# 323 Upper Grassy Hill Road, Woodbury, CT 06798 > **TL;DR:** 3bd/3ba single family, $574,900 ($175/sqft), built 1986, 3,282 sqft. > Fireplace, 2-car garage. Est. $3,075/mo. Listed 70 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $574,900 | | Price/sqft | $175 | | Bedrooms | 3 | | Bathrooms | 2 full, 1 half | | Square Feet | 3,282 | | Year Built | 1986 | | Lot Size | 40,511 sqft (0.93 acres) | | Garage | 2-car | | Property Type | Single Family (Other) | | Status | Pending | | Days on Market | 70 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,907 | | Estimated Insurance | $168 | | **Total** | **$3,075** | ## Nearby Schools - **Elementary:** Mitchell - **High:** Nonnewaug ## Key Amenities - Fireplace - 2-car garage ## Property Highlights - Built in 1986 - 0.93 acre lot - 4 parking spaces - Fireplace ## Description ### Agent Description A Fresh Look at a Home with So Much Flexibility! Come take a look at this versatile and beautifully maintained home, where generous living spaces and unexpected possibilities give you room to make it your own. The first floor offers a wonderful layout with a comfortable living room, spacious great room, and separate dining room, creating plenty of flexibility for everyday living and entertaining. The kitchen has been thoughtfully updated, from the main living spaces, step outside onto the deck - a natural extension of the home for relaxing, dining, or enjoying the outdoors. Upstairs, you'll find generously sized bedrooms with the space and comfort today's buyers are looking for. But the real surprise is downstairs. The walk-out lower level offers even more usable space, including a large room currently used as a workout area and another area that can serve as storage, recreation space, or additional living space. Step outside to the screened-in deck, adding another terrific spot to enjoy the property. And for those looking for flexibility, the large lower-level room has its own separate entrance and offers intriguing potential to create a private studio or guest suite with the addition of a kitchen and bathroom. Whether you envision a home office, gym, creative studio, guest quarters, or future additional living space, the possibilities are here. Turn-key, versatile, and full of potential - this is a home that can adapt to the way you live. Come see! Electronic dog fence conveys with property. ## Location - **Address:** 323 Upper Grassy Hill Road, Woodbury, CT 06798 - **County:** Litchfield - **Coordinates:** 41.537967, -73.254508 - **Google Maps:** https://www.google.com/maps?q=41.537967,-73.254508 ## Listing Agent - **Name:** Gabby Addison - **Brokerage:** Keller Williams Realty - **Broker Phone:** (203) 438-9494 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/323-Upper-Grassy-Hill-Rd_Woodbury_CT_06798_M45529-53637?f=listhub&s=CTMLS&m=24200605&c=propsimple) ## Photos ![323 Upper Grassy Hill Road - Photo 1](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f3813578081r.jpg) ![323 Upper Grassy Hill Road - Photo 2](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f198911587r.jpg) ![323 Upper Grassy Hill Road - Photo 3](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f4031653314r.jpg) ![323 Upper Grassy Hill Road - Photo 4](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f3308105601r.jpg) ![323 Upper Grassy Hill Road - Photo 5](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f4109476846r.jpg) ![323 Upper Grassy Hill Road - Photo 6](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f3755314122r.jpg) ![323 Upper Grassy Hill Road - Photo 7](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f262994495r.jpg) ![323 Upper Grassy Hill Road - Photo 8](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f2156687394r.jpg) ![323 Upper Grassy Hill Road - Photo 9](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f3529810464r.jpg) ![323 Upper Grassy Hill Road - Photo 10](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f830167904r.jpg) ![323 Upper Grassy Hill Road - Photo 11](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f1665995863r.jpg) ![323 Upper Grassy Hill Road - Photo 12](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f57070646r.jpg) ![323 Upper Grassy Hill Road - Photo 13](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f1510658643r.jpg) ![323 Upper Grassy Hill Road - Photo 14](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f2456139487r.jpg) ![323 Upper Grassy Hill Road - Photo 15](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f205505330r.jpg) ![323 Upper Grassy Hill Road - Photo 16](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f3044547720r.jpg) ![323 Upper Grassy Hill Road - Photo 17](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f1617303699r.jpg) ![323 Upper Grassy Hill Road - Photo 18](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f452681455r.jpg) ![323 Upper Grassy Hill Road - Photo 19](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f2029201906r.jpg) ![323 Upper Grassy Hill Road - Photo 20](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f1999773209r.jpg) ![323 Upper Grassy Hill Road - Photo 21](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f24311863r.jpg) ![323 Upper Grassy Hill Road - Photo 22](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f2255001696r.jpg) ![323 Upper Grassy Hill Road - Photo 23](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f2540961625r.jpg) ![323 Upper Grassy Hill Road - Photo 24](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f3411243101r.jpg) ![323 Upper Grassy Hill Road - Photo 25](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f1452657373r.jpg) ![323 Upper Grassy Hill Road - Photo 26](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f4191671307r.jpg) ![323 Upper Grassy Hill Road - Photo 27](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f2872559928r.jpg) ![323 Upper Grassy Hill Road - Photo 28](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f2329515669r.jpg) ![323 Upper Grassy Hill Road - Photo 29](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f2873814850r.jpg) ![323 Upper Grassy Hill Road - Photo 30](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f3141721817r.jpg) ![323 Upper Grassy Hill Road - Photo 31](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f3177421351r.jpg) ![323 Upper Grassy Hill Road - Photo 32](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f633542375r.jpg) ![323 Upper Grassy Hill Road - Photo 33](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f198911587r.jpg) ![323 Upper Grassy Hill Road - Photo 34](http://lh.rdcpix.com/82706b02d9a0aae71cef86449875742fl-f3712615710r.jpg) --- **MLS#:** 24200605 | **Updated:** 2026-10-29 **Source:** listhub *Copyright © 2026 SmartMLS, Inc. 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/323-upper-grassy-hill-road-woodbury-ct-06798-e7c72a26f0c9433b933b006ef9e4de5b) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/323-upper-grassy-hill-road-woodbury-ct-06798-e7c72a26f0c9433b933b006ef9e4de5b#listing", "url": "https://www.propertysimple.ai/listing/323-upper-grassy-hill-road-woodbury-ct-06798-e7c72a26f0c9433b933b006ef9e4de5b", "name": "323 Upper Grassy Hill Road, Woodbury, CT 06798", "description": "A Fresh Look at a Home with So Much Flexibility! Come take a look at this versatile and beautifully maintained home, where generous living spaces and unexpected possibilities give you room to make it your own. 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