Sherman Real Estate

Welcome to Sherman, Connecticut – a hidden gem nestled in the scenic landscapes of Fairfield County. With its charming small-town vibe and stunning natural beauty, Sherman offers an idyllic escape from the hustle and bustle of city life while still being conveniently located near major urban centers.

One of Sherman’s most alluring features is its breathtaking scenery. The town is surrounded by lush forests, rolling hills, and pristine lakes, making it a haven for outdoor enthusiasts. Residents can enjoy hiking, biking, and fishing in the nearby Candlewood Lake, the largest lake in Connecticut, or explore the numerous trails that wind through the picturesque countryside.

Sherman boasts a tight-knit community that values a peaceful, family-oriented lifestyle. With a population of just over 3,500, the town prides itself on its friendly atmosphere and strong sense of belonging. Local events, seasonal farmers' markets, and community gatherings bring residents together, fostering connections and creating lasting memories.

Education is a top priority in Sherman, with highly-rated public schools that provide a solid foundation for children. Families appreciate the town’s commitment to maintaining a safe and nurturing environment for their kids to grow and thrive.

For those who appreciate the arts, Sherman is home to the renowned Sherman Playhouse, where local talent shines through a variety of performances throughout the year.

With its blend of natural beauty, strong community spirit, and a commitment to quality living, Sherman, CT, is more than just a place to live – it’s a place to call home. Whether you’re looking to settle down or simply explore, Sherman invites you to experience its unique charm and welcoming atmosphere.

Newest Listings in Sherman

$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

$275,000

24204536 MLS

Build Your Dream Home in River Oaks Golf Course Living. Gated Privacy. An Exceptional Setting. Imagine stepping out your front door and looking directly onto the 18th hole of River Oaks, with beautiful golf course views and a large pond creating a truly spectacular backdrop. This privately situated homesite offers a rare opportunity to build your dream home in Sherman's premier gated golf and country club community, River Oaks. With approximately 200 feet of road frontage, golf course views, and convenient access for construction, this property provides an ideal canvas for creating a spectacular custom residence in a championship-caliber community. Enjoy the tranquility and privacy of a gated setting while being just 8 minutes from the Wingdale Train Station and approximately 75 minutes from New York City. And with Sherman's attractive property taxes, this is an opportunity to enjoy an exceptional lifestyle without sacrificing convenience. The property also includes deeded rights to optional membership at River Oaks Golf Club. Membership is available for an additional fee and offers access to an impressive array of amenities, including: Championship golf course, Tennis courts, Club pool, Clubhouse & Restaurant, Fitness center/gym, Pro shop, Social activities & more Whether you envision a sophisticated golf retreat, a year-round luxury residence, or a peaceful weekend escape, this is your opportunity to create something truly special.

97 Long River Rd, 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

$299,000

24200446 MLS

This exceptional 5.46-acre parcel, perfectly positioned on Long River Road, is the largest homesite in the private community of River Oaks Country Club. The lightly wooded setting offers privacy and a natural backdrop for your custom residence with potential for sweeping long views that capture the beauty of the Berkshire foothills. Club River Oaks provides access to world-class amenities, including an 18-hole, par-70 golf course, tennis courts, a heated swimming pool, fitness center, and both fine and casual dining options. Located just 60 miles from NYC, 45 miles from White Plains, and only minutes to the Wingdale Metro-North station, this property combines serenity with convenience. Enjoy Sherman's charming town center nearby, offering a library, parks, sandy beach, town boat slips, and easy access to Candlewood Lake. A builder is available to discuss custom home designs that integrate seamlessly with this stunning setting.

41 Long River Rd, 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

$260,000

24198768 MLS

Wooded land.

56 Hubbell Mountain Rd, 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

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