Eastford Homes for Sale

Eastford Homes for Sale

Welcome to Eastford, Connecticut, a hidden gem nestled in the heart of Windham County! This charming town, rich in history and natural beauty, offers the perfect blend of rural tranquility and modern convenience. With a population of just over 1,500 residents, Eastford boasts a tight-knit community atmosphere, where neighbors become friends and local events bring everyone together.

As you explore Eastford, you'll be captivated by its picturesque landscapes, featuring rolling hills, lush forests, and serene ponds. Outdoor enthusiasts will appreciate the abundance of recreational opportunities, from hiking and biking on scenic trails to fishing and kayaking in nearby waterways. The town is also home to several parks and nature reserves, making it an ideal setting for families and nature lovers alike.

When it comes to homes for sale in Eastford, you’ll find a diverse array of properties that cater to various lifestyles and budgets. Whether you’re seeking a charming historic farmhouse, a cozy cottage, or a modern family home, Eastford has something for everyone. Many of these homes are set on spacious lots, allowing for ample outdoor space to enjoy the picturesque surroundings.

With its excellent schools, friendly community, and convenient access to major highways, Eastford offers the perfect balance of rural living and suburban convenience. As you consider your next home, let Eastford welcome you with open arms. Discover the warmth and charm of this delightful town, where your dream home awaits!

Newest Eastford Homes for Sale

54 Westford Rd, Eastford
$574,900
3 Beds ⋅ 2 Baths ⋅ 24212900 MLS
Step onto this property and you are immediately taken with its beauty. Mature landscaping filled with ornamental and native trees including 1000's of spring bulbs, summer lilies, and other perennials surrounded by the stone walls that characterize so much of New England charm. This 1900's home has been carefully updated to highlight its character and history with all the conveniences we have learned to love. The entry way welcomes you with vintage cherry floors, The kitchen has been completely remodeled with new cabinets, quartz countertops, and new appliances. The back ell consists of a walk-in pantry, an oversized mud room with laundry and new 3/4 bath as well as an office with private entrance on the first floor. Spacious Dining room, featuring Washington fir floors is right off the kitchen. The large living room with fireplace, is open to sunroom/family room with ample space for you to spread out and enjoy entertaining. A beautiful staircase leads to three bedrooms, all with wood flooring and remodeled full bathroom. There are possibilities for an in-law suite with not too much effort. Refinished plaster walls and fresh paint throughout. Almost 4 acres gives you room to spread your wings. Open field, perfect for grazing your animals. Concrete pad, ready for your new garage or barn. Most windows replaced; roof on the ell of the house is brand new. Mechanicals are up to date. Ready to for you to move right in!

54 Westford Rd, Eastford
24 Sumner Hill Rd, Eastford
$425,000
3 Beds ⋅ 2 Baths ⋅ 24214021 MLS
IF YOU'VE BEEN WATCHING FOR YOUR DREAM LOG HOME LOCATED ON A QUIET COUNTRY ROAD, YOUR WAIT MIGHT BE OVER! THIS WELL CARED FOR 2000 PLUS SQ FT HOME IS READY FOR IT'S NEW OWNER. YOU'LL LOVE THE SPACIOUS BEAMED CEILING FAMILY ROOM WITH COZY STONE FIREPLACE, REAR DECK ACCESS, AND MINI SPLIT TO KEEP YOU COOL. WIDE PINE FLOORING, COFY DEN, AND OFFICE WHICH COULD BE USED AS A GUEST BEDROOM. LARGE PRIVATE REAR DECK AND OVERSIZE FRONT FARMERS PORCH TO SIT AND RELAX PEACEFULLY. OWNERS HAD RECENTLY REPLACED THE BOILER AND ROOF SO BIG TICKET IMPROVEMENTS WON'T BE NEEDED. COME AND SEE WHAT A RARE FIND THIS IS! NEAR POMFRET AND WOODSTOCK TOWN LINES.

24 Sumner Hill Rd, Eastford
15 Chaplin Rd, Eastford
$299,900
3 Beds ⋅ 1 Baths ⋅ 24213320 MLS
A true gem waiting for its next owner! This Ranch features an oversized attached 2-car garage connected to the house via a breezeway with louvered windows for the perfect spot for your plants and sitting! Sunny and bright living room with floor to ceiling window wall and hardwood floors. 3 bedrooms feature gorgeous hardwood floors. Furnace has a unique ability to be powered by either oil or wood! Newer roof and freshly painted worry free aluminum siding. All of this settled on 2.8 pristine acres! What more could you want?

15 Chaplin Rd, Eastford
32 Ashford Rd, Eastford
$435,000
3 Beds ⋅ 2 Baths ⋅ 24209461 MLS
If you've been searching for true country living, privacy, and land for exploration, this 17-acre property in Eastford delivers all of it. With Bigelow Brook (a Class A trout brook), running through the acreage and the Natchaug Blue Blaze Trail crossing the land, this is a dream setting for outdoor enthusiasts, nature lovers, and anyone seeking a peaceful retreat. The location places you near Natchaug State Forest, Ashford Lake, and between Buell's and Crooks orchards. The Cape Cod home is set back from the road, giving the ultimate sense of privacy. Inside, the large eat-in kitchen features a large moveable island, pantry closet, updated quartz countertops, luxury vinyl flooring, induction stove, newer refrigerator, and an elegant wood hood. Just off the kitchen is a flexible first floor bedroom or home office with double closets and stunning cherry wood floors milled from trees harvested on the property. The living and dining rooms continue the cherry flooring and offer a warm gathering space with a woodstove for alternative heating. A French door leads to the back deck with a ramp from the driveway, and overlooking the backyard and peaceful tree line. A full bath with tub/shower completes the main level. Upstairs are two bedrooms, a full bath, and a walk-in hallway closet. The larger bedroom includes a Jotul woodstove for additional heating, and both rooms feature skylights that fill the space with natural light.

32 Ashford Rd, Eastford
89 John Perry Rd, Eastford
$625,000
4 Beds ⋅ 3 Baths ⋅ 24210501 MLS
The Benjamin Bosworth House has been part of Eastford's landscape for more than two centuries, and there is still nothing quite like it. Set on 3 acres, this Federal-style home, completed around 1800, offers 4,538 square feet, 4 bedrooms, 2.5 baths and 11 fireplaces. Its defining feature is a rare full-height monitor, once used as a Masonic meeting hall, with built-in benches and fireplaces. Throughout the house, hand-carved woodwork, historic finishes and generously scaled rooms tell the story of its past. The main level includes a formal dining room, parlor, sunlit sitting room, kitchen, studio and workshop, with additional flexible space upstairs. Since purchasing the home in May, the current owner has continued restoration work, including new lime plaster in the parlor and second-floor hall, a retiled upstairs bath and fresh paint in several rooms. Listed on the National Register of Historic Places, this is a remarkable opportunity for someone who appreciates early American craftsmanship and wants to carry its story forward.

89 John Perry Rd, Eastford
Start Your Search

IDX information is 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 is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!