$6,700,000
SOLD JUL 10, 2025

27 Macedonia Brook Rd Kent, CT 06757

5 Beds
4.5 Baths
7,632 Sq Ft
41.33 Acres

Recently Sold

$878 Per Sq Ft

4% Below List Price

736 Days on Market

Highlights

  • Guest House
  • Barn
  • Pool House
  • Kent Center School Rated A
  • Tennis Courts
  • Sub-Zero Refrigerator

About This Home

As of July 2025

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.

Last Agent to Sell the Property

Stacey Matthews

W. Raveis Lifestyles Realty License #REB.0794294 Listed on: 06/17/2023

Last Buyer's Agent

Diana Bisselle

William Pitt Sotheby's Int'l License #RES.0799072

William Pitt Sotheby's Int'l

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $76,559

Year Built

  • Built in 1827

Lot Details

  • 41.33 Acre Lot
  • Home fronts a stream
  • Stone Wall
  • Garden

Home Design

  • Colonial Architecture
  • Stone Foundation
  • Stone Frame
  • Wood Shingle Roof
  • Stone Siding
  • Stone

Interior Spaces

  • 7,632 Sq Ft Home
  • 7 Fireplaces
  • French Doors
  • Entrance Foyer
  • Solarium
  • Home Gym
  • Laundry Room
  • Unfinished Basement

Kitchen

  • Built-In Oven
  • Gas Cooktop
  • Sub-Zero Refrigerator
  • Wine Cooler

Bedrooms and Bathrooms

  • 5 Bedrooms
  • Maid or Guest Quarters

Attic

  • Walkup Attic
  • Finished Attic

Parking

  • 4 Car Garage
  • Private Driveway

Pool

  • Pool House
  • Cabana
  • Heated Lap Pool
  • Gunite Pool
  • Fence Around Pool

Outdoor Features

  • Tennis Courts
  • Terrace

Utilities

  • Central Air
  • Heating System Uses Oil
  • Power Generator
  • Private Company Owned Well
  • Electric Water Heater
  • Fuel Tank Located in Basement

Additional Features

  • Guest House
  • Property is near a golf course
  • Barn

Listing and Financial Details

  • Assessor Parcel Number 1942515

Home Details

Home Type

Single Family

Est. Annual Taxes

$76,559

Year Built

Built in 1827

Lot Details

0

Listing Details

  • Neighborhood: Macedonia
  • Property Type: Single Family For Sale
  • Style: Colonial
  • Sq Ft Est Heated Above Grade: 7632
  • Total Sq Ft: 7632
  • Year Built: 1827
  • New Construction: No/Resale
  • Nearby Amenities: Golf Course, Lake, Library, Playground/Tot Lot, Private School(s), Stables/Riding
  • Association Amenities: None
  • Remarks Public Addendum: When you are ready for a break from all that fun, the remnants of the original mill provide a welcome respite w/ a covered perch above the roaring brook (yes fishing!) Distinctive perennial & cutting gardens surround the bldgs & a sunny field across the brook hosts an extensive fenced vegtable garden. Structures are connected by stone terraces, stone walls & covered brick pathways. Macedonia St Park (2300 acres) and Pond Mountain (800 acres) are just up the road w/ miles of spectacular hiking/riding trails which also abut the Appalacian Trail. Kent is one of the most charming historic towns in CT, with chic shops & plentiful fine dining options. Train stop from Grand Central is 10 minutes from house. 1 hr 45 min drive to NYC. Addl land avail. Suitable for horses.
  • Direct Waterfront: Yes
  • Home Warranty Offered: No
  • Radon Mitigation Air Ynu: Unknown
  • Radon Mitigation Water Ynu: Unknown
  • Directions: From Kent Center, Rt 341 to Macedonia Brook Rd to # 27 on left.
  • Financing Used: Withheld
  • In Law Apartment: Possible
  • Spec Assoc Asses: No
  • Street Type: Road
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Room Count: 5
  • Total Bedrooms: 5
  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Fireplaces: 7
  • Attic Description: Walk-up, Finished
  • Basement Description: Unfinished
  • Appliances: Gas Cooktop, Wall Oven, Subzero, Wine Chiller
  • Additional Rooms: Exercise Room, Foyer, Laundry Room, Solarium, Staff Quarters
  • Attic: Yes

