24 Deepwood Rd

Weston, CT 06883

$1,020,000
Last Sold Price
3
Beds
2,310 Sq. Ft.
$442 / Sq. Ft.
2,310
Sq. Ft.
$442
per Sq. Ft.
Closed 6/25/25
Closed 6/25/25

Description

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...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.
  1. Listed by Laura Ancona • William Pitt Sotheby's Int'l
    P: (203)-438-9531 C: (203)-733-7053 lancona@wpsir.com

Property Details for 24 Deepwood Road

Basement Description
Crawl Space
Direct Waterfront
No
Garages Number
1
Neighborhood
Lower Weston
Style
Modern
Garage Parking Info
Attached Garage
Swimming Pool
No
LISTING UPDATED: 06/25/2025 08:21 PM

Property Details for 24 Deepwood Road

StatusClosed
MLS #24088908
Days on Market5
Taxes$12,314 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1984
Lot Size2.28 AC / 99,316 SF
CountyFairfield County

Location

Listing Courtesy of William Pitt Sotheby's Int'l, Laura Ancona

Sold By Compass Connecticut, LLC, Karla Murtaugh

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Building Information for 24 Deepwood Road

Stories-Year Built1984Building Size-Lot Size2.28 AC / 99,316 SF

Payment Calculator

$5,997 per month

30 year fixed, 6.15% Interest

Principal and Interest

$4,971

Property Taxes

$1,026

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 24 Deepwood Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Davis Hill to Hill Farm, left on Deepwood, down private access way to end and then bear right. See signs.
  • Elementary School: Hurlbutt
  • High School: Weston
  • Intermediate School: Weston
  • Latitude: 41.230822
  • Longitude: -73.35414
  • Middle Jr High School: Weston
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2024-June 2025
  • Property Tax: $12,314
Virtual Tour
Interior and Exterior Features
Exterior Features
  • Exterior Features: Deck, Gutters, Lighting, French Doors
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Range, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Storage Space, Access Via Hatch
  • Cooling System: Central Air, Zoned
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Open Floor Plan, Security System
  • Laundry Room Info: Lower Level
  • Rooms Total: 6
Room 1
  • Room Entry Order: 1
  • Room Features: Balcony/Deck,Built-Ins,Fireplace,French Doors,Hardwood Floor
  • Room Length: 23.0
  • Room Level: Main
  • Room Type: Great Room
  • Room Width: 19.0
Room 2
  • Room Entry Order: 2
  • Room Features: Balcony/Deck,French Doors,Hardwood Floor
  • Room Length: 15.5
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 8.0
Room 3
  • Room Entry Order: 3
  • Room Features: Skylight,Vaulted Ceiling,Beams,Breakfast Bar,Pantry
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 9.0
Room 4
  • Room Entry Order: 4
  • Room Features: Balcony/Deck,Dressing Room,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Primary BR Suite
  • Room Width: 13.0
Room 5
  • Listing Key: 32EFD26F9E8FF536E063D501100A1215
  • Room Entry Order: 5
  • Room Features: Balcony/Deck,Sliders,Walk-In Closet,Hardwood Floor
  • Room Length: 14.5
  • Room Level: Lower
  • Room Type: Bedroom
  • Room Width: 12.0
Room 6
  • Room Entry Order: 6
  • Room Features: Hardwood Floor
  • Room Length: 15.0
  • Room Level: Lower
  • Room Type: Bedroom
  • Room Width: 11.0
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Exterior Siding: Clapboard, Wood
  • Foundation Type: Concrete
  • Fuel Tank Location: Above Ground
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1984
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Description: As measured, see floor plans, difference is that the assessor estimated and we measured.
  • Living Area SQFT Per Public Records: 2067
Lot Information
  • Lot Description: Rear Lot, Lightly Wooded, On Cul-De-Sac
  • Parcel Number: 404634
  • Sq Ft Est Heated Above Grade: 2310.0
  • Sq Ft Total: 2310.0
  • Zoning: R
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Electric, Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 24 Deepwood Road

DateEvent & SourcePriceAppreciation
Jun 18, 2025

Closed (Public Record)

Public Record #1904513987

$1,020,000

+7.8% / yr

Oct 22, 2020

Closed (Public Record)

Public Record #682835552

$720,000

+1.2% / yr

Sep 30, 2014

Closed (Public Record)

Public Record #462585281

$668,000

+1.0% / yr

Nov 1, 2007

Closed (Public Record)

Public Record #229331025

$625,000—
Nov 1, 2007

Closed (Public Record)

Public Record #327066080

$1

-80.3% / yr

Oct 25, 1999

Closed (Public Record)

Public Record #91290177

$450,000—
DateEvent & SourcePrice
06/18/2025

Closed (Public Record)

Public Record #1904513987

$1,020,000

+7.8% / yr

10/22/2020

Closed (Public Record)

Public Record #682835552

$720,000

+1.2% / yr

09/30/2014

Closed (Public Record)

Public Record #462585281

$668,000

+1.0% / yr

11/01/2007

Closed (Public Record)

Public Record #229331025

$625,000
11/01/2007

Closed (Public Record)

Public Record #327066080

$1

-80.3% / yr

10/25/1999

Closed (Public Record)

Public Record #91290177

$450,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 24 Deepwood Road

Taxable ValueLand$196,840Additions$327,810Total$524,650
Tax Record2024$12,539 ($1,045 / month)
Home Facts
Beds3Baths3Total Finished SqFt2,067 SqFtAbove Grade Finished SqFt2,067 SqFtStories2Lot Size99,317 SqFtStyleSingle Family ResidenceYear Built1984Year Renovated2004ZoningRCountyFAIRFIELDAPNWSTN M:16 B:2 L:40Fireplace TypeHas Fireplace

Schools near 24 Deepwood Road

This home is within Weston School District.
Rating
School
Type
Grades
Distance
Hurlbutt Elementary School
Public - PK to 2
Weston Intermediate School
Public - 3 to 5
Weston Middle School
Public - 6 to 8
Weston High School
Public - 9 to 12
Rating
School
Distance
Hurlbutt Elementary School
PublicPK to 2

Weston Intermediate School
Public3 to 5

Weston Middle School
Public6 to 8

Weston High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Pitt Sotheby's Int'l, Laura Ancona

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.