76 Deepwood Road, Darien, CT 06820
SOLD
FEB 27, 2026

76 Deepwood Road
Darien, CT 06820

  • 5 Beds
  • 4 Baths
  • 3,897 sqft (on 1.01 acres)

$2,287,500

Last Sold: Feb 27, 2026
3% below list $2.35M
$587/sqft
Est. Refi. Payment $14,864/mo*
Refinance Your Home

$2,287,500

Last Sold: Feb 27, 2026
3% below list $2.35M
$587/sqft
Est. Refi. Payment $14,864/mo*
Refinance Your Home
5 Beds
4 Baths
3,897 sqft
(on 1.01 acres)

Local Information

  • Map ViewExplore the area around 76 Deepwood Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Set on a full acre in one of Darien's most sought-after neighborhoods, this property presents a rare and versatile opportunity for visionary buyers. Whether you choose to undertake a renovation-reviving the charm of mid-century modern design-or build a custom new construction estate from the ground up, the potential here is extraordinary. Surrounded by multi-million dollar homes, this centrally located parcel offers an ideal blend of privacy and convenience. Just moments from the highly regarded Middlesex Middle School and Darien High School, as well as the Noroton Heights train station, shopping, and dining, the location is as practical as it is prestigious. In addition to the main residence, the property features an existing accessory dwelling-perfect for a guest house, home office, or au pair suite-complete with a spacious great room, kitchenette, bedroom, and full bath. Recent comparables in the area attracted multiple offers, underscoring the exceptional value and demand for properties like this. Whether you're an end-user with vision or a developer seeking a standout project, this is an investment that delivers on both lifestyle and long-term value. Don't miss this chance to create something truly special in one of Darien's premier enclaves. Property is being sold as is.
76 Deepwood Road, Darien, CT 06820 is a 5 bedroom, 4 bathroom, 3,897 sqft single-family home built in 1955. It last sold for $2,287,500 on Feb 27, 2026 (3% below the $2,350,000 asking price). It is currently off market. The Trulia Estimate is $2,348,500, with a rent estimate of $7,947/month.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
$587/sqft
Listed
180+ days ago

Home Details for 76 Deepwood Road

Interior Features

Interior Details
Basement: Crawl Space,Partial,Unfinished,Interior Entry,ConcreteNumber of Rooms: 11Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Great Room, Kitchen, Living Room, Rec Play Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 3897 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Water Heater, Electric Water HeaterDishwasherDryerLaundry: Main LevelRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,Radiant,Zoned,OilHas CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace
Levels, Entrance, & Accessibility
Levels: Multi/Split

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Porch, PatioExterior: Rain GuttersFoundation: Block, Concrete PerimeterNo Private Pool
Parking & Garage
GarageParking: Garage Door Opener
Frontage
Waterfront: Beach Access, Water CommunityNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3897 Square Feet

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Split Level
Building
Construction Materials: Shingle Siding, BrickNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 105553

Price & Status

Price
List Price: $2,350,000Price Per Sqft: $587/sqft
Status Change & Dates
Off Market Date: Mon Dec 01 2025Possession Timing: Neg

Active Status

MLS Status: Closed

Location

Direction & Address
City: Darien
School Information
Elementary School: HolmesJr High / Middle School: MiddlesexHigh School: Darien

Building

Building Area
Building Area: 3897 Square Feet

Community

Community Features: Library, Medical Facilities, Paddle Tennis, Playground, Near Public Transport, Shopping/Mall, Tennis Court(s)
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 1.01 Acres

Miscellaneous

BasementMls Number: 24116271Attic: Storage, Pull Down StairsAttribution Contact: (203) 550-0821Above Grade Unfinished Area: 3897

Additional Information

LibraryMedical FacilitiesPaddle TennisPlaygroundNear Public TransportShopping/MallTennis Court(s)
Last check for updates: about 10 hours ago
Listed by Carolyn Brook, (203) 550-0821
William Pitt Sotheby's Int'l, (203) 655-8234
Amy Barsanti, (203) 722-1781
William Pitt Sotheby's Int'l, (203) 655-8234
Bought with: Stacey Delikat, (203) 249-4595, Houlihan Lawrence, (203) 869-0700
Source: Smart MLS, MLS#24116271

Price History for 76 Deepwood Road

DatePriceEventSource
02/27/2026$2,287,500Sold
Smart MLS #24116271
01/31/2026$2,350,000PendingSmart MLS #24116281
08/04/2025$2,350,000Listed For SaleSmart MLS #24116281

Market trends in Darien

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.73M
Sale-to-List Price
105.6%
Price per sq ft
$787
Available listings
54
11MoM
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Property Tax and Assessment

Year2025
Tax$19,325
Assessment$1,248,380
Home facts updated by county records

Comparable Sales for 76 Deepwood Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3 Hickory Lane, Darien, CT
0.09
Single-Family Home
$2,875,000
07/01/26
4
4
2,920
39 Deepwood Road, Darien, CT
0.30
Single-Family Home
$4,022,500
08/01/25
5
3.5
4,932
15 Waterbury Lane, Darien, CT
0.33
Single-Family Home
$4,400,000
04/28/26
5
5
6,052
86 Middlesex Road, Darien, CT
0.21
Single-Family Home
$2,400,000
05/19/26
4
2.5
2,850
261 Hollow Tree Ridge Road, Darien, CT
0.37
Single-Family Home
$4,350,000
12/15/25
5
5.5
6,135
39 Briar Brae Road, Darien, CT
0.54
Single-Family Home
$2,358,000
08/01/25
4
3
3,242
26 Holly Lane, Darien, CT
0.77
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
154 Holmes Avenue, Darien, CT
0.55
Single-Family Home
$2,160,000
07/30/25
5
3.5
3,108

Nearby homes

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Assigned Schools

These are the assigned schools for 76 Deepwood Road.
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"
    0
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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
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  • 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!"
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  • Kathrynquirk445
    "Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
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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
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  • 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 76 Deepwood Road

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Off Market Homes Near 76 Deepwood Road

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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.