55 Winterset Dr , Chatham, MA 02633

How do I schedule a tour of 55 Winterset Dr?

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 55 Winterset Dr.

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 55 Winterset Dr?

Click Ask a Question to talk with our team. You already know it is a 4 bed, 3 bath, listed for $2,245,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Chatham, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 55 Winterset Dr?

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 55 Winterset Dr at around $13,247. 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 55 Winterset Dr?

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 Barnstable 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 55 Winterset Dr?

In most cases, yes. Whether 55 Winterset Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Chatham'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 55 Winterset Dr?

We can handle that for you. Our preferred local agent specializes in residentials in Chatham 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 $2,245,000 with 4,072 sqft of space—that comes out to approximately $551 per square foot.

How long has this property been on the market?

55 Winterset Dr was listed on July 12, 2026, which means it's been on the market for 125 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 1970, making it approximately 56 years old.

What is the lot size of this property?

55 Winterset Dr sits on a 1.94-acre lot, which is 84,506 square feet.

What are the property taxes for 55 Winterset Dr?

The most recent public record shows annual property taxes for 55 Winterset Dr were approximately $5,655. 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 $75 paid annually.

This covers access to community features including: Beach Access.

Is 55 Winterset Dr still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.