27 Tory Hole Road

Closed 10/23/20
Closed 10/23/20
Facade
Front Entry
Front Entry
Rear Exterior
Foyer Virtually Enhanced
Circular Stairway
Living Room fireplace
LR Virtually Staged
Details of limestone FP & aluminum trim
Dining Room
Dining Room virtullystaged
IMG_9768
Vestibule
27 Tory Hole-4
27 Tory Hole-2
Master Bath
Secondary ensuite bedroom
View of house from pond
Facade
Front Door
Rear exterior
Open Floor Plan
Sold
Last Sold Price
$1,962,500
4 beds4,035 sqft
27 Tory Hole Rd, Darien, CT 06820
Single FamilyProperty Type
5.47 acresLot Size
1938Year Built
$486/sq ftPrice per sq ft
$1,000/yrHOA Fees
2 carsParking Spaces

Description

ARCHITECTURALLY SIGNIFICANT designed by Arthur Holden who collaborated with Frank Lloyd Wright on the design of the Guggenheim Museum. This oversized property in prestigious Delafield Island offers privacy within minutes to beaches, downtown Darien and an hour to New York City. The curved walls capture exceptional light and provide great fluidity and views of the garden. The house features original high quality details and finishes. It embodies the elegance and sophistication of 1930's glamour while...ARCHITECTURALLY SIGNIFICANT designed by Arthur Holden who collaborated with Frank Lloyd Wright on the design of the Guggenheim Museum. This oversized property in prestigious Delafield Island offers privacy within minutes to beaches, downtown Darien and an hour to New York City. The curved walls capture exceptional light and provide great fluidity and views of the garden. The house features original high quality details and finishes. It embodies the elegance and sophistication of 1930's glamour while including the space and functionality to support a new generation of modern living.
  • Listed by: Inger Stringfellow • WILLIAM PITT SOTHEBY'S INTL. (NCA)
Listing closed: 10/23/2020 12:00 AM • Source: DARIEN MLS, MLS#: 34737

Recent comparable sales

Median sold price

$2,400,000

Avg days on market

18

Sale-to-list ratio

106.3%

Darien, CT

9 comparable properties found

$1,850,000 | 1745 Post Road, Darien, CT 06820
1

$1,850,000

Sold 07/31/25

4
Bedrooms
3,540
Square Feet
1.04
Acres

1745 Post Road, Darien, CT 06820

$2,440,000 | 45 Brookside Road, Darien, CT 06820
2

$2,440,000

Sold 06/25/25

4
Bedrooms
3,618
Square Feet
0.79
Acres

45 Brookside Road, Darien, CT 06820

a front view of a house with a garden
3

$2,500,000

Sold 08/04/26

4
Bedrooms
3,609
Square Feet
0.2
Acres

11 Walmsley Road, Darien, CT 06820

$2,150,000 | 178 Christie Hill Road, Darien, CT 06820
4

$2,150,000

Sold 07/31/25

4
Bedrooms
3,436
Square Feet
2.86
Acres

178 Christie Hill Road, Darien, CT 06820

$2,400,000 | 85 Hecker Avenue, Darien, CT 06820
5

$2,400,000

Sold 07/31/26

4
Bedrooms
3,547
Square Feet
0.23
Acres

85 Hecker Avenue, Darien, CT 06820

$2,400,000 | 10 McLaren Road South, Darien, CT 06820
6

$2,400,000

Sold 12/12/24

4
Bedrooms
3,183
Square Feet
0.64
Acres

10 McLaren Road South, Darien, CT 06820

$2,750,000 | 31 Pleasant Street, Darien, CT 06820
7

$2,750,000

Sold 07/03/25

4
Bedrooms
4,229
Square Feet
0.33
Acres

31 Pleasant Street, Darien, CT 06820

8

$2,200,000

Sold 12/12/25

4
Bedrooms
3.5
Bathrooms
3,860
Square Feet
1.05
Acres

9 Red Coat Pass, Darien, CT 06820

a house that has a lot of plants in it
9

$3,425,000

Sold 06/30/26

4
Bedrooms
3,560
Square Feet
1.11
Acres

53 Goodwives River Road, Darien, CT 06820

Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of WILLIAM PITT SOTHEBY'S INTL. (NCA), Inger Stringfellow

