299 Upper Cherrytown Rd
Kerhonkson, NY 12446
4 Beds
2 Baths
1,689 sqft (on 3.83 acres)
4 Beds
2 Baths
1,689 sqft
(on 3.83 acres)
Local Information
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Description
This charming farmhouse has infinite possibilities for bringing it back to the gentle ambiance of another time. All the rooms are period except for the kitchen which was installed in 1935 with knotty pine cabinets and modern appliances. The room next to the kitchen with the rustic barn wood siding, hand hewn beams and wide board pine flooring was an addition to the house in the 1970's. It was used as the dining room. The stucco wall is actually the original exterior laid-up stone wall of the house. The reclaimed barn wood siding and wide board flooring came out of an old farm house. The room with the fireplace hearth was used as the living room. The chimney was removed to create a closet upstairs so the fireplace is not functioning. However it is possible to create a new chimney by installing a triple wall metal chimney for a wood stove or pellet stove. The entry way with the brick floor was used as an office. There are three Dutch doors on the first level, two of which lead to the large deck that overlooks the expansive lawn. There is a full bath on each level
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.
Home Highlights
Parking
No Info
Outdoor
Porch, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info
Home Details for 299 Upper Cherrytown Rd
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Interior Details BasementNumber of Rooms: 6 |
Heating & Cooling Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard |
Levels, Entrance, & Accessibility Stories: 1.7000000476837158Floors: Concrete |
Appliances & Utilities Cable ReadyDishwasherDryerRefrigeratorWasher |
Fireplace & Spa Fireplace |
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Year Built Year Built: 1848 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Exterior Home Features DeckExterior: WoodPorch |
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Units in Building: 1 |
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Lot Area: 3.83 acres |
Price History for 299 Upper Cherrytown Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 12/21/2017 | $272,000 | Sold | HVCRMLS #20173182 |
| 12/05/2017 | $299,000 | Pending | Agent Provided |
| 10/05/2017 | $299,000 | PendingToActive | Agent Provided |
| 09/25/2017 | $299,000 | Pending | Agent Provided |
| 08/22/2017 | $299,000 | PriceChange | Agent Provided |
| 07/06/2017 | $349,000 | PriceChange | Agent Provided |
| 07/05/2017 | $379,000 | PriceChange | Agent Provided |
| 06/02/2017 | $550,000 | PriceChange | Agent Provided |
| 12/02/2016 | $400,000 | PriceChange | Agent Provided |
| 06/25/2016 | $429,900 | PriceChange | Agent Provided |
| 06/03/2016 | $579,900 | Listed For Sale | Agent Provided |
| 02/24/1999 | $99,200 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $545,094 |
Home facts updated by county records
Comparable Sales for 299 Upper Cherrytown Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.35 | Single-Family Home | $270,000 | 05/15/26 | 3 | 1 | 1,300 | |
0.80 | Single-Family Home | $615,000 | 06/10/25 | 3 | 2 | 1,416 | |
0.91 | Single-Family Home | $389,900 | 12/08/25 | 4 | 2 | 1,980 | |
0.76 | Single-Family Home | $1,387,500 | 10/17/25 | 2 | 2 | 1,876 | |
0.77 | Single-Family Home | $1,387,500 | 10/08/25 | 2 | 2 | 1,876 | |
0.45 | Single-Family Home | $510,000 | 06/04/25 | 1 | 1 | 904 | |
0.76 | Single-Family Home | $1,150,000 | 12/26/25 | 3 | 3.5 | 2,550 | |
0.97 | Single-Family Home | $620,000 | 11/06/25 | 4 | 2.5 | 2,300 | |
1.55 | Single-Family Home | $324,450 | 01/23/26 | 5 | 2 | 1,600 | |
1.98 | Single-Family Home | $285,000 | 09/25/25 | 4 | 1.5 | 1,495 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
FOR SALEOPEN SAT, 1-2PM
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SOLDNOV 6, 2025Rogo Realty LLC, Closed
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Assigned Schools
These are the assigned schools for 299 Upper Cherrytown Rd.
- Kerhonkson Elementary School
- PK-3
- Public
- 215 Students
6/10GreatSchools RatingParent Rating AverageThey have no clue how to recognize or support students with autism and ADHD. You CANNOT discipline a neurological condition!Parent Review1y ago - Rondout Valley High School
- 9-12
- Public
- 547 Students
5/10GreatSchools RatingParent Rating AverageThis school is terrible. My son went here and he got a 1.8 GPA and was never helped by the teachers. My son is a true genius and it is disgusting what this school has done to his intelligence.Parent Review6mo ago - Rondout Valley Junior High School
- 7-8
- Public
- 278 Students
6/10GreatSchools RatingParent Rating Average
No reviews available for this school. - Rondout Valley Intermediate School
- 4-6
- Public
- 358 Students
6/10GreatSchools RatingParent Rating AverageNo reviews available for this school. 
Check out schools near 299 Upper Cherrytown Rd.
What Locals Say about Kerhonkson
At least 15 Trulia users voted on each feature.
100 % Say car is needed
91 % Say yards are well-kept
88 % Say parking is easy
86 % Say there's wildlife
78 % Say there's holiday spirit
60 % Say it's dog friendly
58 % Say it's quiet
51 % Say neighbors are friendly
50 % Say kids play outside
50 % Say they plan to stay for at least 5 years
44 % Say people would walk alone at night
41 % Say there are community events
21 % Say it's walkable to grocery stores
12 % Say it's walkable to restaurants
11 % Say streets are well-lit
Sourced by Trulia users. Learn more about our methodology.
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NEW - 6 HRS AGOPET FRIENDLYCompass Greater NY, LLC
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Homes for sale near 299 Upper Cherrytown Rd
- 1.94 ACRESListing by: Country House Realty Inc
- 1.2 ACRESListing by: Cedar Properties
- OPEN SAT, 1-2PM5.82 ACRESListing by: Compass Greater NY, LLC, Active
6.1 ACRESListing by: Compass Greater NY, LLC, Active
0.36 ACRESListing by: Weichert, REALTORS The Spiesma, Active- 32 ACRESListing by: Cedar Properties
OPEN SAT, 12-2PM0.73 ACRESListing by: Country House Realty, Active
2.01 ACRESListing by: Coldwell Banker Village GreenN, Active- 0.51 ACRESListing by: Howard Hanna Rand Realty, Active
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Off Market Homes Near 299 Upper Cherrytown Rd
SOLDAPR 13, 2026BHHS HUDSON VALLEY PROP-NP, Closed
SOLDMAR 23, 2026Four Seasons Sotheby's Int., Closed
SOLDMAR 16, 2026Taft Street Realty, Inc., Closed
SOLDMAR 13, 2026
SOLDMAR 6, 2026BHHS HUDSON VALLEY PROP-WDST, Closed
SOLDFEB 23, 2026Compass Greater NY, LLC
SOLDFEB 13, 2026
SOLDFEB 12, 2026Berkshire Hathaway Homeservices Nutshell Realty, Closed- SOLDJAN 23, 2026Weichert, REALTORS The Spiesma, Closed
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Homes for rent near 299 Upper Cherrytown Rd
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See more homes for rent inKerhonkson
299 Upper Cherrytown Rd, Kerhonkson, NY 12446 is a 4 bedroom, 2 bathroom, 1,689 sqft single-family home built in 1848. This property is not currently available for sale. 299 Upper Cherrytown Rd was last sold on Dec 21, 2017 for $272,000. The current Trulia Estimate for 299 Upper Cherrytown Rd is $581,000.