41 Gildersleeve Road
Portland, Connecticut 06480
- Beds
- 3
- Baths
- 3 | 1
- SqFt
- 3,355
- Acres
- 2.03
- Year Built
- 2013
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Rarely available, this exceptional custom built home sits on 2.03 acres bordering the Portland Golf Course. Welcome to 41 Gildersleeve Road an oversized Cape, offering approximately 3,355 square feet of thoughtfully designed living space. The open-concept floor plan features spacious rooms, quality finishes, and an inviting layout designed for both everyday living and entertaining. Beautiful hardwood floors flow throughout the home, complemented by a gas fireplace framed by custom built-ins. On chilly evenings, gather around the fire and enjoy the warmth and comfort of this welcoming space. The thoughtfully designed floor plan creates an easy flow between the living, dining, and entertaining areas. Large windows fill the home with abundant natural light, enhancing the open and airy feel throughout. The home currently offers three bedrooms and three-and-a-half baths, with the flexibility of two potential primary bedroom suites-one on the first floor and another on the second floor. This versatile layout provides options to suit a variety of living arrangements. Convenience continues with laundry hookups on the first floor, as well as a dedicated laundry room in the basement. A spacious first-floor office provides an ideal work-from-home space and could also be used as a fourth bedroom.
Key Facts
- City/Town
- Portland
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 2013
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 3 full · 1 half
- Living Area
- 3,355 sq ft
- Lot Size
- 2.03 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $13,062 / Annually
Market Snapshot
The Portland Market
Single Family · trailing 12 months
Active Listings
11
11 under contract
Median List Price
$393,000
11 active listings
Median Closed Price
$419,900
73 sales
Median Days on Market
16
11 active listings
Median $ / Sq Ft
$223
11 active listings
Sale-to-List Ratio
101.1%
73 sales
How this home compares
List Price
$849,900
vs $393,000 median
2.2× the median
Price / Sq Ft
$253
vs $223 median
13.5% above median
Days on Market
0 days
vs 16 days median
16 days fresher than median
Based on 11 active and 73 closed sales (trailing 12 mo) of single family in Portland. Source: SmartMLS · As of August 30, 2026.
Location
41 Gildersleeve Road, Portland, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per month
- Principal & Interest$4,369
- Property Taxes$1,089
- Insurance$283
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Portland
- Neighborhood
- N/A
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 2013
- New Construction
- No/Resale
- Living Area
- 3,355 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Lower Level
- Laundry Location
- LL separate rm2nd hook up on 1st floor
- Appliances
- Gas RangeRefrigeratorDishwasherWasherElectric Dryer
- Basement
- Full
- Additional Rooms
- Bonus RoomExercise RoomFoyerLaundry Room
Exterior & Lot
- Lot Size
- 2.03 acres
- Zoning
- R25
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- Safety FenceIn Ground Pool
- Construction
- ShakeVinyl Siding
- Color
- Tan
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Underground UtilitiesPorchDeckPatio
- Lot Description
- Golf Course FrontageLightly WoodedGolf Course ViewProfessionally Landscaped
Listing & Financials
- Property Taxes
- $13,062 / Annually
- Days on Market
- 0
- MLS #
- 24200612
- MLS Status
- Coming Soon
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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 8/30/2026. 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 8/30/2026 at 8:15 PM UTC.