Vintage homes for sale & real estate in Sherman, CT

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ABOUT THIS HOME
Vintage Home for sale in Sherman, CT:
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 C

$308,000

1 bed1 bath882 sq ft

101 Route 39 S, Sherman, CT 06784

Cozy wood stove • Heated floor • Renovated kitchen

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Sherman, CT:
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 covere

$384,000

2 beds1 bath1,171 sq ft

150 Route 39 S, Sherman, CT 06784

Updated full bath • Direct beach access • Sprawling backyard

ABOUT THIS HOME
Vintage Home for sale in Sherman, CT:
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 enjoyin

$1,099,000

5 beds4 baths4,200 sq ft

6 Brinsmade Ln, Sherman, CT 06784

Vaulted kitchen • Cathedral ceilings • Wideplank floors

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Sherman, CT:
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 ove

$1,295,000

6 beds5.5 baths4,258 sq ft

201 Route 37 S, Sherman, CT 06784

Bluestone patio • Outdoor shower • 1.42 acre lot

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Sherman, CT:
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

$2,200,000

4 beds2.5 baths2,714 sq ft

32 Leach Hollow Rd, Sherman, CT 06784

Original stone walls • Antique farmhouse • Heated gunite pool

Property at 131 Rte 39 N, Sherman, CT 06784, 2 beds, 1.5 baths

$875,000

2 beds1.5 baths2,400 sq ft

131 Rte 39 N, Sherman, CT 06784

Property at 6 Hoyt Rd, Sherman, CT 06784, 3 beds, 2 baths

$3,200,000

3 beds2 baths1,933 sq ft

6 Hoyt Rd, Sherman, CT 06784

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NEW 18 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Sherman, CT:
Amazing Opportunity to have your own commercial building right in the intersection of New Milford, Sherman, Gaylordsville and minutes to NY border. This building has been renovated top to bottom with over 200k in updates. Potential 9 room dividable rental spaces, full kitchen, 2 full baths and one-half bath. The possibilities are endless here. Wide plank refinished hardwood flooring in main areas. Newly painted inside and out. New Luxury vinyl floors in several of the rooms. 2 baths redone top to bottom. Brand new Roth tanks for efficient/ clean heating. Propane heat and central ac in upstairs apartment, plus brand-new roof over whole right-side apartment. This building is a true gem!! Owne

$777,000

— beds2.5 baths4,617 sq ft

337 Kent Rd, New Milford, CT 06776

Full kitchen • 0.69 acre lot • Built 1925

ABOUT THIS HOME
Vintage Home for sale in Sherman, CT:
Tucked away on . 28 acres with seasonal views of the Housatonic River, this eclectic 1920 cottage is full of character and potential. Featuring 2 bedrooms, hardwood floors, central air, and a cozy woodstove, the home offers a unique opportunity for buyers looking to restore and personalize a property with charm. The detached artist studio provides the perfect space for creative pursuits, while an additional detached shed offers extra storage. In need of updating and repairs, this one-of-a-kind property is ideal for those with vision who appreciate distinctive homes, a peaceful setting, and the chance to create something special.

$299,900

2 beds1.5 baths1,024 sq ft

589 Kent Rd, Gaylordsville, CT 06755

Detached shed • Hardwood floors • 0.28 acre lot

ABOUT THIS HOME
Vintage Home for sale in Sherman, CT:
Welcome to 5 Hickory Lane! This special, charming, log-inspired, Cottage/Ranch home is part of Birch Groves, a lake community bordering the sprawling, scenic Candlewood Lake. Located just minutes from schools, dining, shops and the New Milford's town "Green. " Birch Groves is noted for its privacy, relaxed lifestyle, and close-knit community, and embraces both weekender and full-time residents. With the purchase of this beautiful home, you will enjoy Candlewood Lake rights, clubhouse, sundeck, sandy beach and docks, available for boating and fishing enthusiasts. Special exterior features include: beautiful, level lot with mature perennial gardens, a gazebo whose evening lights emi

$530,000

2 beds2 baths1,567 sq ft

5 Hickory Ln, New Milford, CT 06776

Sandy beach • Docks • Clubhouse

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Sherman, CT:
Beautifully updated ranch offering the ease of single-level living with a bright, open floor plan. This inviting home features 3 bedrooms and is perfectly situated on a desirable corner lot. Gleaming hardwood floors run throughout, creating a warm and welcoming atmosphere. The spacious eat-in kitchen is ideal for both everyday living and entertaining, featuring a center island, granite countertops, stainless-steel appliances, abundant cabinetry, and generous workspace. An updated bathroom and plentiful natural light enhance the home's bright, airy feel while seamlessly blending comfort and modern style. The lower level includes a washer and dryer along with ample storage space. Step outside

