27 Windsor Ave

2,578 Sq. Ft.
$132 / Sq. Ft.
2,578
Sq. Ft.
$132
per Sq. Ft.

Description

Rare opportunity to own a multi-family home that has been cherished by the same owners for generations. Back in the 70's when bell-bottoms and disco were popular, a young couple was renting one of the units when the original owner decided it was time to sell. Instead of listing it publicly, the owner approached them first. They were fortunate to be in a position to say yes-and that decision shaped their future. They purchased the home, raised their large family here, and built a life filled with...Rare opportunity to own a multi-family home that has been cherished by the same owners for generations. Back in the 70's when bell-bottoms and disco were popular, a young couple was renting one of the units when the original owner decided it was time to sell. Instead of listing it publicly, the owner approached them first. They were fortunate to be in a position to say yes-and that decision shaped their future. They purchased the home, raised their large family here, and built a life filled with memories while the second unit provided steady passive income. Now, it's time for the next chapter. This well-maintained multi-family offers both warmth and smart investment potential. Both units feature hardwood flooring, updated windows, two new boilers, and a new water heater. The second-floor unit has been remodeled, and the partially finished attic includes two additional bedrooms that can easily be combined with the second-floor unit-creating a spacious four-bedroom layout and maximizing rental income potential. Whether you're looking to owner-occupy and offset your mortgage with rental income, or expand your investment portfolio, this property delivers flexibility and long-term value. Conveniently located near major transportation, medical facilities, shopping and within walking distance to public transportation-it offers accessibility that tenants and owners alike will appreciate. A home that once gave a young couple their start is ready to do the same for someone new. As-is.
  1. Listed by Amanda S Zorovich • eXp Realty
    P: (203)-886-6600 C: (203)-886-6600 amandazorovich@gmail.com

Property Details for 27 Windsor Avenue

Basement Description
Full, Unfinished, Interior Access, Concrete Floor, Full With Hatchway
Direct Waterfront
No
Expected Active Date
03-06-2026
Garages Number
2
Neighborhood
N/A
Style
Units on different Floors
Garage Parking Info
Detached Garage, Paved, Off Street Parking, Driveway
Swimming Pool
No
LISTING UPDATED: 04/09/2026 11:40 AM

Property Details for 27 Windsor Avenue

StatusUnder Contract
MLS #24156861
Days on Market5
Taxes$4,732 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeMulti Family
MLS TypeMulti-Family / 2 Family
Year Built1895
Lot Size0.15 AC / 6,534 SF
CountyNew Haven County

Location

Listing Courtesy of eXp Realty, Amanda S Zorovich
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Building Information for 27 Windsor Avenue

Stories-Residences2Year Built1895Building Size-Lot Size0.15 AC / 6,534 SF

Payment Calculator

$2,106 per month

30 year fixed, 6.46% Interest

Principal and Interest

$1,712

Property Taxes

$394

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 27 Windsor Avenue

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: West Main St to Windsor
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • Latitude: 41.540282
  • Longitude: -72.812072
  • Middle Jr High School: Per Board of Ed
  • Neighborhood Amenities: Basketball Court, Library, Medical Facilities, Public Transportation, Shopping/Mall
  • State: Connecticut
Parking
  • Parking Total Spaces: 4
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $4,732
Interior and Exterior Features
Exterior Features
  • Exterior Features: Sidewalk, Gutters, Covered Deck
  • Waterfront Description: Not Applicable
Interior Features
  • Attic Description: Partially Finished, Floored, Walk-up
  • Cooling System: None
  • Heat Type: Baseboard
  • Attic YN: Yes
  • Fireplaces Total: 0
  • Rooms Total: 12
Property
Property and Assessments
  • Construction Description: Frame
  • Driveway Type: Private, Paved
  • Exterior Siding: Aluminum
  • Foundation Type: Brick, Stone
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1895
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Est Heated Below Grade: 0
  • Living Area SQFT Per Public Records: 2578
Lot Information
  • Lot Description: Level Lot
  • Parcel Number: 1168782
  • Sq Ft Est Heated Above Grade: 2578.0
  • Sq Ft Total: 2578.0
  • Zoning: R-2
Utilities
  • Energy Features: Thermopane Windows
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Natural Gas, Tank Size Unknown
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Tenant
  • Total Number of Units: 2
  • Total Rooms Multi Family: 12
Unit 1
  • Lease: Monthly
  • Unit Average Sq Ft: 1508
  • Unit Entry Order: 2
  • Unit Full Baths: 1
  • Unit Half Baths: 0
  • Unit Modified Date: 03-04-2026
  • Unit Num Bedrms: 4
  • Unit Num Rooms: 7
  • Unit Occupied By: Tenant
Unit 2
  • Lease: Monthly
  • Unit Average Sq Ft: 1074
  • Unit Entry Order: 1
  • Unit Full Baths: 1
  • Unit Half Baths: 0
  • Unit Modified Date: 03-04-2026
  • Unit Monthly Rent: $1,050
  • Unit Num Bedrms: 2
  • Unit Num Rooms: 5
  • Unit Occupied By: Tenant

Public Records for 27 Windsor Avenue

Taxable ValueLand$25,130Additions$99,680Total$124,810
Tax Record2023$4,806 ($400 / month)
Home Facts
Baths2Total Finished SqFt2,578 SqFtAbove Grade Finished SqFt2,578 SqFtUnfinished Basement SqFt1,074 SqFtStories3Lot Size6,534 SqFtStyleDuplexYear Built1895Year Renovated1971ZoningR-2CountyNEW HAVENAPNMERI M:602 B:156 L:15

Schools near 27 Windsor Avenue

This home is within Meriden School District.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Public - PK to 5
Rating
School
Distance
Casimir Pulaski School
PublicPK to 5

Lincoln Middle School
Public6 to 8

Orville H. Platt High School
Public9 to 12

Stars-Meriden School District
PublicPK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Listing Courtesy of eXp Realty, Amanda S Zorovich

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.