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. 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.
Sold for $6,700,000 on 07/10/25
$6,700,000
27 Macedonia Brook Road, Kent, CT 06757
5beds
7,632sqft
Single Family Residence
Built in 1827
41.33 Acres Lot
$6,722,200 Zestimate®
$878/sqft
$58,481 Estimated rent
What's special
Zillow last checked: 7 hours ago
Listing updated: July 10, 2025 at 11:48am
Listed by:
Stacey Matthews,
W. Raveis Lifestyles Realty
Bought with:
Diana Bisselle, RES.0799072
William Pitt Sotheby's Int'l
Source: Smart MLS,MLS#: 170577139

Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Features: High Ceilings
- Level: Main
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Features: Full Bath
- Level: Upper
Bedroom
- Level: Upper
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Gas Cooktop, Oven, Subzero, Wine Cooler, Electric Water Heater
Features
- Entrance Foyer
- Doors: French Doors
- Basement: Unfinished
- Attic: Walk-up,Finished
- Number of fireplaces: 7
Interior area
- Total structure area: 7,632
- Total interior livable area: 7,632 sqft
- Finished area above ground: 7,632
- Finished area below ground: 0
Property
Parking
- Total spaces: 4
- Parking features: Attached, Private
- Attached garage spaces: 4
- Has uncovered spaces: Yes
Features
- Patio & porch: Terrace
- Exterior features: Garden, Stone Wall, Tennis Court(s)
- Has private pool: Yes
- Pool features: Lap, Heated, Fenced, Gunite
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Brook
Lot
- Size: 41.33 Acres
- Features: Additional Land Avail., Wetlands, Landscaped
Details
- Additional structures: Barn(s), Cabana, Guest House, Pool House
- Parcel number: 1942515
- Zoning: Res
- Other equipment: Generator Ready
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Stone
- Foundation: Stone
- Roof: Wood
Condition
- New construction: No
- Year built: 1827
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & neighborhood
Community
- Community features: Golf, Lake, Library, Playground, Private School(s), Stables/Riding
Location
- Region: Kent
- Subdivision: Macedonia