39 Deepwood Road, Darien, CT 06820
OFF MARKET

$4,334,500

Trulia Estimate
  • 5 Beds
  • 3.5 Baths
  • 4,932 sqft (on 0.77 acres)

39 Deepwood Road, Darien, CT 06820

Est. Refi. Payment $28,970/mo*
Refinance Your Home
Currently Off Market - Sold Aug 1, 2025 for $4,022,500

Home Value

Trulia Estimate
$4.33M
Since last month
Decreased$4K (-0.1%)
Since last year
Increased$256K (+6.3%)
Since last sale
Increased$306K (+7.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +88% in the last 10 years
MonthEstimated value
2026
September 2026$4.33M
August 2026$4.33M
July 2026$4.28M
June 2026$4.26M
May 2026$4.22M
April 2026$4.15M
March 2026$4.14M
February 2026$4.14M
January 2026$4.07M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
261 Hollow Tree Ridge Road, Darien, CT
0.07
Single-Family Home
$4,350,000
12/15/25
5
5.5
6,135
3 Hickory Lane, Darien, CT
0.22
Single-Family Home
$2,875,000
07/01/26
4
4
2,920
76 Deepwood Road, Darien, CT
0.30
Single-Family Home
$2,287,500
02/27/26
5
4
3,897
8 Haskell Ln, Darien, CT
0.21
Single-Family Home
$4,750,000
06/22/26
6
5
6,810
29 Hillcrest Avenue, Darien, CT
0.37
Single-Family Home
$3,352,000
08/19/26
5
3.5
3,621
15 Waterbury Lane, Darien, CT
0.41
Single-Family Home
$4,400,000
04/28/26
5
5
6,052
311 Noroton Avenue, Darien, CT
0.28
Single-Family Home
$3,550,000
12/17/25
5
5.5
5,356
201 Middlesex Road, Darien, CT
0.28
Single-Family Home
$2,760,000
08/20/26
4
2.5
3,293
12 Laurel Lane, Darien, CT
0.21
Single-Family Home
$2,052,000
08/26/26
3
2.5
3,151
14 Revere Road, Darien, CT
0.33
Single-Family Home
$3,250,000
08/07/26
5
5.5
5,226

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
261 Hollow Tree Ridge Road, Darien, CT 06820
0.07
$4,350,000
5
5.5
6,135
Recently Sold
253 Hollow Tree Ridge Road, Darien, CT 06820
0.10
$2,975,100
4
3.5
3,001
Off Market
280 Hollow Tree Ridge Road, Darien, CT 06820
0.12
$4,280,300
5
5
5,579
Off Market
7 Lantern Lane, Darien, CT 06820
0.17
$2,542,300
4
3.5
3,742
Off Market
300 Hollow Tree Ridge Road, Darien, CT 06820
0.17
$5,274,600
5
7
6,118
Off Market
173 Middlesex Road, Darien, CT 06820
0.19
$4,444,500
6
6.5
5,352
Off Market
8 Windsor Road, Darien, CT 06820
0.19
$3,006,900
5
3
3,028
Off Market
23 Peterick Lane, Darien, CT 06820
0.20
$5,527,500
7
7.5
7,083
Off Market
12 Laurel Lane, Darien, CT 06820
0.21
$2,052,000
3
2.5
3,151
Recently Sold
8 Haskell Ln, Darien, CT 06820
0.21
$4,750,000
6
5
6,810
Recently Sold
121 Middlesex Road, Darien, CT 06820
0.22
$2,318,900
4
2.5
3,074
Off Market

Local Information

  • Map ViewExplore the area around 39 Deepwood Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1940
0.77 acre lot
4,932 sqft
$879/sqft
2 Car Garage

About this House

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.
39 Deepwood Road, Darien, CT 06820 is a 5 bedroom, 4 bathroom, 4,932 sqft single-family home built in 1940. It last sold for $4,022,500 on Aug 1, 2025 (4% below the $4,195,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,334,500.
Last check for updates: about 2 hours ago
Listed by Amanda Spatola, (203) 273-8615
Houlihan Lawrence, (203) 655-8238
Christopher Gugelmann, (203) 343-0141
Compass Connecticut, LLC, (203) 343-0141
Bought with: Susheila Starr, (203) 675-2753, Sotheby's International Realty, (203) 869-4343
Source: Smart MLS, MLS#24095468

Home Details for 39 Deepwood Road

Interior Features

Interior Details
Basement: Crawl Space,Interior EntryNumber of Rooms: 11Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Study
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4932 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltFoundation: BlockHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached
Pool
Pool: Gunite, In GroundPool
Frontage
Waterfront: Beach AccessNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 4932 Square Feet

