59-65 Maple Street
Chester, CT 06412
Chester Center
11 Beds
11 Baths
8,500 sqft (on 2.56 acres)
11 Beds
11 Baths
8,500 sqft
(on 2.56 acres)
Home Highlights
Parking
Garage
Climate Control
Heating only
Price/Sqft
$247
Listed
99 days ago
Local Information
- Map ViewExplore the area around 59-65 Maple Street.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
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.
Home Details for 59-65 Maple Street
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Interior Details Basement: FullNumber of Rooms: 34 |
Beds & Baths Number of Bedrooms: 11Number of Bathrooms: 12Number of Bathrooms (full): 10Number of Bathrooms (half): 2 |
Dimensions and Layout Living Area: 8500 Square Feet |
Appliances & Utilities Appliances: Electric Water Heater |
Heating & Cooling Heating: Baseboard,ElectricNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard |
Fireplace & Spa No Fireplace |
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Exterior Home Features Roof: AsphaltFoundation: Concrete PerimeterNo Private Pool |
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 10Parking: Detached,Driveway |
Frontage Not on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 8500 Square Feet |
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Days on Market: 99 |
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Year Built Year Built: 1975 |
Property Type / Style Property Type: Residential IncomeProperty Subtype: Multi FamilyArchitecture: Units on different Floors,Units are Side-by-Side |
Building Construction Materials: Shingle Siding, Vinyl SidingNot a New ConstructionAttached To Another StructureDoes Not Include Home Warranty |
Property Information Parcel Number: 940449 |
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Price List Price: $2,100,000Price Per Sqft: $247 |
Status Change & Dates Possession Timing: Fully Occupied |
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MLS Status: Active |
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Direction & Address City: Chester |
School Information Elementary School: ChesterHigh School: Per Board of Ed |
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Listing Agent Listing ID: 24170551 |
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Building Area Building Area: 8500 Square Feet |
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No HOA |
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Lot Area: 2.56 Acres |
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BasementMls Number: 24170551Attic: NoneAttribution Contact: (860) 343-7800Above Grade Unfinished Area: 8500 |
Last check for updates: about 10 hours ago
Listing courtesy of Connor T. Wenchell, (860) 343-7800
VC Property Group, LLC, (860) 343-7800
Anthony Velez, (860) 300-3102
VC Property Group, LLC, (860) 300-3102
Source: Smart MLS, MLS#24170551
Also Listed on Smart MLS.
Market trends in Chester
Last updated June 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
8
Price History for 59-65 Maple Street
| Date | Price | Event | Source |
|---|---|---|---|
| 04/27/2026 | $2,100,000 | Listed For Sale | Smart MLS #24170551 |
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Comparable Sales for 59-65 Maple Street
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.68 | Multi-Family Home | $285,000 | 08/05/25 | 5 | 2 | 1,553 | |
1.53 | Multi-Family Home | $600,000 | 07/10/26 | 4 | 2 | 8,382 | |
1.05 | Multi-Family Home | $625,000 | 05/19/26 | 4 | 2 | 1,970 | |
4.04 | Multi-Family Home | $1,050,000 | 07/30/26 | 7 | 6 | 2,942 | |
4.21 | Multi-Family Home | $1,150,000 | 07/16/26 | 4 | 4 | 3,036 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
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SOLDJAN 15, 2026William Raveis Real Estate
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SOLDNOV 19, 2025William Raveis Real Estate
Assigned Schools
These are the assigned schools for 59-65 Maple Street.
- John Winthrop Middle School
- 7-8
- Public
- 197 Students
4/10GreatSchools RatingParent Rating AverageI think bullying was the worst problem that happened during my time at JWMS. The adult authorities at the school had a difficult time understanding situations and that often made it worse. I'm also not stating that it was just the kids at the school who would bully but it was also teachers. I remember my 8th grade science teacher would verbally bully girls and pick on them, and it was always girls he was picking on. I was one of them. It didn't help that I had a counselor who couldn't care less if one of there students just jumped off a bridge. They could care less of there students well being, and the same goes with the principles. I honestly would recommend going to a different school, I mean unless you want your child to become depressed.Other Review8y ago - Valley Regional High School
- 9-12
- Public
- 429 Students
7/10GreatSchools RatingParent Rating AverageI enjoyed going to Valley. It is different as a parent I see things differently. However compared to other schools I would say Valley is above the rest.Parent Review7y ago - Chester Elementary School
- PK-6
- Public
- 198 Students
7/10GreatSchools RatingParent Rating AverageCES has a lot of potential with the proper leadership, which it lacks.Other Review6y ago 
Check out schools near 59-65 Maple Street.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Connor T. Wenchell, VC Property Group, LLC, (860) 343-7800
Agent Phone: (860) 343-7800
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
59-65 Maple Street, Chester, CT 06412 is a 11 bedroom, 12 bathroom, 8,500 sqft multi-family built in 1975. 59-65 Maple Street is located in Chester Center, Chester. This property is currently available for sale and was listed by Smart MLS on Apr 27, 2026. The MLS # for this home is MLS# 24170551.