33 Osborn Rd, Sherman, CT 06784
Property image
Property image
OFF MARKET

33 Osborn Rd
Sherman, CT 06784

  • 5 Beds
  • 5.5 Baths
  • 7,000 sqft (on 32 acres)

$1,697,900

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $10,971/mo*
Refinance Your Home

$1,697,900

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $10,971/mo*
Refinance Your Home
5 Beds
5.5 Baths
7,000 sqft
(on 32 acres)

Local Information

  • Map ViewExplore the area around 33 Osborn Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School
  • Shop & Eat
-- mins to
Commute Destination

Description

32 Acre, end of road, estate property surrounded by land preserve. Excellent for security. Great for horse property and possibly a small winery. Low taxes and a top Pre-K thru 8 public school. Secluded yet only a short distance to shopping, restaurants and hospitals.

Sub-Zero and Viking appliances
33 Osborn Rd, Sherman, CT 06784 is a 5 bedroom, 6 bathroom, 7,000 sqft single-family home built in 2000. It last sold for $80,000 on Mar 20, 1997. It is currently off market. The Trulia Estimate is $1,697,900, with a rent estimate of $6,965/month.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 33 Osborn Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 13Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, Recreation RoomWet BarCeiling Fan
Heating & Cooling
Heating: Baseboard, Forced Air, Gas, Oil, Wood PelletAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Carpet, HardwoodGated Entry
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: VinylLawn
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 32.00 acres

Building

Community rooms
Fitness Center
Pool
Sauna

Price History for 33 Osborn Rd

DatePriceEventSource
03/20/1997$80,000Sold
N/A

Market trends in Sherman

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
27
4MoM
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Property Tax and Assessment

Year2025
Tax$11,641
Assessment$698,300
Home facts updated by county records

Comparable Sales for 33 Osborn Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5 Upland Pastures Road, Sherman, CT
0.67
Single-Family Home
$2,000,000
06/15/26
5
4.5
4,250
14 Stilson Lane, New Milford, CT
0.62
Single-Family Home
$735,000
07/31/25
3
3
2,852
4 Hay Meadow Lane, New Milford, CT
0.58
Single-Family Home
$710,000
10/07/25
3
2.5
2,727
20 Crooked Furrows Ln, Sherman, CT
0.50
Single-Family Home
$760,000
10/03/25
2
3
2,112
29 Route 37 East, Sherman, CT
1.18
Single-Family Home
$300,000
10/31/25
10
7.5
5,856
22 Meadowood Drive, New Milford, CT
1.09
Single-Family Home
$720,000
06/03/26
4
3.5
4,214
96 Sherman Road, New Milford, CT
0.78
Single-Family Home
$555,000
08/29/25
3
2
1,740
79 Route 39 North, Sherman, CT
1.13
Single-Family Home
$761,500
09/23/25
4
2.5
3,144
20 Zachary Lane, New Milford, CT
0.88
Single-Family Home
$449,999
03/31/26
3
2
1,867
1 Elena Drive, New Milford, CT
1.11
Single-Family Home
$615,000
06/05/26
4
2.5
1,934

Nearby homes

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Assigned Schools

These are the assigned schools for 33 Osborn Rd.

What Locals Say about Sherman

At least 14 Trulia users voted on each feature.

  • 100 % Say there's wildlife

  • 100 % Say car is needed

  • 93 % Say yards are well-kept

  • 87 % Say parking is easy

  • 83 % Say it's quiet

  • 76 % Say there's holiday spirit

  • 70 % Say neighbors are friendly

  • 67 % Say they plan to stay for at least 5 years

  • 61 % Say people would walk alone at night

  • 52 % Say it's dog friendly

  • 42 % Say there are community events

  • 35 % Say kids play outside

  • 24 % Say it's walkable to grocery stores

  • 13 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Marie L. .
    "No dog park in town but there are parks and trails to walk dogs. On the downside there are potential predators around, coyotes, Bob cats, bears. I have small sized dogs so I’m wary of letting them out on their own."
    0
    Flag
  • ML
    "I’ve lived in this town for almost 20 years. It’s a very supportive community. Everyone knows each other."
    0
    Flag
  • Mbendotti
    "It’s Quite and quaint... been here for seven years and counting... great country town with very friendly people"
    0
    Flag
  • Ila S.
    "Beautiful community- well kept area, safe, clean and serene"
    0
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  • Cheryl F.
    "Sherman: Connecticut’s �Best Small Town� On the northern end of Candlewood Lake, a picturesque, quaint town gives residents and visitors a sense of tranquility and calm. Named �Best Small Town� by Connecticut Magazine, Sherman is a wonderful place for families, singles and retirees. Several golf courses, year-round lake access and beautifully rolling hills make Sherman the ideal place to live. "
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  • Major D.
    "Sherman is quite beautiful, bucolic, and upscale. Many individuals that live in NYC also have second homes in Sherman. It is very quiet and also safe. We have lived here for 19 years and never locked our doors. The only break-in we had was about two years ago when a neighbor's dog put his nose in our back door, opened it, and came in during the night. We live in the country but are only ten minutes from the train station, where you can get an express to Grand Central Station. I taught in the Sherman School for two years and can vouch for its excellence. Not much to do here but there is a playhouse and occasional chamber music. Oh, forgot to mention, we are also on the largest lake in Connecticut, Candlewood, so bring your boat. Overall, Sherman is a great place to unwind and raise a family. People tend to move to Sherman and then never leave..."
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  • Roberta D.
    "Peaceful, beautiful, friendly people."
    0
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  • Lybern
    "Used to escape to Sherman for R&R. Ended up staying."
    0
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Apartments for Rent

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Homes for sale near 33 Osborn Rd

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Off Market Homes Near 33 Osborn Rd

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