Middlebury, CT Triplexes for Sale

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31 properties

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Updated: Sep 15

Four-Unit Multifamily Property with Pool

10 Old Waterbury Road, Middlebury, CT 06762

$699,900

2,345 sqft 0.41 AC lot

Four units across two buildings on a 0.41‑acre parcel
2,345 square feet with a side‑by‑side triplex and detached ranch residence
Detached two‑car garage and in‑ground swimming pool
Triplex includes garages beneath the building and fireplaces in living rooms
Separate heat and utility systems with public water and public sewer

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Updated: Sep 22

Triplex With Detached Three-Bay Garage

160 Edson Avenue, Waterbury, CT 06705

$599,900

3,027 sqft 0.17 AC lot

Triplex with 3,027 square feet on a 0.17‑acre double corner lot
Detached brick garage measures 28 x 22 feet and includes 3 bays
Full above‑ground basement has windows and walk‑out access
Enclosed rear porches and exterior patio area
RM zoning with public water and public sewer

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Triplex with Private Decks

95 Sunnyside Avenue, Waterbury, CT 06708

$464,000

3,044 sqft 0.17 AC lot

Three residential units offer two bedrooms and an eat-in kitchen on each floor.

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Turnkey Six-Unit Residential Income

96 Hill St, Waterbury, CT 06704

$795,000

4,788 sqft

Two three-family buildings on one parcel provide six renovated apartments with on-site laundry and ample off-street parking.

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Three-Unit Triplex with New Roof

23 Plaza Avenue, Waterbury, CT 06710

$450,000

3,245 sqft 0.10 AC lot

Three large apartments with separate utility metering and tenant-paid heat, hot water, and electricity.

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Renovated Three-Unit Triplex

10 Edwards St, Waterbury, CT 06708

$530,000

3,454 sqft

Three spacious residences include private decks, flexible bonus rooms, and separate living, dining, and kitchen areas.

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Renovated Triplex Property

601 Washington Avenue, Waterbury, CT 06708

$559,999

3,192 sqft

Three renovated units near transportation, shopping, restaurants, and highway connections.

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Updated Three-Unit Multifamily Property

256 Hillside Avenue, Waterbury, CT 06710

$450,000

4,016 sqft

Three-unit property with updated electrical service, fresh exterior paint, and a vacant second-floor apartment.

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Turnkey Renovated Three-Family

76 Burton St, Waterbury, CT 06704

$579,000

2,538 sqft

Fully renovated 3-family with modern systems and three 3-bedroom units, plus a detached one-car garage.

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Three-Family Residential Income Property

15 Matson Court, Waterbury, CT 06704

$469,900

4,003 sqft

Fully occupied three-unit home with off-street parking and a backyard, with each unit featuring 2 bedrooms and 1 full bath.

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Three-Unit Residential Property

84 Wheeler Street, Waterbury, CT 06704

$664,000

3,383 sqft

Classic 3-unit home with separate utilities and upgraded kitchens and bathrooms, featuring hardwood floors on upper levels.

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Renovated First-Floor Triplex

16 Fairview Street, Waterbury, CT 06710

$375,000

3,594 sqft

Three apartments offer separate gas and electric utilities, hardwood flooring, and practical layouts across the building.

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Fully Occupied Triplex

23 Plaza Ave, Waterbury, CT 06710

$450,000

3,245 sqft 0.10 AC lot

Three separately metered apartments provide tenant-paid utilities and off-street parking.

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Renovated Triplex with Parking

12 Aetna Street, Waterbury, CT 06704

$469,900

3,163 sqft

Three residential units offer updated interiors, separate utilities, and off-street parking.

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Three-Unit Triplex with Parking

230 Bishop St, Waterbury, CT 06704

$295,000

2,145 sqft

Three residential units feature separate utilities, off-street parking, and individual living areas.

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Three-Family Income Property

95 Sunnyside Avenue, Waterbury, CT 06708

$464,000

3,044 sqft

Spacious three-family residence with two bedrooms and eat-in kitchens on each floor, plus private decks.

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Fire-Damaged Triplex

11 Pearl St, Waterbury, CT 06704

$179,900

3,635 sqft

Three-family property requiring comprehensive rehabilitation after fire damage.

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Updated Triplex with Parking

237 Bishop St, Waterbury, CT 06704

$450,000

2,555 sqft

Three-unit residential property with two refreshed apartments, gas utilities, and off-street parking in Waterbury.

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Waterbury Three-Family Investment Opportunity

225 Bishop St, Waterbury, CT 06704

$295,000

2,673 sqft

Three-family property in Waterbury, Connecticut, with income potential.

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Waterbury Three-Family Investment Opportunity

23 Vermont St, Waterbury, CT 06704

$295,000

2,886 sqft

Three-unit property with income potential near amenities and highways.

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Remodeled 3-Unit Triplex

348 Oak Street, Waterbury, CT 06705

$499,900

4,559 sqft

Three-bedroom apartments are complemented by garages, off-street parking, and a private yard.

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Triplex Property Requiring Renovation

230 Plaza Avenue, Waterbury, CT 06710

$210,000

4,698 sqft 0.09 AC lot

Three-unit residential income property requiring major renovation and structural repair.

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Triplex with Two-Car Garage

38 Ives Street, Waterbury, CT 06704

$374,999

3,042 sqft

Three residential units offer separate utilities, off-street parking, basement storage, and outdoor space.

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Renovated 3-Unit Multifamily

23 Wall St, Waterbury, CT 06705

$474,000

3,840 sqft

Beautifully renovated three-family with 4-bedroom, 1.5-bath units and tenant-paid utilities.

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Middlebury, CT Triplexes Market Trends and Statistics

Explore 31 triplexes for sale in Middlebury, CT, showcased through 31 active listings on our real estate platform. These investment opportunities span a total of 93,165 square feet of properties for sale, with an estimated market value of $13,396,398.

Sale prices for three-family homes in Middlebury, CT start at $179,900, averaging $461,944, and reaching up to $795,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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Top Commercial Asset Segments

Commercial property segments ranked by active listings on the market

Demographics Overview

Population 7,736

Population Growth (5Y) +1.0%

Median Household Income $142,750

College Educated 77.8%

Taxes & Financing

Tax Rate (average for all types) 3.29%

Property Tax per SF $57.07 per SF

Tax Rate vs County Average 0.43 pp below county avg

Average Loan-to-Value 65.0%

Listings Trend

New vs delisted commercial listings in New Haven County

New Delisted

Total CRE Inventory on Market (SF)

Average Property Price per SF

For-sale pricing trends across core commercial property types in New Haven County

Residential Income

Property Size Breakdown

The majority of commercial real estate listings in Middlebury fall within the 100,000+ square foot range.

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