Sold
Last Sold Price
4 beds4,184 sqft$502/sqft
5 Crooked Mile Rd, Westport, CT 06880
Single FamilyProperty Type
2.08 acresLot Size
1930Year Built
$502/sq ftPrice per sq ft
4 carsParking Spaces

Description

Exquisite Country Home With Magnificent Gardens. Pool/Spa Onthe Saugatuck River. Waterfall, Foot Bridge. Totally Privatecompletely Renovated - Elegant Decor.Exquisite Country Home With Magnificent Gardens. Pool/Spa Onthe Saugatuck River. Waterfall, Foot Bridge. Totally Privatecompletely Renovated - Elegant Decor.
  • Listed by: Nancy Dolan 203.258.2303 ndolan@williampitt.com • William Pitt Sotheby's Int'l
Listing closed: 10/07/1999 12:00 AM • Source: SMARTMLS, MLS#: 98048096

Recent comparable sales

Median sold price

$2,365,000

Avg days on market

36

Sale-to-list ratio

100.6%

Westport, CT

9 comparable properties found

a front view of a house with a yard
1

$2,418,000

Sold 06/30/26

4
Bedrooms
4,554
Square Feet
2.04
Acres
$1,635,000 | 12 Crooked Mile Road, Westport, CT 06880
2

$1,635,000

Sold 08/18/25

4
Bedrooms
3,664
Square Feet
1.31
Acres
a living room with furniture and a fireplace
3

$2,035,000

Sold 01/14/26

4
Bedrooms
3,716
Square Feet
0.51
Acres
$2,365,000 | 44 Charcoal Hill Road, Westport, CT 06880
4

$2,365,000

Sold 05/30/25

4
Bedrooms
3,900
Square Feet
1.82
Acres
a view of a house with a yard
5

$2,375,000

Sold 04/23/26

4
Bedrooms
4,013
Square Feet
2.07
Acres
$1,808,000 | 9 Marilane, Westport, CT 06880
6

$1,808,000

Sold 09/23/24

4
Bedrooms
4,394
Square Feet
1.07
Acres
$2,400,000 | 24 Blue Ribbon Drive, Westport, CT 06880
7

$2,400,000

Sold 07/30/26

4
Bedrooms
3,584
Square Feet
1
Acres
$2,150,000 | 4 Cardinal Lane, Westport, CT 06880
8

$2,150,000

Sold 08/05/26

4
Bedrooms
4,651
Square Feet
2.02
Acres
$2,591,000 | 6 Weathervane Hill, Westport, CT 06880
9

$2,591,000

Sold 08/07/25

4
Bedrooms
4,771
Square Feet
1.07
Acres

Location

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Payment Calculator

$11,477 per month

30 year fixed, 6.55% Interest

Principal and Interest

$10,674

Property Taxes

$803

HOA Dues

$0

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Property Information for 5 Crooked Mile Road

Property Details
  • Taxes: $9,635 / year
  • MLS Type: Residential
  • Basement Description: Garage Access, Interior Access, Partial, Sump Pump, Unfinished
  • Direct Waterfront: No
  • Garages Number: 4
  • Style: Colonial
  • Garage Parking Info: Attached Garage, Detached Garage
  • Swimming Pool: Yes
Building Information
  • Year Built: 1930
  • Lot Size: 2.08 AC / 90,604 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Newtown Tpke. Or Calvary To Crooked Mile
  • Elementary School: PBED
  • High School: STAPLES
  • Latitude: 41.178898
  • Longitude: -73.37855
  • Middle Jr High School: PBED
  • State: Connecticut
HOA and Fees
  • HOA Fee Amount: 0
  • Home Owner's Assocation: No
  • Property Tax: $9,635
Virtual Tour
  • Virtual Tour: No
Interior and Exterior Features
Exterior Features
  • Exterior Features: Barn, Deck, Hot Tub, Lighting, Patio, Porch, Shed, Underground Sprinkler
  • Pool Description: In Ground Pool
  • Waterfront Description: Frontage, River, Direct Waterfront
Interior Features
  • Appliances Included: Compactor, Dishwasher, Oven/Range, Refrigerator
  • Cooling System: Central Air, Zoned
  • Heat Type: Baseboard, Hot Air, Radiator, Zoned
  • Attic YN: No
  • Fireplaces Total: 3
  • Interior Features: Security System
  • Laundry Room Location: First Floor
  • Rooms Additional: Foyer, Laundry Room
  • Room Count: 9
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Level: Upper
  • Room Type: Bedroom
Room 2
  • Room Entry Order: 10
  • Room Features: Full Bath
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 3
  • Room Entry Order: 2
  • Room Level: Upper
  • Room Type: Bedroom
Room 4
  • Room Entry Order: 3
  • Room Level: Upper
  • Room Type: Bedroom
Room 5
  • Room Entry Order: 5
  • Room Features: Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Den
Room 6
  • Room Entry Order: 6
  • Room Features: Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 7
  • Room Entry Order: 7
  • Room Features: Stone Floor
  • Room Level: Main
  • Room Type: Family Room
Room 8
  • Room Entry Order: 8
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Kitchen
Room 9
  • Room Entry Order: 9
  • Room Features: Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Property
Property and Assessments
  • Color: TAUPE
  • Exterior Siding: Clapboard
  • Foundation Type: Masonry
  • Gross SQFT Per Public Records: 8553
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Sq Ft Source: Public Records
  • Year Built: 1930
  • Year Built Source: Public Records
  • Living Area SQFT Per Public Records: 4133
Lot Information
  • Documents Available: Property Disclosure
  • Parcel Number: 414862
  • Sq Ft Est Heated Above Grade: 4184.0
  • Sq Ft Total: 4184.0
  • Zoning: 1A
Utilities
  • Energy Features: Storm Doors, Storm Windows
  • Heat Fuel Type: Electric, Oil, Propane
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Total Unit Count: 0

Property History for 5 Crooked Mile Road

DateEvent & SourcePriceAppreciation
Aug 20, 1993

Closed (Public Record)

Public Record #91306391

$1,050,000
DateEvent & SourcePrice
08/20/1993

Closed (Public Record)

Public Record #91306391

$1,050,000

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

Public Records for 5 Crooked Mile Road

Taxable ValueLand$444,300Additions$616,400Total$1,060,700
Tax Record2024$20,005 ($1,667 / month)
Home Facts
Beds4Baths3.5Total Finished SqFt4,133 SqFtAbove Grade Finished SqFt4,133 SqFtUnfinished Basement SqFt1,210 SqFtStories2Lot Size90,605 SqFtStyleSingle Family ResidenceYear Built1930Year Renovated1930ZoningAACountyWESTERN CONNECTICUTAPNWPRT M:B16 L:028-000

Schools near 5 Crooked Mile Road

This home is within Westport School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Coleytown Elementary School
PublicK to 5

Coleytown Middle School
Public6 to 8

Staples 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.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 5 Crooked Mile Road, Westport, CT 06880
$2,100,000
4
4,184
90,604
$610,000
4
3,608
43,560
$1
4
3
3,310
43,560
$625,000
4
2,676
46,173
$576,500
4
3,902
43,560
$1,043,000
4
3,867
46,609

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.

Listing Courtesy of William Pitt Sotheby's Int'l, Nancy Dolan

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.