39 Deepwood Road

Closed 8/1/25
Closed 8/1/25
Gallery Image 1
Sold
Last Sold Price
$4,022,500
5 beds4,932 sqft

39 Deepwood Rd, Darien, CT 06820

Single FamilyProperty Type
0.77 acresLot Size
1940Year Built
$816/sq ftPrice per sq ft
2 carsParking Spaces

Description

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...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.
Listing closed: 08/01/2025 12:00 AM • Source: SMARTMLS, MLS#: 24095468

Recent comparable sales

Median sold price

$3,625,000

Avg days on market

16

Sale-to-list ratio

109.5%

Darien, CT

9 comparable properties found

1

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5
Bedrooms
3.5
Bathrooms
5,595
Square Feet
1.01
Acres

30 Stephanie Lane, Darien, CT 06820

$3,600,000 | 19 Thomasina Lane, Darien, CT 06820
2

$3,600,000

Sold 05/15/26

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Bedrooms
4,170
Square Feet
0.37
Acres

19 Thomasina Lane, Darien, CT 06820

$3,250,000 | 11 McLaren Road South, Darien, CT 06820
3

$3,250,000

Sold 09/15/26

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Bedrooms
4,301
Square Feet
0.38
Acres

11 McLaren Road South, Darien, CT 06820

$3,625,000 | 9 Beach Drive, Darien, CT 06820
4

$3,625,000

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9 Beach Drive, Darien, CT 06820

$4,500,000 | 20 Buttonwood Lane, Darien, CT 06820
5

$4,500,000

Sold 08/03/26

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1.25
Acres

20 Buttonwood Lane, Darien, CT 06820

$3,150,000 | 20 Walmsley Road, Darien, CT 06820
6

$3,150,000

Sold 07/21/26

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4,173
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20 Walmsley Road, Darien, CT 06820

$4,460,000 | 1 Brush Island Road, Darien, CT 06820
7

$4,460,000

Sold 02/28/25

5
Bedrooms
4,542
Square Feet
2.94
Acres

1 Brush Island Road, Darien, CT 06820

an aerial view of a house with a garden and plants
8

$3,000,750

Sold 06/30/25

5
Bedrooms
4,376
Square Feet
0.68
Acres

50 Mansfield Avenue, Darien, CT 06820

$3,800,000 | 20 Leeuwarden Road, Darien, CT 06820
9

$3,800,000

Sold 11/05/24

5
Bedrooms
4,765
Square Feet
1.15
Acres

20 Leeuwarden Road, Darien, CT 06820

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$23,621 per month

30 year fixed, 7.03% Interest

Principal and Interest

$21,474

Property Taxes

$2,147

HOA Dues

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Property Information for 39 Deepwood Road

Property Details

  • Taxes: $25,759 / year
  • MLS Type: Residential
  • County: Fairfield County
  • Basement Description: Crawl Space, Interior Access
  • Direct Waterfront: No
  • Expected Active Date: 05-16-2025
  • Garages Number: 2
  • Style: Colonial
  • Garage Parking Info: Attached Garage
  • Swimming Pool: Yes
  • Expected On Market Date: 05-16-2025

Building Information

  • Year Built: 1940
  • Lot Size: 0.77 AC / 33,541 SF

Summary

Property and Location
  • Acres Source: Public Records
  • Directions: hollow tree to deepwood
  • Elementary School: Holmes
  • High School: Darien
  • Latitude: 41.079093
  • Longitude: -73.498916
  • Neighborhood Amenities: Golf Course, Library, Private School(s), Public Transportation, Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $25,759

