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157 Baileyville Road

Middlefield, Connecticut 06455

COMING SOON - NEW$699,900
Beds
4
Baths
4
SqFt
1,871
Acres
0.53
Year Built
1880
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Waterfront4-Car Garage

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 CMA

Based 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

Property + 1 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,573

per 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

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Listed By

Steven Joseph

(860) 707-5634

Coldwell Banker Realty

(860) 668-4589

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.