Sherman, CT homes for sale & real estate

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ABOUT THIS HOME
Sherman, CT Homes for Sale
Contemporary home located on a cul de sac. Property is currently occupied and the occupants are not to be disturbed. Property will be sold as is on a reserve auction site. Review all terms on the auction site. Cash only or a hard money loan. This property is now under auction terms. All Bids must be submitted during the auction via the property's listing page at www. servicelinkauction.com. This sale is subject to a 5% or $2,500 minimum buyer's premium pursuant to the auction Terms & Conditions. All bids will be subject to seller approval (minimums may apply). Chase Employee's: please see the Chase Acknowledgement for restrictions. Buyer must sign at offer/contract.

$631,750

4 beds4 baths5,342 sq ft

7 Glenview Dr, Sherman, CT 06784

1.87 acre lot • 2 garage spots • Built 1983

ABOUT THIS HOME
Sherman, CT Homes for Sale
Once a beloved gathering place known as The Timber Trails Inn, this storied home now stands as a testament to time, craftsmanship, and quiet beauty. Set upon 1.4 private, level acres, it offers a sanctuary where history whispers through every beam and floorboard, and modern life unfolds in effortless harmony. All just 65 miles from NYC and lower Fairfield County destinations. Step inside, and you'll feel it immediately-the sense of grace that lingers in homes built with heart. Wide-board chestnut and white pine floors, dual staircases, and charming hidden nooks invite you to wander, to slow down, to imagine the lives that came before. The generous yet intimate flow of the main level makes i

$1,600,000

6 beds5.5 baths4,258 sq ft

201 Route 37 S, Sherman, CT 06784

Hidden nooks • Reimagined kitchen • Dual staircases

ABOUT THIS HOME
Sherman, CT Homes for Sale
Cape on Quaker Ridge! Looking for an affordable entry into Sherman? This 4-bedroom, 2-bath Cape, set at the end of a quiet cul-de-sac on sought-after Quaker Ridge Road, offers just that-plus a premium 2.28-acre lot. Owned by the same owner for over 40 years, this home is ready for its next chapter and new owners to enjoy for decades to come. Opportunities for expansion are plentiful, with an unfinished lower level and additional unfinished loft space above the 2-car attached garage (plus a 2-car under-house garage for even more flexibility). The serene lot includes a shed and promises lasting peace and quiet. Inside, the main level features a vaulted-ceiling family room with wood-burning fi

$489,900

4 beds2 baths1,613 sq ft

49 Quaker Ridge Rd, Sherman, CT 06784

New dishwasher • 2.28 acre lot • 4 garage spots

ABOUT THIS HOME
Sherman, CT Homes for Sale
Welcome to this charming 4 Bedroom, 2.5 Bath Colonial tucked away in the desirable pastoral town of Sherman, offering both comfort and versatility. Inside, you'll find a bright and inviting layout with spacious living areas, a well-appointed kitchen, and a cozy family room perfect for gatherings. The primary suite includes a private bath, while three additional bedrooms provide space for family, guests, or a home office. The basement is fully finished to create whatever your need might be, media room, rec room, office etc. .. What truly sets this property apart is the separate 1,200 sq. ft. barn - a dream for the car collector, woodworking enthusiast, or anyone in need of a workshop or crea

$799,900

4 beds2.5 baths3,214 sq ft

12 Sunny Ln, Sherman, CT 06784

Separate barn • Cul de sac road • 1.85 acre lot

ABOUT THIS HOME
Sherman, CT Homes for Sale
Grand FULLY FURNISHED 6,700 SF Mediterranean, direct waterfront on two seriously private acres in Sail Harbor Club. Entertainer's paradise offers unlimited possibilities. Dramatic NEW 26x13 Sun Room displays exciting wall of glass that overlooks NEW 36x14 porcelain tiled deck above sprawling NEW 39x21 covered porcelain tiled patio. NEW 90' deck surrounds 45' saltwater gunite pool having its own path for golf cart transport. Most desirable quiet end of Candlewood Lake advantageous to make unencumbered use of any kind of boat, water or jet ski. Soak in your privacy assured by towering cover of vintage trees, with serene views of undeveloped Deer Island. "Turn-Key" opportunity to imm

