Discover this premier compound prospect in the Old Main Street district in South Windsor. This special property features two completely independent dwellings with three separate units, on a level 0.56-acre parcel, offering an ideal configuration for owner-occupants and savvy investors alike. The primary residence, with 2 units in the stately, fully updated main dwelling colonial, boasts 2,094 sq. ft. of timeless character. The 2-bedroom lower part of the home is a dream for those seeking the charm of yesteryear without sacrificing space. The upper unit has a distinctly cozier feel, while giving more separation than an average 1-bedroom. Tucked privately behind the main house is the second dwelling: a versatile 856 sq. ft. cottage-colonial. Whether you utilize this space as a high-performing rental unit to add to a portfolio, or an in-law suite, the flexibility of two separate legal homes on one lot is a true rarity in this market and presents several options. Live in the grand main house while the second and third units provide supplemental income. Enjoy the "country feel" of Old Main St, one of the most picturesque and historically significant stretches in Connecticut, with its nearby farm stands and scenic river views, while being only 10 minutes from the high-end shopping and dining at Evergreen Walk. Experience the best of both worlds: a heritage home with a modern financial edge. Virtual tours available for both homes.
Accepting backups
Price cut: $30K (4/28)
$634,900
90-92 Main Street, South Windsor, CT 06074
5beds
2,950sqft
Multi Family
Built in 1920
-- sqft lot
$606,200 Zestimate®
$215/sqft
$-- HOA
What's special
Grand main houseThree separate unitsTwo completely independent dwellings
- 107 days |
- 156 |
- 0 |
Zillow last checked:
Listing updated:
Listed by:
Rachel Nadolny-Sipes (860)918-7330,
Berkshire Hathaway NE Prop. 860-648-2045
Source: Smart MLS,MLS#: 24161195
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 3
Heating
- Radiator, Oil
Cooling
- None
Appliances
- Included: Water Heater
Features
- Basement: Full,Dirt Floor
- Attic: Walk-up
- Has fireplace: No
Interior area
- Total structure area: 2,950
- Total interior livable area: 2,950 sqft
- Finished area above ground: 2,950
Video & virtual tour
Property
Parking
- Total spaces: 6
- Parking features: Attached, Unassigned
- Attached garage spaces: 2
Lot
- Size: 0.56 Acres
- Features: Historic District
Details
- Parcel number: 706699
- Zoning: A40
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Other
- Property subtype: Multi Family
Materials
- Vinyl Siding
- Foundation: Brick/Mortar
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1920
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
Community & HOA
Community
- Features: Library, Park, Pool, Public Rec Facilities, Near Public Transport, Stables/Riding
HOA
- Has HOA: No
Location
- Region: South Windsor
Financial & listing details
- Price per square foot: $215/sqft
- Tax assessed value: $283,500
- Annual tax amount: $10,095
- Date on market: 3/20/2026
Estimated market value
$606,200
$576,000 - $637,000
$1,881/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/31/2026 | Contingent | $634,900$215/sqft |
Source: | ||
| 4/28/2026 | Price change | $634,900-4.5%$215/sqft |
Source: | ||
| 4/10/2026 | Price change | $664,900-2.9%$225/sqft |
Source: | ||
| 3/20/2026 | Listed for sale | $684,900$232/sqft |
Source: | ||
Public tax history
Tax history is unavailable.
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 06074
Nearby schools
GreatSchools rating
- 9/10Pleasant Valley SchoolGrades: PK-5Distance: 1.9 mi
- 8/10Timothy Edwards SchoolGrades: 6-8Distance: 5.6 mi
- 10/10South Windsor High SchoolGrades: 9-12Distance: 4.8 mi
Schools provided by the listing agent
- Elementary: Philip R. Smith
- High: South Windsor
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- Hartford County
- South Windsor
- 06074
- 90-92 Main Street




