26 Upper Samsonville Rd
Olive, NY 12461
4 Beds
3 Baths
2,748 sqft (on 52.66 acres)
4 Beds
3 Baths
2,748 sqft
(on 52.66 acres)
Local Information
- Map ViewExplore the area around 26 Upper Samsonville Rd.
- Schools1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1985
Lot Size
52.66 acres
Living Area
2,748 sqft
Price/Sqft
$656
Parking
Garage
About this House
Absolutely extraordinary! This impeccable, custom built, contemporary is just that. The setting of this home creates the whole vibe as it's nestled within 52+ majestic park like acres. Travel up the long driveway while taking in the perfectly green lavished lawns, beautiful landscaping, rock outcroppings, lush trees and the most spectacular views of the mountains and beyond! Looking for privacy? Then this hidden oasis is just what you want! The front entrance welcomes you in through sophisticated double doors and into a bright and open foyer complete with plenty of natural light, high ceilings, skylights and one of a kind winding staircase. The layout of this home is perfectly situated so you can take in the beauty of the grounds from every room. The formal living room is cozy and comforting, a great place to read, entertain or unwind. The kitchen is beyond open and bright with plenty of skylights, vaulted ceilings and doors leading you out to the full deck that runs along the entire side of the house offering mountain views from every angle. The abundance of cabinets, the island and counter space make it easy to create wonderful meals for any amount of guests. Dine in luxury as the formal dining room with big long windows offers amazing views of the mountains and endless sky. There are 2 half baths located on the main floor as well as the laundry room, discretely placed so no one would ever know it was there and success to the 2 car garage. The den offers a very relaxing warm and cozy vibe with a grand stone fireplace embraced by two large windows, high ceilings, skylights and glass doors leading you out onto the deck. Off to the side a spiral staircase carries you up to a small loft, with the best views in the house! It's the perfect spot for a reading nook, small study or office space. From there you have access to the master suite. The amount and uniqueness of the window placement is so grand in this room it really is amazing. There's plenty of space, plenty of light, side by side closets and a large master bath with a jetted soaking tub, shower and double vanity. Also on the 2nd level, down the hallway, there are 3 well sized guest bedrooms, all offering lovely views from the window. One bedroom has a door connecting to the full bathroom. There is a gigantic full basement, that can be accessed from both inside and outside the house, ready to be used as a workshop, workout room or just used for storage space. This exquisite property backs up to state land and High Point so privacy will never be an issue. There is also a guest house, in construction, halfway up the driveway that could be finished and become the perfect spot for your weekend guests, Airbnb rentals, or your own daily use as an office, art studio, yoga studio, whatever your heart desires. This property is truly one of a kind, built by the current owners with love, it stands strong and true.
26 Upper Samsonville Rd, Olive, NY 12461 is a 4 bedroom, 4 bathroom, 2,748 sqft single-family home built in 1985. It last sold for $1,040,000 on Oct 6, 2020. It is currently off market. The Trulia Estimate is $1,802,700, with a rent estimate of $5,871/month.