$3,795,000

4 beds5 baths6,704 sq ft

5 Sail Harbour Dr, Sherman, CT 06784

Two private acres • New sun room • Direct waterfront

Property at 7 Sunset Dr, Sherman, CT 06784, 3 beds, 1.5 baths

$449,000

3 beds1.5 baths1,508 sq ft

7 Sunset Dr, Sherman, CT 06784

Property at 5 Bridgeworth Ln, Sherman, CT 06784, 4 beds, 2.5 baths

$869,900

4 beds2.5 baths2,613 sq ft

5 Bridgeworth Ln, Sherman, CT 06784

Property at 73 Long River Rd, Sherman, CT 06784, 4 beds, 3.5 baths

$1,395,000

4 beds3.5 baths3,247 sq ft

73 Long River Rd, Sherman, CT 06784

Property at 2 Autumn Dr, Sherman, CT 06784, 4 beds, 3 baths

$1,225,000

4 beds3 baths4,509 sq ft

2 Autumn Dr, Sherman, CT 06784

Coldwell Banker Realty

Property at 5 Stone Wall Ln, Sherman, CT 06784, 4 beds, 4.5 baths

$1,999,000

4 beds4.5 baths5,427 sq ft

5 Stone Wall Ln, Sherman, CT 06784

Property at 4 Deer Run Trl, Sherman, CT 06784, 3 beds, 2.5 baths

$575,000

3 beds2.5 baths1,758 sq ft

4 Deer Run Trl, Sherman, CT 06784

Property at 21 Holiday Point Rd, Sherman, CT 06784, 4 beds, 3.5 baths

$1,199,000

4 beds3.5 baths4,854 sq ft

21 Holiday Point Rd, Sherman, CT 06784

Property at 42 Long River Rd, Sherman, CT 06784, 4 beds, 3.5 baths

$1,049,000

4 beds3.5 baths3,350 sq ft

42 Long River Rd, Sherman, CT 06784

Property at 86 Route 37 Rd S, Sherman, CT 06784, 4 beds, 2.5 baths

$899,000

4 beds2.5 baths2,900 sq ft

86 Route 37 Rd S, Sherman, CT 06784

Property at 60 Long River Rd, Sherman, CT 06784, 4 beds, 4.5 baths

$1,195,000

4 beds4.5 baths3,675 sq ft

60 Long River Rd, Sherman, CT 06784

$250,000

— beds— baths— sq ft

2 Coburn Rd W, Sherman, CT

Coldwell Banker Realty

Property at LOT 30 Long River Rd, Sherman, CT 06784

$279,000

— beds— baths— sq ft

LOT 30 Long River Rd, Sherman, CT 06784

Property at Wagon Wheel Rd, Sherman, CT 06784

$525,000

— beds— baths— sq ft

Wagon Wheel Rd, Sherman, CT 06784

Property at 00 Anderson Rd, Sherman, CT 06784

$1,495,000

— beds— baths— sq ft

00 Anderson Rd, Sherman, CT 06784

Property at Rte 39 South, State Rte, Sherman, CT 06784

$850,000

— beds— baths— sq ft

Rte 39 South, State Rte, Sherman, CT 06784

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ABOUT THIS HOME
Sherman, CT Homes for Sale
Nestled in the heart of the highly sought-after Candlewood Hill community, this enchanting 1-bedroom, 1-bath cottage offers the perfect combination of rustic charm and peaceful seclusion. Whether you're seeking a quiet weekend escape or a cozy full-time residence, this home provides immediate comfort with the added bonus of expansion potential. Set on a generous, private lot, the home welcomes you into a warm and inviting Great Room, the true centerpiece of the home. A classic wood-burning fireplace creates a cozy focal point, while surrounding windows flood the space with natural light and views of the surrounding landscape. Cathedral ceilings with exposed rustic beams add height and chara

$285,000

1 bed1 bath528 sq ft

35 Candle Hill Rd, New Fairfield, CT 06812

0.77 acre lot • Car-dependent

Houlihan Lawrence Inc.

