59-65 Maple Street
Chester, Connecticut 06412
- Beds
- 11
- Baths
- 10 | 2
- SqFt
- 8,500
- Acres
- 2.56
- Year Built
- 1975
- Property Type
- 5+ Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
A mixed-use and multifamily package located in Chester and Deep River, two of the most desirable towns in the Lower Connecticut River Valley. The offering includes: 59 Maple Street (Chester): 7-unit multifamily asset with an additional ~1,500 SF commercial warehouse on 2.5+ acres. 163 Main Street (Deep River): 5-unit mixed-use property positioned at the gateway to the downtown retail corridor. The portfolio is fully occupied and generates approximately $210,000+ in current gross income, with upside to over $280,000 stabilized, driven by residential and commercial rent growth. At stabilization, the portfolio delivers approximately $175,748 NOI and a 8.37% cap rate, supported by a strong 1.58x DSCR. The possibility to develop the 3rd floor of 163 Main Street into additional units can drive returns even higher! This is a rare opportunity to acquire scale across two supply-constrained markets, combining in-place cash flow with clear mark-to-market upside across both residential and commercial components.
Key Facts
- City/Town
- Chester
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units on different Floors,Units are Side-by-Side
- Year Built
- 1975
- Days on Market
- 92 days
- Beds
- 11
- Baths
- 10 full · 2 half
- Living Area
- 8,500 sq ft
- Lot Size
- 2.56 acres
- Garage / Parking
- 1 garage · 10 total
- Property Taxes
- $12,134 / Annually
Market Snapshot
The Chester Market
Multi-Family · trailing 12 months
Active Listings
1
Chester inventory
Median List Price
$2.10M
1 active listing
Median Closed Price
$600,000
1 sale
Median Days on Market
92
1 active listing
Median $ / Sq Ft
$247
1 active listing
Sale-to-List Ratio
70.6%
1 sale
How this home compares
List Price
$2.10M
vs $2.10M median
In line with median
Price / Sq Ft
$247
vs $247 median
In line with median
Days on Market
92 days
vs 92 days median
In line with median
Based on 1 active and 1 closed sales (trailing 12 mo) of multi-family in Chester. Source: SmartMLS · As of July 28, 2026.
Location
59-65 Maple Street, Chester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$10,707
- Property Taxes$1,011
- Insurance$700
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Chester
- Neighborhood
- N/A
- County
- Middlesex
Residence
- Property Type
- Multi-Family
- Subtype
- 5 Family+
- Style
- Units on different Floors,Units are Side-by-Side
- Year Built
- 1975
- New Construction
- No/Resale
- Living Area
- 8,500 sq ft
Schools
- Elementary
- Chester
- High
- Per Board of Ed
Interior
- Heating
- Baseboard
- Heat Fuel
- Electric
- Cooling
- None
- Basement
- Full
Exterior & Lot
- Lot Size
- 2.56 acres
- Zoning
- PRD
- Garage / Parking
- 1 garage space10 total parking spacesDetached GarageDrivewayUnpaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water ConnectedPrivate Well
- Sewer
- Septic
- Construction
- ShingleVinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Treed
Listing & Financials
- Property Taxes
- $12,134 / Annually
- Days on Market
- 92
- MLS #
- 24170551
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Anthony Velez
VC Property Group, LLC
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 7:01 AM UTC.