139 Wepawaug Drive
Milford, Connecticut 06461
- Beds
- 4
- Baths
- 3
- SqFt
- 2,362
- Acres
- 0.24
- Year Built
- 1955
- Neighborhood
- Wheeler Farms
- Property Type
- Single 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
Discover this beautifully renovated Colonial in Milford's desirable Northern Mathewson neighborhood, where timeless charm meets sophisticated design. Thoughtfully transformed, this 4 bedroom, 3 full bathroom home offers exceptional finishes and move in ready living. The stunning kitchen features premium appliances, an oversized island, abundant cabinetry, farmhouse sink, striking backsplash and tile flooring. An inviting open layout connects the dining area and living room with its classic wood burning fireplace. The impressive primary suite features cathedral ceilings, a beautifully remodeled bathroom and an extraordinary walk in dressing room with custom storage. Additional bedrooms and updated bathrooms offer flexibility, including space for a home office. A thoughtfully designed mudroom provides ample storage, while the 2 car garage features upgraded flooring. Outside, a professionally landscaped, fully fenced backyard offers an exceptional setting for entertaining with a paver patio, covered dining area, outdoor kitchen, grilling stations and bar area. Conveniently located near Milford's beaches, downtown, shopping and restaurants, this meticulously updated home is designed for effortless living indoors and out.
Key Facts
- City/Town
- Milford
- Neighborhood
- Wheeler Farms
- Property / Style
- Single Family · Colonial
- Year Built
- 1955
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 3 full
- Living Area
- 2,362 sq ft
- Lot Size
- 0.24 acres
- Garage / Parking
- 2 garage · 4 total
- Property Taxes
- $8,684 / Annually
Market Snapshot
The Milford Market
Single Family · trailing 12 months
Active Listings
86
61 under contract
Median List Price
$642,000
86 active listings
Median Closed Price
$572,000
466 sales
Median Days on Market
36
86 active listings
Median $ / Sq Ft
$330
86 active listings
Sale-to-List Ratio
100.0%
466 sales
How this home compares
List Price
$925,000
vs $642,000 median
44.1% above median
Price / Sq Ft
$392
vs $330 median
18.8% above median
Days on Market
0 days
vs 36 days median
36 days fresher than median
Based on 86 active and 466 closed sales (trailing 12 mo) of single family in Milford. Source: SmartMLS · As of November 10, 2026.
Location
139 Wepawaug Drive, Milford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$5,013
- Property Taxes$724
- Insurance$308
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Milford
- Neighborhood
- Wheeler Farms
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1955
- New Construction
- No/Resale
- Living Area
- 2,362 sq ft
Schools
- Elementary
- Mathewson
- High
- Jonathan Law
Interior
- Heating
- Wall Unit
- Cooling
- Split System
- Fireplaces
- 1
- Laundry
- Upper Level
- Appliances
- Electric RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- None
- Interior Features
- Auto Garage Door Opener
- Additional Rooms
- Laundry RoomMud Room
Exterior & Lot
- Lot Size
- 0.24 acres
- Zoning
- R10
- Garage / Parking
- 2 garage spaces4 total parking spacesAttached GaragePavedDrivewayPaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Pool
- Above Ground Pool
- Construction
- Vinyl Siding
- Color
- white
- Roof
- Asphalt Shingle
- Foundation
- Slab
- Exterior Features
- GrillSidewalkDeckGuttersGarden AreaPatio
- Lot Description
- Level LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $8,684 / Annually
- Days on Market
- 0
- MLS #
- 24220309
- MLS Status
- Active
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 11/10/2026. 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 11/10/2026 at 3:50 PM UTC.