Sherman Homes under $1.25 million

Welcome to Sherman, Connecticut, a picturesque gem nestled in the heart of Fairfield County. Known for its stunning landscapes and serene atmosphere, Sherman offers a unique blend of rural charm and modern convenience, making it an ideal place to call home. With a rich history dating back to the 18th century, this quaint New England town boasts beautiful colonial architecture, lush greenery, and a tight-knit community that welcomes newcomers with open arms.

For those seeking a new residence, Sherman presents an array of charming homes priced under $1.25 million. Whether you're looking for a cozy cottage, a spacious family home, or a luxurious retreat, the real estate options in Sherman cater to diverse tastes and lifestyles. Many of these homes feature expansive yards, scenic views, and modern amenities, ensuring that you can enjoy the tranquility of nature without sacrificing comfort.

Living in Sherman means embracing a lifestyle filled with outdoor adventures, from hiking and biking along scenic trails to fishing in the pristine lakes. The town is also conveniently located near major highways, providing easy access to nearby cities like Danbury and Newtown, where you can enjoy shopping, dining, and cultural experiences.

In Sherman, you’ll find not just a house, but a place where memories are made, and community bonds are cherished. Explore the enchanting properties available under $1.25 million and discover the perfect home that fits your lifestyle in this idyllic Connecticut town. Your dream home awaits in Sherman!

Newest Sherman Homes under $1.25 million

$308,000

1 Beds ⋅ 1 Baths ⋅ 24214214 MLS

Escape to your own personal treehouse in Sherman! This charming 1-bedroom, 1-bath home features a fabulous west-facing deck for enjoying spectacular sunsets, and a screened porch surrounded by nature. Inside, a cozy wood stove adds warmth and character, while a spacious loft provides abundant storage. The renovated kitchen features granite counters and a newer refrigerator; the updated bath includes a heated floor and towel warmer. Big-ticket improvements include 200-amp electric with sub panel for a generator, roof, bathroom plumbing, oil tank, water heater, and well pump. This home is ideal for weekend escapes or full-time living, with recreation in every season! Sherman residents enjoy Candlewood Lake access, including a sandy beach, pavilion, playground, and kayak racks. The town recreation area offers tennis courts, a walking path, playground, baseball fields, and a basketball court. Enjoy shopping and dining in nearby New Milford and Danbury, with NYC just 90 minutes away by car or train and the Berkshires 75 minutes away. Ski at Thunder Ridge, just 15 minutes away, or Mohawk Mountain, only 40 minutes away. Discover this special Sherman retreat. Schedule your private showing today!

101 Rte 39 S, Sherman

$1,098,000

3 Beds ⋅ 5 Baths ⋅ 24216220 MLS

One-of-a-Kind Contemporary with Spectacular Timber Lake Views! Wake up to shimmering lake views, enjoy sun-drenched afternoons on multiple decks, and unwind surrounded by nature. Embrace the Timber Lake lifestyle while enjoying Sherman's notably low property taxes, approximately 90 minutes from NYC with convenient access to Metro-North rail service. Tucked along a serene country lane, this distinctive contemporary offers exceptional privacy, striking rock formations, a new driveway, and a three-car garage. Inside, three bedrooms and four and 1/2 full bathrooms provide flexibility for family and guests, including a main-level bedroom and full bath. Beautiful hardwood floors and a distinctive compass inlay in the welcoming foyer add character, while an open, flowing floor plan, expansive windows, and four sets of sliders bring abundant natural light and captivating lake views indoors. The main level office has large closets and can be used as a bedroom. The finished walk-out lower level expands the possibilities with a separate entrance, sliding glass doors, a full bathroom, and beautiful lake views. Ideal for extended family, guests, recreation, or a potential in-law arrangement, this versatile space offers excellent flexibility. Whether envisioned as a peaceful weekend escape or a year-round residence, this exceptional property combines distinctive architecture, spectacular views, privacy, and the best of lake and country living.

