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$3,800
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24194237 MLS
Enjoy the beauty of lakefront living during the academic year at this furnished waterfront home on the quiet end of Squantz Pond in Sherman, CT. Wake up to stunning water views and take a stroll to your private beach for swimming, kayaking, fishing, paddleboarding, or simply relaxing by the water. The home features a main-level primary bedroom with a full en-suite bath, an oversized deck with a barbecue grill, two kayaks and water toys, and ample off-street parking. Just minutes from restaurants and shopping in nearby New Fairfield and only 85 minutes from New York City, this peaceful retreat offers the perfect balance of comfort, recreation, and convenience. Academic-year lease preferred. Available beginning September 1, 2026.

18 Pinewood Shrs, Sherman
$739,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24191473 MLS
Welcome home! Nestled in the desirable Pinewood Shores lake community, this charming 3-bedroom, 3 full bathroom home perfectly blends serene outdoor living with exceptional interior flexibility. The main living areas feature a bright and welcoming layout, complemented by a fully finished, walkout lower level boasting a private entrance and full bath-an ideal space for a potential in-law suite, home office, or guest quarters. Outside, the property transforms into a private sanctuary where you can relax on the porch, entertain on the spacious deck, and take a walk through the peaceful, mature gardens. The exterior is completed by an oversized two-car garage and neighborhood access to a community beach and dock.Offering incredible value, the residence features the unique financial advantage of low Sherman taxes. This turnkey lakeside retreat balances modern comforts, versatile living spaces, and low-maintenance perks in an unbeatable community setting. Purchase includes boat slip on the association's dock!

16 Pinewood Shrs, Sherman
$2,250,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24187861 MLS
Beautifully sited on nearly eight private acres with spectacular views, this turn-key Sherman estate encompasses an amenity-filled main residence, renovated guest house, spring-fed pond, classic stone walls, and exquisite English gardens. Offering luxurious resort-style living in one of Sherman's most captivating settings, the home welcomes you with a marble foyer leading to a dramatic double-height living room, where a wall of glass frames the breathtaking vistas. There are two luxurious primary suites - one on each level - with the main-level BR featuring a fireplace and French doors opening to the expansive deck. The top-of-the-line eat-in kitchen features custom cherry cabinetry, a sun-filled dining area, adjoining butler's pantry, and formal dining room. Upstairs are the second ensuite primary bedroom, two additional bedrooms, a den, full bath, and flexible space/artist's studio. The walk-out lower level is an exceptional space, with custom millwork, marble floors, an antique English bar, gas fireplace, sauna, and gym. Pocket doors reveal a spectacular in-home spa featuring a 24' x 14' heated Gunite spa pool, radiant heated floors, a Desert Aire climate-control system, and walls of glass overlooking the mountains and gardens. Outside, stone pathways meander through beautifully landscaped English gardens to the spring-fed pond and guest house, while classic stone walls and a circular driveway connect the main residence, guest house, and attached and detached garages.

30 Cozier Hill Rd, Sherman
$345,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24189208 MLS
This 1890 Cape-style residence in Sherman, CT, offers a combination of historic charm and updated features. The interior includes hardwood floors throughout and two fireplaces. The kitchen is equipped with granite countertops, an updated dishwasher, and a modern range. The property features double-insulated windows in both the home and the expansive garage. Climate control is managed by forced oil hot air heat and central air conditioning. The primary bedroom includes built-in storage solutions. The garage provides remote access. Den offering views of the surrounding natural landscape. Additionally, the garage has dry storage space underneath. Located approximately one mile from Sherman town center, the home offers convenient access to community tennis courts and beach access to Candlewood Lake. The backyard features a fire pit. The property also benefits from low property taxes. Charming!!!

