564 Main Street
Portland, Connecticut 06480
- Beds
- 4
- Baths
- 1 | 1
- SqFt
- 1,378
- Acres
- 0.74
- Year Built
- 1934
- Neighborhood
- Gildersleeve
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
*** Highest and Best Tomorrow 7.15.26 by Noon*** Welcome to 564 Main St. Portland. This is the one you%27ve been waiting for! Brimming with Charm and Character, a spacious Eat In Kitchen and an Oversized Two Car Garage with electricity for Enthusiasts. This Well Built Quintessential Cape offers 4 bedrooms with a Main floor Primary loacated off the Living room for Privacy, or an In-Law situation, while the half bath is Conveniently located off the kitchen. A Full Dining room gives extra options for space, including a three season sunroom with a heater that stays. Hardwood Flooring throughout including under the brand new carpets. Upstairs you%27ll find three bedrooms and a full bathroom. Other Features include a Newer Furnace, Newer windows, Newer roof on home, Fridge approx. 2Y old, Dishwasher 6Y old, New Shed in 2020, and a clean unfinished basement with Tall ceilings giving an abundance of storage. Natural gas and public utilities complete your worry free living. Set on almost an acre, this Lush Private flat level yard is perfect for Sports, Entertaining Huge Outdoor bashes, or just relaxing in your private Oasis among tall trees including a historic Holly bush. Portland is home to many golf courses, The Ct River for Boating enthusiasts, and Minutes away from Downtown Middletown restaurants and shopping, yet quietly tucked away for the best of both worlds. Come see What this hometown has to offer!
Key Facts
- City/Town
- Portland
- Neighborhood
- Gildersleeve
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1934
- Days on Market
- 21 days
- Beds
- 4
- Baths
- 1 full · 1 half
- Living Area
- 1,378 sq ft
- Lot Size
- 0.74 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $4,423 / 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
$389,000
vs $420,000 median
7.4% below median
Price / Sq Ft
$282
vs $304 median
7.2% below median
Days on Market
21 days
vs 17 days median
4 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
564 Main Street, Portland, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,983
- Property Taxes$369
- Insurance$130
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Portland
- Neighborhood
- Gildersleeve
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1934
- New Construction
- No/Resale
- Living Area
- 1,378 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Portland
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- Window Unit
- Laundry
- Lower Level
- Laundry Location
- Basement
- Appliances
- Oven/RangeRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinished
- Interior Features
- Auto Garage Door Opener
Exterior & Lot
- Lot Size
- 0.74 acres
- Zoning
- R10
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl SidingAluminum
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Shed
- Lot Description
- Level LotOpen Lot
Listing & Financials
- Property Taxes
- $4,423 / Annually
- Days on Market
- 21
- MLS #
- 24189489
- MLS Status
- Under Contract - Continue to Show
- Financing
- FHA,VA,CHFA,USDA
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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 4:25 AM UTC.