45 Timber Lake Rd, Sherman

$410,000

2 Beds ⋅ 2 Baths ⋅ 24214386 MLS

Set on 2+ acres, this single level 2 bed 1.5 bath home makes everyday living easy. The spacious, light filled living room is anchored by a wood burning stove, and the well laid out kitchen has views with a patio just outside the door. It's an easy spot for morning coffee or dinner outdoors. A fully fenced yard gives you secure outdoor space for pets, play, or garden plants, plus a nice swath of land in the front yard adds even more room to spread out. A garage and carport cover your vehicles, plus the walkout basement adds plenty of storage. The detached workshop, with its large windows, is brimming with potential. Picture a studio, hobby space, or workshop. Located in Sherman with a small corner of the parcel in New Fairfield, this home offers beach access on Candlewood Lake through both towns, a rare perk. Minutes to the charming town center w/ community amenities, hiking trails, library & playhouse. One level, loads of space, and a location that gives you the best of both towns - but the low taxes of Sherman! THIS IS ONE OF 2 HOMES FOR SALE NEXT DOOR TO EACH OTHER #210 & #208.

210 Rte 37 S, Sherman

$338,000

2 Beds ⋅ 1 Baths ⋅ 24214342 MLS

Built in the 1920s and wrapped in cedar shingles, this 2 bed 1 bath cottage was designed to harmonize with its surroundings. It sits right beside a protected land trust parcel, so your view stays green with privacy insured. Step onto the front deck and take in the mountain views with your morning coffee. Inside, the living room is cozy and full of character with custom built-ins and a wood burning stove for cold New England nights. The large eat-in kitchen is the heart of the home with a convenient laundry closet tucked to the side. Out back, a gravel patio and tiered backyard make a great spot for gardening, gathering, or a fire pit. A cabin/shed adds flexible space for a studio, workshop, or storage. The walkout basement has room to finish into a home gym or office. Charming, private, and full of potential! Located in Sherman just steps from the New Fairfield line, this is small-town Connecticut at its best. Residents enjoy access to Candlewood Lake through the Sherman Town Beach. Minutes to charming town center w/ community amenities, library & playhouse. Sherman is known for low taxes and K-8 school. And when you need more than country life offers, major shopping and routes in both CT & NY are only a short drive away. THIS IS ONE OF 2 HOMES FOR SALE NEXT DOOR TO EACH OTHER #210 & #208

208 Rte 37 S, Sherman

$550,000

3 Beds ⋅ 3 Baths ⋅ 24213711 MLS

Magical setting and so much character, uniqueness and potential! 3 bedroom 3 bath 3 fireplace contemporary home on private 2 plus acre lot with inground pool and ponds. 2 car detached garage. Living room with vaulted ceilings, hardwood floors, beams, walls of glass and fireplace. Vaulted eat in kitchen with skylite and brick floor and breakfast bar. Super cool den with fireplace, loft, brick floor and great windows. Primary bedroom with distressed pine floors, walk in closet and full bath. 2 sets of stairs to the lower level (one spiral) where you will find an awesome family room/gameroom with slate floors, fireplace and bar plus 3rd bedroom. The outside has indefinite potential and character. Spring fed ponds with patios and walking bridges and dock. Perfect weekend retreat or year round paradise! Great schools and low taxes and minutes to the train station!!

8 Rte 55 W, Sherman

$799,000

4 Beds ⋅ 3 Baths ⋅ 24210881 MLS

Discover the perfect blend of space, privacy, and refined country living in this impressive four- bedroom, three-bath residence offering approximately 3,588 square feet on two serene acres in sought-after Sherman, CT. Privately situated on a peaceful cul-de-sac, the home features generously proportioned rooms designed for comfortable living and effortless entertaining. The beautifully updated kitchen is appointed with stainless steel appliances, abundant cabinetry, and a welcoming breakfast bar. An expansive additional living space provides the ideal setting for entertaining, gathering with loved ones, or simply relaxing and lounging in comfort. Outdoors, a spacious deck and swimming pool create your own private retreat, ideal for summer entertaining and enjoying the tranquil surroundings. Complete with a two-car garage, expansive grounds, and access to Sherman's highly regarded schools, this exceptional property offers the space and serenity of country living with convenient proximity to the New York border.

20 Mauweehoo Hl, Sherman

$699,999

4 Beds ⋅ 4 Baths ⋅ 24211155 MLS

Welcome home to this exceptional 4-bedroom, 3.5-bath Custom Colonial nestled on 4.5 scenic acres in sought-after Sherman. Featuring an expansive wraparound covered porch, a beautifully updated kitchen with stone countertops, and an inviting den with a fireplace, every space is designed for comfortable living and effortless entertaining. Upon entering, you'll find a flexible main-level suite that serves perfectly as a fourth bedroom, guest quarters, au pair setup, or an amazing family room. Upstairs, you'll discover three spacious bedrooms, a convenient laundry area, and two additional full baths. The primary suite is a true retreat, featuring a walk-in closet with custom built-ins, a luxurious soaking tub, and a separate stand-up shower. An unfinished basement provides endless possibilities for future living space, a home gym, media room, workshop, or whatever your vision may be. Enjoy low Sherman taxes and a peaceful setting just 10 minutes from New Fairfield, 12 minutes from downtown Pawling, NY, moments from Candlewood Lake, Quaker Hill Country Club, several equestrian facilities and Great Hollow Nature Preserve. Offering privacy, flexibility, and a serene country setting, this property is more than a home, it's a true getaway.

34 Hardscrabble Rd, Sherman

$850,000

3 Beds ⋅ 4 Baths ⋅ 24209808 MLS

Discover the perfect blend of architectural character, modern updates, and tranquil surroundings in this beautifully refreshed mid-century modern home offering over 2,800 square feet of living space. Soaring ceilings, an open-concept floor plan, and 12 skylights fill the home with abundant natural light, creating a bright, airy, and welcoming atmosphere. The remodeled kitchen blends contemporary style with everyday functionality, while the versatile loft offers the perfect setting for a home office, creative studio, or peaceful retreat. Two striking spiral staircases add a distinctive architectural touch, enhancing the home's unique mid-century appeal. Numerous recent improvements provide comfort, style, and peace of mind, including a new roof, a new septic system installed in April 2026, a new furnace, a new boiler, fresh interior and exterior paint on the house, deck, and doors, and updated sink fixtures. Outside, the private garden setting offers a serene escape surrounded by nature. The inviting pool has also received an impressive refresh, featuring a brand-new liner, new filter system, new water pump, fresh water, and a conversion to saltwater for easier maintenance. Whether enjoying a quiet afternoon in the garden, taking a refreshing swim, or entertaining family and friends, this exceptional property offers a wonderful balance of distinctive design, thoughtful updates, and relaxed living-ready to be enjoyed for years to come.

1 Eagles Nest Dr, Sherman

$1,099,000

5 Beds ⋅ 4 Baths ⋅ 24207822 MLS

Originally part of the historic Brinsmade Dairy Farm, this Sherman estate blends classic New England charm with modern comfort. Set on approximately 8 acres with a Main House and separate Pool House, the property offers approx. 4,500 sq ft across both dwellings, featuring 5 bedrooms and 4 full baths-ideal for multigenerational living, weekend retreats, or entertaining. The Main House showcases cathedral ceilings, exposed beams, wideplank floors, a vaulted kitchen, and large picture windows framing rolling lawns, mature trees, and peaceful countryside views. Outdoor living is exceptional with a sparkling inground pool, tennis court, pond, and multiple spaces for dining, relaxing, and enjoying nature. Candlewood Lake is minutes away for boating, kayaking, and paddleboarding. The Pool House provides a comfortable guest retreat with its own bedroom, bath, and living area. Six garages offer abundant storage for vehicles, boats, and recreational equipment. A rare opportunity to own a private estate combining recreation, history, and natural beauty-all with low Sherman taxes. Experience the space, privacy, and lifestyle that make this property truly unique.

