TWO-FAMILY BRICK HOUSE or SINGLE-FAMILY with SEPARATE APARTMENT in WOOSTER SQUARE AREA Rare opportunity to own a beautifully renovated (circa 10 years ago) 6-bedroom, 4-full-bath high income-producing two-family house or used as a single-family-style home with a legal income-producing apartment, as it was used by previous owners. The larger residence offers 4 bedrooms and 3 full baths, while the separate apartment includes 2 bedrooms and 1 full bath. Enjoy––or let enjoy your tenants––spacious living areas, custom finishes, and a large attic-level 4th bedroom (or study) with its own full bath, closet, and generous storage. The larger unit (or owners’ quarters) span three levels and feature central A/C and a private washer/dryer. The 2-bedroom, 1-bath apartment—on two levels and privately located with its own gated entrance—has separate utilities, A/C, in-unit laundry, and a secluded garden patio, making it ideal for rental income. A large basement provides additional storage, along with a small shed. Zoned and currently used as a legal two-family, this property has been a reliable investment for the current Yale-affiliated owners over nine years, with zero vacancy—consistently rented to academics and medical residents. Located in East Rock–Wooster Square, near most Yale buildings, downtown New Haven, Union Station, and neighborhood parks, this home blends historic charm with modern versatility. A rare opportunity for both investors and homeowners. Limited, discreet showings by appointment only, and after we answer your initial questions to help preview the home’s full potential for your needs. Text or call Dr. K.
Off market
$373,800
83 Olive St, New Haven, CT 06511
6beds
3,080sqft
SingleFamily
Built in 1890
1,742 Square Feet Lot
$-- Zestimate®
$121/sqft
$5,485 Estimated rent
What's special
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 4
- Full bathrooms: 4
Heating
- Forced air, Gas
Cooling
- Central, Other
Appliances
- Included: Dishwasher, Dryer, Freezer, Garbage disposal, Microwave, Range / Oven, Refrigerator, Trash compactor, Washer
Features
- Flooring: Tile, Hardwood
- Basement: Partially finished
- Has fireplace: Yes
Interior area
- Total interior livable area: 3,080 sqft
Property
Parking
- Parking features: Off-street, On-street
Features
- Exterior features: Shingle, Brick, Cement / Concrete
- Has view: Yes
- View description: City
Lot
- Size: 1,742 sqft
Details
- Parcel number: NHVNM208B0549L02800
Construction
Type & style
- Home type: SingleFamily
Materials
- Roof: Asphalt
Condition
- Year built: 1890
Community & neighborhood
Location
- Region: New Haven
Other
Other facts
- Cats Allowed
- Flooring: Hardwood
- Granite countertop
- Heating system: Heat
- Living room
- Secured entry
- Stainless steel appliances
- Street Parking
- Vintage