Welcome to 99 Old Academy Road, a distinguished Cape originally reimagined by local architect Richard Swann and thoughtfully expanded in 2019 by Alex Esposito. Arched-top dormers elevate the architecture, blending tradition with luxury. This residence offers 6 bedrooms plus a private two-level guest suite, 7 full / 3 half baths, all set on 2+ acres in lower Greenfield Hill. At the heart of the home, the kitchen offers an open layout with a spacious dining area, custom cabinetry, a floor-to-ceiling glass wine display, and walk-in pantry. The kitchen flows seamlessly onto a bluestone patio with a double-sided fireplace, perfect for indoor-outdoor living. The kitchen leads to the lower level, featuring a stone bar in the game room, a 10-seat cinema, and ample storage. The family room, with its built-ins, poolside views, and gas fireplace, offers an inviting year-round retreat, the main level also includes a private office. Upstairs, every bedroom is paired with its own private bath, each with a unique design. The custom mahogany library serves as a passage to the East Wing, where the main level offers a gym, poolside lounge, & outdoor shower, while the upper-level features three additional en-suite bedrooms and a second laundry room. Outdoors, enjoy wrap-a-round mahogany decks, multiple bluestone patios, a heated pool, volleyball court, pergola gardens, and fruit trees. 99 Old Academy Road isn't just a home, it's a lifestyle of elegance, comfort, and unforgettable spaces.
Single-familyProperty Type
1937Year Built
2.17 acresLot Size
$488Est. Price/Sq.Ft.
3 car garageParking
Listed by Christine Howard• William Raveis Real Estate
A truly recognizable & admired home, this absolute stunner wows at every turn. The original 1937 home was reimagined, redesigned & expanded by renowned local architect, Richard Swann in 2006 & offers a sophisticated, yet timeless appeal both inside & out. Surrounded by beautiful stone walls and pillars with white picket gate enclosures, this 2+ acre lot is level, professionally landscaped & features an in-ground pool perfectly situated on the lot. With more than 3700 square feet of wrap around Mahogany porches, Bluestone patios, Cedar roof, copper gutters & a classic architectural design, the outdoor spaces on this property are perfect for outdoor living & entertaining. Once inside, the home offers a flexible & smart layout, with open & intimate spaces. The luxe kitchen is the heart of the house & features a large dining area, flowing to a casual family room with fireplace perfect for entertaining. The main level is completed by a formal dining room, living room with gas fireplace, study, full & half bath, laundry room & massive mudroom with built-ins. The master suite oasis, two additional beds (en suite bath), full bath, separate guest suite & bonus room/den complete the second level. A lower level playroom rounds out the main living space. Just thru the breezeway, there is a spacious pool house/exercise room facing the pool area. One of the most spectacular homes & grounds in the area-truly a special offering that does not come around often & will not disappoint.
