320 Chestnut Hill Rd

Stamford, CT 06903

$1,480,000
Price
3
Beds
3,342 Sq. Ft.
$443 / Sq. Ft.
3,342
Sq. Ft.
$443
per Sq. Ft.
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Open: 4/12 12:00PM - 02:00PM
Open: 4/12 12:00PM - 02:00PM

Description

Completely rebuilt from the studs in 2008, this one-of-a-kind Contemporary blends sleek modern design with classic New England exterior charm. Set on 3+ private acres, the home was designed to capture beautiful views from every room, with walls of windows creating a bright, open, and airy feel throughout. The main living space features soaring cathedral ceilings and dramatic two-story windows with water views. A chef's kitchen with expansive island, Viking double ovens, and a sunlit breakfast room...Completely rebuilt from the studs in 2008, this one-of-a-kind Contemporary blends sleek modern design with classic New England exterior charm. Set on 3+ private acres, the home was designed to capture beautiful views from every room, with walls of windows creating a bright, open, and airy feel throughout. The main living space features soaring cathedral ceilings and dramatic two-story windows with water views. A chef's kitchen with expansive island, Viking double ovens, and a sunlit breakfast room surrounded by windows overlooks your own waterfall. The layout flows seamlessly from a formal dining room to spacious living areas and out to wraparound decks, ideal for everyday living and entertaining. Outside, enjoy a resort-style setting with a heated gunite pool, spa, and tranquil natural surroundings. Three private bedroom suites include two updated baths, while the primary suite features vaulted ceilings, a sitting area, and serene pond views. Custom storage maximizes functionality throughout. Ideally located just 2 miles from the Merritt Parkway and LaRocca's Market, and within walking distance to Chestnut Hill Park, this property delivers superior construction, privacy and a lifestyle that you will love.
  1. Listed by Penny Schwartz • William Raveis Real Estate
    P: (203)-762-8300 C: (203)-253-6851 penny.schwartz@raveis.com

Property Details for 320 Chestnut Hill Road

Basement Description
Full, Unfinished, Sump Pump, Interior Access, Concrete Floor
Direct Waterfront
Yes
Expected Active Date
04-09-2026
Garages Number
2
Neighborhood
North Stamford
Style
Contemporary
Garage Parking Info
Attached Garage, Under House Garage, Off Street Parking, Driveway, Unpaved
Swimming Pool
Yes

Open Houses

Sunday, Apr 12th12:00 PM - 2:00 PM
PublicView contact
LISTING UPDATED: 04/09/2026 04:05 AM

Property Details for 320 Chestnut Hill Road

StatusActive
MLS #24157806
Days on Market1
Taxes$19,348 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1985
Lot Size3.15 AC / 137,214 SF
CountyFairfield County
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Location

Listing Courtesy of William Raveis Real Estate, Penny Schwartz
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Building Information for 320 Chestnut Hill Road

