557 Upper Grassy Hill Road
Woodbury, CT, 06798 $ 895,000
Bedrooms4 Baths3.1 Sq 3,784 Monthly Estimate*
$ 5,511
for $895,000 with 4 bedrooms and 3 full baths, 1 half bath. This 3,784 square foot home was built in 1999 on a lot size of 2.73.
Welcome to Upper Grassy Hill Living! This stunning Colonial offers 3784 sf on three levels of thoughtfully designed living space in the sought-after Upper Grassy Hill community. From the moment you enter the grand two-story foyer with gleaming marble floors, you'll be captivated by the home's timeless elegance and comfort.The main level features a formal, front-to-back living and dining room perfect for entertaining, along with a private home office ideal for today's lifestyle. The sun-drenched kitchen boasts granite countertops, stainless steel appliances, a pantry, and a skylight and flows effortlessly into the spacious sunken family room with vaulted ceiling and a cozy pellet stove. Just off the kitchen, step out onto the expansive deck, offering privacy and distant views-your own private outdoor escape. Upstairs, you'll find three generous bedrooms, including a luxurious primary suite with hardwood floors, trey ceiling, dual walk-in closets, and a beautifully remodeled spa bath. A dressing room/sitting room adds the perfect finishing touch to this serene retreat. The fully finished walk-out lower level is an exceptional in-law or au pair setup. It features hardwood floors throughout, a kitchen area with granite counters, a bedroom with built-ins, a Murphy bed and a decorative gas fireplace. There is also a spa-like marble bath complete with a steam shower, and a spacious great room with built-in seating. French doors lead to a stunning bluestone patio with a plunge pool/spa-perfect for relaxing or entertaining. Additional highlights include: surround sound, a Belgium block-lined driveway, stone walls, irrigation system, and a generator. Located just 90 minutes from NYC, this home is part of the self-managed Cardinal Hill HOA ($100/year), and backs up to designated open space for added privacy and peace of mind. This is more than a home-it's a lifestyle. PLEASE NOTE: interior/exterior security cameras/video. 24/7 monitoring
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FeaturesGeneralZoning OS80
Neighborhood N/A
County Litchfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 2.73
Directions Transylvania to Upper Grassy Hill
High School Nonnewaug
City Woodbury
Elementary School Per Board of Ed
Sq Ft Total 3784
DOM 11
Year Built 1999
Style Colonial Contemporary
Year Built Source Public Records
Pool Description Safety Fence In Ground Pool
Energy Features Generator
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InteriorCooling System Central Air Zoned
Total Rooms 11
Basement Description Full Heated Fully Finished Cooled Walk-out Liveable Space Full With Walk-Out
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ExteriorWater Source Private Well
Lot Description Borders Open Space Dry Level Lot Sloping Lot Professionally Landscaped Open Lot
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* Excluded FeaturesList BySusan CorletoListing Agent
William Pitt Sotheby's Int'lBroker
Affordability Calculator
- Monthly Principal & Interest
- $5,511
- Monthly Property Taxes
- $1,090
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Woodbury, CT
Average List Price $816,461
Percent of Sale Price 9%
About Woodbury, CT 9,775 Population
6% Since 2002
$ 82,000 Median Income
50.35 Median Age
26% Households with Children
Trends Information provided by ATTOM Data Solutions.
2060456 Elementary School
1232807 Middle School
Nonnewaug High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 4/1/2026 | $895,000 | | Listed Price |