Sherman Real Estate

Welcome to Sherman, a picturesque town nestled in Fairfield County, Connecticut. Known for its scenic beauty and small-town charm, Sherman offers a tranquil escape from the hustle and bustle of city life.

Situated in the rolling hills of western Connecticut, Sherman boasts a rich history dating back to the 18th century. With its historic buildings, quaint downtown area, and close-knit community, Sherman exudes a sense of timeless elegance.

Nature lovers will appreciate Sherman's abundance of outdoor recreational opportunities. From hiking and biking along the scenic trails to boating and fishing on Candlewood Lake, there's no shortage of ways to enjoy the great outdoors in Sherman.

In addition to its natural beauty, Sherman is also home to a thriving arts and culture scene. The town hosts a variety of events and festivals throughout the year, showcasing local artists, musicians, and performers.

With its top-rated schools, safe neighborhoods, and strong sense of community, Sherman is a wonderful place to call home. Whether you're looking to settle down and raise a family or seeking a peaceful retreat, Sherman has something to offer everyone.

Come discover the beauty and charm of Sherman, Connecticut – where small-town living meets modern convenience.

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 proximity to 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

$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

$2,200,000

4 Beds ⋅ 3 Baths ⋅ 24208909 MLS

Private Country Compound. Utterly charming c.1900 perfectly restored Antique Farmhouse privately located up a long driveway on 15 +/- verdant acres w/beautiful long views, established perennial gardens, ancient specimen trees, original stone walls & a picturesque pond. The magnificent property includes a 4 bedroom/2.5 baths Main House w/period details such as original hardwood floors, 3 antique fireplaces, period hardware and windows & a classic wrap-around porch; a newly renovated loft-like guest house w/ full kitchen & bath over 2-car garage; heated Gunite pool w/cabana & a re-surfaced tennis court. A pretty stone foyer opens to a gracious family room w/a wood-burning fireplace & 3 sets of French doors provide access to a brick-laid patio w/stone walls, a charming, screened porch & a handsome custom-built home office. Cozy living room w/Fieldstone wood-burning fireplace w/insert & built-in bookshelves. Spectacular open kitchen/dining room w/marble center island, top appliances, bespoke cabinetry, pantry, large dedicated dining area & doors to the covered, wraparound porch overlooking the pond & lush grounds w/distant views. Convenient mudroom w/new skylights. Adorable powder room accessed by kitchen & living room. Upstairs, a stunning primary bedroom suite w/vaulted ceiling, wood-burning fireplace, windows on 3 sides, custom dressing room and an elegant, renovated bath. Three delightful bedrooms share a pretty hall bath. A perfect country sanctuary w/easy commute to NYC.

32 Leach Hollow Rd, 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

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Sherman Real Estate

Newest Listings in Sherman

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