99 Olive St New Haven, CT 06511
Wooster Square NeighborhoodEstimated payment $6,287/month
Highlights
- City View
- 4-minute walk to New Haven-State Street Station
- Tankless Water Heater
- Attic
- 4 Fireplaces
- 2-minute walk to Wooster Square Park
About This Home
Step into timeless elegance at 99 Olive Street, a rare Queen Anne Victorian style three-family in the heart of Wooster Square! This striking brick home showcases the best of 19th-century craftsmanship, with its intricate detailing, patterned facade, and beautifully preserved historic character. This lovingly maintained, legal 3 family with a bonus owners unit/office space, has been thoughtfully updated. The property features a newer roof, rebuilt chimney, updated mechanicals, and recent repointing of the whole brick exterior, preserving its beauty and ensuring long-term integrity! Inside, each spacious unit offers high ceilings, hardwood floors, fireplaces, and large windows that fill the rooms with natural light. Private backyard with garden boxes and community grill is great for entertaining and relaxing in the heart of the city. Separate utilities and flexible layouts make it ideal for both investors and owner-occupants. Enjoy everything Wooster Square has to offer right outside your door- the park, weekend farmers market, cafes, and the legendary Sally's and Pepe's Apizza. Just minutes to Yale, downtown, and Union Station, this home perfectly blends Queen Anne elegance with modern reliability and city convenience. A true Wooster Square gem, full of charm, character, and opportunity.
Listing Agent
eXp Realty Brokerage Phone: (203) 228-3554 License #RES.0826450 Listed on: 10/27/2025
Property Details
Home Type
- Multi-Family
Est. Annual Taxes
- $18,801
Year Built
- Built in 1870
Lot Details
- 3,049 Sq Ft Lot
Home Design
- Brick Exterior Construction
- Stone Foundation
- Stone Frame
- Asphalt Shingled Roof
- Masonry Siding
- Masonry
- Stone
Interior Spaces
- 2,885 Sq Ft Home
- 4 Fireplaces
- Concrete Flooring
- City Views
Bedrooms and Bathrooms
- 6 Bedrooms
- 4 Full Bathrooms
Attic
- Unfinished Attic
- Attic or Crawl Hatchway Insulated
Unfinished Basement
- Basement Fills Entire Space Under The House
- Interior Basement Entry
- Basement Hatchway
- Basement Storage
Utilities
- Central Air
- Mini Split Air Conditioners
- Window Unit Cooling System
- Heating System Uses Natural Gas
- Tankless Water Heater
Community Details
- 3 Units
- Gross Income $95,640
Listing and Financial Details
- Assessor Parcel Number 1245751
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $18,801 | $477,190 | $170,030 | $307,160 |
| 2024 | $18,372 | $477,190 | $170,030 | $307,160 |
| 2023 | $17,751 | $477,190 | $170,030 | $307,160 |
| 2022 | $18,968 | $477,190 | $170,030 | $307,160 |
| 2021 | $15,290 | $348,460 | $87,430 | $261,030 |
| 2020 | $15,290 | $348,460 | $87,430 | $261,030 |
| 2019 | $14,977 | $348,460 | $87,430 | $261,030 |
| 2018 | $14,977 | $348,460 | $87,430 | $261,030 |
| 2017 | $13,478 | $348,460 | $87,430 | $261,030 |
| 2016 | $12,731 | $306,390 | $97,160 | $209,230 |
| 2015 | $12,731 | $306,390 | $97,160 | $209,230 |
| 2014 | $12,731 | $306,390 | $97,160 | $209,230 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 10/27/2025 10/27/25 | For Sale | $899,999 | +109.3% | $312 / Sq Ft | |
| 09/13/2013 09/13/13 | Sold | $430,000 | -10.4% | $149 / Sq Ft | View Prior Sale |
| 07/31/2013 07/31/13 | Pending | -- | -- | -- | |
| 10/10/2012 10/10/12 | For Sale | $479,900 | -- | $166 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $430,000 | -- |
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $50,000 | Credit Line Revolving | |
| Open | $392,250 | Stand Alone Refi Refinance Of Original Loan | |
| Closed | $375,000 | Stand Alone Refi Refinance Of Original Loan | |
| Closed | $393,772 | FHA |
Source: SmartMLS
MLS Number: 24136128
APN: NHVN-000208-000560-002600
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