99 Old Academy Rd Fairfield, CT, 06824

single family home
$ 3,292,000 Sold Oct 2, 2025
74 days on market, 109% sale-to-list ratio
  • 6 beds
  • 8 baths
  • 7,062 sq ft
  • 2.17 acres
  • 1937 year built
  • pool house
  • 3 cars garage

About the Home

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.

Rooms & Interior

6 bedrooms beds
7 full + 1 half baths
7,062 square feet sq ft

Room Details

  • Rec/Play Room (Lower Level) Dry Bar, Laminate Floor
  • Primary Br Suite (Upper Level) Dressing Room, Full Bath, Walk-In Closet, Hardwood Floor
  • Bedroom (Upper Level) Palladian Window(s), Vaulted Ceiling, Full Bath, Walk-In Closet, Hardwood Floor
  • Bedroom (Upper Level) Palladian Window(s), Vaulted Ceiling, Full Bath, Walk-In Closet, Hardwood Floor
  • Kitchen (Main Level) Quartz Counters, Dining Area, Wet Bar, French Doors, Island, Pantry
  • Dining Room (Main Level) Fireplace, French Doors, Hardwood Floor
  • Bedroom (Upper Level) Palladian Window(s), Full Bath, Hardwood Floor
  • Family Room (Main Level) Built-Ins, Gas Log Fireplace, French Doors, Patio/Terrace, Hardwood Floor
  • Office (Main Level) Built-Ins, Hardwood Floor
  • Rec/Play Room (Upper Level) Palladian Window(s), Built-Ins, Hardwood Floor
  • Other (Upper Level) Palladian Window(s), Bedroom Suite, Dressing Room, French Doors, Full Bath, Hardwood Floor
  • Bedroom (Upper Level) Palladian Window(s), 9 ft+ Ceilings, Ceiling Fan, Full Bath, Walk-In Closet
  • Sun Room (Main Level) Built-Ins, Wet Bar, French Doors, Engineered Wood Floor
  • Media Room (Lower Level) Wall/Wall Carpet
  • Bedroom (Upper Level) Palladian Window(s), Book Shelves, Full Bath, Hardwood Floor
  • Other Rooms Bonus room, Foyer, Greenhouse, Gym, Laundry room, Mud room, Sitting room

Home Features

Heating

  • Fireplaces: 3
  • Heating: hot air
  • Heat fuel type: natural gas

Cooling

  • Ceiling fans
  • Central air
  • Zoned

Interior Features

  • Audio system
  • Auto garage door opener
  • Cable - available
  • Open floor plan
  • Security system

Appliances

  • Gas range
  • Microwave
  • Refrigerator
  • Freezer
  • Icemaker
  • Dishwasher
  • Washer
  • Dryer
  • Wine chiller

Home Automation

  • Lighting
  • Thermostat(s)

Attic

  • Crawl space
  • Storage space
  • Pull-down stairs

Basement

  • Partial
  • Partially finished

Laundry

  • Main level
  • Upper level

Energy Features

  • Fireplace insert
  • Generator
  • Programmable thermostat
  • Thermopane windows

Exterior Features

  • Breezeway
  • Wrap around deck
  • Gutters
  • Hot tub
  • French doors
  • Patio
  • Fruit trees
  • Gazebo
  • Garden area

Property Details

Parking

  • Garage spaces: 3
  • Attached garage

Swimming Pool

  • Pool house
  • Vinyl
  • In ground pool

Lot Details

  • Lot surface: 2.17 acres
  • Level lot
  • Cleared
  • Professionally landscaped

Utilities

  • Water: public water connected
  • Sewage: septic

Near-by Amenities

  • Golf course
  • Health club
  • Library
  • Paddle tennis
  • Private school(s)
  • Shopping/mall

Construction Details

Style
cape cod

Construction year
1937

Exterior Siding
clapboard

Foundation
block, concrete

Roof
wood shingle


Area & Town

This home is located in Greenfield Hills neighborhood, in the town of Fairfield.

Finance & Listing Info

Status Closed
Listing date October 02, 2025
Closed date December 15, 2025
Days on market 74 days
List price $ 2,999,000
Close price $ 3,292,000
Sale-to-list ratio 109%
Tax amount $ 37,341
Tax year july 2025-june 2026
Financing used Assumed conventional
MLS ID #24130154
List Agent Christine Howard
List Office William Raveis Real Estate

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