$4,022,500
SOLD AUG 1, 2025

39 Deepwood Rd Darien, CT 06820

5 Beds
3.5 Baths
4,932 Sq Ft
0.77 Acres

Recently Sold

$816 Per Sq Ft

4% Below List Price

19 Days on Market

Highlights

  • Beach Access
  • In Ground Pool
  • Property is near public transit
  • Holmes Elementary School Rated A
  • Colonial Architecture
  • Attic

About This Home

As of August 2025

Set in one of Darien's most desirable neighborhoods, this impeccably renovated home blends timeless charm with modern luxury- all within walking distance to schools, the train station, and the shops and restaurants of Noroton Commons. The location simply can't be beat. Sitting on nearly one flat acre, the stunning and ultra-private backyard feels like your own secluded retreat. Mature landscaping offers complete privacy, while two elegant bluestone patios and a gunite pool make this outdoor space perfect for entertaining or relaxing in style. Inside, every room has been thoughtfully updated, preserving the classic architecture while enhancing functionality and design. The spacious, sunlit kitchen features a walk-in pantry and high-end finishes, seamlessly connecting to the rest of the home. The first floor is made for entertaining, with a formal living room with a wood-burning fireplace, a vaulted-ceiling family room with direct backyard access, a striking dining room (with its own fireplace), and a cozy library - each space as inviting as the next. Upstairs, the primary suite is a true sanctuary, complete with a newly renovated bathroom and walk-in closet. Four additional bedrooms and two full baths complete the second floor, offering the perfect layout for family and guests. This is a rare opportunity to own a turnkey, magazine-worthy home in a truly unbeatable location. Classic charm, thoughtful updates, and exceptional indoor/outdoor living- this one has it all.

Last Agent to Sell the Property

Amanda Spatola

Houlihan Lawrence License #RES.0809813 Listed on: 05/14/2025

Houlihan Lawrence

Co-Listed By

Christopher Gugelmann

Compass Connecticut, LLC License #RES.0809299

Last Buyer's Agent

Susheila Starr

Sotheby's International Realty License #RES.0829830

Sotheby's International Realty

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $25,759

Year Built

  • Built in 1940

Parking

  • 2 Car Garage

Home Design

  • Colonial Architecture
  • Block Foundation
  • Frame Construction
  • Asphalt Shingled Roof
  • Wood Siding

Interior Spaces

  • 4,932 Sq Ft Home
  • 3 Fireplaces
  • Pull Down Stairs to Attic

Kitchen

  • Oven or Range
  • Dishwasher

Bedrooms and Bathrooms

  • 5 Bedrooms

Laundry

  • Dryer
  • Washer

Basement

  • Interior Basement Entry
  • Crawl Space

Pool

  • In Ground Pool
  • Gunite Pool

Location

  • Property is near public transit
  • Property is near a golf course

Schools

  • Holmes Elementary School
  • Darien High School

Utilities

  • Central Air
  • Hot Water Heating System
  • Heating System Uses Oil
  • Hot Water Circulator
  • Fuel Tank Located in Garage

Additional Features

  • Beach Access
  • 0.77 Acre Lot

Community Details

  • Public Transportation

Listing and Financial Details

  • Assessor Parcel Number 105576

Home Details

Home Type

Single Family

Est. Annual Taxes

$25,759

Year Built

Built in 1940

Lot Details

0

Listing Details

  • Neighborhood: N/A
  • Property Type: Single Family For Sale
  • Style: Colonial
  • Sq Ft Est Heated Above Grade: 4932
  • Total Sq Ft: 4932
  • Year Built: 1940
  • New Construction: No/Resale
  • Nearby Amenities: Golf Course, Library, Private School(s), Public Transportation, Tennis Courts
  • Direct Waterfront: No
  • Home Warranty Offered: No
  • Directions: hollow tree to deepwood
  • Financing Used: Cash
  • Street Type: Road
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 5
  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Fireplaces: 3
  • Attic Description: Pull-Down Stairs
  • Basement Description: Crawl Space, Interior Access
  • Appliances: Oven/Range, Refrigerator, Freezer, Dishwasher, Washer, Dryer
  • Attic: Yes

