27 Macedonia Brook Road

Closed 7/10/25
Closed 7/10/25
Gallery Image 1
Sold
Last Sold Price
$6,700,000
5 beds7,632 sqft$878/sqft
27 Macedonia Brook Rd, Kent, CT 06757
Single FamilyProperty Type
41.33 acresLot Size
1827Year Built
$878/sq ftPrice per sq ft
4 carsParking Spaces

Description

A truly rare opportunity to own “Dragonfly Farm”, one of the most unique estates in New England which has been featured in House & Garden and many architectural books. The estate compound began in the 1700s with the construction of the mill and the millkeeper's house (which now serves as the guest house). The Federal style stone house was added to the property in the early 19th century. In the 20th century, this main house was expanded by owner and architect Heathcote Woolsey. It was then owned by...A truly rare opportunity to own “Dragonfly Farm”, one of the most unique estates in New England which has been featured in House & Garden and many architectural books. The estate compound began in the 1700s with the construction of the mill and the millkeeper's house (which now serves as the guest house). The Federal style stone house was added to the property in the early 19th century. In the 20th century, this main house was expanded by owner and architect Heathcote Woolsey. It was then owned by the Hammerstein family (of Rogers & Hammerstein fame). The current compound includes the 5 bedroom residence, 2 bedroom guest house, antique barn, office/gym/game room complex above the 4+ car garage, caretaker's house and a stone cabana. Unique features of the main house include a gracious foyer w/ curving staircase, dining room w/ opposing fireplaces, vaulted kitchen w/ stone walls/opposing fireplaces/hand hewn beams & a stunning solarium/family room. Leisure time will find you enjoying tennis, soccer, basketball, golf chipping, archery & the gunite heated pool.
  • Listed by: Stacey Matthews 203.671.9067 stacey.matthews@raveis.com • W. Raveis Lifestyles Realty
Listing closed: 07/10/2025 12:00 AM • Source: SMARTMLS, MLS#: 170577139

Recent comparable sales

Median sold price

$1,300,000

Avg days on market

71

Sale-to-list ratio

95.8%

Kent, CT

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$2,075,000 | 221 Fuller Mountain Road, Kent, CT 06757
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Location

Listing Courtesy of W. Raveis Lifestyles Realty, Stacey Matthews

Sold By William Pitt Sotheby's Int'l, Diana Bisselle

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$40,435 per month

30 year fixed, 6.55% Interest

Principal and Interest

$34,055

Property Taxes

$6,380

HOA Dues

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Property Information for 27 Macedonia Brook Road

Property Details
  • Taxes: $76,559 / year
  • MLS Type: Residential
  • County: Litchfield County
  • Basement Description: Unfinished
  • Direct Waterfront: Yes
  • Garages Number: 4
  • Neighborhood: Macedonia
  • Style: Colonial
  • Garage Parking Info: Attached Garage
  • Swimming Pool: Yes
Building Information
  • Year Built: 1827
  • Lot Size: 41.33 AC / 1,800,334 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Association Amenities: None
  • Directions: From Kent Center, Rt 341 to Macedonia Brook Rd to # 27 on left.
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.744699
  • Longitude: -73.495318
  • Middle Jr High School: Per Board of Ed
  • Neighborhood Amenities: Golf Course, Lake, Library, Playground/Tot Lot, Private School(s), Stables/Riding
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Special Association Assessment: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $76,559
Interior and Exterior Features
Exterior Features
  • Exterior Features: Barn, Cabana, French Doors, Garden Area, Guest House, Stone Wall, Tennis Court, Terrace
  • Pool Description: Pool House, Lap Pool, Heated, Safety Fence, Gunite
  • Waterfront Description: Brook
Interior Features
  • Appliances Included: Gas Cooktop, Wall Oven, Subzero, Wine Chiller
  • Attic Description: Walk-up, Finished
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 7
  • Rooms Additional: Exercise Room, Foyer, Laundry Room, Solarium, Staff Quarters
  • Room Count: 5
  • Rooms Total: 12
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 2
  • Room Entry Order: 2
  • Room Features: Full Bath
  • Room Level: Upper
  • Room Type: Bedroom
Room 3
  • Room Entry Order: 3
  • Room Level: Upper
  • Room Type: Bedroom
Room 4
  • Room Entry Order: 4
  • Room Level: Upper
  • Room Type: Bedroom
Room 5
  • Listing Key: FE5642F018F74F41E0531401100A010A
  • Room Entry Order: 5
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: stone
  • Construction Description: Stone
  • Driveway Type: Private
  • Exterior Siding: Stone
  • Foundation Type: Stone
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Wood Shingle
  • Year Built: 1827
  • Year Built Source: Owner
  • Bank Owned Property: No
  • In Law Apartment: Possible
  • Sq Ft Est Heated Below Grade: 0
  • Living Area SQFT Per Public Records: 0
Lot Information
  • Lot Description: Additional Land Avail., Some Wetlands, Water View, Professionally Landscaped
  • Parcel Number: 1942515
  • Sq Ft Est Heated Above Grade: 7632.0
  • Sq Ft Total: 7632.0
  • Zoning: Res
Utilities
  • Energy Features: Generator Ready
  • Heat Fuel Type: Oil
  • Hot Water Description: Electric
  • Radon Mitigation Air: Unknown
  • Radon Mitigation Water: Unknown
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 27 Macedonia Brook Road

DateEvent & SourcePriceAppreciation
Jul 10, 2025

Closed (Public Record)

Public Record #1908625587

$6,700,000

+0.9% / yr

Jul 2, 2002

Closed (Public Record)

Public Record #101708496

$5,400,000—
DateEvent & SourcePrice
07/10/2025

Closed (Public Record)

Public Record #1908625587

$6,700,000

+0.9% / yr

07/02/2002

Closed (Public Record)

Public Record #101708496

$5,400,000

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

Public Records for 27 Macedonia Brook Road

Taxable ValueLand$688,000Additions$3,850,200Total$4,538,200
Tax Record2025$76,559 ($6,380 / month)
Home Facts
Beds0Lot Size1,800,335 SqFtStyleMiscellaneous ResidentialCountyNORTHWEST HILLSAPNKENT M:0003 B:0005 L:17

Schools near 27 Macedonia Brook Road

This home is within Regional School District 01.
Rating
School
Type
Grades
Distance
Kent Center School
Public - PK to 8
Housatonic Valley Regional High School
Public - 9 to 12
Selc
Public - 6 to 8
Kent School
Private - 9 to 12
Rating
School
Distance
Kent Center School
PublicPK to 8

Housatonic Valley Regional High School
Public9 to 12

Selc
Public6 to 8

Kent School
Private9 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: 27 Macedonia Brook Road, Kent, CT 06757
$6,700,000
5
7,632
1,800,334
61 Macedonia Brook Road, Kent, CT 06757
–
4
1
1,596
267,023
162 A Macedonia Road, Kent, CT 06757
$430,000
3
1,988
78,408
19 Macedonia Brook Road, Kent, CT 06757
–
3
2.5
2,132
53,579
15 Macedonia Brook Road, Kent, CT 06757
$498,500
3
1.5
2,038
61,855
162 B Macedonia Road, Kent, CT 06757
$346,000
3
3.5
2,292
108,900

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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 W. Raveis Lifestyles Realty, Stacey Matthews

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.