18 Tokeneke Trail - Darien, CT

$8,500,000

Beds

10.00

Baths

9,649

SqFt

5.35

Acres

Pricing Insight: Originally listed for $9,350,000, the price was last adjusted to $8,500,000 on March 17, 2026, a –$850,000 (9.1%) change, approximately 0 days ago. This property has been on the market for approximately 194 days.

18 Tokeneke Trail, Darien, CT is a 7-bed, 10-bath, 9,649 square foot home built in 1928 , featuring colonial,mediterranean architecture. This home is part of a homeowners association, with dues of $2,298 paid annually. The HOA fee includes: security service and road maintenance. Community amenities include: security services.

This home is within the Darien school district. Local, with nearby schools including Tokeneke.

MLS #: 24122386

Offered Price: $8,500,000

Residence Type: Single Family

Architectural Style: Colonial,Mediterranean

Living Area: 9,649 Sq. Ft.

Lot Size: 5.35 Acres

Neighborhood: Tokeneke

County: Fairfield

Year Built: 1928

Design & Construction: Frame,Steel

Heating: Hot Air,Radiant,Zoned

Cooling: Central Air

Garage Spaces: 3

Price per Sq Ft as listed: $881

Estimated Tax: $55,174

Days on Market: 194

$6,595,000

6 Beds · 8 Baths · 6,959 Sq Ft

10 Cross Road, Darien

Home Automation: Wired For Audio

Energy Features: Generator, Programmable Thermostat

Solar Contract: Not specified

Heating Fuel: Propane

Fuel Type: Hot Air, Radiant, Zoned

Fuel Tank Location: In Ground

Cooling System: Central Air

Hot Water System: Propane, Domestic

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $881 / Sq. Ft.

Tax assessed value: $3,564,190

Estimated Tax: $55,174

Architectural Style: Colonial,Mediterranean

Design & Construction: Frame,Steel

Residence Type: Single Family

Year Constructed: 1928

Living Area: 9,649 Sq. Ft.

Lot Size: 5.35 Acres

Fuel: Propane

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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 Darien
Statistical modeling algorithms

Local Market Context

Active Listings: 36

Average Price: $2,988,911

Average DOM: 194 days

Complimentary CMAs, no obligation

This magnificent Round Meadows estate with a fantastic 9700 sf house on 5.346 acres of private property is now on the market for the first time in more than 54 years. Located in the private Tokeneke Association with protected land trust property to the East and West of it, Round Meadows is the ultimate in privacy and natural beauty. The owners had the vision to preserve, restore and ultimately combine the best of an elegant and storied past of the original grandeur of its early twentieth century origins with new and soaring modern spaces. They meticulously recreated the splendor of the arches, moldings, windows, light fixtures and even the original sweeping driveway while updating it for the state-of-the-art fine living of today. Round Meadows' totally renovated 19 room home has 7 bedrooms, 7 full baths, including a spectacular primary suite with spa, 3 half baths, library, office and guest suite. Enter through the 2 story foyer with soaring ceilings to the 3 large entertaining rooms, comprised of the living room, sunroom with bar, and an elegant formal dining room with fireplace. The inviting gourmet kitchen is seamlessly connected to a cozy family room with a fireplace which opens onto extensive terraces that overlook acres of manicured lawns and gardens. Add the 3 car garage off a grand mud hall with bath and laundry. Round Meadows honors the past as it pays forward an aspirational essence in the new construction feel, anchored by old world sophistication.

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Flood Risk Assessment

Location Analysis:

Inland Darien location

Water Proximity:

No direct water access

Topography:

Standard terrain • 5.4 acres

Recommendations:

Consult FEMA Flood Maps for accurate zone info
Consider flood insurance based on professional assessment
Evaluate property drainage during inspection
Review local flood history with town officials

Risk Level: Low

Minimal flood risk indicators. Verify with FEMA flood maps.

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.

36

Homes For Sale

$2,988,911

Average List Price

Mechanicals & Utilities: Hot Air,Radiant,Zoned • Propane • Central Air • Public Water Connected water • 5 fireplaces

Exterior Features

Exterior Construction: Stucco

Roof Type: Tile

Foundation: Concrete,Stone

Driveway: Private,Circular,Gravel

Garage: Attached Garage,Driveway (3 car)

Parking: 12 Total

Patio/Deck: Terrace,Gutters,Stone Wall,French Doors,Underground Sprinkler,Patio

Utilities: Water: Public Water Connected

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Darien • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

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18 Tokeneke Trail, Darien, Connecticut

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