99 Old Academy Rd

Fairfield, CT 06824

$3,292,000
Last Sold Price
6
Beds
7,062 Sq. Ft.
$466 / Sq. Ft.
7,062
Sq. Ft.
$466
per Sq. Ft.
Closed 12/15/25
Closed 12/15/25

Description

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...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.
  1. Listed by Christine Howard • William Raveis Real Estate
    P: (646)-239-5676 C: (646)-239-5676 christine.howard@raveis.com

Property Details for 99 Old Academy Road

Basement Description
Partial, Partially Finished
Direct Waterfront
No
Garages Number
3
Neighborhood
Greenfield Hill
Style
Cape Cod
Garage Parking Info
Attached Garage
Swimming Pool
Yes
LISTING UPDATED: 12/16/2025 05:21 PM

Property Details for 99 Old Academy Road

StatusClosed
MLS #24130154
Days on Market6
Taxes$37,341 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1937
Lot Size2.17 AC / 94,525 SF
CountyFairfield County

Location

Listing Courtesy of William Raveis Real Estate, Christine Howard

Sold By Compass Connecticut, LLC, Veronica Monahan

Add your commute

Building Information for 99 Old Academy Road

Stories-Year Built1937Building Size-Lot Size2.17 AC / 94,525 SF

Payment Calculator

$19,156 per month

30 year fixed, 6.15% Interest

Principal and Interest

$16,045

Property Taxes

$3,112

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 99 Old Academy Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Burr to Old Academy Road
  • Elementary School: Burr
  • High School: Fairfield Warde
  • Latitude: 41.182384
  • Longitude: -73.277893
  • Middle Jr High School: Tomlinson
  • Neighborhood Amenities: Golf Course, Health Club, Library, Paddle Tennis, Private School(s), Shopping/Mall
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $37,341
Interior and Exterior Features
Exterior Features
  • Exterior Features: Breezeway, Wrap Around Deck, Gutters, Hot Tub, French Doors, Patio, Fruit Trees, Gazebo, Garden Area
  • Pool Description: Pool House, Vinyl, In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Range, Microwave, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
  • Attic Description: Crawl Space, Storage Space, Pull-Down Stairs
  • Cooling System: Ceiling Fans, Central Air, Zoned
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 3
  • Home Automation: Lighting, Thermostat(s)
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Open Floor Plan, Security System
  • Laundry Room Info: Main Level, Upper Level
  • Rooms Additional: Bonus Room, Foyer, Greenhouse, Gym, Laundry Room, Mud Room, Sitting Room
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Features: Built-Ins,Gas Log Fireplace,French Doors,Patio/Terrace,Hardwood Floor
  • Room Length: 29.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 15.0
Room 2
  • Room Entry Order: 10
  • Room Features: Palladian Window(s),9 ft+ Ceilings,Ceiling Fan,Full Bath,Walk-In Closet
  • Room Length: 16.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 3
  • Room Entry Order: 11
  • Room Features: Palladian Window(s),Vaulted Ceiling,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 19.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 4
  • Room Entry Order: 12
  • Room Features: Palladian Window(s),Vaulted Ceiling,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 20.0
Room 5
  • Listing Key: 3FFB109CBF8EC250E063E201100A37FA
  • Room Entry Order: 13
  • Room Features: Built-Ins,Wet Bar,French Doors,Engineered Wood Floor
  • Room Length: 22.0
  • Room Level: Main
  • Room Type: Sun Room
  • Room Width: 15.0
Room 6
  • Room Entry Order: 14
  • Room Features: Wall/Wall Carpet
  • Room Length: 29.0
  • Room Level: Lower
  • Room Type: Media Room
  • Room Width: 15.0
Room 7
  • Room Entry Order: 15
  • Room Features: Dry Bar,Laminate Floor
  • Room Length: 29.0
  • Room Level: Lower
  • Room Type: Rec/Play Room
  • Room Width: 17.0
Room 8
  • Room Entry Order: 2
  • Room Features: Quartz Counters,Dining Area,Wet Bar,French Doors,Island,Pantry
  • Room Length: 29.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 29.0
Room 9
  • Listing Key: 3FFB109CBF8EC250E063E201100A37FA
  • Room Entry Order: 3
  • Room Features: Fireplace,French Doors,Hardwood Floor
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 17.0
Room 10
  • Room Entry Order: 4
  • Room Features: Built-Ins,Hardwood Floor
  • Room Length: 13.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 12.0
Room 11
  • Room Entry Order: 5
  • Room Features: Dressing Room,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 29.0
  • Room Level: Upper
  • Room Type: Primary BR Suite
  • Room Width: 15.0
Room 12
  • Room Entry Order: 6
  • Room Features: Palladian Window(s),Bedroom Suite,Dressing Room,French Doors,Full Bath,Hardwood Floor
  • Room Length: 21.0
  • Room Level: Upper
  • Room Type: Other
  • Room Width: 20.0
Room 13
  • Room Entry Order: 7
  • Room Features: Palladian Window(s),Book Shelves,Full Bath,Hardwood Floor
  • Room Length: 24.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 14
  • Room Entry Order: 8
  • Room Features: Palladian Window(s),Full Bath,Hardwood Floor
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 15
  • Room Entry Order: 9
  • Room Features: Palladian Window(s),Built-Ins,Hardwood Floor
  • Room Length: 28.0
  • Room Level: Upper
  • Room Type: Rec/Play Room
  • Room Width: 20.0
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Exclusions: Gas Grill,
  • Exterior Siding: Clapboard
  • Foundation Type: Block, Concrete
  • New Construction Type: No/Resale
  • Roof: Wood Shingle
  • Year Built: 1937
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: First Floor, Second Floor
  • In Law Apartment: Possible
  • Living Area SQFT Per Public Records: 7062
Lot Information
  • Lot Description: Level Lot, Cleared, Professionally Landscaped
  • Parcel Number: 129507
  • Sq Ft Est Heated Above Grade: 7062.0
  • Sq Ft Total: 7062.0
  • Zoning: AAA
Utilities
  • Energy Features: Fireplace Insert, Generator, Programmable Thermostat, Thermopane Windows
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Natural Gas, Tankless Hotwater
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 99 Old Academy Road

