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564 Main Street

Portland, Connecticut 06480

PENDING$389,000
Beds
4
Baths
1 | 1
SqFt
1,378
Acres
0.74
Year Built
1934
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,482

per 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

Similar Properties

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

Listed By

Andrea Hanrahan

(860) 818-0946

SalCal Real Estate Connections

(860) 828-1783

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.