1416 Windward Rd, Unit 1416

Milford, CT 06461

$435,000
Price
2
Beds
1,645 Sq. Ft.
$264 / Sq. Ft.
1,645
Sq. Ft.
$264
per Sq. Ft.
Coming SoonOpen: 1/4 01:00PM - 03:00PM
Coming SoonOpen: 1/4 01:00PM - 03:00PM

Description

Welcome to 1416 Windward - located in the popular Caswell Cove Condominium that overlooks the Housatonic River. If you are looking for unparallel water views coupled with dreamy evening sunsets - look no further. Incredibly spacious 2 bedroom 2 full updated bath ranch style offers 1645 sqare feet of easy living space. Extend your living space outside onto the patio to grill dinner overlooking the open common area that feels like a huge backyard. The entertaining space is generous with a chefs kitchen...Welcome to 1416 Windward - located in the popular Caswell Cove Condominium that overlooks the Housatonic River. If you are looking for unparallel water views coupled with dreamy evening sunsets - look no further. Incredibly spacious 2 bedroom 2 full updated bath ranch style offers 1645 sqare feet of easy living space. Extend your living space outside onto the patio to grill dinner overlooking the open common area that feels like a huge backyard. The entertaining space is generous with a chefs kitchen offering granite counters and stainless appliances - note the natural gas stove. The primary suite offers plenty of room to allow for a sitting area coupled with a nook for your desk with amazing water views. Updated primary bath and a walk in closet complete the suite. Unbelievable closet space, beautiful crown molding and space for all is found within this special unit. Caswell Cove is one of Milford's best kept secrets for waterfront living with an exciting lifestyle of swimming at the pool, playing tennis or pickle ball, exercise room / Clubhouse. Consider making Milford your new home with its vibrant & walkable downtown, historic Milford Green and stunning beaches. Contingent upon finding suitable housing.
  1. Listed by Kate Meyer • William Raveis Real Estate
    P: (203)-581-3599 C: (203)-581-3599 Kate.meyer@raveis.com

Property Details for 1416 Windward Road, Unit 1416

Basement Description
None
Direct Waterfront
Yes
Expected Active Date
01-02-2026
Garages Number
0
Neighborhood
N/A
Style
Ranch
Garage Parking Info
None, Paved, Assigned Parking
Swimming Pool
Yes

Open Houses

Sunday, Jan 4th

1:00 PM - 3:00 PM

Public

LISTING UPDATED: 01/01/2026 12:05 AM

Property Details for 1416 Windward Road, Unit 1416

StatusComing Soon
MLS #24146366
Days on Market-
Taxes$6,135 / year
HOA Fees$585 / month
Condo/Co-op Fees-
Compass TypeCondo
MLS TypeCondo/Co-Op / Condominium
Year Built1995
CountyNew Haven County

Location

Listing Courtesy of William Raveis Real Estate, Kate Meyer
Add your commute

Building Information for 1416 Windward Road, Unit 1416

Building/Complex1416 Windward RdFloor14Stories-Residences204Pet PolicyAllowedPet Policy DetailsYesYear Built1995

Payment Calculator

$3,246 per month

30 year fixed, 6.28% Interest

Principal and Interest

$2,149

Property Taxes

$511

HOA Dues

$585

The Payment Calculator is for illustrative purposes only.

Property Information for 1416 Windward Road, Unit 1416

Summary
Property and Location
  • Directions: Sub way to Bic Drive - take left into complex - Popes Island to windward road.
  • Elementary School: Mathewson
  • End Unit: No
  • High School: Jonathan Law
  • Latitude: 41.216731
  • Longitude: -73.105646
  • Pets Allowed Info: Pets allowed
  • Pets Allowed: Yes
  • State: Connecticut
Parking
  • Parking Total Spaces: 2
HOA and Fees
  • Association Fee Includes: Club House, Tennis, Grounds Maintenance, Trash Pickup, Snow Removal, Water, Property Management, Pest Control, Insurance
  • HOA Fee Amount: 585
  • HOA Fee Frequency: Monthly
  • Home Owner's Assocation: Yes
  • Special Association Assessment: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $6,135
Interior and Exterior Features
Exterior Features
  • Exterior Features: Covered Deck
  • Pool Description: Pool House, Power Lift, Safety Fence, In Ground Pool
  • Waterfront Description: River, Walk to Water, View
Interior Features
  • Appliances Included: Gas Range, Refrigerator, Dishwasher, Washer, Electric Dryer
  • Cooling System: Ceiling Fans, Central Air
  • Heat Type: Hot Air
  • Attic YN: No
  • Fireplaces Total: 0
  • Laundry Room Location: Spacious full laundry in unit
  • Rooms Total: 5
Room 1
  • Room Entry Order: 1
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Level: Main
  • Room Type: Kitchen
Room 4
  • Room Entry Order: 4
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 5
  • Listing Key: 471DCBD69D36A4A5E0631A01100A80B5
  • Room Entry Order: 5
  • Room Level: Main
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: Grey
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Levels In Unit: 4
  • New Construction Type: No/Resale
  • Year Built: 1995
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Apartment: No
  • Living Area SQFT Per Public Records: 1645
Lot Information
  • Lot Description: Level Lot, Water View
  • Parcel Number: 1207108
  • Sq Ft Est Heated Above Grade: 1645.0
  • Sq Ft Total: 1645.0
  • Zoning: WDD
Utilities
  • Energy Features: Thermopane Windows
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Natural Gas, 50 Gallon Tank
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner
  • Total Number of Units: 204

Schools near 1416 Windward Road, Unit 1416

This home is within Milford School District.
Rating
School
Type
Grades
Distance
Mathewson School
Public - K to 5
West Shore Middle School
Public - 6 to 8
Jonathan Law High School
Public - 9 to 12
White Oak Baptist Academy
Private - K to 12
Rating
School
Distance
Mathewson School
PublicK to 5

West Shore Middle School
Public6 to 8

Jonathan Law High School
Public9 to 12

White Oak Baptist Academy
PrivateK to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1416 Windward Road, Unit 1416, Milford, CT 06461

1416 Windward Road, Unit 1416 is a condo Coming Soon in Milford, CT 06461. This property is currently priced at $435,000. This listing's school district is Milford School District. Nearby schools include Mathewson School, West Shore Middle School and Jonathan Law High School. 1416 Windward Road, Unit 1416 is a 2-bed, 2-bath, 1,645 sqft condo built in 1995.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Raveis Real Estate, Kate Meyer

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.