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$874,999

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 3,303 Sq. Ft.
  • 1 Car Garage
  • Updated 12 days ago
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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. This opportunity will not last long, schedule your showing today!

Full Property Details for 25 Hillside Dr

General

  • Price: $874,999
  • HOA FEE: $90/month
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24168886
  • Updated: 5/27/2026
  • Added to Site: 48 day(s) ago

Interior

  • Number of Rooms: 7
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Electric Range, Microwave, Refrigerator, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom, Upper
  • Bedroom 1: Bedroom, Main
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Dining Room: Dining Room, Main
  • Laundry: Lower Level

Additional Information

  • Pool: Yes
  • Pool Description: Heated, Vinyl, In Ground Pool

Exterior

  • Exterior Features: Balcony, Shed, Deck, French Doors

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Total Spaces: 5
  • Parking: Detached Garage, Driveway, Off Street Parking

Location

  • County: Fairfield
  • Neighborhood: Holiday Point
  • Driving Directions: Holiday Point Rd to Right on Hillside

School Information

  • Elementary School: Per Board of Ed
  • Middle School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • High School: Per Board of Ed

Community

  • Community Name: Holiday Point
  • Association: Yes
  • Home Owners Assn.: 1
  • Assoc. Fees Include: Lake/Beach Access, Grounds Maintenance, Snow Removal, Road Maintenance

Heating & Cooling

  • Cooling Type: Central Air, Heat Pump, Zoned
  • Heating Type: Heat Pump, Hot Air, Zoned, Electric, Oil
  • Heating Fuel: Electric, Oil
  • Water Heater: Electric, 50 Gallon Tank

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vertical Siding
  • Basement Desc.: Full
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,303
  • Above Ground: 2,420 Sq. Ft.
  • Below Ground: 883 Sq. Ft.
  • Year Built: 1955

Lot Features

  • Lot Size (Acres): 0.63
  • Driveway/Sidewalk: Private, Paved
  • Zoning: RES
  • Lot Description: Secluded, In Subdivision, Sloping Lot, On Cul-De-Sac, Water View

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Lake, Dock or Mooring, Beach Rights, Association Required, Water Community, Access

Financial Considerations

  • Association Fee: $90
  • Assoc Fee Freq.: Monthly
  • Assessment Amount: $341,500
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 310854

Listed by Re/Max Rise, CONNEX TEAM AT REMAX RISE, Gary Crawford

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Listing agent

— 25 Hillside Dr —

  • Gary Crawford

    Re/Max Rise

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 25 Hillside Dr

School District:Sherman School District
NameGradesDistance
Sherman School, Sherman, CT
2 Route 37 East, Sherman, CT 06784
PK-80.2 mi
New Fairfield High School
54 Gillotti Road, New Fairfield, CT 06812
9-128 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 25 Hillside Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/27/2026
Price Reduced
$874,999
-1.66%
MLS
5/15/2026
Price Reduced
$889,777
-1.11%
MLS
4/24/2026
Listed
$899,777
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 25 Hillside Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$5,693
2%
$341,500
—
2023
$5,587
-8%
$341,500
—
2023
$6,086
-2%
$341,500
—
2022
$6,208
-2%
$341,500
—
2021
$6,366
-2%
$341,500
—
2020
$6,526
-4%
$341,500
—
2019
$6,765
3%
$341,500
6%
2018
$6,575
—
$323,400
—
2017
$6,575
—
$323,400
—
2016
$6,575
1%
$323,400
—
2015
$6,481
1%
$323,400
—
2014
$6,416
14%
$323,400
-3%
2011
$5,629
—
$334,250
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 25 Hillside Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Re/Max Rise, CONNEX TEAM AT REMAX RISE, Gary Crawford

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25 Hillside Drive, Sherman, CT 06784 (MLS# 24168886) is a Single Family property with 4 bedrooms and 4 full bathrooms. 25 Hillside Drive is currently listed for $874,999 and was received on April 21, 2026. Want to learn more about 25 Hillside Drive? Do you have questions about finding other Single Family real estate for sale in Sherman? You can browse all Sherman real estate or contact a Coldwell Banker agent to request more information.

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