Sherman Homes for Sale

Welcome to Sherman, a charming town located in Fairfield County, Connecticut. Known for its picturesque landscapes and tight-knit community, Sherman offers a peaceful retreat from the hustle and bustle of city life.

In Sherman, you'll find a variety of homes for sale that cater to different tastes and preferences. Whether you're looking for a cozy cottage, a spacious family home, or a luxurious estate, Sherman has something for everyone. With its serene surroundings and proximity to nature, Sherman is the perfect place to find your dream home.

From historic properties with character to modern houses with all the amenities, Sherman's real estate market has something to offer every homebuyer. With beautiful views, top-rated schools, and a strong sense of community, Sherman is a wonderful place to put down roots and create lasting memories.

If you're looking for a place that combines small-town charm with modern conveniences, look no further than Sherman, CT. Explore the homes for sale in Sherman today and discover the perfect place to call home.

Newest Sherman Homes for Sale

$440,000

3 Beds ⋅ 1 Baths ⋅ 24197820 MLS

Are LOW TAXES and privacy your priority? Buyers, this is a great opportunity to bring your vision and create your perfect home! Set back from the road and situated on a little over 3 acres of park-like property, this home offers open space, a deck for entertaining, and exceptional privacy. With Deer Pond Farm Sanctuary bordering the back of the property, no one can build behind you. Inside, you'll find an easy one-level layout with no stairs, cathedral ceilings, and plenty of natural light throughout the open-concept kitchen and living room. The pellet stove keeps the home warm and cozy all winter long. A newer roof means you can focus your attention on updating the interior to match your style and preferences. Enjoy lake life all summer at Sherman Town Beach, available exclusively to residents. Conveniently located for commuting to New York and just a short drive to the charming downtowns of Kent and New Milford. Don't miss this opportunity, schedule your showing today!

33 Rte 55 W, Sherman

$1,295,000

6 Beds ⋅ 6 Baths ⋅ 24202896 MLS

Tucked back from the road behind a privacy screen of mature evergreens on almost an acre and a half of level property, is the c. 1862 Charles A. Briggs House-famously known as the Timber Trails Inn of the early 1900s. This historic Sherman landmark has been thoughtfully modernized to pair 19th-century soul with 21st-century luxury. Antique wide-board floors, authentic exposed beams, and original working fireplaces are perfectly juxtaposed by modern upgrades, including a new steam boiler and newly installed multi-zone HVAC system with heat pump technology-painstakingly fitted to preserve historical details-and a new 26kw whole house standby generator. A timeless center-hall colonial with over 4,200 square feet of living space, this 6-bedroom, 5 1/2-bath home has all the classic features you'd expect to find, from the oversized living room, private study, double staircases and formal dining room to the original blown glass windows, ornate trim, and cast-iron radiators. But you'll be pleasantly surprised to also discover a modern chef's kitchen outfitted with premium appliances, not one, but two en-suite bedrooms, a large main-level media/rec room, and a heated/cooled, semi-finished walk-up attic-the perfect art studio, workout space, or storage haven. A wall of windows in the open-concept kitchen/sunroom overlooks a backyard oasis featuring a bluestone patio, outdoor shower, and a heated saltwater Gunite pool with an automatic cover and new propane heater.

201 Rte 37 S, Sherman

$998,000

4 Beds ⋅ 3 Baths ⋅ 24204129 MLS

Distinctive architecture, abundant natural light, and a strong connection to the outdoors define this unique home. Set on 2.2 acres at the end of a quiet road, overlooking picturesque lawns and pastures. Cathedral ceilings, large windows, sliders, skylights, and a semi-open floor plan create a light filled, spacious interior. A welcoming foyer opens to the vaulted family room, with an inviting living room off to the right. French glass-paneled doors connect the foyer, living, and dining rooms, allowing natural light to flow throughout, 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 incorporated into the stairways, creates a unique connection between levels. An open upper-level landing serves as a bridge between the private 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 versatile lower level, has new plank 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

