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.
Sold for $435,000
$435,000
1416 Windward Road #1416, Milford, CT 06461
2beds
1,645sqft
Condominium
Built in 1995
-- sqft lot
$436,700 Zestimate®
$264/sqft
$3,076 Estimated rent
Home value
$436,700
$393,000 - $485,000
$3,076/mo
Zestimate® history
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List your homeWhat's special
Zillow last checked: 7 hours ago
Listing updated: February 26, 2026 at 06:46am
Listed by:
Team AFA at William Raveis Real Estate,
Kate Meyer (203)581-3599,
William Raveis Real Estate 203-255-6841
Bought with:
Lance Longo, RES.0796138
S.E.L. Realty
Source: Smart MLS,MLS#: 24146366
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Level: Main
Bedroom
- Level: Main
Dining room
- Level: Main
Kitchen
- Level: Main
Living room
- Level: Main
Heating
- Forced Air, Natural Gas
Cooling
- Ceiling Fan(s), Central Air
Appliances
- Included: Gas Range, Refrigerator, Dishwasher, Washer, Dryer, Gas Water Heater, Water Heater
Features
- Windows: Thermopane Windows
- Basement: None
- Attic: None
- Has fireplace: No
Interior area
- Total structure area: 1,645
- Total interior livable area: 1,645 sqft
- Finished area above ground: 1,645
Property
Parking
- Total spaces: 2
- Parking features: Paved, Assigned
Features
- Stories: 4
- Patio & porch: Covered
- Has private pool: Yes
- Pool features: Power Lift, Fenced, In Ground
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, River Front, Walk to Water
Lot
- Features: Level
Details
- Additional structures: Pool House
- Parcel number: 1207108
- Zoning: WDD
Construction
Type & style
- Home type: Condo
- Architectural style: Ranch
- Property subtype: Condominium
Materials
- Vinyl Siding
Condition
- New construction: No
- Year built: 1995
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Green energy
- Energy efficient items: Windows
Community & neighborhood
Location
- Region: Milford
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $585 monthly
- Amenities included: Clubhouse, Tennis Court(s), Management
- Services included: Maintenance Grounds, Trash, Snow Removal, Water, Pest Control, Insurance
Price history
| Date | Event | Price |
|---|---|---|
| 2/25/2026 | Sold | $435,000$264/sqft |
Source:  Smart MLS #24146366 Report a problem | ||
| 1/2/2026 | Listed for sale | $435,000+58.8%$264/sqft |
Source: Smart MLS #24146366 Report a problem | ||
| 10/2/2017 | Sold | $274,000-2.1%$167/sqft |
Source: Smart MLS #99178608 Report a problem | ||
| 5/8/2017 | Listed for sale | $279,900$170/sqft |
Source: William Pitt Sotheby's International Realty #99178608 Report a problem | ||
| 5/7/2017 | Pending sale | $279,900$170/sqft |
Source: William Pitt Sotheby's International Realty #99178608 Report a problem | ||
Public tax history
Tax history is unavailable.
Find assessor info on the county website
Neighborhood: 06461
Nearby schools
GreatSchools rating
- 6/10J. F. Kennedy SchoolGrades: PK-5Distance: 0.9 mi
- 7/10West Shore Middle SchoolGrades: 6-8Distance: 1.8 mi
- 6/10Jonathan Law High SchoolGrades: 9-12Distance: 1.2 mi
Schools provided by the listing agent
- Elementary: Mathewson
- High: Jonathan Law
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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$436,700
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$445,434
- Connecticut
- New Haven County
- Milford
- 06461
- 1416 Windward Road Unit 1416