123 Rte 37 S, Sherman
$799,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24186663 MLS
Welcome to this sprawling 5 bedroom Antique Colonial in the beautiful town of Sherman. The property invites you with many gardens, flowers and a serene coy pond. Plenty of parking for year round entertainment. Separate heated and cooled detached garage has been converted to a studio or home office. Can also be converted back to garage if that suits your needs. As you enter the large open foyer, you will see that this home has been tastefully upkept with tons of charm. Enter the newly remodeled living room with beams and beautiful fireplace to keep you nice and warm in the months of winter wonderland. Super versatile layout has option for private master bedroom wing or inlaw/au-pair on Oppposite side of the house. Tons of parking. Brand new septic. Fenced yard. Has its own well plus access to community water if necessary. Great Southern Sherman location for New York commute and directly across from large pond for row boating/fishing. This is great value and a must see. Low taxes

172 Rte 37 S, Sherman
$199,000
ACTIVE UNDER CONTRACT Status ⋅ 24186403 MLS
Approved Building Lot Near Center of Sherman. Lot #2 in Small Subdivision, Shared Driveway, Potential Views. Almost 5 acres. Septic approval in place for 4-bedroom home.

6 Alfredson Ln, Sherman
$1,100,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24183159 MLS
Impeccably maintained home in desirable Southern Sherman on 3.8 private, flat acres, right along the CT/ NY border. Welcome to 2 Hollow Brook Road! A rare find where every major mechanical, structural and cosmetic update has already been expertly handled. Truly turn-key and ready for its next chapter. This meticulously updated home blends smart infrastructure with a resort-style backyard. Inside find fresh paint, new interior doors and a stunning chef's kitchen with premium GE Cafe appliances. The primary suite is a true sanctuary with new hardwood floors, a completely remodeled spa-like bath with a walk-in glass shower, spacious walk-in closet and a large office that could also be used as a dressing room. Upstairs features new carpets while the finished basement boasts a private 5th bedroom with full bath - 600 SF of space that could also function as an in-law suite, gym or playroom. Outside is an entertainer's dream: a bluestone patio with a built-in grill, heated salt water pool with new LED lighting and a Sundance hot tub, all framed by professional landscaping & irrigation. Mechanicals are top-tier: 2-year-old roof & solar system, 5 new ductless mini-splits, Nest-controlled heating, epoxy-floor garage, constant-pressure well pump, UV water system and a whole-home alarm. There is nothing left to do but move in and enjoy your private country oasis! Sherman boasts a town beach on Candlewood Lake with boat slips. Easy commutes: 45 min to White Plains, 60 miles to NYC.

2 Hollow Brook Rd, Sherman
$9,950
5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24183720 MLS
Your private retreat awaits. Situated to capture breathtaking, panoramic views of Candlewood Lake and the lush surrounding hills, this elegant estate offers the ultimate in privacy and peace. The expansive deck provides a flawless setting for sunset entertaining, while the interior layout-featuring 5 bedrooms and six bathrooms-offers flexible, well-designed space for any lifestyle. With the added luxury of 5 garage bays and grounds that promise total seclusion, this property represents the perfect harmony of nature and architectural refinement. Available furnished on a month-to-month basis, for the summer, or longer!

12 Fox Run, Sherman
$899,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24182903 MLS
COMPLETED New Construction!! Quick closing available. Custom 4 bedroom colonial with lots of upgrades. 9 Ft ceilings on the main level. Propane heat and central air. Fireplace. Center island kitchen. Large dinette/breakfast nook. Hardwood floors throughout. Oversized deck. Primary with awesome bath and walk in closet with custom built ins. Beautiful tile and glass shower doors. Convenient upper level laundry room with quartz counters. Oversized composite deck. 2 car attached garage. Walk out basement. Pond Views in the winter!

86 Rte 37th Rd S, Sherman
$119,900
ACTIVE Status ⋅ 24179102 MLS
Escape the ordinary and build your dream retreat on this spectacular **5.86-acre canvas** in the quintessential New England town of Sherman. Perfectly positioned to offer the ultimate blend of pristine privacy and elevated living, this rare parcel of land boasts breathtaking, panoramic vistas overlooking the protected lush canopy of The Wimisink Preserve and rolling hills. The expansive acreage offers a private, natural sanctuary with the perfect backdrop for a striking architectural masterpiece or a classic country estate. While the property feels remarkably secluded, it places an outdoor enthusiast's paradise right at your doorstep. You are just minutes from the boating and fishing of **Candlewood Lake**, the iconic hiking of the **Appalachian Trail**, and scenic fly fishing along the **Housatonic River**. Offering true country living without sacrificing convenience, this exceptional lot is just a short drive from Sherman's charming town center and local amenities, yet sits within easy commuting distance to New York City. Bring your architect, bring your vision and claim this beautiful lot today.

