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Set within Darien's coveted private Tokeneke Association, 5 Cross Road is a quintessential stone Colonial gracefully positioned on a private .70 acre property. Timeless architectural character, exceptional privacy, and inviting living spaces define this distinctive residence in one of the town's most sought-after coastal neighborhoods.The thoughtfully updated kitchen serves as the heart of the home, while an extraordinary family room with soaring ceilings and abundant natural light offers a dramatic yet welcoming setting for everyday living and entertaining. A desirable first-floor primary suite provides comfort and convenience, creating an ideal layout for modern living. Classic details and generous rooms throughout complement the home's enduring stone facade and beautifully secluded grounds. Enjoy the rare combination of a tranquil residential setting, private association lifestyle, and convenient access to Darien's village, schools, train, beaches, and waterfront. A special Tokeneke offering where classic New England charm meets effortless, refined living.

  • Bedrooms
    4
  • Bathrooms
    3 full · 2 half
  • Year Built
    1932
  • Architectural Style
    Colonial
  • Construction Materials
    Stone
  • Foundation
    Stone, Concrete Perimeter
  • Garage Spaces
    2.0
  • Parking Features
    Attached
  • Living Area
    4361.0
  • Interior Features
    Entrance Foyer
  • Appliances
    Dryer, Dishwasher, Refrigerator, Washer, Gas Range, Range Hood
  • Exterior Features
    Garden
  • Patio And Porch
    Patio
  • Cooling
    Central Air
  • Heating
    Hot Water, Oil
  • Basement
    Crawl Space, Unfinished

  • Acres
    0.7
  • Lot Features
    Level, Corner Lot
  • Water
    Public

  • County
    Fairfield
  • City
    Darien
  • Zip Code
    06820
  • High School
    Darien
  • Middle School
    Middlesex
  • Elementary School
    Tokeneke

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Frequently Asked Questions

How do I schedule a tour of 5 Crossroad?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 5 Crossroad.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 5 Crossroad?

Click Ask a Question to talk with our team. You already know it is a 4 bed, 3 bath, listed for $3,795,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Darien, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 5 Crossroad?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 5 Crossroad at around $24,216. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 5 Crossroad?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Fairfield County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 5 Crossroad?

In most cases, yes. Whether 5 Crossroad is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Darien's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 5 Crossroad?

We can handle that for you. Our preferred local agent specializes in residentials in Darien and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $3,795,000 with 4,361 sqft of space—that comes out to approximately $870 per square foot.

How long has this property been on the market?

5 Crossroad was listed on September 28, 2026, which means it's been on the market for 46 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1932, making it approximately 94 years old.

What is the lot size of this property?

5 Crossroad sits on a 0.7-acre lot, which is 30,492 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Tokeneke
  • Middle: Middlesex
  • High: Darien

Want to see how these schools compare? Check out our Fairfield County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 5 Crossroad?

The most recent public record shows annual property taxes for 5 Crossroad were approximately $31,441. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is there an HOA fee for this property, and what does it cover?

This home has an HOA fee of $1,349 paid annually.

Is 5 Crossroad still available for sale?

This home is pending sale, which means the seller has accepted an offer. You can favorite it to track status or ask our expert to help you find similar homes in this area. We'll also let you know if this property comes back on the market.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, SmartMLS. All rights reserved.

Last Updated: November 13, 2026 at 02:23PM | Source: SmartMLS | MLS#: 24210059