# 32 Old Route 199, Red Hook, NY 12571 > **TL;DR:** 6bd/7ba residential multi family, $849,000 ($243/sqft), built 1976, 3,500 sqft. > Fireplace. Est. $4,541/mo. Listed 146 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $849,000 | | Price/sqft | $243 | | Bedrooms | 6 | | Bathrooms | 5 full, 2 half | | Square Feet | 3,500 | | Year Built | 1976 | | Lot Size | 174,240 sqft (4.00 acres) | | Stories | 1 | | Property Type | Residential Multi Family (Other) | | Status | Active | | Days on Market | 146 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $4,293 | | Estimated Insurance | $248 | | **Total** | **$4,541** | ## Key Amenities - Fireplace ## Property Highlights - Built in 1976 - 4.00 acre lot - Fireplace ## Description ### Agent Description Tucked away at the end of a long, private driveway, yet just a short stroll to the village, Shepard's Knoll offers a rare and compelling combination of seclusion, character, and versatility. Set on four picturesque acres framed by mature trees and vibrant gardens, this distinctive property invites you to enjoy both peaceful retreat and everyday convenience. Originally conceived as a single-family residence, the home has been thoughtfully converted into two spacious units, separated by just one wall, making it simple to return to a grand single-family estate if desired. This flexibility opens the door to a range of possibilities, from multi-generational living to a smart investment opportunity. Unit one features four bedrooms and three bathrooms, along with a finished basement that expands the living space, currently generating steady long-term rental income. Unit two offers two bedrooms and two bathrooms and has a proven track record as a successful Airbnb. Both residences are filled with warmth and charm, each enhanced by a wood-burning fireplace and an additional wood stove, creating an inviting atmosphere. Step outside and the appeal continues. Expansive decks and porches provide the perfect setting for relaxing, entertaining, or simply taking in the serene pastoral views. The grounds are equally impressive, offering a collection of outbuildings that add both function and charm: a quaint cottage ideal for an artist's studio or fitness space, a former sheep barn with abundant storage, chicken coops, and a dedicated area once used for organic vegetable gardening. Whether you envision a private country sanctuary, an income-producing investment, or a flexible living arrangement that evolves with your needs, Shepherd's Knoll delivers on every level. With its proven versatility, natural beauty, and prime location, this is more than a property; it's an opportunity to create the lifestyle you've been looking for. ## Location - **Address:** 32 Old Route 199, Red Hook, NY 12571 - **County:** Dutchess - **Coordinates:** 41.997974, -73.905727 - **Google Maps:** https://www.google.com/maps?q=41.997974,-73.905727 ## Listing Agent - **Name:** Jennifer Fivelsdal - **Brokerage:** JFIVE HOMES REALTY LLC - **Broker Phone:** 8457586842 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/32-Old-Route-199_Red-Hook_NY_12571_M34359-95696?f=listhub&s=NYSMLS&m=11715926&c=propsimple) ## Photos ![32 Old Route 199 - Photo 1](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1254133013r.jpg) ![32 Old Route 199 - Photo 2](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f3278288075r.jpg) ![32 Old Route 199 - Photo 3](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f714624318r.jpg) ![32 Old Route 199 - Photo 4](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f2811428078r.jpg) ![32 Old Route 199 - Photo 5](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1484375564r.jpg) ![32 Old Route 199 - Photo 6](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f267374159r.jpg) ![32 Old Route 199 - Photo 7](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1392101535r.jpg) ![32 Old Route 199 - Photo 8](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f609185803r.jpg) ![32 Old Route 199 - Photo 9](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f2499121219r.jpg) ![32 Old Route 199 - Photo 10](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f2484971327r.jpg) ![32 Old Route 199 - Photo 11](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1953083708r.jpg) ![32 Old Route 199 - Photo 12](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f3641734663r.jpg) ![32 Old Route 199 - Photo 13](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f2913272572r.jpg) ![32 Old Route 199 - Photo 14](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f477322897r.jpg) ![32 Old Route 199 - Photo 15](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f2977586110r.jpg) ![32 Old Route 199 - Photo 16](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f4113613986r.jpg) ![32 Old Route 199 - Photo 17](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f777241627r.jpg) ![32 Old Route 199 - Photo 18](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f4092564825r.jpg) ![32 Old Route 199 - Photo 