Set privately on one of Newtown, Connecticut's most sought-after streets, 29 Greenleaf Farms Road delivers a refined luxury lifestyle with exceptional indoor and outdoor living. Thoughtfully updated throughout, this impressive residence combines timeless craftsmanship with modern amenities designed for comfort, entertaining, and everyday elegance. The heart of the home features a stunning chef's kitchen appointed with premium Miele appliances, including a 36-inch refrigerator and matching 36-inch freezer positioned side-by-side for a seamless custom look. Natural light pours into the dramatic cathedral ceiling great room highlighted by skylights and an open, airy feel. A dedicated home office, wine cellar, and prep area for a future movie theater add flexibility and sophistication. The luxurious primary suite showcases a completely redesigned spa-inspired bath with whirlpool tub and oversized shower. Additional upgrades include all new Andersen windows, all new interior and exterior doors, and a brand new 30KW+ whole-house automatic generator system for peace of mind year-round. Outside, the property transforms into a private resort. Enjoy a newly built heated gunite pool with spa, expansive paver pool deck, outdoor kitchen, gazebo, basketball court, and playset. The walk-out finished basement opens directly to a beautiful paver patio, creating effortless indoor-outdoor flow ideal for entertaining. A 3-car garage and included pool table complete this extraordinary estate.
Luxury, recreation, and comfort come together in one extraordinary Newtown estate.
Single-familyProperty Type
1997Year Built
4 acresLot Size
$240Price/Sq.Ft.
3 car garageParking
Listed by Rudy Pierre (Milford)• YellowBrick Real Estate LLC
Est. $5,029 per month, based on comparable rentals
Sale and tax history for 29 Greenleaf Farms Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24177425
Jul 22, 2026
Sold
$1,340,000
$240/sq ft
Jul 6, 2026
Pending
—
Jun 17, 2026
Price Changed
$1,499,000
$269/sq ft
May 27, 2026
Listed
$1,590,000
$285/sq ft
May 23, 2026
Coming Soon
$1,590,000
$285/sq ft
Smart MLS #170362981
Mar 12, 2021
Sold
$855,000
$153/sq ft
Jan 7, 2021
Contingent
—
Dec 31, 2020
Listed
$859,900
$154/sq ft
Gorgeous, well-appointed home on four acres in desirable Greenleaf Farms neighborhood. Situated in Southwestern Newtown behind Red Gate Farm (premium boarding/training equestrian facility). Elegant details throughout with formal & comfortable living spaces, custom finishes, & modern amenities. Beautiful two story foyer flanked by formal dining & living rooms. Private main level office. Gourmet kitchen (granite counters, ample cabinetry, huge walk-in pantry, newer appls) & large dining area. Open interior spaces with high ceilings & hardwood flooring. The great room is centrally located with vaulted ceiling (two story), interior balcony, skylights, pellet stove & sliders to large deck. 1st floor laundry. The upper-level primary suite offers wood flooring, dressing rm, four walk-in closets & luxury full bath (jet tub, tiled shower stall, dual sink vanity). Three spacious guest rms (one en-suite & the others share a J & J). Additional rm (possible 5th BR, nursery, 2nd office/den). The finished (1000sqft) walk-out lower level features a media/recreation rm (possible in-law set up), half bath & wine closet. The LL transitions easily to the exterior via the pavered patio. Wonderful yard-professional landscaping and basketball court! Great entertaining spaces. Look no further...fabulous home/property in an idyllic setting! Greenleaf Preserve (33 acre sanctuary) in neighborhood. Conveniently located to Huntington State Park, shopping, restaurants & I-84. Just 60 miles to NYC!
Many rooms/images are virtually staged. The images are an impression of what the property ‘might’ look like. As such, the images have been digitally modified. 3D (Matterport) walk through video available.