Date
Details
Price
Change
Source
1/10/2026
Listed
$625,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/31
$625,000 Contingent
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/31
Property Description
This meticulously maintained home is truly an entertainer's dream, offering seamless indoor/outdoor living in a private, setting. The landscaped grounds feature an in-ground pool with pool house, expansive patio, screened-in porch, mature privacy evergreens, and flowering trees-perfect for both lively gatherings and peaceful relaxation. Inside, the thoughtfully designed floorplan includes living and dining rooms, along with a sunroom/family room highlighted by walls of windows that flood the space with natural light. The FR opens to an expansive 3-season/screened in deck w/ views of the rear yard. Two wood-burning fireplaces add warmth and character, one in the living room and the other creating a cozy focal point in the sunroom/family room. The updated kitchen is both stylish and functional, featuring granite countertops and stainless steel appliances. Three spacious bedrooms and one and a half baths, mudroom and laundry complete the main living level. The finished lower level offers an recreation and entertainment space with a custom bar, bar back, and two-burner electric cooktop-ideal for watching the big game or hosting family and friends for holidays or weekend gatherings. This level also includes a private, wood-paneled office with built-in shelving, providing a quiet work-from-home retreat. Ideally located near Trumbull Center and the Fairfield town line, this home offers the perfect balance of privacy, comfort, and convenience.
Full Property Details
Full Property Details for 88 Chestnut Hill Rd
General
- Price: $625,000
- Taxes: (July 2025-June 2026)
- Status: Contingent
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24147217
- Updated: 1/12/2026
- Added to Site: 8 day(s) ago
Interior
- Number of Rooms: 6
- Interior Features: Cable - Available, Open Floor Plan
- Fireplace: Yes
- Number of Fireplaces: 2
- Appliances: Electric Cooktop, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 1
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
- Primary Bedroom: Primary Bedroom - Ceiling Fan, Hardwood Floor, 15 x 13, Main
- Bedroom 1: Bedroom - Ceiling Fan, Hardwood Floor, 11 x 12, Main
- Bedroom 2: Bedroom - Ceiling Fan, Wall/Wall Carpet, 12 x 10, Main
Other Rooms
- Living Room: Living Room - Built-Ins, Combination Liv/Din Rm, Dining Area, Fireplace, Hardwood Floor, 27 x 13, Main
- Family Room: Family Room - Ceiling Fan, Fireplace, Sliders, Hardwood Floor, 17 x 18, Main
- Eat In Kitchen: Eat-In Kitchen - Remodeled, Breakfast Bar, Granite Counters, Dining Area, Tile, 10 x 17, Main
- Office: Office, 12 x 9, Lower
- Game room: Yes
- Game Room: Rec/Play Room - Built-Ins, Cedar Closet, Wet Bar, Vinyl Floor, 17 x 27, Lower
- Rec Room: Built-Ins, Cedar Closet, Wet Bar, Vinyl Floor, 17 x 27, Lower
- Laundry: Main Level
- Other Room 1: Other - Wall/Wall Carpet, 17 x 22, Main
Additional Information
- Pool: Yes
- Pool Description: Vinyl, In Ground Pool
Exterior
- Exterior Features: Porch-Screened, Porch, Gutters, Lighting, Patio
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 4
- Parking: Under House Garage, Paved, Off Street Parking, Driveway
Location
- County: Fairfield
- Neighborhood: St. Theresa&Apos;S
- Driving Directions: Madison Ave to Chestnut Hill Road
School Information
- Elementary School: Frenchtown
- Middle School: Madison
- High School: Trumbull
Community
- Community Name: St. Theresa&Apos;S
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Gas on Gas, Hot Water, Natural Gas
- Heating Fuel: Natural Gas
- Water Heater: Domestic
Utilities
- Sewer: Public Sewer Connected
- Water: Public Water Connected
Structural Information
- Architectural Style: Ranch
- Construction Status: No/Resale
- Exterior Const.: Aluminum, Stone
- Basement Desc.: Full, Unfinished, Storage, Partially Finished
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 2,340
- Above Ground: 1,890 Sq. Ft.
- Below Ground: 450 Sq. Ft.
- Year Built: 1955
Lot Features
- Lot Size (Acres): 0.3
- Driveway/Sidewalk: Paved
- Zoning: A
- Lot Description: Fence - Partial, Professionally Landscaped
Financial Considerations
- Assessment Amount: $298,200
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 393958
Listed by William Raveis Real Estate, The Denise Walsh Team, Denise Walsh
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 88 Chestnut Hill Rd —
Denise Walsh
William Raveis Real Estate
Agent Contact: (203) 650-1583 Office Contact: (203) 255-6841
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 88 Chestnut Hill Rd
School District:Trumbull School District
| Name | Grades | Distance |
|---|---|---|
Frenchtown Elementary 30 Frenchtown Road, Trumbull, CT 06611 | K-5 | 0.8 mi |
Madison Middle School 4630 Madison Avenue, Trumbull, CT 06611 | 6-8 | 1.7 mi |
Trumbull High School 72 Strobel Road, Trumbull, CT 06611 | 9-12 | 2.5 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 88 Chestnut Hill Rd
Tax History
Tax History for 88 Chestnut Hill Rd
Year
Property Taxes
Change
Tax Assessment
Change
2024
$10,957
3%
$298,200
—
2023
$10,648
12%
$298,200
8%
2022
$9,530
20%
$275,660
26%
2021
$7,957
2%
$218,820
—
2020
$7,804
2%
$218,820
—
2018
$7,629
2%
$218,820
—
2017
$7,488
3%
$218,820
—
2016
$7,295
-1%
$218,820
—
2015
$7,347
2%
$219,500
—
2014
$7,191
3%
$219,500
—
2011
$7,000
—
$219,500
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 88 Chestnut Hill Rd
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 6 days ago
- 4Beds
- 3Total Baths
- 2,500Sq. Ft.
- Single Family
- Active
- Updated 8 days ago
- 4Beds
- 2Total Baths
- 1,556Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Townhouse
- Active
- Updated 1 hour ago
- 1Bed
- 2Total Baths
- 837Sq. Ft.
Listed by Aileen O'Connell (203) 231-0935
- Commercial Lease
- Active
- Condo
- Active
- Updated 5 hours ago
- 1Bed
- 1Total Bath
- 784Sq. Ft.
Listed by Anthony Fabrizio (203) 767-3354
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Closed
- Updated 8 days ago
- 3Beds
- 3Total Baths
- 1,733Sq. Ft.
88 Chestnut Hill Road, Trumbull, CT 06611 (MLS# 24147217) is a Single Family property with 3 bedrooms, 1 full bathroom and 1 partial bathroom. 88 Chestnut Hill Road is currently listed for $625,000 and was received on January 08, 2026. Want to learn more about 88 Chestnut Hill Road? Do you have questions about finding other Single Family real estate for sale in Trumbull? You can browse all Trumbull real estate or contact a Coldwell Banker agent to request more information.