Rte 39 N, Sherman
$1,100,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24179851 MLS
Contemporary home in Atchison Cove lake community w/ clubhouse & deeded beach rights perfect for family living and entertaining. This unique residence offers the perfect mix of social hub and private sanctuary for year-round living or weekend escapes, located in Southern Sherman just 60 miles from NYC. The home is anchored by a large kitchen equipped w/ granite countertops, all new appliances, walk-in pantry and a generous dining/sitting area w/ cozy fireplace. Just off the kitchen is a half bathroom, large laundry room w/ cedar-lined closet, plus private home office perfect for remote work. The north wing highlights a dramatic library w/ soaring ceilings, floor-to-ceiling fireplace w/ wall of custom built-ins, alongside formal dining room and a convenient main level Primary Suite. The south wing is built entirely for recreation featuring a family room w/ cathedral ceilings, exposed beams and its own fireplace, plus a lofted game room complete with skylights. The formal dining room opens seamlessly to an incredible 1,200 SF deck which overlooks a Gunite pool and large backyard. Upstairs provides ample space for family and guests, featuring a bedroom w/ ensuite bathroom, plus 2 additional bedrooms w/ full hallway bath. A truly unique property optimized for modern family living and grand-scale entertaining, brimming with potential. Minutes to charming town center w/ community amenities, library & hiking trails. Sherman is known for low taxes and K-8 school.

21 Holiday Point Rd, Sherman
$1,100,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24167644 MLS
Set back on a tranquil cul-de-sac enclave of prestigious Hubbell Mountain Farm North this 4 bedroom, 2.5 bath Custom Colonial offers the ultimate carefree lifestyle, blending modern elegance with vintage character. Situated on 9.24 wooded acres, the property boasts mature, colorful trees, sprawling stone walls, and an expansive composite deck with serene country views. Inside, an open floor plan features gleaming hardwood floors and an artistic flair throughout, French doors, and reproduction antique finishes. The heart of the home is the gourmet kitchen, complete with a center cherry top island, sun-drenched window seat, and stainless steel high- end appliances. It flows seamlessly into the elegant dining and family room area, highlighted by a custom, dual-sided smooth stone wood burning fireplace. A spacious living room, private home office, and powder room complete the main level. A spindle staircase leads upstairs to the primary sanctuary, featuring a walk-in closet and a luxurious marble bath with Edwardian-style console sinks and a soaking tub. Additional guest bedrooms offer generous closet space and ceiling fans, sharing a full bath that blends vintage architectural character with an airy aesthetic. A laundry room completes the upper level. Full walk-out lower level offers finishing potential and storage with 3 car garage. Equipped with a Generac generator. Just minutes to schools and Sherman Town Beach which is a town resident-only beach with pavilion.

3 Partridge Trl, Sherman
$2,395,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24177737 MLS
Custom Dream home that blends modern luxury, comfort and peaceful living. Nestled in a beautiful 18-hole golf course community, this stunning newer-construction residence offers spacious open living, abundant natural light and thoughtfully designed details throughout. From the moment you enter you'll notice the airy layout, oversized windows, 10ft ceilings and seamless flow. The heart of the home features a beautifully appointed kitchen with generous workspace, custom cabinets and finishes with all high-end appliances. This home includes many upgraded systems including whole house generator, whole house water and air filtration systems, water softener and so much more. Upstairs has 4 spacious bedrooms with 3 large bathrooms and laundry room. Primary bedroom is absolute magic... with large balcony overlooking the course and pond. Massive bathroom suite with spa like details including jacuzzi tub and walk in rain shower with 3 shower heads!! His and hers walk in closets with plenty of built ins. Exercise room/bedroom, has new Tonal exercise system that stays with the house. Basement is walk-out and fully finished with full bar, living area, dining area, bedroom, kitchen and second laundry with custom dog bath. Step outside to serene surroundings, manicured property and peaceful setting. Large deck that spans the entire width of the house. The Golf course is under new ownership and newly remodeled with upscale restaurant, pool and workout facility. Opportunity of a lifetime!!

