Nestled in one of Connecticut's most sought-after estate neighborhoods and just minutes from town, this spectacular 1939 Classic Colonial blends timeless elegance with every modern amenity. Set on nearly 5 bucolic acres of rolling lawns, perennial gardens, and mature trees, this pristine property offers unmatched privacy and beauty. The grand approach includes a stately driveway with a central fountain leading to an inviting paneled foyer. Inside, the gracious living room with fireplace and built-ins opens to a formal dining room that overlooks the magnificent grounds. The chef's kitchen, complete with eat-in area, is perfect for both everyday living and entertaining. Unique lifestyle features abound: a spacious game room with cigar ventilation ideal for cards or gatherings, a cozy wood-paneled office with extensive built-ins, and a secondary office featuring a charming circular window with a view of the sprawling front lawn. The luxurious primary suite offers a fireplace, dual walk-in closets, and a spa-inspired bath. Four additional bedrooms provide comfortable accommodations for family and guests. A modern gym and a bonus bunk room with sleeping quarters for up to eight make this home as functional as it is elegant. Outdoors, enjoy an expansive patio perfect for entertaining, a swimming pool, and a tennis/pickle ball/sport court-all surrounded by meticulously manicured landscaping that recalls a bygone era of quiet sophistication. A true Connecticut gem,
offering the enduring charm of the 1930s with today's finest features. Ready for immediate occupancy!
Single-familyProperty Type
1939Year Built
4.64 acresLot Size
$736Price/Sq.Ft.
3 car garageParking
Listed by Melissa Rwambuya• William Raveis Real Estate
Est. $4,809 per month, based on comparable rentals
Sale and tax history for 276 Greenley Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24141707
Apr 2, 2026
Sold
$5,600,000
$736/sq ft
Mar 10, 2026
Pending
—
Mar 7, 2026
Contingent
—
Nov 22, 2025
Listed
$5,995,000
$788/sq ft
Smart MLS #24097853
Aug 12, 2025
Listing Removed
—
May 27, 2025
Listed
$6,495,000
$854/sq ft
Smart MLS #99048850
Jun 13, 2014
Sold
$3,850,000
$506/sq ft
Jan 24, 2014
Listed
$3,999,995
$526/sq ft
Spectacular 1939 Classic Colonial sited on almost 5 private, bucolic acres in a prestigious estate neighborhood convenient to town. Complete with swimming pool & tennis court nestled in the middle of manicured, rolling lawns and perennial gardens.....reminiscent of a quietly elegant bygone era.
Smart MLS #98529885
Jul 16, 2012
Listing Removed
—
Mar 1, 2012
Listed
$3,995,000
$525/sq ft
Smart MLS #98500479
Dec 31, 2011
Listing Removed
—
May 10, 2011
Listed
$4,200,000
$552/sq ft
Smart MLS #98453181
Mar 1, 2011
Listing Removed
—
Mar 1, 2010
Listed
$4,675,000
$615/sq ft
Public Records
Jun 8, 2004
Sold
$3,875,000
$510/sq ft
Public Records
Oct 16, 1986
Sold
$1,500,000
$197/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$45,785 (+3.1%)
$1,158,710 + $1,258,670
$2,417,380
2022
$44,407 (+1.2%)
$1,158,710 + $1,258,670
$2,417,380
2021
$43,900
$1,158,710 + $1,258,670
$2,417,380
2020
$43,900 (−0.4%)
$1,158,710 + $1,258,670
$2,417,380
2019
$44,093 (−2.2%)
$1,158,710 + $1,258,670
$2,417,380
2018
$45,098 (+1.7%)
$1,192,030 + $1,467,060
$2,659,090
2017
$44,327 (+2.2%)
$1,192,030 + $1,467,060
$2,659,090
2016
$43,370 (+37.3%)
$1,192,030 + $1,467,060
$2,659,090
2014
$31,586
$1,192,030 + $840,560
$2,032,590
Public record
Beds
7
Baths
7.5
Stories
2
Lot width
—
Lot depth
—
Lot size
4.64 Acres
Year renovated
—
Sq. Ft.
7,605
Year built
1939
Style
Single Family Residential
County
Fairfield County
APN
184346
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 13, 2023.
Property details
Parking
Garage Information
Garage & Parking: Attached Garage
Garages Number: 3
Interior
Virtual Tour Information
Interior Information
Total Rooms: 12
Laundry Room Info: Upper Level
Interior Features: Auto Garage Door Opener, Cable - Available, Security System
Fireplaces Total: 4
Cooling System: Central Air, Zoned
Appliances Included: Gas Cooktop, Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller