Sherman Homes for Sale

Welcome to Sherman, Connecticut – a hidden gem nestled in the heart of Fairfield County. Known for its picturesque landscapes and charming small-town atmosphere, Sherman offers a unique blend of tranquility and community spirit, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle.

With its rolling hills, serene lakes, and lush forests, Sherman is a haven for nature lovers. The town is dotted with beautiful parks and recreational areas, perfect for hiking, fishing, and enjoying the great outdoors. The nearby Candlewood Lake, Connecticut's largest lake, provides ample opportunities for boating, swimming, and picnicking, ensuring that residents can soak in the beauty of their surroundings year-round.

Sherman boasts a tight-knit community with a strong emphasis on local events and activities. The town hosts various seasonal festivals and farmers' markets, fostering connections among residents and celebrating the rich culture of the area. Families will appreciate the highly-rated schools, which are known for their commitment to academic excellence and personal development.

When it comes to real estate, Sherman offers a diverse range of homes for sale that cater to different lifestyles and budgets. From charming historic homes that reflect the town's rich heritage to modern, spacious residences perfect for growing families, there is something for everyone. With the current real estate market showcasing a variety of listings, now is the perfect time to explore the enchanting homes that Sherman has to offer.

Discover the perfect blend of nature, community, and comfort in Sherman, CT – where your dream home awaits!

Newest Sherman Homes for Sale

$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

Experience the perfect blend of architectural character, thoughtful updates, and peaceful surroundings in this beautifully refreshed mid-century modern home. Soaring ceilings, an open floor plan, and 12 skylights fill the interior with natural light, creating a bright and inviting atmosphere throughout the day. The remodeled kitchen offers updated style and functionality, while the loft provides an inspiring space ideal for creative pursuits, a home office, or quiet retreat. Recent improvements include a new roof, new septic system installed in 4/26, new furnace, new boiler, fresh interior and exterior paint on the house, deck, and doors, updated sink fixtures, and two striking spiral staircases that enhance the home's unique design. Outside, the private garden setting creates a serene escape surrounded by nature, while the pool has been thoughtfully updated with a brand-new liner, new filter system, new water pump, fresh water, and a conversion to saltwater for easier maintenance. The pool offers the perfect place to relax, entertain, and enjoy lasting memories 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

$899,000

4 Beds ⋅ 4 Baths ⋅ 24204636 MLS

Welcome to 17 Curtis Drive, a private and peaceful retreat tucked away on a quiet cul-de-sac in the picturesque town of Sherman, CT. Set on 2.03 beautifully wooded acres, this unique property offers a wonderful combination of privacy, versatility, and convenience, just minutes from Candlewood Lake, the New York border, and approximately 90 minutes from NYC. The main residence features 3 bedrooms and 3 full baths, with a flexible layout designed for comfortable everyday living and entertaining. The sun-filled main level showcases soaring cathedral ceilings, skylights, and oversized windows that bring the surrounding natural beauty indoors. A cozy family room with fireplace and full bath, currently used as a main-level bedroom, provides additional flexibility for guests or one-level living. The open-concept living and dining areas flow into the spacious kitchen, complete with center island and French doors opening to a large deck overlooking the private, wooded setting, perfect for entertaining, relaxing, or enjoying morning coffee surrounded by nature. Upstairs, a charming Juliet balcony overlooks the main living area and leads to the primary suite with vaulted ceilings and en-suite bath. Two additional bedrooms, a full bath, laundry room, and access to a loft complete the upper level. Hardwood floors run throughout the main home, while a full basement provides abundant storage. A two-car garage and generous driveway offer plenty of parking. Adding exceptional versatility,

17 Curtis Dr, Sherman

$399,000

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

$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

This wonderful home is 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 unique home. 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 to the right. French glass-paneled doors connect the foyer, living, and dining rooms, allowing natural light to flow through, 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 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 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

Start Your Search

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.