1433 Windward Road - Milford, CT

$2,950

Beds

2.00

Baths

1,419

SqFt

0.00

Acres

Pricing Insight: Originally listed for $2,950, the price has remained unchanged for approximately 4 days. This property has been on the market for approximately 4 days.

1433 Windward Road, Milford, CT is a 2-bed, 2-bath, 1,419 square foot home built in 1995 , featuring ranch architecture. This residence is part of a 204-unit community. This home is part of a homeowners association. The HOA fee includes: club house, tennis, grounds maintenance, trash pickup, snow removal, property management, pest control, and pool service. Community amenities include: basketball court, bocci court, club house, exercise room/health club, guest parking, pool, and tennis courts.

This home is within the Milford school district. Local, with nearby schools including Mathewson.

MLS #: 24153910

Offered Price: $2,950

Residence Type: Residential Rental

Architectural Style: Ranch

Living Area: 1,419 Sq. Ft.

Lot Size: 0.00 Acres

Neighborhood: N/A

County: New Haven

Year Built: 1995

Design & Construction: N/A

Heating: Hot Air

Cooling: Central Air

Garage Spaces: 1

Price per Sq Ft as listed: $2

Estimated Tax: $0

Days on Market: 4

$435,000

2 Beds · 2 Baths · 1,645 Sq Ft

1416 Windward Road, Milford

$265,000

1 Beds · 1 Baths · 887 Sq Ft

18 Greenview Lane, Milford

$425,000

2 Beds · 2 Baths · 1,419 Sq Ft

532 Popes Island Road, Milford

Home Automation: Not specified

Energy Features: Not specified

Solar Contract: Not specified

Heating Fuel: Natural Gas

Fuel Type: Hot Air

Fuel Tank Location: Not specified

Cooling System: Central Air

Hot Water System: Natural Gas, Upright Tank

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $2 / Sq. Ft.

Tax assessed value: $0

Estimated Tax: $0

Architectural Style: Ranch

Design & Construction: N/A

Residence Type: Residential Rental

Year Constructed: 1995

Living Area: 1,419 Sq. Ft.

Lot Size: 0.00 Acres

Fuel: Natural Gas

Loading automated valuation...

AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

Request CMA Schedule Tour

Understanding This Valuation

The RPR AVM considers:

Recent sales of comparable properties
Property characteristics and location
Market trends in Milford
Statistical modeling algorithms

Local Market Context

Active Listings: 111

Average Price: $386,770

Average DOM: 4 days

Complimentary CMAs, no obligation

Waterfront Living at Caswell Cove! Discover this stunning waterfront condo along the Housatonic River, complete with a private garage and captivating views. This beautifully updated 2-bedroom, 2-bathroom rental features an open-concept layout connecting the living room, dining area, and kitchen-all designed to maximize the breathtaking water views. Step through the sliding glass doors in the spacious living room onto your private deck, where you can unwind while overlooking the waterfront and the community amenities. The primary bedroom offers serene water views, a walk-in closet, and a full ensuite bathroom. The second bedroom is conveniently located near the second full bathroom. Hardwood floors run throughout the condo, which has been freshly painted for a modern and inviting feel. Enjoy resort-style living with access to a pool, tennis, pickleball, and basketball courts, as well as a fitness center and a clubhouse overlooking the river. Experience the best of waterfront living at Caswell Cove-your serene escape awaits!

Continue reading ▾

Flood Risk Assessment Water Body Detected Nearby

Water Proximity Detected: This property exhibits indicators suggesting nearby or referenced water features

Location Analysis:

Water features noted

Water Proximity:

Near water body

Topography:

Standard terrain

Water Indicators Found:

Water-related features referenced in listing details

Recommendations:

Professional flood assessment advised
Based on identified water-related indicators, flood insurance may warrant consideration
Consult FEMA Flood Maps for zone verification
Evaluate drainage systems
Review local flood history

Risk Level: Moderate

Property near water bodies. Consider flood insurance.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

Dining & Café Access: Low to Moderate
Daily Services: Limited
Recreational Space: Limited Nearby

How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

111

Homes For Sale

$386,770

Average List Price

Mechanicals & Utilities: Hot Air • Natural Gas • Central Air • Public Water Connected water

Exterior Features

Exterior Construction: Vinyl Siding

Garage: Detached Garage,Unassigned Parking,Assigned Parking (1 car)

Parking: 2 Total

Patio/Deck: Deck

Pool: Pool House,In Ground Pool

Utilities: Water: Public Water Connected

Only motif connects you to a certified
"Local Market Expert"

Steve Simos

Real Estate Advisor

Milford • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

Verified Motif Advisor

(800) 555-0003

george@appzentric.com

Good evening Steve, I'm interested in
1433 Windward Road, Milford, Connecticut

By proceeding, you consent to receive calls and texts at the number you provided, and artificial voice, and email, from motif about your inquiry and similar properties. Your personal information will never be sold or given to a 3rd party.

motif, the motif logo, and other various trademarks, logos, designs, and slogans are the registered and unregistered trademarks of motif, LLC. dba Motif Luxe International Realty in the U.S. and/or other countries. Corporate Responsibility, Privacy & Legal Notices: motif is a licensed real estate broker, licensed to do business as Motif LLC. 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 conditions), such should be independently verified, and Motif expressly disclaims any liability in connection therewith. No financial or legal advice provided. Equal Housing Opportunity.

The data relating to real estate for sale on this website appears in part through the SmartMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SmartMLS through a licensing agreement. Listing information is from various brokers who participate in the SmartMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. MLS

. Designed by Appzentric for motif

Good evening. Welcome to 1433 Windward Road, Milford, CT