237 Chestnut Hill Road, Stamford, Connecticut 06903

About this home

***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.

Flood risk: check the FEMA flood map for this address.

Schools

Taxes

Interior

Building & Exterior

Lot & Land

Energy

What it would cost per month

An estimate you can adjust — not a quote, and not an offer of credit. Principal and interest only, plus the taxes and HOA already on this listing. Insurance, PMI and closing costs are not included. Rate seeded at 6.5% (August 2026); change it to whatever your lender quotes.

What's nearby

Distances are straight-line from the property, not driving or walking routes. Places data © OpenStreetMap contributors.

Recent comparable sales

The 5 closest recent sales to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded sale prices from the MLS, not estimates. No automated valuation is shown, because what a home is worth depends on condition, layout and timing that a formula cannot see — call John at 203·883·3399 to read them properly against this home.

5 comparable sales — median $1,000,000, ranging $775,000 to $1,250,000.

Within a 15-minute walk, sold in the last year
• 23 Ethan Allen Lane4 bd · 3 ba · 3,022 sq ft · 0.2 mi away
  $1,150,000$380/sq ft2025-10-27
• 14 Chestnut Hill Road2 bd · 2 ba · 2,088 sq ft · 0.4 mi away
  $775,000$371/sq ft2026-04-23
• 164 Janes Lane4 bd · 3 ba · 3,119 sq ft · 0.6 mi away
  $1,250,000$400/sq ft2026-01-27
• 96 Surrey Road4 bd · 3 ba · 2,815 sq ft · 0.6 mi away
  $1,000,000$355/sq ft2025-08-21
• 177 Old Logging Road4 bd · 2 ba · 2,396 sq ft · 0.6 mi away
  $898,500$375/sq ft2025-10-30

Public record

From the Stamford assessor's public property record. These figures describe the property as the town has it on file and can differ from the listing — a finished basement or an addition may not be reflected in the assessor's living area.

Recorded sales

Deed transfers on file with the Stamford land records, newest first. These are recordings rather than MLS sales, so they include transfers that were never listed. Nominal and $0 transfers (estate, trust and family conveyances) are excluded.

• 2015-12-21$744,000Single Family

More homes in Stamford

Closest in price to this one.

• 45 Hemlock Drive3 bed · 3 bath · 2,183 sq ft$1,075,000
• 518 Woodbine Road4 bed · 5 bath · 5,162 sq ft$1,050,000
• 19 Crestview Avenue4 bed · 3 bath · 2,826 sq ft$1,049,000
• 58 Briar Woods Trail3 bed · 5 bath · 4,388 sq ft$1,099,000
• 132 Webbs Hill Road3 bed · 2 bath · 1,933 sq ft$1,015,000
• 24 Smoke Hill Drive3 bed · 2 bath · 3,383 sq ft$1,000,000

← Back to all Stamford listings