Surreal, private, promontory setting surrounds this tree-top modern, designed & built by esteemed architect, Michael Greenberg, whose passion for artistry is reflected throughout this one of a kind home. The home's multi-level design combines balconies & decks w/expansive glass windows & skylights to blend seamlessly into the spectacular natural backdrop of massive rock outcroppings, pillowy moss & mature woodland, complete w/babbling brook & waterfall. While inspired by the likes of Philip Johnson & Mies van der Rohe, this sophisticated home maintains the warmth of a CT country house featuring inviting great room w/hardwood floors & native fieldstone fireplace. The open floor plan is ideal for entertaining w/multiple atrium glass doors to the wrap around deck, sunny dining area, plus updated kitchen w/handmade tile backsplash by Bantam Tileworks, new fridge, D/W, & fixtures. Over $200K of recent improvements incl. new HVAC, electrical panel, water systems, rebuilt chimney/flu, structural repairs to decks w/new staircase & more. Total 2,310 sf w/3 BRs & 3 full baths including the stunning "penthouse" primary suite comprising the entire top floor w/walls of glass for panoramic sunrise/moonrise views. The suite's spa bath features a deep soaking tub, large frameless glass shower, radiant heated floor plus spacious dressing room. Top lower Weston location plus access to Compo Beach in neighboring Westport, with world-class shopping, dining, cultural venues & two train stations.
Single-familyProperty Type
1984Year Built
2.28 acresLot Size
$464Est. Price/Sq.Ft.
1 car garageParking
Listed by Laura Ancona• William Pitt Sotheby's Int'l
Bought with Karla Murtaugh• Compass Connecticut, LLC
Source:Smart MLS #24088908
Redfin Estimate
$1,072,049
$52K since sold in June 2025$43K since August
Recently sold homes
Estimate history
Homes for sale
This home's estimate is 23.8% lower than the average sale price ($1.41M) of 6 comparable homes.
Welcome to this stunning, one-of-a-kind home. This chic, modern residence was designed and built by the well-known architect, Michael Greenberg. The home is architecturally a contemporary yet maintains the warmth of a Connecticut country house, while revealing influences of the modernist era; the likes of Philip Johnson and Mies van der Rohe as the extensive use of glass, outdoor living spaces, and purposeful capture of light reveals nature at its best. The master suite is the entire top floor, eastern views bring the sunrise and the moonrise into this unique space. The suite is complete with a very well-appointed spa bath with deep soaking tub, large frameless glass shower, heated floor and dressing room. The main living level offers an open flow for entertaining and gallery space for art display. Gaze through any window and experience panoramic, breathtaking views - or step out to the large decks. A recent renovation melds beautifully with the original design concept. This is a unique opportunity to live in the prominent town of Weston, which is among the most highly-desired communities in the United States. Weston homeowners have access to passes for Compo Beach in the neighboring sister town of Westport, which is another cosmopolitan community with world-class shopping, dining, arts and culture venues plus two Metro North Railroad stations to Grand Central. Weston was just featured in the Wall Street Journal & New York Times.
The residents of the shared driveway leading to the house share the expenses of snow removal and road repairs.
Smart MLS #99074240
Sep 29, 2014
Sold
$668,000
$289/sq ft
Jul 22, 2014
Listed
$675,000
$292/sq ft
Incredible Michael Greenberg original that has been taken to the next level. The stunning renovation of this home offers a sleek and contemporary feel that takes advantage of the natural environment. Spectacular vistas can be enjoyed from every room, while 4 decks offer outdoor enjoyment from sunrise to sunset. Relaxing in the master bedroom suite makes you feel as if you were in a 5 star hotel, the exquisite features and spa bath offer a peaceful and tranquil setting. The gourmet kitchen and open floor plan make this home perfect for entertaining or casual everyday living.