DateEvent & SourcePriceAppreciation
Jul 25, 2019

Closed (Public Record)

Public Record #650444755

$1,620,000

-2.4% / yr

May 9, 2016

Closed (Public Record)

Public Record #571550976

$1,750,000

+1.0% / yr

Feb 10, 2003

Closed (Public Record)

Public Record #119993836

$1,525,000

+15.3% / yr

Jan 31, 1997

Closed (Public Record)

Public Record #90962901

$645,000—
DateEvent & SourcePrice
07/25/2019

Closed (Public Record)

Public Record #650444755

$1,620,000

-2.4% / yr

05/09/2016

Closed (Public Record)

Public Record #571550976

$1,750,000

+1.0% / yr

02/10/2003

Closed (Public Record)

Public Record #119993836

$1,525,000

+15.3% / yr

01/31/1997

Closed (Public Record)

Public Record #90962901

$645,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 99 Old Academy Road

Taxable ValueLand$374,430Additions$940,870Total$1,315,300
Tax Record2024$37,341 ($3,112 / month)
Home Facts
Beds6Baths4.5Total Finished SqFt7,062 SqFtAbove Grade Finished SqFt7,062 SqFtUnfinished Basement SqFt1,817 SqFtStories2Lot Size94,525 SqFtStyleSingle Family ResidenceYear Built1937ZoningAAACountyFAIRFIELDAPNFFLD M:150 B:25Fireplace TypeHas Fireplace

Schools near 99 Old Academy Road

This home is within Fairfield School District.
Rating
School
Type
Grades
Distance
Burr Elementary School
Public - K to 5
Tomlinson Middle School
Public - 6 to 8
Fairfield Warde High School
Public - 9 to 12
Fairfield Country Day School
Private - K to 9
Rating
School
Distance
Burr Elementary School
PublicK to 5

Tomlinson Middle School
Public6 to 8

Fairfield Warde High School
Public9 to 12

Fairfield Country Day School
PrivateK to 9

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Raveis Real Estate, Christine Howard

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.