$328,200
2 Beds
1 Bath
720 sqft (on 2.30 acres)
265 Oakland Valley Road, Cuddebackville, NY 12729
Est. Refi. Payment $2,339/mo*
Refinance Your HomeCurrently Off Market - Sold Dec 5, 2025 for $324,000 (2% below list price)
Home Value
Trulia Estimate
$328KSince last month
Decreased$2K (-0.5%)Since last year
Decreased$3K (-0.9%)Since last sale
Increased$4K (+1.3%)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 +177% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $328K |
| August 2026 | $330K |
| July 2026 | $333K |
| June 2026 | $332K |
| May 2026 | $332K |
| April 2026 | $330K |
| March 2026 | $327K |
| February 2026 | $326K |
| January 2026 | $327K |
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 |
|---|---|---|---|---|---|---|---|
0.51 | Single-Family Home | $355,000 | 12/29/25 | 3 | 1.5 | 1,456 | |
0.15 | Single-Family Home | $530,000 | 10/30/25 | 3 | 2.5 | 2,020 | |
1.04 | Single-Family Home | $270,000 | 04/13/26 | 5 | 1.5 | 3,312 | |
1.32 | Single-Family Home | $472,000 | 06/30/26 | 3 | 3 | 2,360 | |
1.69 | Single-Family Home | $400,000 | 09/29/25 | 3 | 2 | 1,674 | |
1.55 | Single-Family Home | $500,000 | 04/09/26 | 3 | 2 | 2,352 | |
1.95 | Single-Family Home | $355,000 | 12/30/25 | 2 | 2 | 1,904 | |
1.91 | Single-Family Home | $315,000 | 03/23/26 | 3 | 1 | 1,540 | |
1.95 | Single-Family Home | $100,000 | 12/19/25 | 2 | 1 | 824 |
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 |
|---|---|---|---|---|---|---|
0.15 | $539,900 | 3 | 2.5 | 2,020 | Off Market | |
0.24 | $348,200 | 4 | 1 | 1,458 | Off Market | |
0.29 | - | - | - | - | Off Market | |
0.51 | $355,000 | 3 | 1.5 | 1,456 | Recently Sold | |
0.78 | - | - | - | - | Off Market | |
0.78 | $434,500 | 3 | 2 | 1,240 | Off Market | |
0.95 | $1,500,000 | 13 | 5 | 3,000 | For Sale | |
1.04 | $270,000 | 5 | 1.5 | 3,312 | Recently Sold | |
1.07 | $375,500 | 9 | 4 | - | Off Market | |
1.18 | $429,800 | 4 | 2 | 2,731 | Off Market | |
1.14 | $502,300 | 3 | 2.5 | 1,813 | Off Market |
Local Information
- Map ViewExplore the area around 265 Oakland Valley Road.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Single-Family Home
Built in 1940
2.3 acre lot
720 sqft
$450/sqft
Open Parking
About this House
What's unique:Creek accessTwo bright bedroomsBuilt-in bench seatingBeautiful mature forest backdropPrivate outdoor retreat
One Property. Two Homes. Unlimited Possibilities.
Welcome to 265 Oakland Valley Road...a nature lover’s dream with a unique bonus you don’t find every day: a second home on the property! Set on over 2 peaceful acres, this unique offering includes a charming main residence and a picture-perfect brookside cottage, perfect for rental income, guests, or your own private retreat.
The main home is warm and inviting, featuring two bedrooms and a bonus room, one bath, and an eat-in kitchen on the main level (720 sq. ft.). Downstairs, you’ll find a cozy living room (an additional 320 sq. ft) with sliding glass doors leading to a quaint patio overlooking the expansive backyard where you can sip your morning coffee and listen to the birds sing. You will also find an above-ground pool for summer fun and fruit trees, such as apple, peach & pear that adorn the property!
Wander across the lawn and discover the sweetest surprise: a legal one-bedroom cottage (640 sq. ft) that sits alongside a babbling brook that echoes the sounds of tranquility right outside the sliding glass doors. Whether you're envisioning a guest retreat, multi-generational living, a rental opportunity, or a peaceful place to write your next chapter, this cottage has endless charm and potential.
And there’s more...a rustic shed with a covered porch creates yet another outdoor oasis, and a private trail winds along the back of the property, following the brook, and inviting you to slow down and soak in the beauty of your surroundings.
A property with two separate living quarters and natural serenity doesn’t come along often, so this one is definitely worth the look and will definitely charm you!
90 miles from NYC, easy access to the train (NJ Transit/Otisville), close to all of the area's attractions such as The Forestburgh Playhouse, Bethel Woods, Resorts World Casino, The Kartrite Waterpark, Delaware River Rafting and so much more!