$599,900

3 Beds ⋅ 3 Baths ⋅ 24202669 MLS

Exceptional Opportunity in Southern Sherman! Tucked away on a scenic 1.84-acre parcel, this spacious 2,700 square foot custom-built home offers incredible upside for end users, builders, and investors alike. Bring your vision to life-all of the major items are already in place. Featuring a newer roof, top-of-the-line European Buderus boiler, hot water heater, Roth double-wall oil tank, and a premium well system with pump, pressure tank, and water treatment system. Hardwood oak floors and quality Andersen windows throughout. The interior highlights include an open concept layout with a dramatic two-story living room anchored by a fireplace, an expansive front-to-back living and dining space, and a versatile floor plan offering 3 to 4 bedrooms with flexible home office/guest suite options. A massive full walkout lower level with soaring ceilings offers tremendous potential for additional finished area. Outside, a huge deck overlooks a beautiful lot with mature trees and seasonal lake views. Just minutes to Squantz Pond, Candlewood Lake, and commuter lines. A solid, well-built home with excellent core systems-simply bring your finishing touches and make it your own.

158 Rte 39 S, Sherman

$1,180,000

3 Beds ⋅ 1 Baths ⋅ 24199717 MLS

DIRECT WATERFRONT, rarely available, LAKEFRONT HOME ON CANDLEWOOD LAKE - SHERMAN, CT Experience the best of lakefront living in this charming 3-bedroom, 1 bath home nestled on a private .43- acre lot. An adjacent .63-acre wooded, sloping lot is included. New kitchen with new appliances and new bathroom. New washer and dryer and hot water tank. Located on a cul-de-sac and next to Orchard Beach. This property has a deep-water dock and mooring. Access to Green Pond and Candlewood Lake Community beaches. Excellent opportunity for a seasonal getaway or full-time lakefront living. Located in the picturesque town of Sherman, just minutes from local shops, dining and an easy drive from Westchester and New York City

18 Orchard Beach Rd, Sherman

$599,000

3 Beds ⋅ 3 Baths ⋅ 24199443 MLS

Beautifully maintained, move-in ready +1890 sf raised ranch with a deeded boat dock and private sandy beach in desirable Pinewood Shores at Squantz Pond! Enjoy the best of water-community living with a gorgeous, level yard surrounded by perennial plantings & a spacious deck perfect for outdoor entertaining, dining alfresco or simply relaxing after a day on the water. Light and bright throughout, this inviting home features hardwood floors throughout most of the main level. The spacious living room offers a ceiling fan and flows into the dining room with sliders opening to the deck and backyard. The eat-in kitchen features white cabinetry, granite counters, tile flooring, ceiling fan and a comfortable dining area. The main level offers two spacious bedrooms with hardwood floors and ceiling fans, a full hall bath with tub/shower combination, and a lovely primary bedroom with hardwood flooring, ceiling fan, two closets and private full bath with tile floor and shower. The finished lower level provides additional living space with a family room featuring tile flooring and a wood-burning fireplace-perfect for movie nights, entertaining or relaxing by the fire. A half bath, laundry room and large walk-in storage/pantry area add convenience, with direct access to the two-car garage. Central air and zoned electric heat make it easy to control the temperature throughout the home. Beautifully cared for inside and out, this home offers wonderful curb appeal & a peaceful country setting.

8 Pinewood Shrs, Sherman

$935,000

3 Beds ⋅ 3 Baths ⋅ 24197741 MLS

Nestled on nearly 5 acres of picturesque countryside, this 3-bedroom, 2.5-bathroom home delivers the rare and coveted balance of dense, private woodlands and big-sky pastoral meadow views. Offering approximately 2,445 square feet of light-filled living space, this sanctuary provides a seamless blend of everyday comfort, natural beauty, and thoughtful accessibility. Step inside to an inviting layout where warm interior spaces frame panoramic vistas of the surrounding landscape. The heart of the main living area features a cozy woodstove-perfect for crisp evenings and adding timeless rustic charm to the open, airy atmosphere. The well-appointed layout includes spacious main-level living, complemented by thoughtful wheelchair accessibility features that ensure effortless flow and long-term convenience throughout the home. Outside, the 4.92-acre grounds are a true high point. Enjoy sun-drenched pastoral acreage perfect for gardening, outdoor entertaining, or simply taking in the open skies, while the mature woodland backdrop ensures total tranquility and privacy. Additional highlights include a spacious 2-car attached garage with direct entry and ample storage. Meticulously situated to capture the best of country living without sacrificing comfort-schedule your private tour to experience this countryside retreat firsthand.

