157 Baileyville Road
Middlefield, Connecticut 06455
- Beds
- 4
- Baths
- 4
- SqFt
- 1,871
- Acres
- 0.53
- Year Built
- 1880
- Neighborhood
- Lake Beseck
- Property Type
- 2 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
Keep your boat in the backyard! Rare opportunity to own a beautifully updated Multi family property with waterfront, exceptional outdoor spaces, and outstanding income potential. Whether you're looking for an owner-occupied investment, multigenerational living, or an income-producing property, this home offers incredible versatility. Recent improvements include a brand-new roof, new siding, a beautifully renovated second floor, and brand-new fencing, giving the property a fresh, updated feel while taking care of many of the major improvements a new owner would typically face. The main two-family residence features beautiful balconies overlooking the lake, creating the perfect setting for morning coffee, outdoor dining, or simply relaxing and enjoying the view. Outside, you'll find a charming courtyard area, landscaped grounds, and inviting spaces for entertaining. Adding tremendous value is the separate four-car garage with a carriage house above, complete with its own beautiful balconies and additional possibilities for living space, guests, a home office, or potential rental income, subject to applicable approvals. With two-family home and a additional carriage house home and four-car garage, multiple balconies, lake views, a private courtyard, and extensive recent renovations, this is a truly unique opportunity to live on the property while generating rental income and building long-term value all while enjoying an incredible lakeside setting.Brand new Metal Dock.
Key Facts
- City/Town
- Middlefield
- Neighborhood
- Lake Beseck
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1880
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 4 full
- Living Area
- 1,871 sq ft
- Lot Size
- 0.53 acres
- Garage / Parking
- 4 garage · 8 total
- Property Taxes
- $8,898 / Annually
Market Snapshot
The Middlefield Market
Multi-Family · trailing 12 months
Median Days on Market
--
0 active listings
Median $ / Sq Ft
--
0 active listings
Sale-to-List Ratio
--
0 sales
How this home compares
This home is distinctive enough in Middlefieldthat comparable market data is limited. For a precise read on value, we'd recommend a private CMA — Matt can typically prepare one within 24 hours.
Request a CMABased on 0 active and 0 closed sales (trailing 12 mo) of multi-family in Middlefield. Source: SmartMLS · As of August 28, 2026.
Location
157 Baileyville Road, Middlefield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per month
- Principal & Interest$3,598
- Property Taxes$742
- Insurance$233
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Middlefield
- Neighborhood
- Lake Beseck
- County
- Middlesex
Residence
- Property Type
- Multi-Family
- Subtype
- Duplex
- Style
- Units on different Floors
- Year Built
- 1880
- New Construction
- No/Resale
- Living Area
- 1,871 sq ft
Schools
- Elementary
- John Lyman
- High
- Coginchaug Regional
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Ductless
- Basement
- Full
Exterior & Lot
- Lot Size
- 0.53 acres
- Zoning
- HD1
- Garage / Parking
- 4 garage spaces8 total parking spacesAttached GaragePaved
- Waterfront
- Direct waterfront
- Waterfront Details
- Lake
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Masonry
- Lot Description
- Water View
Listing & Financials
- Property Taxes
- $8,898 / Annually
- Days on Market
- 0
- MLS #
- 24202689
- MLS Status
- Coming Soon
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 8/28/2026. 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 8/28/2026 at 6:20 AM UTC.