Welcome to 28 Crooked Mile Road! Privately sited at the end of a quiet cul-de-sac in North Darien on a private road in the Ox Ridge school district, this handsome cedar shingle-clad colonial sits on two beautifully manicured acres with mature trees and planting beds. The property offers wonderful western and southern exposure, the house is truly flooded with sunshine throughout the day. The home underwent a major renovation in 2007 and more recently, in 2020, the kitchen and bar area had a fabulous redo!. The classic shaker style kitchen shares an adjacent family room with a fireplace and access to the patio beyond. Formal living and dining rooms and an office anchor the first floor, along with a magazine worthy, newly renovated sunroom (complete with wet bar)! The second floor holds 5 bedrooms. Four are en-suite and positioned along the south side of the house, while a 5th (and potential 6th) bedroom sit on the North side - well suited for guests, older children or an au pair. Also, up the back stairs, is a generous bonus room, perfect for any number of activities! In 2025 the entire roof was replaced, and an array of solar panels were installed on the rear of the home. An electric car charger in the 3-car garage and generator complete this very well-equipped house. Don't miss the chance to make this well maintained and beautifully updated colonial your forever home! Crooked Mile Tax District is a "special tax district" in the Town of Darien under Connecticut Law. The tax bill for 28 Crooked Mile for the fiscal year 2025-2026 was $1467.69. Funds collected are used for road & property maintenance, plowing, etc.
Under contract
$3,975,000
28 Crooked Mile Road, Darien, CT 06820
5beds
4,653sqft
Est.:
Single Family Residence
Built in 1961
2 Acres Lot
$-- Zestimate®
$854/sqft
$-- HOA
What's special
Cedar shingle-clad colonialClassic shaker style kitchenGenerous bonus roomTwo beautifully manicured acres
- 54 days |
- 144 |
- 3 |
Zillow last checked: 7 hours ago
Listing updated: February 07, 2026 at 07:06am
Listed by:
Nan Peter (203)247-1188,
Houlihan Lawrence 203-655-8238
Source: Smart MLS,MLS#: 24148496
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 7
- Full bathrooms: 5
- 1/2 bathrooms: 2
Rooms
- Room types: Bonus Room, Laundry
Primary bedroom
- Features: Bedroom Suite, Built-in Features, Full Bath, Stall Shower, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 293.91 Square Feet
- Dimensions: 24.25 x 12.12
Bedroom
- Features: Bedroom Suite, Full Bath, Hardwood Floor, Tile Floor
- Level: Upper
- Area: 185.25 Square Feet
- Dimensions: 14.25 x 13
Bedroom
- Features: Bedroom Suite, Full Bath, Hardwood Floor, Tile Floor
- Level: Upper
- Area: 153 Square Feet
- Dimensions: 12.75 x 12
Bedroom
- Features: Bedroom Suite, Full Bath, Hardwood Floor, Tile Floor
- Level: Upper
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 183.75 Square Feet
- Dimensions: 12.25 x 15
Bathroom
- Features: Tile Floor
- Level: Main
- Area: 21.88 Square Feet
- Dimensions: 3.5 x 6.25
Bathroom
- Features: Ceiling Fan(s), Stone Floor
- Level: Main
- Area: 22.75 Square Feet
- Dimensions: 7 x 3.25
Bathroom
- Level: Upper
- Area: 63 Square Feet
- Dimensions: 9 x 7
Dining room
- Features: Patio/Terrace, Sliders, Hardwood Floor
- Level: Main
- Area: 222.75 Square Feet
- Dimensions: 16.5 x 13.5
Family room
- Features: Skylight, Cathedral Ceiling(s), Built-in Features, Fireplace, Sliders
- Level: Main
- Area: 193.88 Square Feet
- Dimensions: 11.75 x 16.5
Kitchen
- Features: Built-in Features, Quartz Counters, Dining Area, Double-Sink, Eating Space, Kitchen Island
- Level: Main
- Area: 438.75 Square Feet
- Dimensions: 19.5 x 22.5
Living room
- Features: Fireplace, Hardwood Floor
- Level: Main
- Area: 444.19 Square Feet
- Dimensions: 17.25 x 25.75
Office
- Features: Hardwood Floor
- Level: Main
- Area: 150 Square Feet
- Dimensions: 12.5 x 12
Other
- Features: Built-in Features, Wet Bar
- Level: Main
- Area: 70.5 Square Feet
- Dimensions: 11.75 x 6
Other
- Level: Upper
- Area: 139.75 Square Feet
- Dimensions: 13 x 10.75
Rec play room
- Features: Vaulted Ceiling(s), Bookcases, Built-in Features, Hardwood Floor
- Level: Upper
- Area: 831.79 Square Feet
- Dimensions: 22.33 x 37.25
Sun room
- Features: Remodeled, Ceiling Fan(s), Wet Bar, Parquet Floor