Welcome to 265 Oakland Valley Road...a nature lover’s dream with a unique bonus you don’t find every day: a second home on the property! Set on over 2 peaceful acres, this unique offering includes a charming main residence and a picture-perfect brookside cottage, perfect for rental income, guests, or your own private retreat.
The main home is warm and inviting, featuring two bedrooms and a bonus room, one bath, and an eat-in kitchen on the main level (720 sq. ft.). Downstairs, you’ll find a cozy living room (an additional 320 sq. ft) with sliding glass doors leading to a quaint patio overlooking the expansive backyard where you can sip your morning coffee and listen to the birds sing. You will also find an above-ground pool for summer fun and fruit trees, such as apple, peach & pear that adorn the property!
Wander across the lawn and discover the sweetest surprise: a legal one-bedroom cottage (640 sq. ft) that sits alongside a babbling brook that echoes the sounds of tranquility right outside the sliding glass doors. Whether you're envisioning a guest retreat, multi-generational living, a rental opportunity, or a peaceful place to write your next chapter, this cottage has endless charm and potential.
And there’s more...a rustic shed with a covered porch creates yet another outdoor oasis, and a private trail winds along the back of the property, following the brook, and inviting you to slow down and soak in the beauty of your surroundings.
A property with two separate living quarters and natural serenity doesn’t come along often, so this one is definitely worth the look and will definitely charm you!
90 miles from NYC, easy access to the train (NJ Transit/Otisville), close to all of the area's attractions such as The Forestburgh Playhouse, Bethel Woods, Resorts World Casino, The Kartrite Waterpark, Delaware River Rafting and so much more!
265 Oakland Valley Road, Cuddebackville, NY 12729 is a 2 bedroom, 1 bathroom, 720 sqft single-family home built in 1940. It last sold for $324,000 on Dec 5, 2025 (2% below the $329,000 asking price). More recently, it was listed as a rental in February 2026 with an asking price of $2,400 per month. That rental listing was removed on March 29, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $328,200, with a rent estimate of $1,698/month.
Last check for updates: about 20 hours ago
Listed by Dominick J Tufano, (914) 443-7622
RE/MAX Benchmark Realty Group, (845) 341-0004
Amy Skellett, (917) 697-2266
RE/MAX Benchmark Realty Group, (845) 341-0004
Bought with: Danielle Bartula, (646) 639-0077, Howard Hanna Rand Realty, (845) 744-2095
Source: OneKey® MLS as distributed by MLS GRID, MLS#897085
Home Details for 265 Oakland Valley Road
|
|---|
Interior Details Basement: Partially Finished,Walk-Out AccessNumber of Rooms: 4Types of Rooms: Bedroom 1, Bedroom 2, Bathroom 1, Bonus Room, Kitchen, Laundry, Living Room |
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 1Number of Bathrooms (full): 1 |
Dimensions and Layout Living Area: 720 Square Feet |
Appliances & Utilities Utilities: Water AvailableAppliances: Dishwasher, Dryer, Microwave, Other, Oven, RefrigeratorDishwasherDryerLaundry: In BasementMicrowaveRefrigerator |
Heating & Cooling Heating: Oil,PropaneHas CoolingAir Conditioning: DuctlessHas HeatingHeating Fuel: Oil |
Fireplace & Spa Number of Fireplaces: 1Fireplace: Free Standing, GasHas a Fireplace |
Gas & Electric Has Electric on Property |
|
|---|
Exterior Home Features Patio / Porch: Deck, PatioOther Structures: Guest HouseFoundation: BlockHas a Private Pool |
Parking & Garage No CarportNo GarageHas Open ParkingParking: Driveway |
Pool Pool: Above GroundPool |
Frontage WaterfrontWaterfront: Stream, WaterfrontOn Waterfront |
Water & Sewer Sewer: Septic Tank |
|
|---|
Cumulative Days on Market: 67 |
|
|---|
Year Built Year Built: 1940 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Bungalow,Cottage |
Building Construction Materials: T111Not Attached Property |
Property Information Not Included in Sale: Washer in Primary HomeParcel Number: 3328000200000001064.1100000 |
|
|---|
Price List Price: $329,000Price Per Sqft: $450/sqft |
Status Change & Dates Off Market Date: Tue Oct 14 2025 |
|
|---|
MLS Status: Sold |
|
|---|
Direction & Address City: Cuddebackville |