Exterior Features

  • Exterior Features: Barn, Cabana, French Doors, Garden Area, Guest House, Stone Wall, Tennis Court, Terrace
  • Exterior Siding: Stone
  • Foundation Type: Stone
  • Roof Information: Wood Shingle
  • Waterfront Description: Brook
  • Swimming Pool: Yes
  • Pool: Pool House, Lap Pool, Heated, Safety Fence, Gunite
  • Construction Description: Stone

Garage/Parking

  • Garages Number: 4
  • Driveway Type: Private
  • Garage And Parking: Attached Garage

Utilities

  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Heat Fuel Type: Oil
  • Fuel Tank Location: In Basement
  • Hot Water Description: Electric
  • Water Source: Private Well
  • Sewer: Septic

Green Features

  • Energy Features: Generator Ready

Lot Info

  • Acres: 41.33
  • Lot Description: Additional Land Avail. Some Wetlands Water View Professionally Landscaped
  • Zoning: Res
  • Parcel #: 1942515

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 76559

MLS Schools

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

Ownership History

Date Name Owned For Owner Type

Purchase Details

Listed on
Jun 17, 2023
Closed on
Jul 10, 2025
Sold by
Keswin Jeffrey A and Keswin Erica
Bought by
Barney Hefner House T and Barney Ambrosino
Seller's Agent
Stacey Matthews
W. Raveis Lifestyles Realty
Buyer's Agent
Diana Bisselle
William Pitt Sotheby's Int'l
List Price
$6,995,000
Sold Price
$6,700,000
Premium/Discount to List
-$295,000
-4.22%
Views
759
Current Estimated Value
$6,827,393

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
$127,393
Avg. Annual Appreciation
5.37%

Purchase Details

Closed on
Jul 2, 2002
Sold by
Levine Richard L and Levine Lark Navez
Bought by
Keswin Jeffrey A and Keswin Erica
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
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Average Value
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List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Purchase History

Date Type Sale Price Title Company
Warranty Deed $6,700,000 --
Warranty Deed $6,700,000 --
Warranty Deed $5,400,000 --
Warranty Deed $5,400,000 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Previous Owner $3,500,000 No Value Available
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
07/10/2025 07/10/25 Sold $6,700,000 -2.9% $878 / Sq Ft
06/22/2025 06/22/25 Pending -- -- --
12/14/2024 12/14/24 Price Changed $6,900,000 +6.2% $904 / Sq Ft
04/12/2024 04/12/24 Price Changed $6,495,000 -7.1% $851 / Sq Ft
12/16/2023 12/16/23 For Sale $6,995,000 +4.4% $917 / Sq Ft
12/16/2023 12/16/23 Off Market $6,700,000 -- --
06/17/2023 06/17/23 For Sale $6,995,000 -- $917 / Sq Ft
Source: SmartMLS

Tax History Compared to Growth

Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $76,559 $4,538,200 $688,000 $3,850,200
2024 $70,751 $4,538,200 $688,000 $3,850,200
2023 $63,730 $3,397,100 $743,500 $2,653,600
2022 $63,084 $3,397,100 $743,500 $2,653,600
2021 $63,084 $3,397,100 $743,500 $2,653,600
2020 $63,220 $3,397,100 $743,500 $2,653,600
2019 $63,220 $3,397,100 $743,500 $2,653,600
2018 $66,479 $3,572,200 $961,900 $2,610,300
2017 $66,406 $3,568,300 $961,900 $2,606,400
2016 $65,407 $3,568,300 $961,900 $2,606,400
2015 $63,730 $3,568,300 $961,900 $2,606,400
2014 $60,768 $3,568,300 $961,900 $2,606,400
Source: Public Records

Agents Affiliated with this Home

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Map

Source: SmartMLS

MLS Number: 170577139

SmartMLS

APN: KENT-000003-000005-000017