Sherman Homes for Sale

Welcome to Sherman, Connecticut – a hidden gem nestled in the picturesque Fairfield County. Known for its idyllic charm and inviting community spirit, Sherman offers a serene escape from the hustle and bustle of city life while still being conveniently located near major metropolitan areas. Surrounded by lush forests and tranquil lakes, this quaint town is perfect for nature lovers and those seeking a peaceful lifestyle.

The heart of Sherman is its vibrant community, where residents enjoy a tight-knit atmosphere and a strong sense of belonging. With a rich history and a commitment to preserving its natural beauty, Sherman is a place where you can truly feel at home. The local schools are highly regarded, making it an excellent choice for families looking to settle down in a supportive environment.

As for real estate, Sherman boasts a diverse selection of homes for sale, catering to various tastes and budgets. From charming historic houses that echo the town's rich past to modern new constructions that offer all the latest amenities, you'll find a property that fits your lifestyle perfectly. Many homes are nestled on spacious lots, providing ample outdoor space for gardening, entertaining, or simply enjoying the peaceful surroundings.

Whether you’re searching for a cozy cottage by the lake or a sprawling estate with breathtaking views, Sherman has something for everyone. With its enchanting landscape, welcoming community, and an array of beautiful homes, Sherman, CT, is the ideal place to start your next chapter. Explore the current listings and discover your dream home in this delightful corner of Fairfield County!

Newest Sherman Homes for Sale

$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

$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

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.

Sherman Homes for Sale

Newest Sherman Homes for Sale

How much is your home worth?

How much is your home worth?