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Welcome to 27 Circle Drive, a charming 2-bedroom, 1-bath home nestled in the desirable Lake Chaffee community! Offering a wonderful blend of comfort, character, and potential, this inviting home features a spacious living room with an open layout, creating a warm and welcoming atmosphere for everyday living and entertaining. The generously sized kitchen offers ample space for cooking and gathering, along with a separate dining area. The main-level bathroom features both a separate shower and whirlpool tub, providing the perfect place to relax and unwind. Upstairs, you'll find two spacious bedrooms, including one with the potential to be reconfigured to accommodate an additional room, ideal for a home office, nursery, or guest space. While the home offers a comfortable and functional layout, it also presents a wonderful opportunity for buyers to bring their own style and personal touches through cosmetic updates and improvements. Step outside to enjoy the deck overlooking the expansive yard, with property extending to the opposite side of Circle Drive, offering plenty of room for outdoor activities, gardening, and entertaining. Enjoy all that the Lake Chaffee community has to offer, including access to two beaches and a boat launch, perfect for swimming, kayaking, and enjoying the outdoors. Conveniently located near I-84, approximately 30 minutes to Hartford and 35 minutes to Worcester, this property offers a wonderful balance of peaceful lake community living.

Highlights

  • Residential
  • Single Family Residence
  • Built in 1959
  • 0.19 Acre Lot
  • 2 days on Market

  • Bedrooms
    2
  • Bathrooms
    1
  • Year Built
    1959
  • Architectural Style
    Cottage
  • Construction Materials
    Frame, Vinyl Siding
  • Foundation
    Concrete Perimeter
  • Living Area
    1070.0
  • Interior Features
    Open Floorplan
  • Appliances
    Dryer, Electric Water Heater, Refrigerator, Washer, Range, Oven
  • Patio And Porch
    Deck
  • Cooling
    Ceiling Fan(s)
  • Heating
    Forced Air, Oil
  • Basement
    Crawl Space, Unfinished

  • Acres
    0.19
  • Lot Features
    Level
  • Water Front Features
    Beach Access
  • Water
    Well

  • County
    Windham
  • City
    Ashford
  • Zip Code
    06278
  • High School
    Smith
  • Elementary School
    Ashford

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Frequently Asked Questions

How do I schedule a tour of 27 Circle 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 27 Circle 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 27 Circle Dr?

Click Ask a Question to talk with our team. You already know it is a 2 bed, 1 bath, listed for $225,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Ashford, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 27 Circle 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 27 Circle Dr at around $1,584. 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 27 Circle 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 Windham 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 27 Circle Dr?

In most cases, yes. Whether 27 Circle Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Ashford'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 27 Circle Dr?

We can handle that for you. Our preferred local agent specializes in residentials in Ashford 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 $225,000 with 1,070 sqft of space—that comes out to approximately $210 per square foot.

How long has this property been on the market?

27 Circle Dr was listed on November 12, 2026, which means it's been on the market for 2 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 1959, making it approximately 67 years old.

What is the lot size of this property?

27 Circle Dr sits on a 0.19-acre lot, which is 8,276 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Ashford
  • High: Smith

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

What are the property taxes for 27 Circle Dr?

The most recent public record shows annual property taxes for 27 Circle Dr were approximately $3,643. 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 27 Circle 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.

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 14, 2026 at 07:37AM | Source: SmartMLS | MLS#: 24221377