29 Hillside Dr, Sherman, CT 06784
Property image
Property image
OFF MARKET

29 Hillside Dr
Sherman, CT 06784

  • 2 Beds
  • 1.5 Baths
  • 1,512 sqft (on 0.50 acres)

$537,100

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $3,527/mo*
Refinance Your Home

$537,100

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $3,527/mo*
Refinance Your Home
2 Beds
1.5 Baths
1,512 sqft
(on 0.50 acres)

Local Information

  • Map ViewExplore the area around 29 Hillside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School
  • Shop & Eat
-- mins to
Commute Destination

Description

Sweet beach property with cozy interiors, direct waterfront / dock available. Ownership gives access to one of Sherman's premiere private beaches - Holiday Point Beach, known for its' magnificent Candlewood Lake views, Association gatherings, picnics & community sensibility. Boating, swimming, volleyball & sunset watching are just a few of the popular activities. Located in quaint Sherman, known for low taxes, educational choices, recreational options & 90 min. to NYC. Many weekend / summer residents retire here or opt to live here full-time for its' serene natural beauty yet minutes to trains, shopping, the Appalachian Trail & more. An investment in your quality of life!
29 Hillside Dr, Sherman, CT 06784 is a 2 bedroom, 2 bathroom, 1,512 sqft single-family home built in 1950. It last sold for $240,000 on May 14, 2018. It is currently off market. The Trulia Estimate is $537,100, with a rent estimate of $3,978/month.

Home Highlights

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

Home Details for 29 Hillside Dr

Interior Features

Heating & Cooling
Heating: Baseboard, ElectricCooling System: OtherHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 4
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1950
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Other
Parking & Garage
Parking: On Street

Lot Information

Lot Area: 0.50 acres

Price History for 29 Hillside Dr

DatePriceEventSource
05/14/2018$240,000Sold
Smart MLS #170044307
01/26/2018$249,900Listed 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$3,852
Assessment$231,100
Home facts updated by county records

Comparable Sales for 29 Hillside Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2 Oak Drive, Sherman, CT
0.32
Single-Family Home
$550,000
09/05/25
4
2
2,239
7 Ridge Road, Sherman, CT
0.38
Single-Family Home
$670,000
01/30/26
3
4
2,450
35 Route 39 South, Sherman, CT
1.12
Single-Family Home
$439,000
06/26/26
2
2
1,400
4 Mary Bee Lane, Sherman, CT
1.19
Single-Family Home
$554,000
10/31/25
3
2
1,189
18 Green Pond Road, Sherman, CT
1.41
Single-Family Home
$399,000
12/18/25
3
2
1,464
3 Gelston Road, Sherman, CT
0.99
Single-Family Home
$336,000
04/24/26
1
1
536
12 Sunny Lane, Sherman, CT
0.59
Single-Family Home
$775,000
11/25/25
4
2.5
3,214
11 Gelston Road, Sherman, CT
1.13
Single-Family Home
$599,000
04/01/26
3
2
1,568
94 Green Pond Rd, Sherman, CT
1.80
Single-Family Home
$215,000
08/27/25
2
2
1,120
139 Candlewood Mountain Road, New Milford, CT
1.56
Single-Family Home
$570,000
05/20/26
3
2
2,392

Nearby homes

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Assigned Schools

These are the assigned schools for 29 Hillside 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 29 Hillside Dr

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Off Market Homes Near 29 Hillside Dr

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