557 Upper Grassy Hill Road Woodbury, CT $ 895,000
557 Upper Grassy Hill Road
$ 895,000
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557 Upper Grassy Hill Road

Woodbury, CT, 06798
$ 895,000
Bedrooms4 Baths3.1 Sq 3,784

Monthly Estimate*

$ 5,511

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Single Family Home for sale in Woodbury, CT

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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Single Family Active

Price

$ 895,000

Bedrooms

4

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 13,082

Style

Lot Size

2.73

Year Built

1999

Town/City

Woodbury

MLS | Web ID

24158380

Features
General
Zoning 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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Interior
Cooling 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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Exterior
Water Source Private Well
Lot Description Borders Open Space Dry Level Lot Sloping Lot Professionally Landscaped Open Lot
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* Excluded Features
List By
Susan Corleto

Listing Agent

William Pitt Sotheby's Int'l

Broker

scorleto@wpsir.com

Email

Affordability Calculator

$6,601
Per Month
83%
17%
0%
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.
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Nearby
2060456 Elementary School
1232807 Middle School
Nonnewaug High School High School
Pricing History
DatePricePrice ChangeDescription
4/1/2026$895,000 Listed Price

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557 Upper Grassy Hill Road, Woodbury, CT, 06798 is a Single Family Home for sale at $895,000 with 3,784 sqft and a lot size of 2.73. 557 Upper Grassy Hill Road has 4 bedrooms, 3.1 baths, and was built in 1999. The property's zip code is 06798 which is in Woodbury, CT