Don Orsini
Don Orsini Realty, LLC
(860) 863-4913
63 Total Sales
2 in Middlebury
$75K - $242K Price Range
Character, charm, and exceptional flexibility come together in this one-of-a-kind Middlebury home. Offering far more space than meets the eye, this property blends timeless craftsmanship with a versatile layout designed to fit today's evolving lifestyle. The main home features expansive living and dining spaces, a full bath, a main-level bedroom, and an additional flexible-use room ideal for a home office, den, guest space, or hobby room. Upstairs, you'll find two generously sized bedrooms with abundant closet space and a convenient half bath. A standout feature is the potential in-law setup, complete with its own living area, bedroom, and full bath, providing endless possibilities for multi-generational living, extended guests, or added privacy. Throughout the home, you'll appreciate the details that make this property truly special-from beautiful built-ins and custom trim work to the character and craftsmanship rarely found today. Outside, enjoy a spacious backyard designed for both relaxation and entertaining, featuring a large above-ground pool with surrounding deck space, perfect for summer gatherings and enjoying the outdoors. The lower level offers additional storage, garage space, and a workshop area complete with a workbench, ideal for hobbyists, craftsmen, or anyone in need of extra room. This is not your average Cape-style home. With its generous living space, unique layout, and endless possibilities, this home it ready for its next chapter!
Last Agent to Sell the Property
William Raveis Real Estate Brokerage Phone: (203) 802-8401 License #RES.0816314 Listed on: 06/24/2026
Don Orsini
Don Orsini Realty, LLC
(860) 863-4913
63 Total Sales
2 in Middlebury
$75K - $242K Price Range
Linda Heinig & Kim O'Donnell
William Raveis Real Estate
(475) 267-4466
55 Total Sales
1 in Middlebury
$389,900 Price
Wayne Watt Jr.
THE CONNECTICUT AGENCY LLC
(860) 590-6997
62 Total Sales
3 in Middlebury
$365K - $530K Price Range
Susan Hotchkiss
Realty ONE Group Connect
(475) 241-7831
67 Total Sales
1 in Middlebury
$292,500 Price
Zach Nichols
West View Properties, LLC
(475) 244-9049
109 Total Sales
2 in Middlebury
$265K - $506K Price Range
Amanda Nemense
Showcase Realty, Inc.
(475) 285-3197
117 Total Sales
2 in Middlebury
$505K - $525K Price Range
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 |
|---|---|---|---|---|---|
| 08/14/2026 08/14/26 | Sold | $485,000 | 0.0% | $215 / Sq Ft | |
| 07/11/2026 07/11/26 | Pending | -- | -- | -- | |
| 06/24/2026 06/24/26 | For Sale | $485,000 | +49.2% | $215 / Sq Ft | |
| 08/12/2022 08/12/22 | Sold | $325,000 | +8.4% | $144 / Sq Ft | View Prior Sale |
| 06/30/2022 06/30/22 | Pending | -- | -- | -- | |
| 06/25/2022 06/25/22 | Price Changed | $299,900 | -14.3% | $133 / Sq Ft | |
| 06/15/2022 06/15/22 | Price Changed | $350,000 | -6.7% | $155 / Sq Ft | |
| 06/03/2022 06/03/22 | Price Changed | $375,000 | -6.2% | $167 / Sq Ft | |
| 05/01/2022 05/01/22 | For Sale | $399,900 | -- | $178 / 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 | $7,613 | $234,100 | $58,700 | $175,400 |
| 2024 | $7,632 | $234,100 | $58,700 | $175,400 |
| 2023 | $7,552 | $234,100 | $58,700 | $175,400 |
| 2022 | $7,318 | $234,100 | $58,700 | $175,400 |
| 2021 | $5,608 | $161,000 | $66,900 | $94,100 |
| 2020 | $5,651 | $161,000 | $66,900 | $94,100 |
| 2019 | $5,377 | $161,000 | $66,900 | $94,100 |
| 2018 | $5,234 | $161,000 | $66,900 | $94,100 |
| 2017 | $5,070 | $161,000 | $66,900 | $94,100 |
| 2016 | $5,166 | $166,600 | $78,200 | $88,400 |
| 2015 | $5,018 | $166,600 | $78,200 | $88,400 |
| 2014 | $4,888 | $166,600 | $78,200 | $88,400 |
Seller's Agent in 2026
Emily Fitzgerald
William Raveis Real Estate
(203) 264-8180
47 Total Sales
DB
Buyer's Agent in 2026
Dawn Bucciarelli
Century 21 Bette Real Estate
(203) 232-9161
18 Total Sales
Seller's Agent in 2022
Pam Famiglietti
William Raveis Real Estate
(203) 560-0753
152 Total Sales
Buyer's Agent in 2022
Nikolaos Koulouris
William Raveis Real Estate
(860) 248-0684
53 Total Sales
Source: SmartMLS
MLS Number: 24185992
APN: MIDD-000510-000000-000056
Ask me questions while you tour the home.