Home Details for 26 Upper Samsonville Rd
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Heating & Cooling Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2Floors: Concrete, Hardwood |
Interior Details Types of Rooms: Dining Room |
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher |
Fireplace & Spa Fireplace |
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Year Built Year Built: 1985Year Updated: 2010 |
Property Type / Style Property Type: Single Family HomeArchitecture: Contemporary |
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Exterior Home Features DeckExterior: StonePatio |
Pool Pool |
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached |
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Lot Area: 52.66 acres |
Price History for 26 Upper Samsonville Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 10/06/2020 | $1,040,000 | Sold | HVCRMLS #20201461 |
| 06/23/2020 | $1,100,000 | ListingRemoved | Agent Provided |
| 05/23/2020 | $1,100,000 | PriceChange | Agent Provided |
| 07/30/2019 | $995,000 | PriceChange | Agent Provided |
| 03/15/2019 | $1,250,000 | PriceChange | Agent Provided |
| 10/11/2018 | $1,565,000 | Listed For Sale | Agent Provided |
Market trends in West Shokan
Last updated June 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $1,451,700 |
Home facts updated by county records
Comparable Sales for 26 Upper Samsonville Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.14 | Single-Family Home | $976,000 | 11/25/25 | 3 | 3 | 1,276 | |
0.44 | Single-Family Home | $1,350,000 | 02/12/26 | 3 | 2 | 1,646 | |
0.14 | Single-Family Home | $1,350,000 | 02/12/26 | 3 | 2 | 1,646 | |
0.14 | Single-Family Home | $750,000 | 09/08/25 | 3 | 2 | 1,720 | |
0.14 | Single-Family Home | $597,000 | 06/23/26 | 3 | 2 | 1,996 | |
0.67 | Single-Family Home | $976,000 | 11/10/25 | 3 | 2.5 | 1,986 | |
0.14 | Single-Family Home | $585,000 | 07/13/26 | 2 | 2 | 1,000 | |
0.88 | Single-Family Home | $860,000 | 05/06/26 | 3 | 2 | 2,184 | |
1.52 | Single-Family Home | $750,000 | 09/08/25 | 3 | 2 | 1,720 | |
0.91 | Single-Family Home | $400,000 | 03/06/26 | 2 | 1 | 1,388 |
Nearby homes
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Assigned Schools
These are the assigned schools for 26 Upper Samsonville Rd.
- Onteora High School
- 9-12
- Public
- 370 Students
7/10GreatSchools RatingParent Rating AverageAn extremely inappropriate cross of boundaries between teachers and students. Numerous teachers have slept with students. Students feel unsafe and watched as if the teachers are predators. When brought to administration, little was done to make the student feel safe. Administration cares more about protecting their reputation than protecting the students.Other Review3y ago - Reginald Bennett Elementary School
- K-5
- Public
- 236 Students
8/10GreatSchools RatingParent Rating AverageI have been very happy with the experience my son has had at Bennett. His teachers have been amazing, and it's a very warm and engaging environment for students and families. Communication is great, and their learning philosophy aligns very well with my own. I love that the children are given the opportunity to learn real instruments and even get to keep them over the summer to practice. There isn't tons of homework either, which is great! They let kids be kids. And the children are SO different here than at my son's previous school. They're generally respectful and pleasant to be around, so I'm glad my child is among kids who are a positive influence.Parent Review10mo ago - Onteora Middle School
- 6-8
- Public
- 248 Students
9/10GreatSchools RatingParent Rating AverageAs a parent of Onteora Middle and High school students who have only been enrolled in the district for the past few years, I was more than pleased with this school, however, the administration is terrible, and I agree with the one parent, the students are horrible and bullying is not addressed, and as of this year a newly appointed Vice president of the middle school, will completely ruin the reputation of this school by the time is done with it.Parent Review9mo ago 
Check out schools near 26 Upper Samsonville Rd.
What Locals Say about West Shokan
At least 1 Trulia users voted on each feature.
100 % Say car is needed
100 % Say it's dog friendly
100 % Say people would walk alone at night
100 % Say there's holiday spirit
100 % Say yards are well-kept
100 % Say parking is easy
100 % Say there's wildlife
75 % Say it's quiet
71 % Say neighbors are friendly
67 % Say there are community events
60 % Say kids play outside
50 % Say they plan to stay for at least 5 years
33 % Say it's walkable to restaurants
33 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
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Homes for sale near 26 Upper Samsonville Rd
- 40 ACRESListing by: Corcoran Country Living, Active
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6.5 ACRESListing by: Hudson Dwellings Realty, Active
2.57 ACRESListing by: Berardi Realty, Active
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Off Market Homes Near 26 Upper Samsonville Rd
SOLDJUL 17, 2026Compass Greater NY, LLC, Closed
SOLDJUN 16, 2026Compass Greater New York, LLC, Closed- SOLDJUN 10, 2026
- SOLDJUN 1, 2026
SOLDMAY 29, 2026Berkshire Hathaway Homeservices Nutshell Realty, Closed
SOLDMAY 20, 2026Compass Greater NY, LLC, Closed- SOLDMAY 19, 2026
- SOLDMAY 11, 2026Anatole House LLC, Closed
SOLDAPR 27, 2026Corcoran Country Living, Closed- SOLDFEB 12, 2026BHHS HUDSON VALLEY PROP-WDST, Closed
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