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235 Middle Haddam Road

Portland, Connecticut 06480

PENDING$699,000
Beds
3
Baths
4
SqFt
2,859
Acres
1.39
Year Built
1907
Matt Caiola

Matt Caiola

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About This Home

Surrounded on three sides by the 90-acre Palmer-Taylor Preserve, this one-of-a-kind home offers an extraordinary combination of history, privacy, and natural beauty. Originally built in 1979 and thoughtfully expanded over the years, the residence incorporates an early 20th-century guesthouse once associated with the Taylor family of nearby St. Clements Castle, creating a home unlike any other. The setting is truly special, with permanently protected conservation land providing exceptional privacy, direct access to walking trails, abundant wildlife, and peaceful views in every season. A nearby stream, bluestone terrace, bocce court, fire pit, and beautifully landscaped grounds create inviting outdoor spaces for relaxing and entertaining. Inside, the flexible floor plan offers multiple living areas, a spacious primary suite with loft, and a finished walkout lower level with a full bath. Recent improvements include updated windows, central air conditioning, a high-efficiency natural gas boiler installed in 2024, and rare underground natural gas service. The existing carport was designed with future expansion in mind and is engineered for conversion to an enclosed garage, with the potential to add a second-story space above. Additional features include a backup generator system, security system, and mature landscaping designed to provide year-round beauty. A remarkable opportunity to own a home where history, architecture, and nature come together.

Key Facts

City/Town
Portland
Neighborhood
N/A
Property / Style
Single Family · Contemporary,Ranch
Year Built
1907
Days on Market
71 days
Beds
3
Baths
4 full
Living Area
2,859 sq ft
Lot Size
1.39 acres
Garage / Parking
2 garage
Property Taxes
$8,394 / Annually

Market Snapshot

The Portland Market

Single Family · trailing 12 months

Median Days on Market

17

7 active listings

Median $ / Sq Ft

$304

7 active listings

Sale-to-List Ratio

101.2%

70 sales

How this home compares

List Price

$699,000

vs $420,000 median

66.4% above median

Price / Sq Ft

$244

vs $304 median

19.7% below median

Days on Market

71 days

vs 17 days median

54 days longer than median

Based on 7 active and 70 closed sales (trailing 12 mo) of single family in Portland. Source: SmartMLS · As of July 28, 2026.

Location

235 Middle Haddam Road, Portland, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,497

per month

  • Principal & Interest$3,564
  • Property Taxes$700
  • Insurance$233
  • 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
Contemporary,Ranch
Year Built
1907
New Construction
No/Resale
Living Area
2,859 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
1
Laundry
Lower Level
Appliances
Cook TopRefrigeratorDishwasherWasherDryer
Basement
FullFull With Walk-Out
Interior Features
Cable - Available

Exterior & Lot

Lot Size
1.39 acres
Zoning
RR
Garage / Parking
2 garage spacesCarport
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Clapboard
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
TreedBorders Open SpaceLevel Lot

Listing & Financials

Property Taxes
$8,394 / Annually
Days on Market
71
MLS #
24176313
MLS Status
Under Contract - Continue to Show

Similar Properties

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Listed By

Carl Guild

(860) 813-2275

Carl Guild & Associates

(860) 474-3500

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 6:10 AM UTC.