25 Hillside Drive - Sherman, CT

$873,999

Beds

4.00

Baths

3,303

SqFt

0.63

Acres

Pricing Insight: Originally listed for $899,777, the price was last adjusted to $873,999 on July 22, 2026, a –$25,778 (2.9%) change, approximately 0 days ago. This property has been on the market for approximately 92 days.

25 Hillside Drive, Sherman, CT is a 4-bed, 4-bath, 3,303 square foot home built in 1955 , featuring colonial architecture. This home is part of a homeowners association, with dues of $90 paid monthly. The HOA fee includes: lake/beach access, grounds maintenance, snow removal, and road maintenance.

This home is within the Sherman school district. Local, with nearby schools including Per Board of Ed.

MLS #: 24168886

Offered Price: $873,999

Residence Type: Single Family

Architectural Style: Colonial

Living Area: 3,303 Sq. Ft.

Lot Size: 0.63 Acres

Neighborhood: Holiday Point

County: Fairfield

Year Built: 1955

Design & Construction: Frame

Heating: Heat Pump,Hot Air,Zoned

Cooling: Central Air,Heat Pump,Zoned

Garage Spaces: 1

Price per Sq Ft as listed: $265

Estimated Tax: $5,693

Days on Market: 89

$20,000

4 Beds · 4 Baths · 3,303 Sq Ft

25 Hillside Drive, Sherman

$1,100,000

4 Beds · 4 Baths · 4,854 Sq Ft

21 Holiday Point Road, Sherman

Home Automation: Not specified

Energy Features: Not specified

Solar Contract: Not specified

Heating Fuel: Electric, Oil

Fuel Type: Heat Pump, Hot Air, Zoned

Fuel Tank Location: In Basement

Cooling System: Central Air, Heat Pump, Zoned

Hot Water System: Electric, 50 Gallon Tank

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $265 / Sq. Ft.

Tax assessed value: $341,500

Estimated Tax: $5,693

Architectural Style: Colonial

Design & Construction: Frame

Residence Type: Single Family

Year Constructed: 1955

Living Area: 3,303 Sq. Ft.

Lot Size: 0.63 Acres

Fuel: Electric,Oil

Loading automated valuation...

AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

Request CMA Schedule Tour

Understanding This Valuation

The RPR AVM considers:

Recent sales of comparable properties
Property characteristics and location
Market trends in Sherman
Statistical modeling algorithms

Local Market Context

Active Listings: 44

Average Price: $865,291

Average DOM: 89 days

Complimentary CMAs, no obligation

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!

Continue reading ▾

Flood Risk Assessment Water Body Detected Nearby

Water Proximity Detected: This property exhibits indicators suggesting nearby or referenced water features

Location Analysis:

Water features noted

Water Proximity:

Near water body

Topography:

Standard terrain • 0.6 acres

Water Indicators Found:

Water-related features referenced in listing details

Recommendations:

Professional flood assessment advised
Based on identified water-related indicators, flood insurance may warrant consideration
Consult FEMA Flood Maps for zone verification
Evaluate drainage systems
Review local flood history

Risk Level: Moderate

Property near water bodies. Consider flood insurance.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

Dining & Café Access: Low to Moderate
Daily Services: Limited
Recreational Space: Limited Nearby

How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

44

Homes For Sale

$865,291

Average List Price

Mechanicals & Utilities: Heat Pump,Hot Air,Zoned • Electric,Oil • Central Air,Heat Pump,Zoned • Private Well water • 2 fireplaces

Exterior Features

Exterior Construction: Vertical Siding

Roof Type: Asphalt Shingle

Foundation: Concrete

Driveway: Private,Paved

Garage: Detached Garage,Driveway,Off Street Parking (1 car)

Parking: 5 Total

Patio/Deck: Balcony,Shed,Deck,French Doors

Pool: Heated,Vinyl,In Ground Pool

Utilities: Water: Private Well

Outbuildings: Balcony,Shed,Deck,French Doors

Only motif connects you to a certified
"Local Market Expert"

Steve Simos

Real Estate Advisor

Sherman • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

Verified Motif Advisor

(203) 915-6183

george@appzentric.com

Good afternoon Steve, I'm interested in
25 Hillside Drive, Sherman, Connecticut

By proceeding, you consent to receive calls and texts at the number you provided, and artificial voice, and email, from motif about your inquiry and similar properties. Your personal information will never be sold or given to a 3rd party.

Good afternoon. Welcome to 25 Hillside Drive, Sherman, CT