25 Hillside Drive
Sherman, Connecticut 06784
Reduced from $899,777
- Beds
- 4
- Baths
- 4
- SqFt
- 3,303
- Acres
- 0.63
- Year Built
- 1955
- Neighborhood
- Holiday Point
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
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!
Key Facts
- City/Town
- Sherman
- Neighborhood
- Holiday Point
- Property / Style
- Single Family · Colonial
- Year Built
- 1955
- Days on Market
- 98 days
- Beds
- 4
- Baths
- 4 full
- Living Area
- 3,303 sq ft
- Lot Size
- 0.63 acres
- Garage / Parking
- 1 garage · 5 total
- Property Taxes
- $5,693 / Annually
- HOA Fee
- $90 / Monthly
Market Snapshot
The Sherman Market
Single Family · trailing 12 months
Active Listings
28
5 under contract
Median List Price
$1.05M
28 active listings
Median Closed Price
$672,500
42 sales
Median Days on Market
61
28 active listings
Median $ / Sq Ft
$333
28 active listings
Sale-to-List Ratio
96.7%
42 sales
How this home compares
List Price
$873,999
vs $1.05M median
16.7% below median
Price / Sq Ft
$265
vs $333 median
20.4% below median
Days on Market
98 days
vs 61 days median
37 days longer than median
Based on 28 active and 42 closed sales (trailing 12 mo) of single family in Sherman. Source: SmartMLS · As of July 28, 2026.
Location
25 Hillside Drive, Sherman, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,456
- Property Taxes$474
- Insurance$291
- HOA$90
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Sherman
- Neighborhood
- Holiday Point
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1955
- New Construction
- No/Resale
- Living Area
- 3,303 sq ft
- Below Grade
- 883 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Heat PumpHot AirZoned
- Heat Fuel
- ElectricOil
- Cooling
- Central AirHeat PumpZoned
- Fireplaces
- 2
- Laundry
- Lower Level
- Laundry Location
- Laundry Hook Up In Basement
- Appliances
- Electric RangeMicrowaveRefrigeratorDishwasher
- Basement
- Full
Exterior & Lot
- Lot Size
- 0.63 acres
- Zoning
- RES
- Garage / Parking
- 1 garage space5 total parking spacesDetached GarageDrivewayOff Street ParkingPrivatePaved
- Waterfront
- Direct waterfront
- Waterfront Details
- LakeDock or MooringBeach RightsAssociation RequiredWater CommunityAccess
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Pool
- HeatedVinylIn Ground Pool
- Construction
- Vertical Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- BalconyShedDeckFrench Doors
- Lot Description
- SecludedIn SubdivisionSloping LotOn Cul-De-SacWater View
HOA / Association
- Fee
- $90 / Monthly
Listing & Financials
- Property Taxes
- $5,693 / Annually
- Days on Market
- 98
- MLS #
- 24168886
- MLS Status
- Active
- Financing
- FHA,VA,CHFA,Owner Financing
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/28/2026 at 8:02 AM UTC.