1 Overlook Way , Winchester, MA 01890

How do I schedule a tour of 1 Overlook Way?

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 1 Overlook Way.

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 1 Overlook Way?

Click Ask a Question to talk with our team. You already know it is a 4 bed, 2 bath, listed for $1,650,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Winchester, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 1 Overlook Way?

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 1 Overlook Way at around $10,861. 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 1 Overlook Way?

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 Middlesex 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 1 Overlook Way?

In most cases, yes. Whether 1 Overlook Way is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Winchester'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 1 Overlook Way?

We can handle that for you. Our preferred local agent specializes in residentials in Winchester 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 $1,650,000 with 3,604 sqft of space—that comes out to approximately $458 per square foot.

How long has this property been on the market?

1 Overlook Way was listed on September 23, 2026, which means it's been on the market for 51 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 1941, making it approximately 85 years old.

What is the lot size of this property?

1 Overlook Way sits on a 0.36-acre lot, which is 15,682 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

• Elementary: Ambrose
• Middle: Mccall
• High: Whs

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

What are the property taxes for 1 Overlook Way?

The most recent public record shows annual property taxes for 1 Overlook Way were approximately $17,650. 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 1 Overlook Way 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.