5 Sherwood Avenue, Greenwich, Connecticut 06831

About this home

Meticulously restored and reimagined by Fletcher Development in 2023, this classic Tudor sits behind secure gates on 28 magnificent, parklike acres. Beautifully appointed interiors feature a dramatic double-height living room, sunroom, office, formal dining room and gourmet kitchen equipped with Wolf, Sub-Zero and Miele appliances. Four generously sized bedrooms each include a private en-suite bath. Exceptional craftsmanship and thoughtful details honor the home's historic character while introducing every modern comfort. Private, picturesque and remarkably serene, the property offers an elevated country retreat in an extraordinary setting.

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

Availability, Pets & Lease

Schools

Interior

Building & Exterior

Lot & Land

What's nearby

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

Recent comparable rentals

The 5 closest recent leases to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded lease 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 rentals — median $11,500/mo, ranging $9,000/mo to $14,000/mo.

Within a 15-minute walk, leased in the last year
• 9 Sherwood Avenue5 bd · 7 ba · 4,024 sq ft · 0.1 mi away
  $14,000/mo2025-11-26
• 414 Riversville Road4 bd · 3 ba · 4,490 sq ft · 0.7 mi away
  $11,000/mo2025-08-30
Within about a mile and a half, leased in the last 2 years
• 53 Stonehedge Drive South4 bd · 4 ba · 5,341 sq ft · 1.2 mi away
  $9,000/mo2025-06-12
• 15 Bowman Drive4 bd · 4 ba · 3,451 sq ft · 1.3 mi away
  $11,500/mo2026-05-04
• 99 Porchuck Road5 bd · 5 ba · 3,700 sq ft · 1.3 mi away
  $12,500/mo2025-10-17

Listing & sale history

Every time this exact home has come to market in the MLS data this site tracks. Where a sale closed, the recorded sale price is shown; "asking" marks a price the home was listed at rather than what it sold for.

More rentals in Greenwich

Closest in price to this one.

• 1 Crawford Terrace4 bed · 4 bath · 2,819 sq ft$18,000/mo
• 2 Choctaw Lane4 bed · 4 bath · 5,262 sq ft$18,000/mo
• 18 Osee Place5 bed · 6 bath · 3,848 sq ft$17,500/mo
• 189 Davis Avenue Unit A14 bed · 5 bath · 3,256 sq ft$18,500/mo
• 34 Wescott Street4 bed · 5 bath · 4,200 sq ft$16,500/mo
• 97 Riverside Avenue4 bed · 3 bath · 3,517 sq ft$20,000/mo

← Back to all Stamford listings