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41 Gildersleeve Road

Portland, Connecticut 06480

COMING SOON - NEW$849,900
Beds
3
Baths
3 | 1
SqFt
3,355
Acres
2.03
Year Built
2013
Matt Caiola

Matt Caiola

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Pool2-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,741

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Debbie Walden

(860) 559-5176

eXp Realty

(866) 828-3951

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.