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139 Wepawaug Drive

Milford, Connecticut 06461

ACTIVE - NEW$925,000
Beds
4
Baths
3
SqFt
2,362
Acres
0.24
Year Built
1955
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Pool2-Car Garage1 FireplaceVirtual Tour

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,045

per 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.

Listed By

Brandy Hall

(203) 685-9379

Higgins Group Real Estate

(203) 452-5500

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.