758 Smith Ridge Road, New Canaan, Connecticut 06840

About this home

Nestled at the end of a private lane off sought after Smith Ridge Road, this enchanting 1924 Cape exudes timeless elegance and undeniable charm. Set on 2.2 lush, flat acres, the property offers a serene retreat with expansive grounds ideal for relaxation and hosting. The chef's kitchen features top tier appliances and quartz countertops that balance beauty with functionality, and it opens seamlessly into the family room for effortless everyday living. The spacious living room showcases French doors that lead to a breathtaking park-like setting with a built-in outdoor grill and stone fireplace. The first-floor primary suite is approached through a cozy sitting room with a fireplace, creating an intimate and inviting entry. Four beautifully finished bedrooms complete the home, each crafted with thoughtful detail and classic appeal. The expansive bonus room above the garage-complete with a full bathroom and steam shower-offers exceptional versatility, perfect for a home gym, recreation room, private office, or guest suite. Brand new septic system!

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 $2,400,000, ranging $1,000,000 to $3,750,000.

Within a 15-minute walk, sold in the last year
• 232 Sleepy Hollow Road4 bd · 4 ba · 4,436 sq ft · 0.4 mi away
  $1,575,000$355/sq ft2025-10-30
Within about a mile and a half, sold in the last 2 years
• 12 Father Peters Lane4 bd · 5 ba · 5,958 sq ft · 0.4 mi away
  $3,750,000$629/sq ft2025-05-01
• 428 Laurel Road4 bd · 5 ba · 3,396 sq ft · 0.6 mi away
  $3,000,000$883/sq ft2026-08-17
• 1000 Smith Ridge Road2 bd · 3 ba · 3,298 sq ft · 0.6 mi away
  $1,000,000$303/sq ft2024-10-01
• 2 Sleepy Hollow Road5 bd · 3 ba · 5,658 sq ft · 0.8 mi away
  $2,400,000$424/sq ft2026-06-29

Public record

From the New Canaan 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 New Canaan 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.

• 2007-07-02$2,100,000Single Family

More homes in New Canaan

Closest in price to this one.

• 596 Silvermine Road5 bed · 7 bath · 6,373 sq ft$2,780,000
• 44 Benedict Hill Road5 bed · 4 bath · 3,200 sq ft$2,750,000
• 148 West Hills Road5 bed · 5 bath · 5,731 sq ft$2,995,000
• 16 Grace Street5 bed · 5 bath · 3,250 sq ft$2,995,000
• 192 Cross Ridge Road3 bed · 3 bath · 3,096 sq ft$3,000,000
• 145 River Street5 bed · 6 bath · 5,300 sq ft$2,695,000

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