2 Pond View Ln, Sherman
$1,499,000
6 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24174761 MLS
Enjoy the best of country and lake living at this exceptional private estate in Sherman, CT, just 90 minutes from NYC and moments from Candlewood Lake with beach and boat rights. The pool is open and ready for summer fun! Originally the historic Brinsmade Dairy Farm, this remarkable property blends timeless New England charm with modern comfort. Set on two lots with three buildings-the Main House, Carriage House, and Pool House-it offers approximately 5,500 sq ft, 6 bedrooms, and 5 full baths, ideal for multi-generational living, weekend escapes, guests, or entertaining. The Main House features soaring cathedral ceilings, exposed beams, wide-plank floors, a vaulted kitchen, and picture windows overlooking rolling lawns, mature trees, and countryside views. Life here is all about the outdoors. Spend summer days swimming in the sparkling pool, playing tennis, nature spotting by the pond, gathering for outdoor dining, or relaxing beneath the stars. Just minutes away, enjoy boating, kayaking, paddleboarding on Candlewood Lake. The Pool House creates the perfect guest retreat, while the Carriage House offers a fireplace, semi-open kitchen and living area, one bedroom, and a full bath. Six garages provide ample space for vehicles, boats, recreational equipment, or hobbies. A rare opportunity to own a private estate that combines recreation, history, and natural beauty with low Sherman taxes. Experience the space, privacy, and lifestyle that make this property truly unique.

6 Brinsmade Ln, Sherman
$1,495,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24173967 MLS
New construction 5 bedroom 4.5 bath modern farmhouse colonial in gated upscale golf community. River Oaks offers private 18 hole golf course under new ownership. Lots of upgrades to the clubhouse, restaurand/bar, and the course. River Oaks also has a community pool and tennis courts. The custom home has 2 primary bedrooms, one on the main level and one upstairs. 3 car attcahed garage. 9 Ft ceilings. Efficient propane fired heat and central air. 4 inch select red oak hardwod floors throughout. Amazing center island kitchen with quartz counters. Fireplace. Awesome versatile layout with large rooms and gathering space. This is an amazing lovel lot with pond, mountain and golf course views. Farmhouse front porch with metal roof. Even more potential in the walkout lower level that opens to huge patio. Still time to customize some things so hurry!!

4 Pond View Ln, Sherman
$499,000
ACTIVE UNDER CONTRACT Status ⋅ 24172170 MLS
FOUNDATION READY BUILD SITE! Down a quiet stretch of road in the quaint town of Sherman a hidden drive leads you away from the world into 14 acres of absolute tranquility. As you walk the land you'll find the remnants of historic stone walls intertwining through the woods. The air is still, save for the rustle of native trees and the quiet life surrounding a private vernal pond. While the land feels like a wild escape the groundwork for your future has been meticulously laid. There's no need to wonder if you can build, the path has been cleared for you: driveway in place, home site cleared, well installed, septic field, electric and cable run to build site, wetlands and planning & zoning approval - it doesn't get more ready than this! Whether you wish to collaborate with the preeminent local builder who currently holds the permit, or bring your own team to execute a custom design, all the prep work is done and the site is ready for its next chapter. This prime location offers easy commuting to White Plains (just 45 miles away) and New York City (just 60 miles away), as well as easy access to the charming town center, just 2 minutes away. There you'll find community amenities including library, parks, tennis courts, pavilion, and a sandy beach including boat slips on CANDLEWOOD LAKE. Sherman is known for it's low taxes and K-8 school (with a choice of local high schools) thus making this property a rare gem!