19](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f4126324059r.jpg) ![32 Old Route 199 - Photo 20](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1187604081r.jpg) ![32 Old Route 199 - Photo 21](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1633519666r.jpg) ![32 Old Route 199 - Photo 22](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f3543476763r.jpg) ![32 Old Route 199 - Photo 23](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f2324213817r.jpg) ![32 Old Route 199 - Photo 24](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1286636164r.jpg) ![32 Old Route 199 - Photo 25](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f378334538r.jpg) ![32 Old Route 199 - Photo 26](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1474455639r.jpg) ![32 Old Route 199 - Photo 27](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f399562989r.jpg) ![32 Old Route 199 - Photo 28](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1574549555r.jpg) ![32 Old Route 199 - Photo 29](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f3819534262r.jpg) ![32 Old Route 199 - Photo 30](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f860826775r.jpg) ![32 Old Route 199 - Photo 31](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f3409136204r.jpg) ![32 Old Route 199 - Photo 32](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f2573699837r.jpg) ![32 Old Route 199 - Photo 33](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1134941795r.jpg) ![32 Old Route 199 - Photo 34](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f2807153676r.jpg) ![32 Old Route 199 - Photo 35](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1925187151r.jpg) ![32 Old Route 199 - Photo 36](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f2066429401r.jpg) ![32 Old Route 199 - Photo 37](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1798151510r.jpg) ![32 Old Route 199 - Photo 38](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1123734699r.jpg) ![32 Old Route 199 - Photo 39](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f1998552606r.jpg) ![32 Old Route 199 - Photo 40](http://lh.rdcpix.com/92ad70a25346062e613c64698cb0a94al-f2465778951r.jpg) --- **MLS#:** 11715926 | **Updated:** 2026-08-21 **Source:** listhub *Copyright © 2026 My State 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-12571-11715926) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/32-old-route-199-red-hook-ny-12571-11715926#listing", "url": "https://www.propertysimple.ai/listing/32-old-route-199-red-hook-ny-12571-11715926", "name": "32 Old Route 199, Red Hook, NY 12571", "description": "Tucked away at the end of a long, private driveway, yet just a short stroll to the village, Shepard's Knoll offers a rare and compelling combination of seclusion, character, and versatility. Set on four picturesque acres framed by mature trees and vibrant gardens, this distinctive property invites you to enjoy both peaceful retreat and everyday convenience. Originally conceived as a single-family residence, the home has been thoughtfully converted into two spacious units, separated by just one wall, making it simple to return to a grand single-family estate if desired. This flexibility opens the door to a range of possibilities, from multi-generational living to a smart investment opportunity. Unit one features four bedrooms and three bathrooms, along with a finished basement that expands the living space, currently generating steady long-term rental income. Unit two offers two bedrooms and two bathrooms and has a proven track record as a successful Airbnb. Both residences are filled with warmth and charm, each enhanced by a wood-burning fireplace and an additional wood stove, creating an inviting atmosphere. Step outside and the appeal continues. Expansive decks and porches provide the perfect setting for relaxing, entertaining, or simply taking in the serene pastoral views. The grounds are equally impressive, offering a collection of outbuildings that add both function and charm: a quaint cottage ideal for an artist's studio or fitness space, a former sheep barn with abundant storage, chicken coops, and a dedicated area once used for organic vegetable gardening. Whether you envision a private country sanctuary, an income-producing investment, or a flexible living arrangement that evolves with your needs, Shepherd's Knoll delivers on every level. 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"url": "https://www.propertysimple.ai/listing/32-old-route-199-red-hook-ny-12571-11715926", "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-12571-11715926#agent" } }, "provider": { "@type": "Person", "@id": "https://www.propertysimple.ai/listing/32-old-route-199-red-hook-ny-12571-11715926#agent", "name": "Jennifer Fivelsdal", "worksFor": { "@type": "Organization", "@id": "https://www.propertysimple.ai/listing/32-old-route-199-red-hook-ny-12571-11715926#brokerage", "name": "JFIVE HOMES REALTY LLC", "telephone": "8457586842" } } } ```