ABOUT THIS HOME
Sherman, CT Homes for Sale
This three-bedroom (possibly four bedroom), three-bathroom home sits on approximately 6.6 acres of land (originally three building lots). The home offers approximately 3,334 square feet of living space. The primary bedroom features an en-suite bathroom and provides ample space for a seating area or home office. The two additional bedrooms are well-proportioned and have access to the hallway bathroom. The kitchen is outfitted with stainless steel appliances, providing a modern and efficient cooking experience. The open floor plan allows the kitchen to flow seamlessly into the living and dining areas, creating a warm and inviting atmosphere for entertaining or casual gatherings. Outside, the

$875,000

3 beds3 baths3,334 sq ft

31 Cedar Hill Rd, Gaylordsville, CT 06755

6.6 acre lot • 4 garage spots • Pool

ABOUT THIS HOME
Sherman, CT Homes for Sale
Set among the rolling hills of Wingdale, New York, near the Sherman, Connecticut border, 1 Hoyt Road offers the quiet beauty of country living and the artistry of a thoughtfully built home. Morning light filters through tall windows, gliding across hardwood floors on the main level and the wide-plank flooring above. Each window frames views of trees and sky, blending the indoors with the surrounding landscape. The farmhouse combines timeless warmth with subtle sophistication. A brick entryway sets the tone for craftsmanship that continues throughout. The kitchen pairs rustic charm with everyday function, featuring exposed brick accents, built-in cabinetry, and a butcher block island that in

$450,000

2 beds3 baths1,939 sq ft

1 Hoyt Rd, Wingdale, NY 12594

2.39 acre lot • 2 garage spots • Car-dependent

Listing by RE/MAX Classic Realty

ABOUT THIS HOME
Sherman, CT Homes for Sale
Beautiful Twin Oaks community on Route 7 north. Townhouse 2 bedrooms, 1 1/2 bath, 1337 sq ft, finished basement 600 sq ft. Perfect for the office, rec room, or teenager's bedroom. Fireplace with custom mantle. 2 parking spaces. New front paver front walkway to the front porch. Through the wall a/c (3), electric baseboard, and hot water. Deck faces East for morning sun. The condo needs a few updates to personalize it for your style.

$309,900

2 beds1.5 baths1,987 sq ft

2 Twin Oaks #2, New Milford, CT 06776

$538 HOA • 2 garage spots • Car-dependent

ABOUT THIS HOME
Sherman, CT Homes for Sale
Don't miss this newly listed one of a kind home nestled on 8.44 private acres with views so outstanding they could take your breath away. This 5700 plus sq. ft. home w/ 6 generous sized Brs, 5.5 baths is only the start. Its primary Br. 25X18 w/ Fp, Lg. tiled bath w/ jacuzzi & those mountain top views again then to a spacious walk/in closet. There are an additional 4 more bedrooms all with oak floors on this level. ( 2nd Floor ) The main level all with oak floors. (exception tile foyer) features a lg. country equipped kitchen w/ all appliances, center island, dinning area Wolf granite counters and more abutting 23' a family room a w/ 10 ft' ceiling & gas Fp. There is two car g

$1,250,000

6 beds6.5 baths5,710 sq ft

5 Lyric Ln, New Milford, CT 06776

8.44 acre lot • 4 garage spots • Car-dependent

ABOUT THIS HOME
Sherman, CT Homes for Sale
It's All About the Views! Surrounded by lake views, this stately Contemporary, set on a private acre plus an additional lot (. 82 acs), at the end of a cul-de-sac, is just waiting for your customization. This incredible setting hosts this 3 bedroom, 2.5 bath custom designed home with multilevel wrap decks & balconies and an oversized bonus room for great family fun center or studio for the artist/photographer. An open plan showcases. slate floors, custom built-in cabinetry throughout, a great room open to dining room and efficient galley kitchen topped with granite. A second floor primary suite offers a large, walk-in closet, loft sitting area with desks & bookcase