Interior and Exterior Features

Exterior Features
  • Pool Description: Gunite, In Ground Pool
  • Waterfront Description: Beach Rights
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Freezer, Dishwasher, Washer, Dryer
  • Attic Description: Pull-Down Stairs
  • Cooling System: Central Air
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 3
  • Rooms Total: 11
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 25.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 17.0
Room 2
  • Room Entry Order: 10
  • Room Features: Remodeled,Island,Pantry,Hardwood Floor
  • Room Level: Main
  • Room Type: Kitchen
Room 3
  • Room Entry Order: 2
  • Room Features: Fireplace,French Doors,Hardwood Floor
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 15.0
Room 4
  • Room Entry Order: 3
  • Room Features: Fireplace,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 13.0
Room 5
  • Listing Key: 3505404E9C4B6DDAE063E201100A3E4D
  • Room Entry Order: 4
  • Room Length: 16.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 6
  • Room Entry Order: 5
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 7
  • Room Entry Order: 6
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 8
  • Room Entry Order: 7
  • Room Length: 19.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 19.0
Room 9
  • Listing Key: 3505404E9C4B6DDAE063E201100A3E4D
  • Room Entry Order: 8
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Study
  • Room Width: 11.0
Room 10
  • Room Entry Order: 9
  • Room Features: Beams,Fireplace
  • Room Length: 26.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 17.0

Property

Property and Assessments
  • Color: white
  • Construction Description: Frame
  • Exterior Siding: Wood
  • Foundation Type: Block
  • Fuel Tank Location: In Garage
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1940
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 4932
Lot Information
  • Lot Description: Dry, Level Lot, Professionally Landscaped
  • Parcel Number: 105576
  • Sq Ft Est Heated Above Grade: 4932.0
  • Sq Ft Total: 4932.0
  • Zoning: R-1
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected

Multi Family

Income and Expenses
  • Occupied By: Owner

Property History for 39 Deepwood Road

DateEvent & SourcePriceAppreciation
Jul 17, 2025

Closed (Public Record)

Public Record #1909387959

$4,022,500

+7.7% / yr

May 13, 2014

Closed (Public Record)

Public Record #416153308

$1,757,500

+4.7% / yr

Jun 19, 1992

Closed (Public Record)

Public Record #90945656

$646,500—
DateEvent & SourcePrice
07/17/2025

Closed (Public Record)

Public Record #1909387959

$4,022,500

+7.7% / yr

05/13/2014

Closed (Public Record)

Public Record #416153308

$1,757,500

+4.7% / yr

06/19/1992

Closed (Public Record)

Public Record #90945656

$646,500

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

Public records

39 Deepwood Road

Beds

6

Baths

5

Total Finished SqFt

4,932 SqFt

Above Grade Finished SqFt

4,932 SqFt

Unfinished Basement SqFt

600 SqFt

Stories

2

Schools near 39 Deepwood Road

This home is within Darien School District.
Rating
School
Type
Grades
Distance
Holmes Elementary School
Public - PK to 5
Middlesex Middle School
Public - 6 to 8
Darien High School
Public - 9 to 12
Rating
School
Distance
Holmes Elementary School
PublicPK to 5

Middlesex Middle School
Public6 to 8

Darien 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.

Darien
Darien
A coastal Connecticut town with a strong sense of community. Incorporated in 1820, Darien is a popular coastal town situated between Stamford and Norwalk. Just a 1 hour train ride from Manhattan via Metro North, Darien is an ideal commuter town that boasts spectacular shoreline activities...
Darien GuideAll Neighborhoods

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 39 Deepwood Road, Darien, CT 06820
$4,022,500
5
4,932
33,541
11 Deepwood Road, Darien, CT 06820
$1,825,000
5
4,297
30,927
281 Hollow Tree Ridge Road, Unit 52, Darien, CT 06820
$1,610,000
–
–
–
69,260
281 Hollow Tree Ridge Road, Darien, CT 06820
$1,250,000
–
–
–
57,499
27 Deepwood Road, Darien, CT 06820
$2,400,000
5
4,300
44,866
10 Deepwood Road, Darien, CT 06820
$1,875,000
4
3,409
26,571

Explore Nearby Homes

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

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.