- Level: Main
- Area: 358.38 Square Feet
- Dimensions: 23.5 x 15.25
Heating
- Heat Pump, Forced Air, Electric, Oil
Cooling
- Central Air, Heat Pump
Appliances
- Included: Gas Cooktop, Cooktop, Oven, Range Hood, Refrigerator, Subzero, Dishwasher, Disposal, Washer, Dryer, Water Heater
- Laundry: Main Level, Mud Room
Features
- Wired for Data, Entrance Foyer, Smart Thermostat
- Doors: French Doors
- Windows: Thermopane Windows
- Basement: Partial,Unfinished,Storage Space,Interior Entry,Concrete
- Attic: Storage,Walk-up
- Number of fireplaces: 2
Interior area
- Total structure area: 4,653
- Total interior livable area: 4,653 sqft
- Finished area above ground: 4,653
Property
Parking
- Total spaces: 5
- Parking features: Attached, Paved, Off Street, Driveway, Garage Door Opener, Private, Asphalt
- Attached garage spaces: 3
- Has uncovered spaces: Yes
Features
- Patio & porch: Patio
- Exterior features: Rain Gutters, Underground Sprinkler
Lot
- Size: 2 Acres
- Features: Dry, Level, Cul-De-Sac, Landscaped, Open Lot
Details
- Parcel number: 102896
- Zoning: R2
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Shingle Siding, Cedar
- Foundation: Block
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1961
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Underground Utilities
Green energy
- Energy efficient items: Thermostat, Windows
- Energy generation: Solar
Community & HOA
Community
- Features: Golf, Park, Near Public Transport, Shopping/Mall, Tennis Court(s)
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Darien
Financial & listing details
- Price per square foot: $854/sqft
- Tax assessed value: $2,106,090
- Annual tax amount: $32,602
- Date on market: 1/26/2026
- Exclusions: Draperies in living room and primary suite, wine fridge and freezer in basement, workbench in basement, televisions. All negotiable.
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 2/7/2026 | Pending sale | $3,975,000$854/sqft |
Source:  Smart MLS #24148496 Report a problem | ||
| 1/26/2026 | Listed for sale | $3,975,000+109.2%$854/sqft |
Source: Smart MLS #24148496 Report a problem | ||
| 9/1/2012 | Listing removed | $9,500$2/sqft |
Source: Kelly Associates Real Estate, Inc. #17192 Report a problem | ||
| 5/3/2012 | Listed for rent | $9,500$2/sqft |
Source: Kelly Associates Real Estate, Inc. #17192 Report a problem | ||
| 6/24/2002 | Sold | $1,900,000+132.4%$408/sqft |
Source: Smart MLS #98123121 Report a problem | ||
| 2/28/1991 | Sold | $817,500$176/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $32,602 +5.4% | $2,106,090 |
| 2024 | $30,938 +13.4% | $2,106,090 +36% |
| 2023 | $27,276 +2.2% | $1,548,890 |
| 2022 | $26,687 +2.3% | $1,548,890 |
| 2021 | $26,083 +3.1% | $1,548,890 |
| 2020 | $25,293 -0.9% | $1,548,890 |
| 2019 | $25,510 -12.3% | $1,548,890 -14.4% |
| 2018 | $29,097 -0.5% | $1,809,500 |
| 2017 | $29,242 +2.5% | $1,809,500 |
| 2016 | $28,536 +2.7% | $1,809,500 |
| 2015 | $27,776 +2.3% | $1,809,500 |
| 2014 | $27,161 +3.9% | $1,809,500 -8.8% |
| 2013 | $26,140 +3.9% | $1,984,850 |
| 2012 | $25,168 +3.9% | $1,984,850 |
| 2011 | $24,215 +3.9% | $1,984,850 |
| 2010 | $23,302 +3.3% | $1,984,850 |
| 2009 | $22,568 +10.4% | $1,984,850 +41.2% |
| 2008 | $20,448 +29.3% | $1,405,390 +23.3% |
| 2007 | $15,815 +3.5% | $1,140,230 |
| 2006 | $15,279 -28% | $1,140,230 -30% |
| 2005 | $21,208 +55.6% | $1,628,900 +42.9% |
| 2004 | $13,626 +25.5% | $1,140,230 +37.2% |
| 2003 | $10,855 -6.8% | $831,180 |
| 2001 | $11,653 +7.4% | $831,180 -30% |
| 2000 | $10,855 +4.9% | $1,187,400 +103.4% |
| 1999 | $10,344 | $583,770 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$26,097/mo
Principal & interest
$20499
Property taxes
$5598
More affordability tools
Climate risks
Neighborhood: 06820
Nearby schools
GreatSchools rating
- 9/10Ox Ridge Elementary SchoolGrades: PK-5Distance: 0.6 mi
- 9/10Middlesex Middle SchoolGrades: 6-8Distance: 2.2 mi
- 10/10Darien High SchoolGrades: 9-12Distance: 1.4 mi
Schools provided by the listing agent
- Elementary: Ox Ridge
- Middle: Middlesex
- High: Darien
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Local experts in 06820
- Connecticut
- Fairfield County
- Darien
- 06820
- 28 Crooked Mile Road
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