Richard Higgins
Higgins Group Bedford Square
(855) 923-4476
19 Total Sales
2 in Greenfield Hill
$1.5M - $3.6M Price Range
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.
Last Agent to Sell the Property
William Raveis Real Estate Brokerage Phone: (646) 239-5676 License #RES.0798049 Listed on: 10/02/2025
Richard Higgins
Higgins Group Bedford Square
(855) 923-4476
19 Total Sales
2 in Greenfield Hill
$1.5M - $3.6M Price Range
Pam Toner
Berkshire Hathaway NE Prop.
(973) 604-2163
25 Total Sales
1 in Greenfield Hill
$1,625,000 Price
Hyleri Katzenberg
Compass Connecticut, LLC
(475) 889-7112
46 Total Sales
2 in Greenfield Hill
$1.5M - $3.7M Price Range
Roni Agress
William Pitt Sotheby's Int'l
(914) 875-2948
34 Total Sales
1 in Greenfield Hill
$800,000 Price
Sam Granata
Preston Gray Real Estate
(475) 265-6341
39 Total Sales
1 in Greenfield Hill
$760,000 Price
Linda Dunsmore
Coldwell Banker Realty
(475) 258-8711
90 Total Sales
1 in Greenfield Hill
$910,000 Price
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 12/15/2025 12/15/25 | Sold | $3,292,000 | +9.8% | $466 / Sq Ft | |
| 10/09/2025 10/09/25 | Pending | -- | -- | -- | |
| 10/02/2025 10/02/25 | For Sale | $2,999,000 | +85.1% | $425 / Sq Ft | |
| 07/26/2019 07/26/19 | Sold | $1,620,000 | -4.4% | $303 / Sq Ft | View Prior Sale |
| 06/25/2019 06/25/19 | Pending | -- | -- | -- | |
| 05/01/2019 05/01/19 | For Sale | $1,695,000 | -3.1% | $317 / Sq Ft | |
| 05/09/2016 05/09/16 | Sold | $1,750,000 | 0.0% | $317 / Sq Ft | View Prior Sale |
| 04/09/2016 04/09/16 | Pending | -- | -- | -- | |
| 02/16/2016 02/16/16 | For Sale | $1,750,000 | -- | $317 / Sq Ft |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $37,341 | $1,315,300 | $374,430 | $940,870 |
| 2024 | $36,697 | $1,315,300 | $374,430 | $940,870 |
| 2023 | $36,184 | $1,315,300 | $374,430 | $940,870 |
| 2022 | $35,829 | $1,315,300 | $374,430 | $940,870 |
| 2021 | $35,487 | $1,315,300 | $374,430 | $940,870 |
| 2020 | $25,845 | $964,740 | $454,860 | $509,880 |
| 2019 | $25,845 | $964,740 | $454,860 | $509,880 |
| 2018 | $25,431 | $964,740 | $454,860 | $509,880 |
| 2017 | $24,910 | $964,740 | $454,860 | $509,880 |
| 2016 | $24,553 | $964,740 | $454,860 | $509,880 |
| 2015 | $24,077 | $971,250 | $512,890 | $458,360 |
| 2014 | $23,699 | $971,250 | $512,890 | $458,360 |
Seller's Agent in 2025
Christine Howard
William Raveis Real Estate
(646) 239-5676
5 in this area
41 Total Sales
Buyer's Agent in 2025
Veronica Monahan
Compass Connecticut, LLC
(203) 520-1568
15 in this area
74 Total Sales
Seller's Agent in 2019
Denise Walsh
William Raveis Real Estate
(203) 650-1583
15 in this area
159 Total Sales
J
Seller Co-Listing Agent in 2019
Jessica Walsh
William Raveis Real Estate
(617) 501-5320
2 in this area
28 Total Sales
C
Seller's Agent in 2016
Carol/Ann Langeland And Small
Higgins Group Real Estate
A
Seller Co-Listing Agent in 2016
Ann Small
William Raveis Real Estate
Source: SmartMLS
MLS Number: 24130154
APN: FAIR-000150-000000-000025
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