Exterior Features

  • Exterior Siding: Wood
  • Foundation Type: Block
  • Roof Information: Asphalt Shingle
  • Waterfront Description: Beach Rights
  • Swimming Pool: Yes
  • Pool: Gunite, In Ground Pool
  • Construction Description: Frame

Garage/Parking

  • Garages Number: 2
  • Garage And Parking: Attached Garage

Utilities

  • Cooling System: Central Air
  • Heat Type: Hot Water
  • Heat Fuel Type: Oil
  • Fuel Tank Location: In Garage
  • Hot Water Description: Domestic
  • Water Source: Public Water Connected
  • Sewer: Public Sewer Connected

Lot Info

  • Acres: 0.77
  • Lot Description: Dry Level Lot Professionally Landscaped
  • Zoning: R-1
  • Parcel #: 105576

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 25759

MLS Schools

  • Elementary School: Holmes
  • High School: Darien

Ownership History

Date Name Owned For Owner Type

Purchase Details

Listed on
May 14, 2025
Closed on
Jul 17, 2025
Sold by
Gugelmann Christopher P and Gugelmann Margaret W
Bought by
Mitchell T T and Mitchell M
Seller's Agent
Amanda Spatola
Houlihan Lawrence
Buyer's Agent
Susheila Starr
Sotheby's International Realty
List Price
$4,195,000
Sold Price
$4,022,500
Premium/Discount to List
-$172,500
-4.11%
Views
30
Current Estimated Value
$4,027,313

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
$4,813
Avg. Annual Appreciation
0.29%

Purchase Details

Listed on
Jan 20, 2014
Closed on
May 13, 2014
Sold by
Murphy James S
Bought by
Gugelmann Christopher P and Gugelmann Margaret W
Seller's Agent
Julie Peters
Coldwell Banker Realty
List Price
$1,825,000
Sold Price
$1,757,500
Premium/Discount to List
-$67,500
-3.7%

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
7.65%
Original Mortgage
$700,000
Interest Rate
4.41%
Mortgage Type
Purchase Money Mortgage

Purchase Details

Closed on
Jun 19, 1992
Sold by
Weimer Richard
Bought by
Murphy Kevin and Murphy Jamey
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
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Average Value
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List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Purchase History

Date Type Sale Price Title Company
Warranty Deed $4,022,500 --
Warranty Deed $1,757,500 --
Warranty Deed $1,757,500 --
Deed $646,500 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Previous Owner $700,000 Purchase Money Mortgage
Previous Owner $331,400 No Value Available
Previous Owner $50,000 No Value Available
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft Prior Sale
08/01/2025 08/01/25 Sold $4,022,500 -4.1% $816 / Sq Ft
06/05/2025 06/05/25 Pending -- -- --
05/16/2025 05/16/25 For Sale $4,195,000 +138.7% $851 / Sq Ft
05/12/2014 05/12/14 Sold $1,757,500 -3.7% $378 / Sq Ft View Prior Sale
04/12/2014 04/12/14 Pending -- -- --
01/20/2014 01/20/14 For Sale $1,825,000 -- $393 / Sq Ft
Source: SmartMLS

Tax History Compared to Growth

Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $25,759 $1,664,040 $913,990 $750,050
2024 $24,445 $1,664,040 $913,990 $750,050
2023 $22,053 $1,252,300 $609,350 $642,950
2022 $21,577 $1,252,300 $609,350 $642,950
2021 $21,089 $1,252,300 $609,350 $642,950
2020 $7,954 $1,252,300 $609,350 $642,950
2019 $8,245 $1,252,300 $609,350 $642,950
2018 $20,194 $1,255,870 $612,920 $642,950
2017 $20,295 $1,255,870 $612,920 $642,950
2016 $19,805 $1,255,870 $612,920 $642,950
2015 $17,173 $1,118,740 $612,920 $505,820
2014 $16,792 $1,118,740 $612,920 $505,820
Source: Public Records

Agents Affiliated with this Home

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Map

Source: SmartMLS

MLS Number: 24095468

SmartMLS

APN: DARI-000026-000000-000049