Shingle style home with horse barn, paddocks & riding arena, set on over 9 acres with a gorgeous westerly view of Roxbury's bucolic rolling hills! Separate 2.05 acre building lot will convey with this property. You can build another house, outbuildings, or whatever zoning will permit! This property is an equestrian's dream. Horse barn w 5 stalls w waterers. 2nd level in barn loft for additional space. 6 horse paddocks w waterers & electric fence. Perfectly set riding arena w views. Built in 2013, no expense was spared on the construction of this home. Sprawling kitchen w marble countertops, stainless appliances, butler's pantry & breakfast nook opens to a sun-drenched 2-story great room w views. Tastefully done formal living & dining rooms. Dining room w trey ceilings & wood paneling. Charming office w bookshelves & built-ins. Cozy, multi-purpose den w fireplace & french doors. Mudroom & powder room. Upstairs, master suite w bookshelves, built-ins, sitting area, walk-in closet w center island & stunning master bath w heated marble floors, marble countertops, double vanities, stand-up shower & jetted tub. 3 additional bedrooms all amply sized w walk-in closets & attached baths. Oversized rec room currently used as a home gym & play area. Additional room on 3rd floor. This home is set on several cleared acres but is secluded from all neighboring properties and backs up to 34 acres of open space. Plenty of room for a pool. Taxes reflect PA490 tax exemption for 5.22 acres. The westerly views of rolling hills offer stunning sunsets from bluestone patios. The setting and land are serene and surreal!
For sale
Price cut: $145K (8/7)
$2,349,999
562 Upper Grassy Hill Road, Woodbury, CT 06798
4beds
6,459sqft
Est.:
Single Family Residence
Built in 2013
9.11 Acres Lot
$2,202,200 Zestimate®
$364/sqft
$-- HOA
What's special
Breakfast nookRiding arena w viewsDouble vanitiesStainless appliances
- 73 days
- on Zillow |
- 905 |
- 49 |
Zillow last checked: 7 hours ago
Listing updated: August 07, 2025 at 07:43am
Listed by:
John Donato Jr,
Showcase Realty, Inc.
Source: Smart MLS,MLS#: 24098508

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Features: High Ceilings, Cathedral Ceiling(s), Built-in Features, Fireplace, Full Bath, Walk-In Closet(s)
- Level: Upper
Bedroom
- Features: Full Bath, Walk-In Closet(s)
- Level: Upper
Bedroom
- Features: Jack & Jill Bath, Walk-In Closet(s)
- Level: Upper
Bedroom
- Features: Jack & Jill Bath, Walk-In Closet(s)
- Level: Upper
Den
- Features: High Ceilings, Fireplace, French Doors, Hardwood Floor
- Level: Main
Dining room
- Features: High Ceilings, Hardwood Floor
- Level: Main
Great room
- Features: 2 Story Window(s), High Ceilings, Fireplace, Hardwood Floor
- Level: Main
Kitchen
- Features: High Ceilings, Breakfast Nook, Kitchen Island, Pantry, Hardwood Floor
- Level: Main
Living room
- Features: High Ceilings, Hardwood Floor
- Level: Main
Office
- Features: High Ceilings, Bookcases, Built-in Features, Hardwood Floor
- Level: Main
Other
- Level: Third,Upper
Rec play room
- Level: Upper
Heating
- Hydro Air, Propane
Cooling
- Central Air
Appliances
- Included: Gas Cooktop, Oven, Range Hood, Refrigerator, Washer, Dryer, Water Heater, Tankless Water Heater
- Laundry: Upper Level
Features
- Sound System, Wired for Data, Central Vacuum
- Windows: Thermopane Windows
- Basement: Full,Unfinished
- Attic: Finished,Walk-up
- Number of fireplaces: 4
Interior area
- Total structure area: 6,459
- Total interior livable area: 6,459 sqft
- Finished area above ground: 6,459
- Finished area below ground: 0
Video & virtual tour
Property
Parking
- Total spaces: 3
- Parking features: Attached, Garage Door Opener
- Attached garage spaces: 3
Lot
- Size: 9.11 Acres
- Features: Secluded, Additional Land Avail., Borders Open Space, Level, Landscaped
Details
- Additional structures: Barn(s)
- Parcel number: 2491077
- Zoning: OS80
- Other equipment: Generator Ready
- Horses can be raised: Yes
- Horse amenities: Paddocks
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Other
- Property subtype: Single Family Residence
Materials
- Shake Siding, Cedar
- Foundation: Concrete Perimeter
- Roof: Asphalt,Shingle
Condition
- New construction: No
- Year built: 2013
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Underground Utilities
Green energy
- Energy efficient items: Windows
Community & HOA
Community
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Woodbury
Financial & listing details
- Price per square foot: $364/sqft
- Tax assessed value: $964,670
- Annual tax amount: $22,786
- Date on market: 6/9/2025
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