School Information Elementary School: N A Hamilton Bicentennial SchoolJr High / Middle School: Port Jervis Middle SchoolHigh School: Port Jervis Senior High SchoolHigh School District: Port Jervis |
|
|---|
Building Area Building Area: 1680 Square Feet |
|
|---|
Not Senior Community |
|
|---|
No HOA |
|
|---|
Lot Area: 2.3 Acres |
|
|---|
Special Conditions: None |
|
|---|
Listing Agreement Type: Exclusive Right To Sell |
|
|---|
BasementMls Number: 897085Attic: ScuttleAttribution Contact: 845-341-0004Showing Requirements: Appointment Only |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Mar 29, 2026 Source: Zillow Rentals | ListingRemoved | $2,200 |
Mar 23, 2026 Source: Zillow Rentals | PriceChange | $2,200 Price decreased by 4% |
Feb 23, 2026 Source: Zillow Rentals | PriceChange | $2,300 Price decreased by 4% |
Feb 3, 2026 Source: Zillow Rentals | Listed For Rent | $2,400 |
Dec 5, 2025 Source: OneKey® MLS as distributed by MLS GRID #897085 | Sold | $324,000 |
Oct 14, 2025 Source: OneKey® MLS as distributed by MLS GRID #908709 | Pending | $329,000 |
Aug 8, 2025 Source: OneKey® MLS as distributed by MLS GRID #897085 | Listed For Sale | $329,000 |
Aug 13, 2016 Source: Agent Provided | ListingRemoved | $1,000 |
Aug 20, 2014 Source: Agent Provided | ListingRemoved | $950 |
Aug 5, 2014 Source: Agent Provided | Listed For Rent | $950 |
Apr 29, 1993 Source: N/A | Sold | $70,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | Unavailable | $207,000 |
Home facts updated by county records
Market trends in Cuddebackville
Last updated August 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
7
4MoM
Around this home
What Locals Say about Cuddebackville
At least 3 Trulia users voted on each feature.
100 % Say car is needed
83 % Say there's wildlife
80 % Say yards are well-kept
80 % Say parking is easy
75 % Say there's holiday spirit
60 % Say they plan to stay for at least 5 years
33 % Say there are community events
25 % Say it's quiet
25 % Say kids play outside
25 % Say it's dog friendly
17 % Say it's walkable to grocery stores
16 % Say neighbors are friendly
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Based on information submitted to the MLS GRID as of 2026-09-22 12:33:17 PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information
Frequently asked questions about 265 Oakland Valley Road
- What is 265 Oakland Valley Road estimated to be worth?Trulia's estimated value for 265 Oakland Valley Road in Cuddebackville, NY is $328,200.
- What is the price history for 265 Oakland Valley Road?265 Oakland Valley Road in Cuddebackville, NY last sold for $324,000 in December 2025.
- Is Cuddebackville a buyer's or seller's market?Cuddebackville is currently a buyer's market, based on recent for-sale activity.
- What are the closest schools to 265 Oakland Valley Road?The closest schools to 265 Oakland Valley Road in Cuddebackville, NY are N A Hamilton Bicentenial School (Pre-K/Elementary, rated 4/10), Port Jervis Middle School (rated 5/10), Port Jervis Senior High School (rated 5/10).
- Does 265 Oakland Valley Road have air conditioning?Yes, 265 Oakland Valley Road in Cuddebackville, NY has air conditioning.
- Does 265 Oakland Valley Road have a pool?Yes, 265 Oakland Valley Road in Cuddebackville, NY has a pool.
Apartments for Rent
PET FRIENDLYAJ3 Management Services LLC
APPLY INSTANTLYHomes by Yara Realty Group llc
PET FRIENDLYFURNISHED
See more homes for rent inCuddebackville
Off Market Homes Near 265 Oakland Valley Road
SOLDSEP 16, 2026KW Hudson Valley United
SOLDSEP 14, 2026KW Hudson Valley United
SOLDAUG 31, 2026RE/MAX Benchmark Realty Group
SOLDJUL 28, 2026Jackie Henry Realty LLC- SOLDJUL 27, 2026
SOLDJUL 16, 2026KW Hudson Valley United
See more homes for sale inCuddebackville
Homes for sale near 265 Oakland Valley Road
1.9 ACRESListing by: KW Hudson Valley United
0.82 ACRESListing by: Homes By Yara Realty Group LLC
Listing by: Skipping Stones Realty
0.4 ACRESListing by: Hawk's Nest Realty Inc
149.5 ACRESListing by: Gibson E McKean Inc
0.51 ACRESListing by: Century 21 Geba Realty
0.38 ACRESListing by: KW Hudson Valley United
2.9 ACRESListing by: Xiomara Marrero, REALPRO 100 LLC, NY State MLS
698 ACRESListing by: Compass Greater NY LLC- See more homes for sale inCuddebackville
- Results are loading