Public Records
Nov 1, 2007
Sold
$625,000
$271/sq ft
Smart MLS #98329907
Apr 26, 2007
Listed
$665,000
$288/sq ft
Smart MLS #98315225
Apr 26, 2007
Listing Removed
—
Jan 10, 2007
Listed
$665,000
$288/sq ft
Smart MLS #98273037
Nov 30, 2006
Listing Removed
—
Mar 7, 2006
Listed
$665,000
$288/sq ft
Smart MLS #98029261
Nov 10, 1998
Listed
$465,000
$201/sq ft
Smart MLS #98021093
Nov 3, 1998
Listing Removed
—
Aug 3, 1998
Listed
$519,000
$225/sq ft
Public Records
Jun 1, 1988
Sold
$497,500
$215/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$13,179 (+0.3%)
$159,040 + $239,600
$398,640
2022
$13,143 (+0.2%)
$159,040 + $239,600
$398,640
2021
$13,123 (+29.2%)
$159,040 + $239,600
$398,640
2020
$10,161
$159,040 + $154,860
$313,900
2019
$10,161 (+5.4%)
$159,040 + $154,860
$313,900
2018
$9,643 (+1.7%)
$173,900 + $154,200
$328,100
2017
$9,485 (+1.2%)
$173,900 + $154,200
$328,100
2016
$9,371 (+1.1%)
$173,900 + $154,200
$328,100
2014
$9,266
$173,900 + $154,200
$328,100
Tax history for 24 Deepwood Rd
Year
Property tax
Land + Additions
Assessment*
2023
$13,179 (+0.3%)
$159,040 + $239,600
$398,640
2022
$13,143 (+0.2%)
$159,040 + $239,600
$398,640
2021
$13,123 (+29.2%)
$159,040 + $239,600
$398,640
2020
$10,161
$159,040 + $154,860
$313,900
2019
$10,161 (+5.4%)
$159,040 + $154,860
$313,900
2018
$9,643 (+1.7%)
$173,900 + $154,200
$328,100
2017
$9,485 (+1.2%)
$173,900 + $154,200
$328,100
2016
$9,371 (+1.1%)
$173,900 + $154,200
$328,100
2014
$9,266
$173,900 + $154,200
$328,100
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Beds
3
Baths
3
Stories
2
Lot width
—
Lot depth
—
Lot size
2.28 Acres
Year renovated
2004
Sq. Ft.
2,067
Year built
1984
Style
Single Family Residential
County
Fairfield County
APN
404634
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 12, 2023.
Property details
Parking
Garage Information
Garage & Parking: Attached Garage
Garages Number: 1
Interior
Virtual Tour Information
Interior Information
Total Rooms: 6
Laundry Room Info: Lower Level
Interior Features: Open Floor Plan, Security System
Fireplaces Total: 1
Cooling System: Central Air, Zoned
Appliances Included: Gas Range, Refrigerator, Dishwasher, Washer, Dryer
Bathroom Information
# of Baths (Full): 3
Bedroom Information
Beds Total: 3
Room Information
Basement Description: Crawl Space
Has Attic
Attic Description: Storage Space, Access Via Hatch
Exterior
Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Clapboard, Wood
Exterior Features: Deck, Gutters, Lighting, French Doors
Lot Information
Lot Description: Rear Lot, Lightly Wooded, On Cul-De-Sac
Building Information
Foundation Type: Concrete
Construction Description: Frame
Color: White
Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2067
Financial
Assessments Information
Assessed Value: $524,650
Utilities
Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Oil, Electric, Domestic
Heat Type: Hot Air
Heat Fuel Type: Oil
Fuel Tank Location: Above Ground
Location
School Information
Middle Jr High School: Weston
Intermediate School: Weston
High School: Weston
Elementary School: Hurlbutt
Location Information
State: Connecticut
Directions: Davis Hill to Hill Farm, left on Deepwood, down private access way to end and then bear right. See signs.
County: Fairfield
Public facts
Beds: 3
Baths: 3.0
Sq. Ft.: 2,067
Stories: 2.0
Lot Size: 2.28 acres
Style: Single Family Residential
Year Built: 1984
Year Renovated: 2004
County: Fairfield County
APN: 404634
Home facts updated by county records on Jul 12, 2023
Other
Documents & Disclosures
Supplement Count Public: 4
Around this home
Schools
Weston Intermediate School
Public 3-5 • Assigned • 2.1mi
10/10
Weston Middle School
Public 6-8 • Assigned • 1.9mi
9/10
Weston High School
Public 9-12 • Assigned • 2.0mi
10/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 99° expected this year, 15 days in 30 years
6/10 Wind Factor
27% chance of strong winds in next 30 years
4/10 Air Factor
3 unhealthy days expected this year, 5 days in 30 years
Provided by First Street
Historical weather
Weston, CT • 06883
Average low and high temperatures (°F)
35
21
37
23
53
33
62
43
69
52
81
61
84
67
81
60
76
57
67
46
55
37
40
26
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 8.7 hours in
June and 4.3 hours in December, placing it below the
U.S. average for solar exposure.
8.7 hrs
4.3 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.02M – $1.23M
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