Major improvements and expansions include: 2003: Kitchen, family room, master bedroom, bath and barn garage additions, new oil tank with compliant removal of oil tank in the ground, central A/C and septic system, formally, professionally landscaped the entire property with well-known landscape architect, two large Bluestone terraces, full underground sprinkler systems, specimen trees, many pine trees removed, stone wall and pillars repointed and extensive exterior lighting, Belgium block and circular driveway, privacy fencing along sides and rear of property, CT Basement System new sump pumps and Waterguard French drain 2003-2006: Additions: wrap around Mahogany (3,767sqft with 37 columns), dormers, exercise/pool room, guest bedroom, bonus room, breezeway, playroom upgrade, staircases, All new Marvin windows, new exterior wood siding, numerous new doors, new Cedar shingle roof, new copper gutters, mudroom with numerous cubbies and hooks and extra hallway which used to be the original garage 2006-2012: New pool liner and decorative overlay around pool, new HVAC zones, new fireplace surrounds and new staircase railings, Generac Guardian gas generator with automatic turn on, study with built-ins created from an original bedroom on the main level 2012-2016: Majority of rooms freshly painted, refaced kitchen cabinetry and family room trim painted Linen White, new designer carpeting in upstairs hallway and staircase, Cedar roof preservation and stain, Mahogany porch re-stained and sanded, new pool pump, heater and cover, new carpeting in lower level playroom 2016: Floor re-stained throughout the house, but for the pool house, washer and dryer, playground, smoke detectors (all good for 10 years) 2017: New basement dehumidifier, exterior painting, all siding and trim, porch repairs, conversion to LED lights, two downstairs low flow toilets installed 2018: Custom screen/storm doors, 2 new dishwashers, beverage refrigerator, rear sump pump replacement
Smart MLS #99134585
May 9, 2016
Sold
$1,750,000
$248/sq ft
Mar 19, 2016
Listing Removed
—
Feb 16, 2016
Listed
$1,750,000
$248/sq ft
Sophisticated Farmhouse Colonial w/spectacular architecture & gorgeous grounds in Lower Greenfield Hill. Rich in NE character & award-winning curb appeal, this highly coveted property is highlighted by a mahogany wrap-around porch, large windows & open flr plan. Magnificent kitchen w/black granite, soap stone sink, Bosch & Sub-Zero appls, wet bar w/Carrera marble. French doors galore! Lavish master suite w/gas FP & dressing rm. Two more en-suite BRs, guestroom/Au Pair w full BA, study, office, playroom, laundry & mud rms, pool house/gym. Stunning 2 flat acres. Retreat-like pool area w/gardens. Bluestone patios, gazebo, & exterior lighting build a setting that will take your breath away. Very convenient location! See Video.
Public Records
Feb 10, 2003
Sold
$1,525,000
$216/sq ft
Smart MLS #98140477
Sep 3, 2002
Listed
$1,695,000
$240/sq ft
Public Records
Jan 31, 1997
Sold
$645,000
$91/sq ft
Smart MLS #96032971
Oct 9, 1996
Listed
$695,000
$98/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$36,184 (+1.0%)
$374,430 + $940,870
$1,315,300
2022
$35,829 (+1.0%)
$374,430 + $940,870
$1,315,300
2021
$35,487 (+37.3%)
$374,430 + $940,870
$1,315,300
2020
$25,845
$454,860 + $509,880
$964,740
2019
$25,845 (+1.6%)
$454,860 + $509,880
$964,740
2018
$25,431 (+2.1%)
$454,860 + $509,880
$964,740
2017
$24,910 (+1.5%)
$454,860 + $509,880
$964,740
2016
$24,553 (+3.6%)
$454,860 + $509,880
$964,740
2014
$23,699
$512,890 + $458,360
$971,250
Tax history for 99 Old Academy Rd
Year
Property tax
Land + Additions
Assessment*
2023
$36,184 (+1.0%)
$374,430 + $940,870
$1,315,300
2022
$35,829 (+1.0%)
$374,430 + $940,870
$1,315,300
2021
$35,487 (+37.3%)
$374,430 + $940,870
$1,315,300
2020
$25,845
$454,860 + $509,880
$964,740
2019
$25,845 (+1.6%)
$454,860 + $509,880
$964,740
2018
$25,431 (+2.1%)
$454,860 + $509,880
$964,740
2017
$24,910 (+1.5%)
$454,860 + $509,880
$964,740
2016
$24,553 (+3.6%)
$454,860 + $509,880
$964,740
2014
$23,699
$512,890 + $458,360
$971,250
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Beds
6
Baths
7.5
Stories
2
Lot width
—
Lot depth
—
Lot size
2.17 Acres
Year renovated
—
Sq. Ft.
7,062
Year built
1937
Style
Single Family Residential
County
Fairfield County
APN
129507
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
Interior Information
Total Rooms: 10
Laundry Room Info: Main Level, Upper Level
Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Open Floor Plan, Security System