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Street View
$399,900
Monthly Est:$1,990
3 Beds
- 2 Baths
1 full bath + 1 half bath
2,048sqft
4 Plains Rd, Montgomery, NY 12586
$399,900
$1,990/moEst:
Get Pre-Approved
Single Family Residence
Built in 1790
$-- HOA
1.3 acres lot
$195/sq.ft
Description
Some people walk into a house built in 1790 and see only what they would want to change. You are not one of those people. You look up and find hand-hewn beams running the length of the ceiling, the axe marks still visible in the wood, and you understand immediately that no budget on earth can manufacture that. You look down at wide plank floors, boards far wider than anything milled today, worn to a soft glow by more than two centuries of footsteps. Something in you settles. You have been holding out for a house that was actually made by hand, and they almost never come up for sale.
This is a home that rewards people who notice things. The deep window casings that hold the afternoon light. The painted wainscoting and the papered walls that someone chose with real care. The fireplaces you gather around when the weather turns, every one of them working, and down in the stone cellar, the original walk-in cooking hearth where every meal in this house was once made, still standing exactly as it was built. You do not restore a detail like that. You inherit it, and you become the person lucky enough to live alongside it.
At the end of the day you retreat to a primary suite that feels like its own quiet corner of the house, beams overhead, wide boards underfoot, and a fireplace of its own for the nights you want to read until the fire dies down. Waking up here does not feel like waking up anywhere else.
Here is the part that lets you exhale. Loving an old house usually means bracing for the big-ticket surprises, but the important things here are already handled. The windows were replaced about 8 years ago, the cesspool was updated in the same stretch, and the home runs on natural gas heat. So you get all the soul of 1790 with far less of the worry, free to spend your attention on the details you fell for rather than the systems behind the walls.
Step outside and the land does the rest. There is a pond on your own 1.30 acres, willows leaning over the water, the kind of view that makes a Sunday disappear. A great old shade tree spreads over the lawn, wide enough to sit under all afternoon, with room to plant a garden, build a fire pit by the water, and spread out in a way you cannot in town. Come evening you can take the porch, listen to the quiet, and feel a good distance from everything you needed a break from.
The location quietly works in your favor. This sits in the Valley Central school district, one of the most sought-after and genuinely affordable in the county, which helps the value hold. Angry Orchard's cider house is practically down the road for a slow afternoon in the Wallkill Valley, the shops and cafes of the village of Montgomery are minutes away, and when the city calls you are roughly 70 miles from the George Washington Bridge with the Thruway and I-84 close at hand.
Houses like this were built to outlast everyone who lives in them. The people who love old homes understand that owning one is less about buying a property and more about becoming its next caretaker. If that is you, this one has been waiting a long time for someone who would see it.
- Houzeo last checked: 9 minutes ago
- Listing updated: September 9, 2026 at 4:49 pm
- Listing Provided by: Brian J Caplicki (845) 460-0879 | KW Hudson Valley United (845) 610-6065
- Source: OneKey MLS-NY | MLS#: 1024006

Property Details
Status
Pending
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1790
HOA Fees
-
Finished Area
2,048 sqft
Lot Size
1.3 acres lot
Basement Area
- sqft
MLS Name
OneKey MLS
MLS Number
1024006
MLS Status
Pending
Days on Market
87
Cumulative Days on Market
320

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 3
Bathrooms: 2
Interior
Interior Features
Beamed Ceilings, Built In Features, Chandelier, Double Vanity, Entrance Foyer, Natural Woodwork
Appliances
Convection Oven, Cooktop, Dishwasher, Refrigerator, Stainless Steel Appliance(s)
Heating
Baseboard, Natural Gas
Sewer
Cesspool
Cooling
None
Flooring
Carpet, Hardwood
Window Features
Bay Window(s)
Construction
Year Built
Year Built: 1790
Home type
Single Family Residence
Architectural Style
Colonial, Farmhouse
Construction Materials
Clapboard, Frame
Utilities & Energy
Fireplace Features
Basement, Bedroom, Family Room, Living Room
Utilities
Electricity Connected
Basement
Full, Unfinished, Walk Out Access
Water Source
Well
Parking Features
Off Street
Other Features
Patio And Porch Features
Covered, Porch
Price History
| Date | Event | Price |
|---|---|---|
09/09/2026 Source: | Pending | $399,900 $195/sqft |
08/12/2026 Source: | Listed for Sale | $399,900 $195/sqft |
08/12/2026 Source: | Listing Removed | $399,900 -9.09% $195/sqft |
07/15/2026 Source: | Listed for Sale | $439,900 $215/sqft |
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Based on information from OneKey MLS, through Oct 10, 2026, 09:46PM. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 OneKey® MLS. All rights reserved.
Advertising Broker: Derek Greene | The Greene Realty Group









