27 Macedonia Brook Road, Kent, CT 06757 - Photo 1

1/1

$6,700,000

Sold
Closed
Single Family
5 Beds
4 Full Baths
1 Partial Bath
7,632 Sq. Ft.
4 Car Garage

1/1

Property 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 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.

Full Property Details

Full Property Details for 27 Macedonia Brook Rd

General

Sold For: $6,700,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 170577139
Added to Site: 949 day(s) ago

Interior

Number of Rooms: 12
Rooms/Areas: Exercise Room, Foyer, Laundry Room, Solarium, Staff Quarters
Fireplace: Yes
Number of Fireplaces: 7
Appliances: Gas Cooktop, Wall Oven, Subzero, Wine Chiller

Rooms

Bathrooms

Total Bathrooms: 5
Full Bathrooms: 4
Half Bathrooms: 1

Bedrooms

Total Bedrooms: 5
Primary Bedroom: Primary Bedroom - 9 ft+ Ceilings, Main
Bedroom 1: Bedroom - Full Bath, Upper
Bedroom 2: Bedroom, Upper
Bedroom 3: Bedroom, Upper
Bedroom 4: Bedroom, Upper

Additional Information

Shared Amenities: None
Pool: Yes
Pool Description: Pool House, Lap Pool, Heated, Safety Fence, Gunite

Exterior

Exterior Features: Barn, Cabana, French Doors, Garden Area, Guest House, Stone Wall, Tennis Court, Terrace
Color: stone

Parking

Garage: Yes
Attached garage: Yes
Garage Spaces: 4
Parking: Attached Garage

Location

County: Litchfield
Neighborhood: Macedonia
Driving Directions: From Kent Center, Rt 341 to Macedonia Brook Rd to # 27 on left.

School Information

Elementary School: Per Board of Ed
Middle School: Per Board of Ed
High School: Per Board of Ed

Community

Community Name: Macedonia

Heating & Cooling

Cooling Type: Central Air
Heating Type: Hot Air, Oil
Heating Fuel: Oil
Water Heater: Electric

Utilities

Sewer: Septic
Water: Private Well

Structural Information

Architectural Style: Colonial
Construction Status: No/Resale
Exterior Const.: Stone
Basement Desc.: Unfinished
Roof: Wood Shingle
Attic: Yes
Square Feet: 7,632
Above Ground: 7,632 Sq. Ft.
Year Built: 1827

Lot Features

Lot Size (Acres): 41.33
Driveway/Sidewalk: Private
Zoning: Res
Lot Description: Additional Land Avail., Some Wetlands, Water View, Professionally Landscaped

Water Features

Water Front: Yes
Water View: Yes
Water Front Desc.: Brook

Green Features

Energy Features: Generator Ready

Financial Considerations

Assessment Amount: $4,538,200
Tax Year: July 2025-June 2026

Disclosures and Reports

Property ID: 1942515

Listed by W. Raveis Lifestyles Realty, Stacey Matthews
Sold by William Pitt Sotheby's Int'l, THE LEGACY TEAM AT WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, Diana Bisselle

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Listing agent

— 27 Macedonia Brook Rd —

Stacey Matthews

W. Raveis Lifestyles Realty

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Schools

Schools serving 27 Macedonia Brook Rd

School Districts:Kent School District, Regional High School District 01

Name	Grades	Distance
Kent Center School 9 Judd Avenue, Kent, CT 06757	PK-8	1.6 mi
Housatonic Valley Regional High School 246 Warren Turnpike Rd., Canaan, CT 06031	9-12	14.9 mi

Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 27 Macedonia Brook Rd

Date

Details

Price

Change

Source

7/10/2025

Sold

$6,700,000

-2.9%

MLS

12/14/2024

Price Increased

$6,900,000

6.24%

MLS

4/12/2024

Price Reduced

$6,495,000

-7.15%

MLS

6/17/2023

Listed

$6,995,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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27 Macedonia Brook Road, Kent, CT 06757 (MLS# 170577139) is a Single Family property that was sold at $6,700,000 on July 10, 2025. Want to learn more about 27 Macedonia Brook Road? Do you have questions about finding other Single Family real estate for sale in Kent? You can browse all Kent real estate or contact a Coldwell Banker agent to request more information.

27 Macedonia Brook Rd Kent, CT 06757