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$435,000 Contingent

  • For Sale
  • Contingent
  • Condo
  • 2 Beds
  • 2 Full Baths
  • 1,645 Sq. Ft.
  • Updated 5 days ago
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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.

Full Property Details for 1416 Windward Rd #1416

General

  • Price: $435,000
  • HOA FEE: $585/month
  • Taxes: (July 2025-June 2026)
  • Status: Contingent
  • Type: Condo
  • Source: SMARTMLS
  • MLS ID: 24146366
  • Updated: 1/12/2026
  • Added to Site: 19 day(s) ago

Interior

  • Number of Rooms: 5
  • Appliances: Gas Range, Refrigerator, Dishwasher, Washer, Electric Dryer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2
  • Primary Bedroom: Primary Bedroom, Main
  • Bedroom 1: Bedroom, Main

Other Rooms

  • Living Room: Living Room, Main
  • Kitchen: Kitchen, Main
  • Dining Room: Dining Room, Main

Additional Information

  • Pool: Yes
  • Pool Description: Pool House, Power Lift, Safety Fence, In Ground Pool

Exterior

  • Exterior Features: Covered Deck
  • Color: Grey

Parking

  • Total Spaces: 2
  • Parking: Paved, Assigned Parking

Location

  • County: New Haven
  • Driving Directions: Sub way to Bic Drive - take left into complex - Popes Island to windward road.

School Information

  • Elementary School: Mathewson
  • High School: Jonathan Law

Community

  • Association: Yes
  • Home Owners Assn.: 1
  • Assoc. Fees Include: Club House, Tennis, Grounds Maintenance, Trash Pickup, Snow Removal, Water, Property Management, Pest Control, Insurance
  • Pets Allowed: Yes
  • Pet Restrictions: Pets allowed

Heating & Cooling

  • Cooling Type: Ceiling Fans, Central Air
  • Heating Type: Hot Air, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Natural Gas, 50 Gallon Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Ranch
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: None
  • Square Feet: 1,645
  • Above Ground: 1,645 Sq. Ft.
  • Year Built: 1995

Lot Features

  • Zoning: WDD
  • Lot Description: Level Lot, Water View

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: River, Walk to Water, View

Green Features

  • Energy Features: Thermopane Windows

Financial Considerations

  • Association Fee: $585
  • Assoc Fee Freq.: Monthly
  • Assessment Amount: $207,630
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1207108

Listed by William Raveis Real Estate, Team AFA at William Raveis Real Estate, Kate Meyer

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Listing agent

— 1416 Windward Rd #1416 —

  • Kate Meyer

    William Raveis Real Estate

Agent Contact: (203) 581-3599 Office Contact: (203) 255-6841

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1416 Windward Rd #1416

School District:Milford School District
NameGradesDistance
J. F. Kennedy School
404 West Ave., Milford, CT 06460
K-20.9 mi
Pumpkin Delight School
27 Art Street, Milford, CT 06460
3-51.7 mi
West Shore Middle School
70 Kay Avenue, Milford, CT 06460
6-81.8 mi
Jonathan Law High School
20 Lansdale Avenue, Milford, CT 06460
9-121.2 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1416 Windward Rd #1416 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/02/2026
Listed
$435,000
20.83%
MLS
1/26/2023
Sold
$360,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1416 Windward Rd #1416

Year
Property Taxes
Change
Tax Assessment
Change
2024
$6,135
1%
$207,630
—
2023
$6,050
7%
$207,630
—
2023
$5,641
2%
$207,630
—
2022
$5,533
8%
$207,630
12%
2021
$5,113
—
$184,920
—
2020
$5,119
-4%
$184,920
—
2019
$5,307
3%
$184,920
—
2018
$5,130
—
$184,920
—
2017
$5,139
-2%
$184,920
-2%
2016
$5,247
—
$188,470
—
2015
$5,255
6%
$188,470
—
2011
$4,953
—
$188,470
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 1416 Windward Rd #1416

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by William Raveis Real Estate, Team AFA at William Raveis Real Estate, Kate Meyer

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1416 Windward Road #1416, Milford, CT 06461 (MLS# 24146366) is a Condo property with 2 bedrooms and 2 full bathrooms. 1416 Windward Road #1416 is currently listed for $435,000 and was received on December 29, 2025. Want to learn more about 1416 Windward Road #1416? Do you have questions about finding other Condo real estate for sale in Milford? You can browse all Milford real estate or contact a Coldwell Banker agent to request more information.

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