265 Oakland Valley Road, Cuddebackville, NY 12729
SOLD
DEC 5, 2025

265 Oakland Valley Road
Cuddebackville, NY 12729

  • 2 Beds
  • 1 Bath
  • 720 sqft (on 2.30 acres)

$324,000

Last Sold: Dec 5, 2025
2% below list $329K
$450/sqft
Est. Refi. Payment $2,217/mo*
Refinance Your Home

$324,000

Last Sold: Dec 5, 2025
2% below list $329K
$450/sqft
Est. Refi. Payment $2,217/mo*
Refinance Your Home
2 Beds
1 Bath
720 sqft
(on 2.30 acres)

Local Information

  • Map ViewExplore the area around 265 Oakland Valley Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1940
Lot Size
2.3 acres
Living Area
720 sqft
Price/Sqft
$450/sqft
Parking
Open Parking

About this House

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!
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. It is currently off market. The Trulia Estimate is $332,500, with a rent estimate of $1,737/month.

Home Details for 265 Oakland Valley Road

Interior Features

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 Features

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

Days on Market

Cumulative Days on Market: 67

Property Information

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 & Status

Price
List Price: $329,000Price Per Sqft: $450/sqft
Status Change & Dates
Off Market Date: Tue Oct 14 2025

Active Status

MLS Status: Sold

Location

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

Building Area
Building Area: 1680 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 2.3 Acres

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 897085Attic: ScuttleAttribution Contact: 845-341-0004Showing Requirements: Appointment Only
Last check for updates: 44 minutes 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

Price History for 265 Oakland Valley Road

DatePriceEventSource
03/29/2026$2,200ListingRemovedZillow Rentals
03/23/2026$2,200PriceChange
Zillow Rentals
02/23/2026$2,300PriceChange
Zillow Rentals
02/03/2026$2,400Listed For RentZillow Rentals
12/05/2025$324,000Sold
OneKey® MLS as distributed by MLS GRID #897085
10/14/2025$329,000PendingOneKey® MLS as distributed by MLS GRID #908709
08/08/2025$329,000Listed For SaleOneKey® MLS as distributed by MLS GRID #897085
08/13/2016$1,000ListingRemovedAgent Provided
08/20/2014$950ListingRemovedAgent Provided
08/05/2014$950Listed For RentAgent Provided
04/29/1993$70,000Sold
N/A

Market trends in Cuddebackville

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
9
1MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$207,000
Home facts updated by county records

Comparable Sales for 265 Oakland Valley Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
146 Oakland Valley Road, Cuddebackville, NY
0.51
Single-Family Home
$355,000
12/29/25
3
1.5
1,456
278 Oakland Valley Road, Cuddebackville, NY
0.15
Single-Family Home
$530,000
10/30/25
3
2.5
2,020
19 Oakland Valley Road, Cuddebackville, NY
1.04
Single-Family Home
$270,000
04/13/26
5
1.5
3,312
88 Kennel Road, Cuddebackville, NY
1.17
Single-Family Home
$489,000
08/25/25
3
2.5
1,813
944 Us Route 209, Cuddebackville, NY
1.32
Single-Family Home
$472,000
06/30/26
3
3
2,360
660 Oakland Valley Road, Cuddebackville, NY
1.69
Single-Family Home
$400,000
09/29/25
3
2
1,674
109 3rd Street, Godeffroy, NY
1.55
Single-Family Home
$500,000
04/09/26
3
2
2,352
62 Guymard Turnpike, Godeffroy, NY
1.95
Single-Family Home
$355,000
12/30/25
2
2
1,904
8 Fourth Street, Godeffroy, NY
1.91
Single-Family Home
$315,000
03/23/26
3
1
1,540

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Assigned Schools

These are the assigned schools for 265 Oakland Valley Road.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
  • Samantha Gonzalez
    "I’ve lived in the area for over 18 years and we love it in the area I wish we could find a place in this area "
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Apartments for Rent

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Homes for sale near 265 Oakland Valley Road

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Off Market Homes Near 265 Oakland Valley Road

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Based on information submitted to the MLS GRID as of 2026-08-04 07:23:33 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