103 Glenbrook Drive
Cheshire, Connecticut 06410
- Beds
- 3
- Baths
- 3 | 1
- SqFt
- 3,736
- Acres
- 0.92
- Year Built
- 1951
- 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
Welcome to Honeypot Glen, a one-of-a-kind property on nearly an acre in Cheshire. This 3-bedroom, 3.5-bath home blends thoughtful craftsmanship, smart-home technology, and exceptional indoor-outdoor living. The chef's kitchen features quartz countertops, custom oak cabinetry, stainless steel appliances, a wet bar, and walk-in pantry. The family room offers hardwood floors, a wood-burning stove, surround sound, and access to a flexible office/in-law suite with a full bath and kitchenette. The primary suite includes a private terrace, custom built-ins, jetted tub, and spa-like bath. Outside, enjoy a heated pool with hot tub overflow and waterfall, outdoor kitchen, fire-pit terraces, pool house snack bar, and park-like setting backing to town land. Smart-home controls, whole-house generator, 400-amp service, irrigation, landscape lighting, and more complete this exceptional property.
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Ranch
- Year Built
- 1951
- Days on Market
- 50 days
- Beds
- 3
- Baths
- 3 full · 1 half
- Living Area
- 3,736 sq ft
- Lot Size
- 0.92 acres
- Property Taxes
- $11,358 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
24
54 under contract
Median List Price
$642,000
24 active listings
Median Closed Price
$553,750
238 sales
Median Days on Market
33
24 active listings
Median $ / Sq Ft
$270
24 active listings
Sale-to-List Ratio
101.6%
238 sales
How this home compares
List Price
$699,900
vs $642,000 median
9.0% above median
Price / Sq Ft
$187
vs $270 median
30.7% below median
Days on Market
50 days
vs 33 days median
17 days longer than median
Based on 24 active and 238 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of July 28, 2026.
Location
103 Glenbrook Drive, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,569
- Property Taxes$947
- Insurance$233
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Cheshire
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Ranch
- Year Built
- 1951
- New Construction
- No/Resale
- Living Area
- 3,736 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Cheshire
Interior
- Heating
- Hot Water
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry Location
- Living room - bathroom
- Appliances
- Oven/RangeMicrowaveRange HoodRefrigeratorDishwasherDisposalWasherDryerWine Chiller
- Basement
- PartialSump PumpStorageInterior AccessPartially Finished
- In-Law Apartment
- PossibleSecond Floor
- Interior Features
- Audio SystemOpen Floor PlanSecurity System
- Accessibility
- Ramps
Exterior & Lot
- Lot Size
- 0.92 acres
- Zoning
- R-20
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Pool
- Pool HouseSpaSafety FenceIn Ground Pool
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- GrillTerracePorchLightingUnderground SprinklerPatio
- Lot Description
- Corner LotTreedProfessionally Landscaped
Listing & Financials
- Property Taxes
- $11,358 / Annually
- Days on Market
- 50
- MLS #
- 24181888
- MLS Status
- Under Contract
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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 7:01 AM UTC.