Sold By Brown Harris Stevens, NANCY DAUK

Add your commute

Payment Calculator

Get preapproved with Rocket Mortgage1

$12,414 per month

30 year fixed, 6.71% Interest

Principal and Interest

$10,141

Property Taxes

$2,190

HOA Dues

$83

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 27 Tory Hole Road

Property Details
  • Taxes: $26,274 / year
  • MLS Type: Residential
  • County: Fairfield County
  • Town: Darien
  • Sub-Area: Delafield Island
  • Style: Other
  • Basement: Full
  • Garage #: 2
  • Garage Description: Under
  • Pool: No
  • Pool Description: None
Building Information
  • Stories: 3
  • Year Built: 1938
  • Lot Size: 5.47 AC / 238,273 SF
Summary
Location and General Information
  • Directions: Map quest
  • Miles to Station: 1.5
  • Elementary School: Tokeneke
  • Middle School: Middlesex
  • High School: Darien
  • Equipment Included: Cable TV Conn, Washer, Self Clean Oven, Refrigerator, Microwave, Freezer, Dryer, Dishwasher, Cooktop, Ceiling Fan
  • Handicap Access: No
  • House Color: White
  • Mill Rate: $16
  • Possession: Negotiable
  • Property Also for Rent: No
Parking
  • Garage: Under
Virtual Tour
Property
Lot Information
  • Lot Description: Some Wetlands, Secluded, Lightly Wooded, Treed
  • Parcel Number: 06517
  • Waterfront: No
  • Zoning: R-1
Property and Assessments
  • Assessed Value: $1,941,940
  • Assessment - Building: $614,600
  • Assessment - Land: $1,327,340
  • Amenities: Deck, Pond, Wet Bar, Terrace, Shed, Lawn Sprinkler
  • SqFt Source: Town
  • Water: Public Connected
  • Wetlands: Partial
  • Year Renovated: 1998
Utilities
  • Cooling: Central Air
  • Air Conditioning: Central
  • Heat Zone: 3
  • Heating: Radiator, Steam
  • Water Heater: Boiler
  • Fuel: Oil
  • Sewer: Septic
  • Cable: Yes
Interior and Exterior Features
Exterior Features
  • Exterior: Stucco
  • Exterior Features: Balcony, Garden
  • Porch: None
  • Swimming Pool: None
Interior Features
  • Exclusions: Wall system shelving in guest room
  • Rooms: 9
  • Living Room: Fireplace
  • Living Room: Dimensions: 33x17
  • Bedroom 2: Built-Ins, Upper, Full Bath
  • Bedroom 2: Dimensions: 16x14
  • Bedroom 3: Built-Ins, Upper, Full Bath
  • Bedroom 3: Dimensions: 17x14
  • Bedroom 4: First, Full Bath
  • Bedroom 4: Dimensions: 18x12
  • Dining Room: Bay
  • Dining Room: Dimensions: 19x15
  • Family Room: Book Shelves, Lower Level
  • Family Room: Dimensions: 13x22
  • Baths: First Floor Full Baths: 1
  • Baths: First Floor Half Baths: 1
  • Baths: Second Floor Full Baths: 3
  • Kitchen: Eat-In, Remodeled, Island
  • Kitchen: Dimensions: 28x17
  • Laundry Location: Lower
  • Additional Rooms: Office
  • Additional Rooms: Office Dimensions: 15x12
  • Flooring: Carpet, Hardwood, Tile, Slate, Other
  • Interior Features: Balcony, Wet Bar, Workshop, Foyer, Ceiling Fan
  • Roof: Other
  • Walls: Plaster
  • Windows: Partial, Storm, Thermal, Screens
  • Additional SqFt: 500.0
  • Addl Exterior Feats: Deck, Terrace
  • Appliances Included: Cooktop, Wall Oven, Washer, Microwave, Refrigerator, Freezer, Dryer, Dishwasher
  • Attic: None
  • Basement Finish: Partial Finished
Room Information
Room 1
  • Room Type: Living Room
  • Room Level: 1
  • Level: 1
  • length: FP
  • width: Walk Out
  • area: Built-Ins
Room 2
  • Room Type: Dining Room
  • Room Level: 1
  • Level: 1
Room 3
  • Room Type: Kitchen
  • Room Level: 1
  • Level: 1
  • length: Eat In
  • width: Island
  • area: Walk Out
Room 4
  • Room Type: Bedroom 4
  • Room Level: 1
  • Level: 1
Room 5
  • Room Type: Primary Bedroom
  • Room Level: 2
  • Level: 2
  • length: Bath
  • width: FP
  • area: Balcony
Room 6
  • Room Type: Bedroom 2
  • Room Level: 2
  • Level: 2
  • length: Bath
Room 7
  • Room Type: Bedroom 3
  • Room Level: 2
  • Level: 2
  • length: Bath
  • width: Built-Ins
Room 8
  • Room Type: Office
  • Room Level: 2
  • Level: 2
  • length: Built-Ins
Room 9
  • Room Type: Media Room
  • Room Level: L
  • Level: L
  • length: Built-Ins
Multi Family
Multi-Family Information
  • Oil Tank: In Ground

