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

$349,000

24216863 MLS

Exceptional opportunity to purchase a three-lot package totaling 9.62 acres in the gated community of The Club at River Oaks in Sherman, CT. The offering includes 4 River Oaks Lane (3.12 acres), 10 River Oaks Lane (3.07 acres), and 12 River Oaks Lane (3.42 acres), all bordering the 9th green of the community's 18-hole, par-70 golf course. Lot 12 includes a 4-bedroom septic design and offers frontage on the Housatonic River. The Club at River Oaks consists of 66 home sites on approximately 350 acres and offers amenities including an 18-hole golf course, driving range, putting green, pro shop, 26,000-square-foot clubhouse with locker rooms and bag storage, tennis courts, heated swimming pool, fitness center, Mahogany Bar & Grille Room, banquet facilities, and an outdoor terrace overlooking the 18th green. The combined assessment for the three lots is $202,500 with annual property taxes of $3,313. Located approximately 10 minutes from the Wingdale Metro-North station and close to the Appalachian Trail and the Berkshires. Buyer is responsible for all due diligence regarding permits, approvals, deed restrictions, memberships, fees, utilities, and building requirements

12 River Oaks Ln, Sherman

$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

$1,375,000

4 Beds ⋅ 5 Baths ⋅ 24213489 MLS

Sexy on Sunset! Stunning, 2-year-old Modern Contemporary set on over 3 secluded acres with breathtaking western views and spectacular sunsets! Custom-built by its craftsman owner with exceptional attention to detail, this architectural beauty offers 3,200 sq. ft. of finished living space across 3 levels, with 4 bedrooms, 3 full and 3 half baths. Soaring ceilings and walls of glass flood the home with natural light while framing magnificent views. The open-concept main level features a private primary suite, media room, and expansive deck capturing sunshine by day and sunsets by night. Upstairs, 3 spacious bedrooms include flexible space with custom barn doors and access to a GIANT rooftop terrace overlooking the western horizon! The finished lower level offers a recreation room, half bath, and cleverly concealed storage. Designed with the future in mind, the home is solar power and energy system ready, offering exciting potential for enhanced efficiency. A gated circular pebble driveway welcomes you to this private retreat, complete with a detached 4-car garage/workshop and potential pool site. Minutes from Sherman Center and downtown New Milford, yet a world away from the everyday. Whether your full-time residence or weekend escape, this extraordinary property delivers privacy, craftsmanship, dramatic architecture, and unforgettable sunsets!

7 Sunset Ter, 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

$3,400,000

5 Beds ⋅ 6 Baths ⋅ 24208088 MLS

This contemporary cedar and stone construction home occupies one of Sherman's most spectacular settings. Set on 102.2 acres, the property provides complete privacy, panoramic mountain views, rolling open meadows, a tennis court, and a recently refinished gunite pool. The home features five bedrooms, five and a half bathrooms, and three levels of living space. Double teak entry doors open to a two-story foyer and an expansive, open-concept main level. At its center is a sunken living room with a floor-to-ceiling fieldstone fireplace and dramatic walls of windows. The adjoining dining room and kitchen both provide direct access to the wraparound deck. Also on the main level are a heated three-car garage, powder room, and spacious en-suite bedroom. Upstairs, a second primary suite offers exceptional flexibility and includes a generously sized bathroom, office area, dressing room with two walk-in closets and a sink, sauna, and sliding glass doors opening to a private deck overlooking the rolling hills. Two additional bedrooms and a Jack-and-Jill bathroom complete the upper floor. Designed for both entertaining and relaxation, the lower level includes a large family room, reading nook, gym area, laundry room, two bedrooms, and two full bathrooms. Sliding glass doors open to a pathway leading directly to the freeform pool, which was fully restored this summer to be enjoyed for years to come.

9 Ashley Ln, Sherman

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Sherman Real Estate

Newest Listings in Sherman

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