Stories-Year Built1985Building Size-Lot Size3.15 AC / 137,214 SF

Payment Calculator

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$9,065 per month

30 year fixed, 6.46% Interest

Principal and Interest

$7,453

Property Taxes

$1,612

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 320 Chestnut Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Take Long Ridge to Chestnut Hill House on right.
  • Elementary School: Roxbury
  • Flood Zone: No
  • High School: Westhill
  • Latitude: 41.126064
  • Longitude: -73.569004
  • Middle Jr High School: Cloonan
  • Neighborhood Amenities: Basketball Court, Golf Course, Library, Medical Facilities, Park, Playground/Tot Lot, Private School(s), Stables/Riding
  • State: Connecticut
Parking
  • Parking Total Spaces: 4
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $19,348
Interior and Exterior Features
Exterior Features
  • Exterior Features: Wrap Around Deck, Lighting, Underground Sprinkler
  • Pool Description: Gunite, Heated, In Ground Pool
  • Waterfront Description: Pond, View, Access
Interior Features
  • Appliances Included: Electric Cooktop, Wall Oven, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Electric Dryer
  • Cooling System: Ceiling Fans, Central Air, Zoned
  • Heat Type: Hot Air, Zoned
  • Attic YN: No
  • Fireplaces Total: 1
  • Interior Features: Auto Garage Door Opener, Open Floor Plan
  • Laundry Room Info: Main Level
  • Laundry Room Location: Laundry Room off Kitchen
  • Rooms Additional: Foyer, Laundry Room
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Features: Sliders,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Features: 2 Story Window(s),Cathedral Ceiling,Balcony/Deck,Granite Counters,Island,Hardwood Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 4
  • Room Entry Order: 4
  • Room Features: 2 Story Window(s),Cathedral Ceiling,Balcony/Deck,Fireplace,Sliders,Hardwood Floor
  • Room Level: Main
  • Room Type: Great Room
Room 5
  • Listing Key: 4C4DC58760F9EDF5E0631A01100A5107
  • Room Entry Order: 5
  • Room Features: Full Bath,Hardwood Floor,Stall Shower,Tile Floor
  • Room Level: Main
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 6
  • Room Features: 2 Story Window(s),Cathedral Ceiling,Ceiling Fan,Walk-In Closet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Primary BR Suite
Room 7
  • Room Entry Order: 7
  • Room Features: Double-Sink,Stall Shower,Whirlpool Tub,Travertine Floor
  • Room Level: Upper
  • Room Type: Primary Bath
Room 8
  • Room Entry Order: 8
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Loft
Room 9
  • Listing Key: 4C4DC58760F9EDF5E0631A01100A5107
  • Room Entry Order: 9
  • Room Features: 2 Story Window(s),Cathedral Ceiling,Full Bath,Walk-In Closet,Hardwood Floor,Stall Shower
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: Beige
  • Construction Description: Frame
  • Driveway Type: Private, Gravel
  • Exclusions: Please see exclusion document
  • Exterior Siding: Shingle, Stone, Wood
  • Foundation Type: Block
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1985
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Apartment: No
  • Sq Ft Description: Unfinished Basement Space 1746 per property records
Lot Information
  • Lot Description: Some Wetlands, Interior Lot, Treed, Level Lot, Professionally Landscaped, Water View
  • Parcel Number: 337400
  • Sq Ft Est Heated Above Grade: 3342.0
  • Sq Ft Total: 3342.0
  • Zoning: RA1
Utilities
  • Energy Features: Generator, Programmable Thermostat
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Domestic
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 320 Chestnut Hill Road

DateEvent & SourcePriceAppreciation
Apr 9, 2026

Listed (Active)

SMARTMLS #24157806

$1,480,000—
Oct 18, 2020

Closed (Public Record)

Public Record #681700889

$969,000

-2.1% / yr

Aug 28, 2008

Closed (Public Record)

Public Record #254610349

$1,260,000

+26.6% / yr

Jun 18, 2007

Closed (Public Record)

Public Record #223366164

$950,000—
DateEvent & SourcePrice
04/09/2026

Listed (Active)

SMARTMLS #24157806

$1,480,000
10/18/2020

Closed (Public Record)

Public Record #681700889

$969,000

-2.1% / yr

08/28/2008

Closed (Public Record)

Public Record #254610349

$1,260,000

+26.6% / yr

06/18/2007

Closed (Public Record)

Public Record #223366164

$950,000

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

Public Records for 320 Chestnut Hill Road

Taxable ValueLand$369,560Additions$461,880Total$831,440
Tax Record2024$19,348 ($1,612 / month)
Home Facts
Beds3Baths3.5Total Finished SqFt3,342 SqFtAbove Grade Finished SqFt3,342 SqFtUnfinished Basement SqFt1,746 SqFtStories2Lot Size137,214 SqFtStyleSingle Family ResidenceYear Built1985ZoningRA1CountyFAIRFIELDAPNSTAM M:002 B:8531Fireplace TypeHas Fireplace

Schools near 320 Chestnut Hill Road

This home is within Stamford School District.
Rating
School
Type
Grades
Distance
Northeast School
Public - K to 5
Turn Of River School
Public - 6 to 8
Westhill High School
Public - 9 to 12
Rogers International School
Public - K to 8
Rating
School
Distance
Northeast School
PublicK to 5

Turn Of River School
Public6 to 8

Westhill High School
Public9 to 12

Rogers International School
PublicK to 8

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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More information about 320 Chestnut Hill Road, Stamford, CT 06903

320 Chestnut Hill Road is a single family home for sale in Stamford, CT 06903. This listing's school district is Stamford School District. Nearby schools include Northeast School, Turn Of River School and Westhill High School. 320 Chestnut Hill Road is a 3-bed, 3-bath, 3,342 sqft single family home built in 1985.

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, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Raveis Real Estate, Penny Schwartz

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.