557 Upper Grassy Hill Road, Woodbury, CT 06798
Local realty services provided by:Better Homes and Gardens Real Estate Gaetano Marra Homes



557 Upper Grassy Hill Road,Woodbury, CT 06798
$949,900
- 4 Beds
- 4 Baths
- 3,784 sq. ft.
- Single family
- Active
Listed by:susan corleto
Office:william pitt sotheby's int'l
MLS#:24104194
Source:CT
Price summary
- Price:$949,900
- Price per sq. ft.:$251.03
About this home
Nestled in the Upper Grassy Hill community of Woodbury, CT, 557 Upper Grassy Hill Road offers a lifestyle of luxury and comfort. This stunning Colonial residence spans 3784 square feet across three meticulously designed levels. As you step into the grand two-story foyer with gleaming marble floors, you are immediately enveloped in a sense of timeless elegance. The main level features a gracious living and dining room, ideal for entertaining, a private home office, and a sun-drenched kitchen equipped with granite countertops, stainless steel appliances, and a skylight. The kitchen seamlessly flows into the spacious family room, complete with a cozy pellet stove. Step outside to the expansive deck for a serene outdoor escape with distant views, perfect for relaxation and entertainment.
Moving upstairs, you'll discover three generous bedrooms, including a luxurious primary suite with hickory hardwood floors, trey ceiling, dual walk-in closets, and a beautifully remodeled spa bath. A dressing room/sitting room adds a touch of luxury to this peaceful retreat. The fully finished walk-out lower level is a standout feature of the home, offering an exceptional in-law or au pair setup. With hickory floors throughout, a kitchen area with granite counters, a bedroom with built-ins and a Murphy bed, a marble full bath with a steam shower, and a spacious great room with built-in seating, this space is perfect for extended family or guests. French doors lead to a stunning bluestone patio with a plunge pool/spa, creating a space for both relaxation and entertainment. Additional highlights of this property include surround sound, a Belgium block-lined driveway, stone walls, an irrigation system, and a generator for added convenience and peace of mind.
Situated just 90 minutes from NYC, this home is part of the self-managed Cardinal Hill HOA and backs up to designated open space, offering privacy and tranquility. The Cardinal Hill HOA provides access to a range of amenities for residents to enjoy. This property is not just a home; it's a lifestyle. Impeccably maintained and thoughtfully designed, 557 Upper Grassy Hill Road presents a rare opportunity to own a piece of Woodbury's premier real estate. Experience the perfect blend of sophistication, comfort, and tranquility in this exquisite residence.
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Home facts
- Year built:1999
- Listing Id #:24104194
- Added:45 day(s) ago
- Updated:August 15, 2025 at 11:27 AM
Rooms and interior
- Bedrooms:4
- Total bathrooms:4
- Full bathrooms:3
- Half bathrooms:1
- Living area:3,784 sq. ft.
Heating and cooling
- Cooling:Central Air, Zoned
- Heating:Hot Air, Zoned
Structure and exterior
- Roof:Asphalt Shingle
- Year built:1999
- Building area:3,784 sq. ft.
- Lot area:2.73 Acres
Schools
- High school:Nonnewaug
- Elementary school:Per Board of Ed
Utilities
- Water:Private Well
Finances and disclosures
- Price:$949,900
- Price per sq. ft.:$251.03
- Tax amount:$13,082 (July 2025-June 2026)
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