5 Brinsmade Ln, Sherman
$2,199,000
10 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24172461 MLS
PRICE REDUCTION ALONG WITH NEW 10 BEDROOM SEPTIC! Exceptional Renovated 7 Bedroom Farmhouse with 3 Bedroom In-Law Apartment. Expansive Living & Unforgettable Views Bordering the 70 Acre Naromi Land Trust. Welcome to this Stunning, Fully Renovated Farmhouse with In-law Apartment, where Timeless Character meets Modern Comfort on a Grand Scale. Offering 10 spacious Bedrooms and 8 Beautifully Updated Bathrooms, this One-of-a-Kind Property is Perfectly Suited for Extended Living, Guest Accommodations, or Income Potential as a Bed & Breakfast. At the Heart of the Home is a Massive, Light-Filled Kitchen and Eat-in Area, thoughtfully Redesigned with New Cabinetry and Premium Bosch Appliances, Creating the Perfect Space for Entertaining and Everyday Living. A Generous Walk-in Pantry provides Exceptional Storage and Functionality. The Home Features Multiple Inviting Living Spaces, including a Warm and Welcoming Family Room and a separate Living Room, Ideal for both Relaxation and Hosting. Multiple Entrances throughout the Property offer Flexibility, Privacy, and Ease of Access. Extensive Upgrades ensure Peace of Mind and Modern Efficiency: 3 Laundry Areas, New Windows, Interior Doors, and Flooring throughout. Contemporary Light Fixtures. Central Heating and Cooling for Year-Round Comfort. Newer Oil Tanks. Massive Basement with Upgraded Foundation, Offering Incredible Storage or Future Expansion Potential.

29 Rte 37 E, Sherman
$390,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24164142 MLS
Circa 1900 antique property offering character, history, and opportunity, set on a picturesque parcel with a babbling brook. The home has seen additions over the years and features 3 bedrooms and 2 full baths, ready for restoration and updating. A detached twocar barn/garage includes a spacious loft and a basement workshop-ideal for hobbyists, storage, or future conversion possibilities. Both the house and outbuildings are in need of work, making this an excellent project for contractors, investors, or buyers looking to create their dream country retreat. Centrally located in desirable Sherman, close to town amenities, schools, and outdoor recreation. A charming setting with tremendous potential awaits. Property being sold "AS IS"

2 Sawmill Rd, Sherman
$1,595,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24159584 MLS
This impeccable 4 bedroom home is sited on 7.7 private acres w/four fenced paddocks and a 3/4 stall stable for horses at the end of a quiet country lane.The home has a sought after open floor plan on the 1st level. The large, eat-in kitchen has a vast granite center island & includes a 6 burner/two oven range w/egress to the outdoor stone terrace. The open flow to the family room and dining room is ideal for today's lifestyle. The family room features built-ins & an Extraordinaire Fireplace capable of heating the entire home! It is back to back with the outdoor fireplace on the expansive stone terrace. A convenient first floor bedroom with a newly renovated full bath can also be used as a gym, office or library. There is an additional room at that end of the home that is perfect for a home office, den or music room. The upper level has 3 bedrooms including the primary ensuite bedroom w/3 walk-in closets. There is a hall bath for the other two bedrooms to share. The walk-out lower level/basement has high ceilings & a poured concrete foundation. The beautifully appointed 4 stall/3 stalls plus tack room, center aisle stable has large stalls with a stone aisle. The stalls have rubber matting & the 4 fenced paddocks are all adjacent to the barn. There is a fenced round pen as well as access to the Naromi trail system. The in-ground pool is heated and fenced with lovely gardens surrounding it. A charming, in character garage/storage building graces the property as well.

27 Osborn Rd, Sherman
$2,100
1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24095820 MLS
One of a kind rental opportunity. Set on 10 magical acres with pond and brook. Private 1 bedroom above garage rental. Open concept with hardwood floors throughout. Center island kitchen opens to living room. Bedroom with built ins, walk in closet and small storage area. Laundry room (washer/dryer not included-front loader needed). Private entrance and mudroom/foyer. Beautiful tiles bathroom. Excellent credit expected. No smokers or pets. Must have renters insurance and sign waiver for land/pond usage. Heat included but separate electric. Central air.

21 Rte 39 S Unit A, Sherman
$1,195,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24112249 MLS
River Oaks Golf Course New Construction!! Sherman's best value. New construction 4 bedroom 4.5 bath colonial with open floorplan and 2 primary bedrooms. (main level and upper) Propane heat and Central Air. Composite decking. 9 Ft ceilings on the main level. 3 car attached garage. Hardwood floors throughout. Center island kitchen with large pantry and granite/quartz counters. All bedrooms have full baths. Awesome lot on with golf course view. Gated community. 18 hole golf course, community pool, tennis, restaurant, gym is optional.

60 Long River Rd, Sherman

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