# 32 Old Route 199, Red Hook, NY 12571

> **TL;DR:** 6bd/5ba multi-family, $849,000, built 1976.
> Pool, Fireplace, A/C. Est. $4,541/mo. Listed 150 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $849,000 |
| Bedrooms | 6 |
| Bathrooms | 5 full |
| Year Built | 1976 |
| Lot Size | 174,240 sqft (4.00 acres) |
| Property Type | Multi-Family (Duplex) |
| Status | Active |
| Days on Market | 150 |

## Why This Home Stands Out

- **Pool** - Pool listed; type not specified

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $4,293 |
| Estimated Insurance | $248 |
| **Total** | **$4,541** |

## Nearby Schools

- **Elementary:** Mill Road-Primary Grades
- **Middle:** Linden Avenue Middle School
- **High:** Red Hook Senior High School

## Key Amenities

- Pool
- Fireplace
- A/C

## Property Highlights

- Built in 1976
- 4.00 acre lot
- 4 parking spaces
- Private pool
- Fireplace

## Description

### Agent Description
Shepherd's Knoll offers rare privacy and flexibility, located less than two miles from the village. Set on four beautiful acres that include lawns, pastures, and lightly wooded areas, this distinctive property sits at the end of a long private drive. It includes two spacious living units that could easily be converted back into a single-family home. Unit One features four bedrooms, three bathrooms, and a finished lower level. Unit Two offers two bedrooms and two bathrooms with a strong history as a short-term rental. Both spaces include wood-burning fireplaces and a wood stove, creating a warm, inviting atmosphere. Outdoor living shines here. expansive decks and porches overlook pastoral views, while the grounds include a charming studio cottage, a former sheep barn with storage, chicken coops, and established garden areas. Located just minutes from Bard College, a campus that includes the Fisher Center, and Montgomery Place. The property blends country seclusion with access to Hudson Valley cultural life. Whether you need multi-generational flexibility, a home plus a guest setup, or a private sanctuary close to town, Shepherd's Knoll offers a lifestyle that's increasingly hard to find.

## Location

- **Address:** 32 Old Route 199, Red Hook, NY 12571
- **County:** Dutchess County
- **Coordinates:** 41.998551, -73.906096
- **Google Maps:** https://www.google.com/maps?q=41.998551,-73.906096

## Listing Agent

- **Name:** Jennifer Fivelsdal
- **Brokerage:** JFIVE Homes Realty LLC
- **Phone:** 8455949947
- **Broker Phone:** (845) 758-6842
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/32-Old-Route-199_Red-Hook_NY_12571_M34359-95696?f=listhub&s=MLSLINY&m=985647&c=propsimple)

## Photos

![32 Old Route 199 - Photo 1](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f819829327r.jpg)

![32 Old Route 199 - Photo 2](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f1981886616r.jpg)

![32 Old Route 199 - Photo 3](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f2458992229r.jpg)

![32 Old Route 199 - Photo 4](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f1313469993r.jpg)

![32 Old Route 199 - Photo 5](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f3652104293r.jpg)

![32 Old Route 199 - Photo 6](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f362397044r.jpg)

![32 Old Route 199 - Photo 7](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f612024195r.jpg)

![32 Old Route 199 - Photo 8](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f4184219148r.jpg)

![32 Old Route 199 - Photo 9](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f2254473647r.jpg)

![32 Old Route 199 - Photo 10](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f3803742982r.jpg)

![32 Old Route 199 - Photo 11](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f348965137r.jpg)

![32 Old Route 199 - Photo 12](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f4031642798r.jpg)

![32 Old Route 199 - Photo 13](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f1775060147r.jpg)

![32 Old Route 199 - Photo 14](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f312759357r.jpg)

![32 Old Route 199 - Photo 15](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f297649180r.jpg)

![32 Old Route 199 - Photo 16](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f2717652851r.jpg)

![32 Old Route 199 - Photo 17](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f3421663572r.jpg)

