44 Deepwood Rd, Darien, CT 06820
Property image
Property image
OFF MARKET

44 Deepwood Rd
Darien, CT 06820

  • 5 Beds
  • 3.5 Baths
  • 5,385 sqft (on 1.93 acres)

$3,648,300

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $23,488/mo*
Refinance Your Home

$3,648,300

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $23,488/mo*
Refinance Your Home
5 Beds
3.5 Baths
5,385 sqft
(on 1.93 acres)

Local Information

  • Map ViewExplore the area around 44 Deepwood Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Welcome to one of the most coveted streets in Darien for its location to everything. This traditional New England home has quintessential cape charm with modern upgrades and an abundance of usable space. Enjoy outdoor entertaining with your custom grill area on the IPE deck, while overlooking the professionally landscaped 1.92 acre property. Endless space to play, entertain and enjoy the sun! The stunning custom kitchen with an oversized island is the center of the home. Indoor/Outdoor living with the newly remodeled 1,300 sf lower level family and game room that is walk out to a generously sized blue stone patio. 2 bar areas, large private office and so much more. This is life on Deepwood.
44 Deepwood Rd, Darien, CT 06820 is a 5 bedroom, 4 bathroom, 5,385 sqft single-family home built in 1950. It last sold for $2,150,000 on May 10, 2021. It is currently off market. The Trulia Estimate is $3,648,300, with a rent estimate of $16,247/month.

Home Highlights

Parking
Garage
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 44 Deepwood Rd

Interior Features

Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 11Types of Rooms: Recreation Room
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1950Year Updated: 2014
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Exterior Features

Exterior Home Features
DeckExterior: WoodPatio
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1.93 acres

Price History for 44 Deepwood Rd

DatePriceEventSource
05/10/2021$2,150,000Sold
Smart MLS #170369805
03/13/2021$2,395,000PendingHalstead / Brown Harris Stevens #170369805
03/08/2021$2,395,000ContingentSmart MLS #170369805
02/01/2021$2,395,000Listed For SaleSmart MLS #170369805
12/03/2009$1,699,000ListingRemovedAgent Provided
11/20/2009$1,699,000Listed For SaleAgent Provided
04/14/2008$1,683,000Sold
Smart MLS #98341706
08/25/1995$590,000Sold
N/A

Market trends in Darien

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
1MoM
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Property Tax and Assessment

Year2025
Tax$27,551
Assessment$1,779,750
Home facts updated by county records

Comparable Sales for 44 Deepwood Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
76 Deepwood Road, Darien, CT
0.23
Single-Family Home
$2,287,500
02/27/26
5
4
3,897
39 Deepwood Road, Darien, CT
0.15
Single-Family Home
$4,022,500
08/01/25
5
3.5
4,932
261 Hollow Tree Ridge Road, Darien, CT
0.18
Single-Family Home
$4,350,000
12/15/25
5
5.5
6,135
326 Hollow Tree Ridge Road, Darien, CT
0.43
Single-Family Home
$3,650,000
08/20/25
5
4.5
6,860
3 Hickory Lane, Darien, CT
0.17
Single-Family Home
$2,875,000
07/01/26
4
4
2,920
26 Holly Lane, Darien, CT
0.65
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
8 Haskell Ln, Darien, CT
0.35
Single-Family Home
$4,750,000
06/22/26
6
5
6,810
86 Middlesex Road, Darien, CT
0.27
Single-Family Home
$2,400,000
05/19/26
4
2.5
2,850
15 Waterbury Lane, Darien, CT
0.45
Single-Family Home
$4,400,000
04/28/26
5
5
6,052
300 Hollow Tree Ridge Road, Darien, CT
0.31
Single-Family Home
$4,900,000
09/02/25
5
7
6,118

Nearby homes

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Assigned Schools

These are the assigned schools for 44 Deepwood Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

  • 81 % 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. "
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  • 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
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  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
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  • 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
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  • 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 "
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  • 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
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  • 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
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  • 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."
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  • 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
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  • Kathrynquirk445
    "Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
    0
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  • 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
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Homes for sale near 44 Deepwood Rd

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Off Market Homes Near 44 Deepwood Rd

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