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

$847,600

Trulia Estimate
as of Sep 23, 2026
  • 4 Beds
  • 4 Baths
  • 3,303 sqft

25 Hillside Dr, Sherman, CT 06784

Home Highlights

Single-Family Home
3,303 sqft
$257/sqft
Garage

Local Information

  • Map ViewExplore the area around 25 Hillside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Private dockHeated in-ground poolFully remodeled homePlenty of storageImpressive vaulted primary suiteFully remodeled bath
Year round rental opportunity! A true waterfront retreat with direct frontage on Candlewood Lake, this hidden gem is tucked away behind a perimeter of mature trees, offering a private and peaceful setting within the private Holiday Point Association. The community invites an active lifestyle with scenic opportunities for walking, hiking, and biking. Outdoor living shines here, featuring an expansive 107' x 12' deck and a heated in-ground pool. A gentle path leads to the water's edge, where a private dock accommodates you. Designed for both entertaining and flexible, multi-generational living, this fully remodeled home is spacious and filled with natural light. Most rooms feature sliding doors that open to decks or balconies. The main level includes a living room with fireplace and deck access, flowing into a dining room and kitchen. A den/additional bedroom with French doors to the deck, along with fully remodeled bath completes this level. Upstairs, the impressive vaulted primary suite offers a gas fireplace, private balcony, oversized walk-in closet, and spa-like bath. An additional vaulted bedroom with its own balcony and loft, along with a full bath, provides ample space. The finished lower level expands the living area even further, with a family room featuring a wet bar a media/game room, a full bath, and plenty of storage. Can come furnished for additional cost
Note: Unable to put large boat at bottom of dock. Dock more suitable jet ski, paddle boards, and kayaking

*Can come furnished for an additional fee

Renter responsible for all utilities. Pet policy handled on case by case basis.
25 Hillside Dr, Sherman, CT 06784 is a 4 bedroom, 4 bathroom, 3,303 sqft single-family home. More recently, it was listed as a rental in August 2026 with an asking price of $6,000 per month. That rental listing was removed on September 22, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $847,600, with a rent estimate of $5,687/month.

Home Details for 25 Hillside Dr

Interior Features

Heating & Cooling
Heating: Forced Air, Heat PumpHeating Fuel: Forced Air
Appliances & Utilities
DishwasherRefrigerator
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Exterior Features

Pool
Pool
Parking & Garage
GarageParking: Detached Garage, On Site

Comparable Sales for 25 Hillside Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
7 Ridge Road, Sherman, CT
0.42
Single-Family Home
$670,000
01/30/26
3
4
2,450 sqft
12 Sunny Lane, Sherman, CT
0.64
Single-Family Home
$775,000
11/25/25
4
2.5
3,214 sqft
18 Fox Run, Sherman, CT
0.89
Single-Family Home
$847,000
01/30/26
3
2.5
3,474 sqft
15 Brinsmade Lane, Sherman, CT
0.62
Single-Family Home
$1,050,000
09/15/26
3
2
1,746 sqft
9 Route 37 Center, Sherman, CT
0.36
Single-Family Home
$515,000
08/31/26
2
2
864 sqft
8 Ledgewood Drive, Sherman, CT
1.04
Single-Family Home
$1,300,000
12/15/25
4
3.5
1,542 sqft
5 Upland Pastures Road, Sherman, CT
1.11
Single-Family Home
$2,000,000
06/15/26
5
4.5
4,250 sqft
12 Fox Run, Sherman, CT
0.83
Single-Family Home
$1,300,000
11/25/25
6
6
6,751 sqft
22 Meadowood Drive, New Milford, CT
1.28
Single-Family Home
$720,000
06/03/26
4
3.5
4,214 sqft
29 Route 37 East, Sherman, CT
0.75
Single-Family Home
$300,000
10/31/25
10
7.5
5,856 sqft

Nearby homes

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Rental Market Trends in Sherman

Last updated Sep 2026
Trulia Rent Estimate$5,687/mo
Average rent
$6K
$500MoM
Available listings
5
View rental market trends in Sherman, CT

Around this home

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
    Flag
  • 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
    Flag
  • Roberta D.
    "Peaceful, beautiful, friendly people."
    0
    Flag
  • Lybern
    "Used to escape to Sherman for R&R. Ended up staying."
    0
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Sep 22, 2026
Source: Zillow Rentals
ListingRemoved
$6,000
Aug 12, 2026
Source: Zillow Rentals
Listed For Rent
$6,000
Aug 11, 2026
Source: Smart MLS #24168886
ListingRemoved
$869,999
Jul 28, 2026
Source: Smart MLS #24168886
PriceChange
$869,999
Price decreased by 0%
Jun 24, 2026
Source: Smart MLS #24168886
PriceChange
$873,999
Price decreased by 0%

Frequently asked questions about 25 Hillside Dr

  • What is 25 Hillside Dr estimated to be worth?
    Trulia's estimated value for 25 Hillside Dr in Sherman, CT is $847,600.
  • Is Sherman a buyer's or seller's market?
    Sherman is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Sherman?
    Residents describe Sherman, CT as well-kept, easy to park in, and quiet. Most residents say you need a car. See recently sold homes in Sherman, CT.
  • What are the closest schools to 25 Hillside Dr?
    The closest schools to 25 Hillside Dr in Sherman, CT are Sherman School (Pre-K/Elementary/Middle, rated 9/10).
  • Does 25 Hillside Dr have a pool?
    Yes, 25 Hillside Dr in Sherman, CT has a pool.
  • Does 25 Hillside Dr have a garage?
    Yes, 25 Hillside Dr in Sherman, CT has a garage.

Homes for rent near 25 Hillside Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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