5 Oriole Dr, Sherman, CT 06784
Property image
Property image
OFF MARKET

5 Oriole Dr
Sherman, CT 06784

  • 3 Beds
  • 2 Baths
  • 1,144 sqft (on 0.93 acres)

$642,100

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $4,195/mo*
Refinance Your Home

$642,100

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $4,195/mo*
Refinance Your Home
3 Beds
2 Baths
1,144 sqft
(on 0.93 acres)

Local Information

  • Map ViewExplore the area around 5 Oriole Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School
  • Shop & Eat
-- mins to
Commute Destination

Description

Opportunity Awaits!! Private, One Acre Squantz Pond Direct Waterfront with Gorgeous Northern, Southern and Western Views. Grassy, Level 150+/- Feet of Waterfront. Three Bedroom, Two Full Bath Home, In Need of Updating, has Hardwood Floors, 4 Sets of New Sliders to Deck and Walk Out Basement. 500 Square Foot Lower Level can be Finished for More Living Space. 2 Car Garage, Fireplace, Low Sherman Taxes, Great School, 75 Minutes to Manhattan. Bring Your Vision, This is the One!!
5 Oriole Dr, Sherman, CT 06784 is a 3 bedroom, 2 bathroom, 1,144 sqft single-family home built in 1971. It last sold for $410,000 on Aug 19, 2019. It is currently off market. The Trulia Estimate is $642,100, with a rent estimate of $3,806/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 5 Oriole Dr

Interior Features

Heating & Cooling
Heating: Baseboard, ElectricCooling System: OtherHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 5Types of Rooms: Recreation Room
Appliances & Utilities
Refrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Stone, Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1971
Property Type / Style
Property Type: Single Family HomeArchitecture: ranch

Lot Information

Lot Area: 0.93 acres

Price History for 5 Oriole Dr

DatePriceEventSource
08/19/2019$410,000Sold
Smart MLS #170209229
07/13/2019$399,000PendingAgent Provided
06/26/2019$399,000Listed For SaleAgent Provided
07/18/2012$350,000Sold
Smart MLS #98523322
05/11/2012$399,500PriceChange
Agent Provided
02/07/2012$449,500PriceChange
Agent Provided
01/01/2012$495,000Listed For SaleAgent Provided

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$4,059
Assessment$243,500
Home facts updated by county records

Comparable Sales for 5 Oriole Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
348 State Route 39, New Fairfield, CT
0.17
Single-Family Home
$515,000
08/08/25
3
2
2,096
4 Wanzer Hill Road, Sherman, CT
0.17
Single-Family Home
$640,000
10/01/25
3
2.5
1,896
14 Hilltop Drive, New Fairfield, CT
0.35
Single-Family Home
$450,000
09/23/25
2
1.5
1,440
5 Candle Hill Road, New Fairfield, CT
0.31
Single-Family Home
$610,000
06/05/26
4
2
1,500
28 Lavelle Avenue, New Fairfield, CT
0.29
Single-Family Home
$690,000
07/23/25
4
3
2,005
16 Oak Street, New Fairfield, CT
0.40
Single-Family Home
$225,000
09/24/25
2
1
813
15 Flak Lane, New Fairfield, CT
0.51
Single-Family Home
$615,500
04/22/26
3
3
2,292
13 Wanzer Hill Road, Sherman, CT
0.29
Single-Family Home
$950,000
07/28/25
4
3.5
4,092
339 State Route 39, New Fairfield, CT
0.46
Single-Family Home
$916,000
11/06/25
3
2
1,976
16 Fair Lane, New Fairfield, CT
0.45
Single-Family Home
$309,900
07/18/25
2
1
1,120

Nearby homes

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Assigned Schools

These are the assigned schools for 5 Oriole Dr.

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
    Flag
  • 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. "
    0
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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..."
    0
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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
    Flag

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Homes for sale near 5 Oriole Dr

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Off Market Homes Near 5 Oriole Dr

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