6 Brinsmade Ln, Sherman

$384,000

2 Beds ⋅ 1 Baths ⋅ 24202184 MLS

Welcome home to this charming 2-bedroom, 1-bath Cape Cod overflowing with character in the desirable Candlewood Echoes community of Sherman, CT. Nestled along the tranquil northern shores of Squantz Pond near New Fairfield, this private beach neighborhood offers an idyllic lifestyle with direct beach access for year-round swimming, kayaking, paddleboarding, fishing, and winter ice sports. Inside, a generous wide-open floor plan seamlessly connects the living and family room spaces to a dining area with custom built-ins and a corner curio and space for an in-home office. The spacious eat-in kitchen features ample cabinetry, a pantry, and rustic vaulted wood ceilings, stepping out to a covered small side porch that leads to a sprawling backyard with a firepit. The main level boasts a serene primary bedroom and an updated full bath with a glass-enclosed brick-tiled shower, wainscoting, and newer fixtures. The upper-level loft bedroom offers built-in drawers and under-eaves storage. Downstairs, the unfinished walk-out lower level includes laundry and abundant storage with direct access to the back lawn. Complete with parking just steps up from the front door, major updates including a brand-new well pump, new hot water heater, and newer asphalt roof, plus low HOA fees and low taxes, this Cape home is just 60 minutes from Manhattan with easy highway and Metro-North access. Efficient oil heat, gravel driveway parking, super value with large open floor plan, just minutes to beach!

150 Rte 39 S, Sherman

$399,000

3 Beds ⋅ 1 Baths ⋅ 24197820 MLS

PRICE ADJUSTMENT! Bring your vision and make this home your own! Priced to reflect the need for cosmetic updates, this property offers a great opportunity for buyers ready to refresh, reimagine, and personalize a home to suit their style. If LOW TAXES are high on your wish list, this one deserves a look! Set back from the road on a little over 3 acres of park-like property, the home offers plenty of open space, a deck for entertaining, and privacy. With Deer Pond Farm Sanctuary bordering the rear of the property, enjoy a peaceful natural setting with no development directly behind you. Inside, the easy one-level layout features cathedral ceilings and plenty of natural light throughout the open-concept kitchen and living room. A pellet stove adds warmth and coziness during the winter months, while a newer roof allows you to focus your energy on putting your personal stamp on the interior. Bring your ideas and unlock the possibilities! Enjoy summers at Sherman Town Beach, available exclusively to residents, along with a convenient location for commuting to New York and easy access to the charming downtowns of Kent and New Milford. Opportunity, privacy, acreage, and potential...come see what you can create!

33 Rte 55 W, Sherman

$998,000

4 Beds ⋅ 3 Baths ⋅ 24204129 MLS

FALL in Love- In every season this home doesn't disappoint. Set on 2.2 acres overlooking picturesque lawns and pastures at the end of a quiet road. Distinctive architecture, abundant natural light, and a strong connection to the outdoors define this home. Cathedral ceilings, large windows, sliders, skylights, and a semi-open floor plan create a light , spacious interior. The welcoming foyer opens to the vaulted family room, to the inviting living room to the right. French glass-paneled doors connect the foyer, living, and dining rooms, allowing the flow of natural light, creating a comfortable setting for everyday living and entertaining. Hardwood floors and two fireplaces add warmth, including a new wood-burning fireplace insert framed by a floor-to-ceiling brick surround. The home's silo-inspired design, with rounded walls in the stairways, creates a unique connection between levels. An open upper-level landing serves as a bridge between the primary suite and three additional bedrooms, adding a sense of openness. The primary suite has a relaxing deck, spacious bathroom with double sinks, shower, and jacuzzi tub. The recently renovated lower level, has new flooring, good-sized windows, abundant storage, and sliders to a side deck and access to the side yard. Recent updates include, new roof, sky lights, wood fireplace insert, heat/AC pump upper level and fresh paint. Enjoy Sherman's low taxes, elementary school, library, market and rural charm, all 90 minutes from NYC

2 Anderson Rd W, Sherman

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Sherman Homes under $1.25 million

Newest Sherman Homes under $1.25 million

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