![32 Old Route 199 - Photo 18](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f1447689754r.jpg)

![32 Old Route 199 - Photo 19](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f197623663r.jpg)

![32 Old Route 199 - Photo 20](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f4189883271r.jpg)

![32 Old Route 199 - Photo 21](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f460276414r.jpg)

![32 Old Route 199 - Photo 22](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f2750758171r.jpg)

![32 Old Route 199 - Photo 23](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f331788294r.jpg)

![32 Old Route 199 - Photo 24](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f3194658566r.jpg)

![32 Old Route 199 - Photo 25](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f2683302467r.jpg)

![32 Old Route 199 - Photo 26](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f1129490245r.jpg)

![32 Old Route 199 - Photo 27](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f1481100803r.jpg)

![32 Old Route 199 - Photo 28](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f3019312514r.jpg)

![32 Old Route 199 - Photo 29](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f4289714777r.jpg)

![32 Old Route 199 - Photo 30](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f4089064751r.jpg)

![32 Old Route 199 - Photo 31](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f2067653104r.jpg)

![32 Old Route 199 - Photo 32](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f3113752132r.jpg)

![32 Old Route 199 - Photo 33](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f196470219r.jpg)

![32 Old Route 199 - Photo 34](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f384697910r.jpg)

![32 Old Route 199 - Photo 35](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f1770732456r.jpg)

![32 Old Route 199 - Photo 36](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f1352963546r.jpg)

![32 Old Route 199 - Photo 37](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f2715425417r.jpg)

![32 Old Route 199 - Photo 38](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f4110871018r.jpg)

![32 Old Route 199 - Photo 39](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f2770318782r.jpg)

![32 Old Route 199 - Photo 40](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f1829112306r.jpg)

![32 Old Route 199 - Photo 41](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f1389878482r.jpg)

![32 Old Route 199 - Photo 42](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f4039424399r.jpg)

![32 Old Route 199 - Photo 43](http://lh.rdcpix.com/3c8dcd73899d08cd73d51255b64df319l-f1517948925r.jpg)

---

**MLS#:** 985647 | **Updated:** 2026-09-13
**Source:** listhub

*Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/32-old-route-199-red-hook-ny-12571-y985647)

---

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        "@type": "LocationFeatureSpecification",
        "name": "Pool",
        "value": true
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Fireplace",
        "value": true
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Air Conditioning",
        "value": true
      }
    ],
    "additionalProperty": [
      {
        "@type": "PropertyValue",
        "name": "Lot Size",
        "value": "4.00 acres"
      },
      {
        "@type": "PropertyValue",
        "name": "Parking Spaces",
        "value": 4
      },
      {
        "@type": "PropertyValue",
        "name": "Property Subtype",
        "value": "Duplex"
      }
    ]
  },
  "offers": {
    "@type": "Offer",
    "@id": "https://www.propertysimple.ai/listing/32-old-route-199-red-hook-ny-12571-y985647#offer",
    "url": "https://www.propertysimple.ai/listing/32-old-route-199-red-hook-ny-12571-y985647",
    "price": 849000,
    "priceCurrency": "USD",
    "businessFunction": "http://purl.org/goodrelations/v1#Sell",
    "availability": "https://schema.org/InStock",
    "seller": {
      "@id": "https://www.propertysimple.ai/listing/32-old-route-199-red-hook-ny-12571-y985647#agent"
    }
  },
  "provider": {
    "@type": "Person",
    "@id": "https://www.propertysimple.ai/listing/32-old-route-199-red-hook-ny-12571-y985647#agent",
    "name": "Jennifer Fivelsdal",
    "telephone": "8455949947",
    "worksFor": {
      "@type": "Organization",
      "@id": "https://www.propertysimple.ai/listing/32-old-route-199-red-hook-ny-12571-y985647#brokerage",
      "name": "JFIVE Homes Realty LLC",
      "telephone": "(845) 758-6842"
    }
  }
}
```