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 105576

Price & Status

Price
List Price: $4,195,000
Status Change & Dates
Off Market Date: Wed Jun 04 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Darien
School Information
Elementary School: HolmesHigh School: Darien

Building

Building Area
Building Area: 4932 Square Feet

Community

Community Features: Golf, Library, Private School(s), Near Public Transport, Tennis Court(s)

HOA

No HOA

Lot Information

Lot Area: 0.77 acres

Miscellaneous

BasementMls Number: 24095468Attic: Pull Down StairsAbove Grade Unfinished Area: 4932

Additional Information

GolfLibraryPrivate School(s)Near Public TransportTennis Court(s)

Price and Tax history

DateEventPrice
Aug 1, 2025
Source: Smart MLS #24095468
Sold
$4,022,500
Jun 5, 2025
Source: Smart MLS #24095468
Pending
$4,195,000
May 16, 2025
Source: Smart MLS #24095468
Listed For Sale
$4,195,000
May 12, 2014
Source: Smart MLS #99051526
Sold
$1,757,500
Jan 22, 2014
Source: Agent Provided
PriceChange
$1,825,000
Price decreased by 4%

Market trends in Darien

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.82M
$155KMoM
Sale-to-List Price
110.3%
1.4%MoM
Price per sq ft
$821
$21MoM
Available listings
29
7MoM

Around this home

What Locals Say about Darien

At least 147 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 89 % Say yards are well-kept

  • 88 % Say parking is easy

  • 87 % Say car is needed

  • 84 % Say there's holiday spirit

  • 82 % Say people would walk alone at night

  • 80 % Say kids play outside

  • 73 % Say there's wildlife

  • 71 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 58 % Say neighbors are friendly

  • 58 % Say there are community events

  • 58 % Say there are sidewalks

  • 55 % Say it's walkable to restaurants

  • 48 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Kimrichardnyc
    "Happy, safe and friendly place to live and raise children. Need more diversification like in wesport CT though. "
    0
    Flag
  • Trulia User
    "This is the best town to raise kids and build friendships. The beaches, parks, restaurants, nature and proximity to NYC also makes a great place to live. We have found the people generally friendly and welcoming. "
    0
    Flag
  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
    0
    Flag
  • Jessica_hatch7
    "NA commute to the city is an easy 65 minute train ride. We have two stations in Darien, both easily accessible. "
    3
    Flag
  • Peter S.
    "Holidays and school events. Dining and activities such as sports, the arts and many many social events"
    0
    Flag
  • Mzengo8
    "My neighborhood plays kid lacrosse/ basketball or football games. And we have parties on almost every holiday. Which is very fun for all of the kids on the block "
    0
    Flag
  • Bill T.
    "Dead end but on a hill and has a loop so kids can run around, play and explore. Lots of trees and woods surround the neighborhood."
    3
    Flag
  • Tad
    "My commute is five minutes to the train station, five minute walk from parking lot to the tracks, then an hour on the train to grand central each work day. "
    1
    Flag
  • Allison w.
    "They would love it, such a friendly area. Dogs are everywhere and appreciated. I have 2 dogs and I am so glad there are a ton of dogs around. "
    0
    Flag
  • Chad W.
    "Darien is as family friendly as it gets. There is a lot of money here. Some are kind, but many are snobby. It's a bit of a bubble, which is why many families move here."
    0
    Flag
  • Jessica_hatch7
    "The people are amazing and the schools are fantastic. We are only 60 minutes from the city and the trains run very frequently. "
    2
    Flag
  • Victoria_belluscio
    "Great place to raise children- excellent schools- everything is 5-10 min away so good for busy schedules! 2 train stations for easy commuting, beaches, parks and more!"
    0
    Flag
  • Kathrynquirk445
    "Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
    0
    Flag
  • Bill T.
    "Big circle where no cars or trucks visit unless they live here or have business in the neighborhood... great place for kids"
    1
    Flag
  • dwenger
    "Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
    0
    Flag

LGBTQ Local Legal Protections

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Frequently asked questions about 39 Deepwood Road

  • What is 39 Deepwood Road estimated to be worth?
    Trulia's estimated value for 39 Deepwood Road in Darien, CT is $4,334,500.
  • What is the price history for 39 Deepwood Road?
    39 Deepwood Road in Darien, CT last sold for $4,022,500 in August 2025.
  • Is Darien a buyer's or seller's market?
    Darien is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Darien?
    The median sale price in Darien is $2.82M. That is down $155K from the prior month.
  • Does 39 Deepwood Road have air conditioning?
    Yes, 39 Deepwood Road in Darien, CT has air conditioning.
  • Does 39 Deepwood Road have a pool?
    Yes, 39 Deepwood Road in Darien, CT has a pool.

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