6 Fox Run, Sherman

$450,000

3 Beds ⋅ 1 Baths ⋅ 24197493 MLS

Welcome to your private retreat nestled on a scenic wooded lot with distant views of Green Pond. Located in a quiet gated community, this charming 3-bedroom, 1-bath ranch offers a peaceful layout designed for relaxed living and effortless indoor-outdoor connection. Step inside to discover a bright, expansive sunroom wrapped in wall-to-wall windows that fill the home with natural light and frame beautiful views of the surrounding trees. Off the back, two spacious decks provide the perfect setting for morning coffee, evening relaxing, or outdoor entertaining. The primary level offers single-story convenience, while the walk-out basement presents fantastic potential to be finished into extra living space, a media room, or a home gym. Enjoy access to Green Pond, a pristine 30-acre private lake where you can spend your weekends kayaking, paddleboarding, and swimming in total tranquility-no motorboats allowed. Combining privacy, natural beauty, and lakeside amenities, this property is a rare find ready for your personal touch.

8 Terrace Dr, Sherman

$749,000

4 Beds ⋅ 4 Baths ⋅ 24195796 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

$1,880,000

2 Beds ⋅ 2 Baths ⋅ 24195480 MLS

Rare opportunity to own a unique waterfront home in the desirable Candlewood Lake Estates. Loved by the same family for over 50 years, this mid-century was designed in the 1960s as a passive solar home and offers amazing lake views from nearly every room. While currently listed as a two bedroom, an addition in the 1970's added rooms and increased the size of the home to approximately 3,345 sq ft. 310 feet of direct shoreline, a private dock and a spacious grassy area...perfect for relaxing, entertaining and enjoying lake life!! Access to two private beaches on Green Pond and two private beaches on Candlewood Lake. Close to shops and restaurants. Easy access to Westchester, 75 miles from NYC and low taxes. Bring your vision and make this special property your own!

40 Sunset Dr, Sherman

$1,995,000

4 Beds ⋅ 5 Baths ⋅ 24187861 MLS

Beautifully sited on nearly eight private acres with spectacular views, this turn-key Sherman estate encompasses an amenity-filled main residence, renovated guest house, spring-fed pond, classic stone walls, and exquisite English gardens. Offering luxurious resort-style living in one of Sherman's most captivating settings, the home welcomes you with a marble foyer leading to a dramatic double-height living room, where a wall of glass frames the breathtaking vistas. There are two luxurious primary suites - one on each level - with the main-level BR featuring a fireplace and French doors opening to the expansive deck. The top-of-the-line eat-in kitchen features custom cherry cabinetry, a sun-filled dining area, adjoining butler's pantry, and formal dining room. Upstairs are the second ensuite primary bedroom, two additional bedrooms, a den, full bath, and flexible space/artist's studio. The walk-out lower level is an exceptional space, with custom millwork, marble floors, an antique English bar, gas fireplace, sauna, and gym. Pocket doors reveal a spectacular in-home spa featuring a 24' x 14' heated Gunite spa pool, radiant heated floors, a Desert Aire climate-control system, and walls of glass overlooking the mountains and gardens. Outside, stone pathways meander through beautifully landscaped English gardens to the spring-fed pond and guest house, while classic stone walls and a circular driveway connect the main residence, guest house, and attached and detached garages.

30 Cozier Hill Rd, Sherman

$310,000

2 Beds ⋅ 1 Baths ⋅ 24189208 MLS

This 1890 Cape-style residence in Sherman, CT, offers a combination of historic charm and updated features. The interior includes hardwood floors throughout and two fireplaces. The kitchen is equipped with granite countertops, an updated dishwasher, and a modern range. The property features double-insulated windows in both the home and the expansive garage. Climate control is managed by forced oil hot air heat and central air conditioning. The primary bedroom includes built-in storage solutions. The garage provides remote access. Den offering views of the surrounding natural landscape. Additionally, the garage has dry storage space underneath. Located approximately one mile from Sherman town center, the home offers convenient access to community tennis courts and beach access to Candlewood Lake. The backyard features a fire pit. The property also benefits from low property taxes. Charming!!!

123 Rte 37 S, Sherman

Start Your Search

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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.