for 44 Upland Dr?
    44 Upland Dr in Garrison, NY last sold for $158,000 in February 1998.
  • Is Garrison a buyer's or seller's market?
    Garrison is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Garrison?
    Residents describe Garrison, NY as well-kept, quiet, and established. Most residents say you need a car. See recently sold homes in Garrison, NY.
  • How big is the lot at 44 Upland Dr?
    The lot at 44 Upland Dr in Garrison, NY is about 1.1 acres.

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