Property History for 27 Tory Hole Road

DateEvent & SourcePriceAppreciation
Sep 18, 1992

Closed (Public Record)

Public Record #90945805

$1,185,000—
DateEvent & SourcePrice
09/18/1992

Closed (Public Record)

Public Record #90945805

$1,185,000

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

Public Records for 27 Tory Hole Road

Taxable ValueLand$1,296,680Additions$646,520Total$1,943,200
Tax Record2025$30,081 ($2,507 / month)
Home Facts
Beds4Baths4.5Total Finished SqFt4,453 SqFtAbove Grade Finished SqFt4,453 SqFtUnfinished Basement SqFt447 SqFtStories2Lot Size238,273 SqFtStyleSingle Family ResidenceYear Built1938Year Renovated1938ZoningR-1CountyWESTERN CONNECTICUTAPNDARI M:63 B:52A

Schools near 27 Tory Hole Road

This home is within Darien School District.
Rating
School
Type
Grades
Distance
Tokeneke Elementary School
Public - PK to 5
Middlesex Middle School
Public - 6 to 8
Darien High School
Public - 9 to 12
Rating
School
Distance
Tokeneke Elementary School
PublicPK to 5

Middlesex Middle School
Public6 to 8

Darien 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.

Neighborhood Map and Transit

Similar Homes

New listings in 06820

$1,895,000 | 13 Chestnut Street, Darien, CT 06820
1/32
Open: 9/19 01:00PM - 03:00PMVirtual Tour

$1,895,000

4
Bedrooms
2,303
Square Feet
0.36
Acres

13 Chestnut Street, Darien, CT 06820

$3,825,000 | 21 Harbor Road, Darien, CT 06820
1/32
Open: 9/19 12:30PM - 03:30PMNew

$3,825,000

5
Bedrooms
4,400
Square Feet
1
Acres

21 Harbor Road, Darien, CT 06820

$2,895,000 | 30 Birch Road, Darien, CT 06820
1/34
New

$2,895,000

4
Bedrooms
4,080
Square Feet
1.02
Acres

30 Birch Road, Darien, CT 06820

$2,195,000 | 14 Edgerton Street, Darien, CT 06820
1/28

$2,195,000

4
Bedrooms
3,104
Square Feet
0.22
Acres

14 Edgerton Street, Darien, CT 06820

$2,095,000 | 103 West Avenue, Darien, CT 06820
1/29
Listed By CompassOpen: 9/19 01:00PM - 03:00PM

$2,095,000

5
Bedrooms
3,543
Square Feet
0.4
Acres

103 West Avenue, Darien, CT 06820

$3,595,000 | 31 Hancock Lane, Darien, CT 06820
1/40
Virtual Tour

$3,595,000

3
Bedrooms
4,733
Square Feet
1.51
Acres

31 Hancock Lane, Darien, CT 06820

$1,200,000 | 145 West Avenue, Darien, CT 06820
1/25
Open: 9/20 02:00PM - 04:00PM

$1,200,000

3
Bedrooms
1,974
Square Feet
0.23
Acres

145 West Avenue, Darien, CT 06820

a view of a white house in front of a big yard with plants and large trees
1/38
Listed By Compass

$3,925,000

4
Bedrooms
4,093
Square Feet
0.52
Acres

20 Lighthouse Way, Darien, CT 06820

$5,995,000 | 67 Peach Hill Road, Darien, CT 06820
1/40

$5,995,000

6
Bedrooms
8,068
Square Feet
2.15
Acres

67 Peach Hill Road, Darien, CT 06820

Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 27 Tory Hole Road, Darien, CT 06820
$1,962,500
4
4,035
238,273
23 Red Coat Pass, Darien, CT 06820
$2,525,000
4
5,757
50,094
9 Morley Lane, Darien, CT 06820
$445,000
4
7
5,124
48,217
2 Morley Lane, Darien, CT 06820
$2,350,000
5
4,009
43,560
33 Tory Hole Road, Darien, CT 06820
$2,525,000
4
3,629
50,529
4 Morley Lane, Darien, CT 06820
$620,000
4
3.5
2,828
45,738

Explore Nearby Homes

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 INTL. (NCA), Inger Stringfellow

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.