235 Middle Haddam Road
Portland, Connecticut 06480
- Beds
- 3
- Baths
- 4
- SqFt
- 2,859
- Acres
- 1.39
- Year Built
- 1907
- 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
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
Active Listings
7
13 under contract
Median List Price
$420,000
7 active listings
Median Closed Price
$417,450
70 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
Homes with a close match in area, property type, and price.
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.