About 237 Chestnut Hill Road
***HIGHEST & BEST: TUES, AUGUST 25TH AT 12PM*** Welcome to this private North Stamford retreat set on 1.58 acres of beautiful, secluded property. This 4-bedroom Colonial offers spacious living areas and an impressive outdoor setting designed for relaxing and entertaining. A 30-foot sunroom with sliders opens to the expansive backyard and pool area. The heated gunite pool is the centerpiece of the property, featuring an expansive stone terrace and waterfall feature. Pool improvements include a new gunite floor and tile in 2021, plus a new filter and electrical box in 2025. The property also offers a pool cabana with electricity, whole-house generator, deer fencing, mature landscaping, and a newly paved and sealed driveway. Inside, the home offers a mix of classic character and updates, including renovated bathrooms, Anderson windows, French doors, updated well systems, and hardwood flooring. A rare 4-car garage setup includes two attached garages plus an oversized detached barn with heat and air conditioning, workshop space, storage, and an additional carport. The barn provides exceptional flexibility for vehicles, hobbies, equipment, or storage. With its private acreage, extensive outdoor amenities, versatile garage and barn spaces, and sought-after North Stamford location, this property offers a unique opportunity to create your own private retreat.
Features of 237 Chestnut Hill Road
| MLS® # | 24197236 |
|---|---|
| Price | $1,066,000 |
| Bedrooms | 4 |
| Bathrooms | 3.00 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 2,527 |
| Acres | 1.58 |
| Type | Single Family For Sale |
| Style | Colonial |
| Status | Active |
Community Information
| Address | 237 Chestnut Hill Road |
|---|---|
| Area | North Stamford |
| City | Stamford |
| County | Fairfield |
| State | Connecticut |
| Zip Code | 06903 |
Amenities
| Features | Generator, Thermopane Windows |
|---|---|
| Parking | Barn, Attached Garage, Detached Garage |
| # of Garages | 4 |
| Is Waterfront | No |
| Waterfront | Not Applicable |
| Has Pool | Yes |
| Pool | Gunite, In Ground Pool |
Interior
| Interior Features | Auto Garage Door Opener, Cable - Available, Security System |
|---|---|
| Appliances | Cook Top, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer |
| Heating | Hot Air, Natural Gas |
| Cooling | Ceiling Fans, Central Air |
| Fireplace | Yes |
| # of Fireplaces | 2 |
| Has Basement | Yes |
| Basement | Crawl Space, Partial |
Exterior
| Exterior | Vinyl Siding |
|---|---|
| Exterior Features | Barn, Cabana, Gutters, Lighting, Underground Sprinkler, Patio |
| Lot Description | Fence - Partial, Some Wetlands, Treed |
| Roof | Asphalt Shingle |
| Foundation | Block |
School Information
| Elementary | Roxbury |
|---|---|
| Middle | Cloonan |
| High | Westhill |
Additional Information
| Date Listed | August 18th, 2026 |
|---|---|
| Days on Market | 15 |
| Zoning | RA1 |
| RE / Bank Owned | No |
Listing Details
| Office | Keller Williams Prestige Prop. |
|---|