$1,595,000

3 beds2.5 baths3,020 sq ft

35 Skyline Dr, Sherman, CT 06784

1.74 acre lot • Garage • Car-dependent

Property at 34 Sherry Ln, New Milford, CT 06776, 3 beds, 2.5 baths

$515,000

3 beds2.5 baths1,872 sq ft

34 Sherry Ln, New Milford, CT 06776

Property at 97 Lake Ellis Rd, Wingdale, NY 12594, 3 beds, 2.5 baths

$399,000

3 beds2.5 baths2,344 sq ft

97 Lake Ellis Rd, Wingdale, NY 12594

Listing by William Pitt Sothebys Int Rlty

Property at 153 Shortwoods Rd, New Fairfield, CT 06812, 3 beds, 2.5 baths

$699,000

3 beds2.5 baths1,885 sq ft

153 Shortwoods Rd, New Fairfield, CT 06812

Property at 15 Misty Brook Ln, New Fairfield, CT 06812, 4 beds, 3.5 baths

$1,295,000

4 beds3.5 baths5,173 sq ft

15 Misty Brook Ln, New Fairfield, CT 06812

Property at 48 Gaylord Rd, Gaylordsville, CT 06755, 4 beds, 2 baths

$539,000

4 beds2 baths2,760 sq ft

48 Gaylord Rd, Gaylordsville, CT 06755

Property at 1 Pinecrest Ln, New Fairfield, CT 06812, 4 beds, 3.5 baths

$1,199,900

4 beds3.5 baths3,204 sq ft

1 Pinecrest Ln, New Fairfield, CT 06812

Property at 16 Gaylord Rd, Gaylordsville, CT 06755, 2 beds, 1 bath

$340,000

2 beds1 bath1,774 sq ft

16 Gaylord Rd, Gaylordsville, CT 06755

Property at 42 Twin Oaks #42, New Milford, CT 06776, 2 beds, 1.5 baths

$345,000

2 beds1.5 baths1,337 sq ft

42 Twin Oaks #42, New Milford, CT 06776

Property at 55 Colonial Ridge Dr, Gaylordsville, CT 06755, 3 beds, 2.5 baths

$534,000

3 beds2.5 baths1,822 sq ft

55 Colonial Ridge Dr, Gaylordsville, CT 06755

Property at 6 Pinewood Dr, New Fairfield, CT 06812, 4 beds, 3 baths

$899,950

4 beds3 baths3,858 sq ft

6 Pinewood Dr, New Fairfield, CT 06812

Property at 32 Sail Harbour Dr, New Fairfield, CT 06812, 4 beds, 5.5 baths

$1,495,000

4 beds5.5 baths6,052 sq ft

32 Sail Harbour Dr, New Fairfield, CT 06812

Property at 15 Flak Ln, New Fairfield, CT 06812, 3 beds, 3 baths

$688,800

3 beds3 baths2,292 sq ft

15 Flak Ln, New Fairfield, CT 06812

Property at 4 Harbour View Dr, New Fairfield, CT 06812, 4 beds, 3.5 baths

$3,195,000

4 beds3.5 baths3,688 sq ft

4 Harbour View Dr, New Fairfield, CT 06812

Property at 73 Lake Ellis Rd, Wingdale, NY 12594, 4 beds, 3 baths

$899,000

4 beds3 baths1,850 sq ft

73 Lake Ellis Rd, Wingdale, NY 12594

Listing by Keller Williams NY Realty

Based on information submitted to the MLS GRID as of Mon Oct 20 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Average home prices near Sherman, CT

Cities

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Minor Civil Divisions

Sherman, CT real estate trends

$696K

Sale price

+27.7%
since last year

$243

Sale $/sq ft

-1.4%
since last year

Under list price

Days on market

Down payment

—

Total homes sold

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