421 Chestnut Hill Road, Stamford, Connecticut 06903

About this home

Contemporary Colonial in a prime Long Ridge location! Move right into this 3-bedroom, and 2.1 bathroom home offering an open floor plan, and flexible living spaces, ideally situated just off Long Ridge Road. The main level features vaulted ceilings, oversized windows, and hardwood floors. Enjoy the modern, light and bright kitchen, a great room with a wood burning fireplace, a formal dining room, a large flex space which is ideal as an office, and a full bathroom. Upstairs offers 3 bedrooms, and a bath and a half. The lower level has a playroom, lots of storage, and an oversized 1 car garage. Step outside to your private outdoor oasis-relax on the spacious deck overlooking a serene backyard with a fire-pit, surrounded by walking trails, and a peaceful brook. Just steps away from Chestnut Hill Park, a 6.6-acre gem featuring a newly renovated playground, wide-open green spaces, and picnic areas. Minutes from shopping, dining, golf courses, and top-rated specialty hospitals, and a 2 minute drive to the Merritt Parkway makes this property ideal for buyers.

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

Schools

Taxes

Interior

Building & Exterior

Lot & Land

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 $810,000, ranging $500,000 to $910,000.

Within a 15-minute walk, sold in the last year
• 247 Chestnut Hill Road2 bd · 2 ba · 1,743 sq ft · 0.4 mi away
  $813,709$466/sq ft2026-08-18
• 1489 Long Ridge Road3 bd · 2 ba · 1,969 sq ft · 0.5 mi away
  $500,000$253/sq ft2025-10-23
• 21 Timber Mill Road4 bd · 3 ba · 2,604 sq ft · 0.6 mi away
  $910,000$349/sq ft2025-12-02
Within about a mile and a half, sold in the last 2 years
• 5 Hunting Ridge Road4 bd · 3 ba · 1,950 sq ft · 0.1 mi away
  $810,000$415/sq ft2025-07-31
• 560 Webbs Hill Road3 bd · 3 ba · 1,742 sq ft · 0.2 mi away
  $740,000$424/sq ft2024-12-18

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.

• 2019-09-30$471,000Single Family
• 2011-07-15$470,000Single Family

More homes in Stamford

Closest in price to this one.

• 15 Muriel Drive3 bed · 1 bath · 1,448 sq ft$725,000
• 65 Interlaken Road4 bed · 2 bath · 2,696 sq ft$729,000
• 114 Webb Avenue3 bed · 2 bath · 2,081 sq ft$732,000
• 55 Dann Drive3 bed · 2 bath · 1,470 sq ft$745,000
• 13 Ledge Lane3 bed · 2 bath · 1,770 sq ft$749,000
• 25 Hillandale Avenue3 bed · 2 bath · 1,852 sq ft$749,000

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