105 Woodside Drive - Greenwich, CT

$6,995,000

Beds

9.00

Baths

7,292

SqFt

0.88

Acres

Pricing Insight: Originally listed for $6,995,000, the price has remained unchanged for approximately 57 days. This property has been on the market for approximately 57 days.

105 Woodside Drive, Greenwich, CT is a 6-bed, 9-bath, 7,292 square foot home built in 1930 , featuring colonial architecture. This home is part of a homeowners association, with dues of $10,826 paid annually. The HOA fee includes: security service and road maintenance. Community amenities include: park and playground/tot lot.

This home is within the Greenwich school district. Local, with nearby schools including Julian Curtiss.

MLS #: 24159292

Offered Price: $6,995,000

Residence Type: Single Family

Architectural Style: Colonial

Living Area: 7,292 Sq. Ft.

Lot Size: 0.88 Acres

Neighborhood: N/A

County: Fairfield

Year Built: 1930

Design & Construction: Stone

Heating: Hot Water

Cooling: Central Air

Garage Spaces: 2

Price per Sq Ft as listed: $959

Estimated Tax: $53,260

Days on Market: 57

$6,700

3 Beds · 2 Baths · 1,631 Sq Ft

33 Circle Drive, Greenwich

Home Automation: Not specified

Energy Features: Not specified

Solar Contract: Not specified

Heating Fuel: Natural Gas

Fuel Type: Hot Water

Fuel Tank Location: Not specified

Cooling System: Central Air

Hot Water System: Natural Gas, Domestic

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $959 / Sq. Ft.

Tax assessed value: $4,309,410

Estimated Tax: $53,260

Architectural Style: Colonial

Design & Construction: Stone

Residence Type: Single Family

Year Constructed: 1930

Living Area: 7,292 Sq. Ft.

Lot Size: 0.88 Acres

Fuel: Natural Gas

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AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

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Understanding This Valuation

The RPR AVM considers:

Recent sales of comparable properties
Property characteristics and location
Market trends in Greenwich
Statistical modeling algorithms

Local Market Context

Active Listings: 88

Average Price: $2,668,545

Average DOM: 57 days

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105 Woodside Drive captures the very best of Country Club Living in Greenwich. Chic fieldstone classic set within the gated Milbrook community, home to the coveted Milbrook Club, with the opportunity to apply for private membership--creating a lifestyle where recreation, relaxation, and social life are just moments from your front door. Perfectly sited overlooking the lake on nearly an acre, the six-bedroom residence blends modern interiors with an effortless indoor-outdoor flow designed for entertaining and everyday enjoyment. Renovated and expanded for seamless living, the crisp, light-filled residence unfolds across four levels, highlighted by a spectacular great room with soaring 19-foot ceilings, elegant formal rooms, and a welcoming family room that opens to a gourmet kitchen with center island, professional appliances and a sunny breakfast room. French doors lead to terraces and a lush backyard--an inviting setting for outdoor dining, gatherings, and play. Upstairs, the serene primary suite offers generous walk-in closets and two luxurious baths, accompanied by three additional ensuite bedrooms. A versatile top floor provides two more bedrooms or a creative retreat, while the finished lower level (additional 1500+ sq ft) has another media area, gym, wine space and much more.

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Flood Risk Assessment Water Body Detected Nearby

Water Proximity Detected: This property exhibits indicators suggesting nearby or referenced water features

Location Analysis:

Water features noted

Water Proximity:

Near water body

Topography:

Standard terrain • 0.9 acres

Water Indicators Found:

Water-related features referenced in listing details

Recommendations:

Professional flood assessment advised
Based on identified water-related indicators, flood insurance may warrant consideration
Consult FEMA Flood Maps for zone verification
Evaluate drainage systems
Review local flood history

Risk Level: Moderate

Property near water bodies. Consider flood insurance.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

Dining & Café Access: Low to Moderate
Daily Services: Limited
Recreational Space: Limited Nearby

How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

88

Homes For Sale

$2,668,545

Average List Price

Mechanicals & Utilities: Hot Water • Natural Gas • Central Air • Public Water Connected water • 4 fireplaces

Exterior Features

Exterior Construction: Stone

Roof Type: Tile

Foundation: Concrete

Garage: Attached Garage (2 car)

Patio/Deck: Terrace,French Doors

Utilities: Water: Public Water Connected

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Greenwich • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

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105 Woodside Drive, Greenwich, Connecticut

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