$399,900

3 beds1 bath960 sq ft

10 Brook Dr, New Fairfield, CT 06812

Open floor plan • Single level living • Corner lot

ABOUT THIS HOME
Vintage Home for sale in Sherman, CT:
Sometimes the best part of coming home is escaping the hustle and bustle and having a little space to call your own! Welcome to this charming 2-bedroom, 1.5-bath ranch, tucked away in a peaceful, private setting on a large, level lot within an exclusive waterfront community. Featuring two marinas, a private community beach, a community basketball court, and a private community dock dedicaded to the residents! Pull into your attached two-car garage, complete with overhead storage and a convenient breezeway connecting to the house-perfect for those rainy New England afternoons. Inside, enjoy the comfort and convenience of single-level living in a solid, well-built home. But the fun doesn't

$399,900

2 beds1.5 baths1,730 sq ft

22 Southview Rd, New Fairfield, CT 06812

Spacious backyard • Two marinas • Private beach

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Sherman, CT:
Quintessential New England Charm. Discover this classic Connecticut Fieldstone Country Retreat, an enchanting 1945 fieldstone home, beautifully situated on 2.24 picturesque acres along the New Fairfield/Sherman border. Rich in character, craftsmanship and timeless appeal, this distinctive country retreat offers over 2,830 square feet of living space, 4 bedrooms, 2 full baths and a setting that captures the very essence of Connecticut country living. From the magnificent stone exterior to the beautiful bluestone patios, walkways, steps and impressive stone walls, every corner of this property exudes charm. Inside, discover spacious, sun-filled rooms featuring hardwood floors, handsome wood t

$599,000

4 beds2 baths2,838 sq ft

363 State Route 37 Ct, New Fairfield, CT 06812

Coffered ceilings • Fieldstone home • Stone walls

Coldwell Banker Realty

Property at 363 State Route 37, New Fairfield, CT 06812, 4 beds, 2 baths

$599,000

4 beds2 baths2,838 sq ft

363 State Route 37, New Fairfield, CT 06812

Property at 9 Chimney Point Rd, New Milford, CT 06776, 4 beds, 3 baths

$725,000

4 beds3 baths1,898 sq ft

9 Chimney Point Rd, New Milford, CT 06776

Property at 44 Lavelle Ave, New Fairfield, CT 06812, 1 bed, 1 bath

$379,899

1 bed1 bath789 sq ft

44 Lavelle Ave, New Fairfield, CT 06812

Property at 656 Kent Rd, Gaylordsville, CT 06755, 3 beds, 2 baths

$599,900

3 beds2 baths2,792 sq ft

656 Kent Rd, Gaylordsville, CT 06755

Property at 823 N Quaker Hill Rd, Pawling, NY 12564, 4 beds, 3.5 baths

$2,400,000

4 beds3.5 baths3,660 sq ft

823 N Quaker Hill Rd, Pawling, NY 12564

Listing by Houlihan Lawrence Inc

Property at 34 Gaylord Rd, Gaylordsville, CT 06755, 3 beds, 2 baths

$319,000

3 beds2 baths1,896 sq ft

34 Gaylord Rd, Gaylordsville, CT 06755

Property at 22 Waller Rd, Gaylordsville, CT 06755, 4 beds, 2 baths

$399,000

4 beds2 baths2,358 sq ft

22 Waller Rd, Gaylordsville, CT 06755

Property at 14 Rocky Hill Rd, New Fairfield, CT 06812, 3 beds, 3 baths

$500,000

3 beds3 baths1,850 sq ft

14 Rocky Hill Rd, New Fairfield, CT 06812

Property at 73 Lake Ellis Rd, Wingdale, NY 12594, 3 beds, 2 baths

$899,000

3 beds2 baths1,686 sq ft

73 Lake Ellis Rd, Wingdale, NY 12594

Listing by Coldwell Banker Realty

Property at 57 Indian Trail Rd, New Milford, CT 06776, 4 beds, 4 baths

$4,850,000

4 beds4 baths6,236 sq ft

57 Indian Trail Rd, New Milford, CT 06776

Property at 23 Echo Dr, New Milford, CT 06776, 4 beds, 2.5 baths

$3,900,000

4 beds2.5 baths2,073 sq ft

23 Echo Dr, New Milford, CT 06776

Property at 15 Kirby Hill Rd, Pawling, NY 12564, 4 beds, 3.5 baths

$14,995,000

4 beds3.5 baths3,942 sq ft

15 Kirby Hill Rd, Pawling, NY 12564

Listing by McGrath Realty Inc

Property at 685 Kent Rd, Gaylordsville, CT 06755, 4 baths

$595,000

— beds4 baths5,952 sq ft

685 Kent Rd, Gaylordsville, CT 06755

Property at Candlewood Mountain Rd, New Milford, CT 06776, 1 bed, 1 bath

$1,390,000

Land3.12 acres (lot)

Candlewood Mountain Rd, New Milford, CT 06776

Vintage Homes for Sale in Sherman

There are currently 7 vintage homes for sale in Sherman at a median listing price of $900K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Sherman stay on the market for 87 days and receive 4 offers. This map is refreshed with the newest listings in Sherman every 15 minutes.

In the past month, 6 homes have been sold in Sherman. In addition to houses in Sherman, there were also 0 condos, 0 townhouses, and 1 multi-family unit for sale in Sherman last month. Find your dream home in Sherman using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Sherman are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Sherman. If you're looking to sell your home in the Sherman area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Sherman with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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