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$450,000
2 Beds ⋅ 2 Baths ⋅ 24200301 MLS ⋅ Caswell Cove BLDG.
Welcome to 1412 Windward Road in Caswell Cove, one of Milford's hidden gems for waterfront living along the Housatonic River. This spacious 1,645 sq. ft. garden-level ranch offers 2 bedrooms, 2 updated full baths, a detached garage and the ease of one-level living, all complemented by beautiful water views and spectacular sunsets. The generous floor plan features a spacious living room with sliders, dining room and additional family room/den, perfect for a home office or sitting room. The kitchen offers granite countertops and a breakfast bar. The oversized primary bedroom enjoys water views, a walk-in closet and private updated full bath. A second bedroom, updated full bath and additional cedar closets complete the interior. Step outside to your patio and enjoy the peaceful waterfront setting, watch the boats pass by and take in gorgeous sunsets over the river. Caswell Cove offers an in-ground pool, clubhouse/fitness center, tennis, pickleball and basketball. Conveniently located near downtown Milford, the train station, beaches, shopping, restaurants and major highways. Enjoy the space of a home with the ease and amenities of waterfront condominium living

1412 Windward Rd Unit 1412, Milford
$449,900
2 Beds ⋅ 1 Baths ⋅ 24204995 MLS
Rare opportunity to own a private coastal home backing directly to Silver Sands State Park, with stunning marsh views and nature right outside your door. Enjoy the views from your private back deck, surrounded by abundant wildlife and exceptional bird watching, all while being just minutes from Milford's beaches, boardwalk, dining, and shoreline attractions. This charming vintage coastal home has been thoughtfully updated with modern touches while retaining its original character. The main level offers an inviting open-concept floor plan perfect for entertaining, along with a heated enclosed front porch and direct access to the back deck. Upstairs are two bedrooms, and the heated full walk-out basement provides valuable additional space. Updated major mechanicals, a brand-new driveway, and a detached shed with electricity complete the property. A unique combination of privacy, character, natural beauty, and an incredible shoreline location that is increasingly hard to find in Milford.

102 Surf Ave, Milford
$449,000
2 Beds ⋅ 1 Baths ⋅ 24198537 MLS
Welcome to this charming ranch-style home offering comfortable one-level living in a desirable location with walkable access to the beach. The spacious kitchen provides plenty of room for everyday living and entertaining, while central air and ceiling fans in every room offer year-round comfort. Enjoy the privacy of the rear and side yards, complete with a patio-perfect for relaxing outdoors, entertaining guests, or enjoying the refreshing ocean breeze. A convenient two-car garage provides ample parking and storage. The surrounding area is ideal for an active lifestyle, with excellent opportunities for walking and biking and easy access to the beach. Conveniently located near I-95, Yale University and its medical system, Sikorsky/Lockheed Martin, Bridgeport Hospital, and St. Vincent's Medical Center. Nearby amenities include new restaurants, a playground, basketball courts, and pickleball courts, providing plenty of options for dining, recreation, and entertainment. A wonderful opportunity to enjoy coastal living with convenience, comfort, and an array of amenities right nearby.

43 Chester St, Milford
$439,000
2 Beds ⋅ 1 Baths ⋅ 24201328 MLS ⋅ Fernwood Estates BLDG.
This is the one you have been waiting for! Welcome home to 150 Forest Rd #41 in the sought after Fernwood Estates Condominium complex. This beautiful ranch style home has been completely renovated in August, 2026. The immaculate 2 Bedroom 1 bathroom home offers spacious single level living. The home is bright and inviting and includes a generous patio off the large sparkling new eat in kitchen. The airy and easy flow provide a serene backdrop for comfortable and convenient living. The location is central to town, major roadways, restaurants, and shopping while feeling quietly tucked away with trees and mature landscaping. There is ample guest parking and a lovely clubhouse for your enjoyment.

150 Forest Road Unit 41, Milford
$439,000
2 Beds ⋅ 1 Baths ⋅ 24204379 MLS
TODAY'S OPEN HOUSE HAS BEEN CANCELLED. WE APOLIGIZE FOR ANY INCONVENIENCE Calling all contractors, investors and buyers with vision! This bank-owned property presents an outstanding renovation opportunity just one block from Walnut Beach. Renovate and resell, create a coastal home of your own with a possible 203(k) rehabilitation loan, or explore its potential as a vacation or short-term rental, subject to local regulations and approvals. The attic offers additional finished space/rooms for added living space. The location is the true highlight-close to the beach, fishing pier, volleyball courts, seasonal concerts and the boardwalk leading to Silver Sands State Park. Walk to neighborhood coffee, ice cream, restaurants and other amenities. A prime location with tremendous potential-bring your plans and make the most of this unique shoreline opportunity.

63 Stowe Ave, Milford
$429,900
2 Beds ⋅ 2 Baths ⋅ 24197666 MLS ⋅ Southwick At Milford BLDG.
Welcome to easy living in this beautifully maintained ranch end unit. Two bedroom, plus a den, two bath condo located in Southwick, one of Milford's most desirable 55+ communities. 1,460 square feet of thoughtfully designed space, this home offers comfort, and a convenient location. Open floor plan, cathedral ceilings, main level laundry, one car garage with plenty of additional parking. Unfinished basement offers an abundance of storage or can be finished for additional living space. Wonderful location to all major highways. A pleasure to show. Subject to Probate Court Approval.

3 Southwick Ct N Unit 3, Milford
$425,000
2 Beds ⋅ 3 Baths ⋅ 24192377 MLS ⋅ Southwind Cove Condominiums BLDG.
Welcome to 450 Naugatuck Ave! This inviting 2-bedroom, 2.5-bath end-unit townhouse offers over 1,400 sq ft of thoughtfully designed living space. An open-concept layout keeps the main level bright and connected, while a breakfast nook off the kitchen leads out to a private patio, perfect for quiet mornings or evening relaxation. This beautifully maintained end-unit sits less than a mile from the sought-after Walnut Beach neighborhood, and just a short drive to I-95, making weekend beach walks and weekday commutes equally easy. The oversized primary bedroom offers flexible space to suit your needs, along with a primary bath featuring a double sink vanity and plenty of cabinet space for toiletries. Additional highlights include generous closet space throughout, a brand-new on-demand water heater, and an upstairs laundry closet with a stackable washer and dryer for everyday convenience. Move-in ready, this coastal gem offers comfort and convenience, all in one coastal package. Spend the afternoon at Walnut Beach, then grab dinner and dessert at the neighborhood's local restaurants and shops, all just a short trip from your front door!

450 Naugatuck Ave Unit 450, Milford
$419,000
3 Beds ⋅ 1 Baths ⋅ 24195450 MLS
A terrific opportunity to take this flex coastal Milford 3BR ranch to the next level. A perfect 1st home, 2nd home or renovation project. Well maintained by the same owner, for almost 40 years, includes updates in the kitchen and bath, central air, attractive fencing, and a SaniDry waterproofing system in the semi-finished heated lower level. The added oversized 2 car garage with attic storage is a big plus! Through the garage is a large unheated room ideal for expansion that leads to the beautiful private fenced in yard! Off the lower level playroom, there is a large workshop room that can have multi-use. There is a bilco door for exterior access. Don't forget the shed for outside storage needs. Just a few blocks away from beaches and the Sound! Near shopping, RR, and all the other amenities found in Milford!

211 Melba St, Milford
$412,000
2 Beds ⋅ 2 Baths ⋅ 24201048 MLS ⋅ Seabreeze Village BLDG.
Beautiful townhouse for sale, just a 2-minute walk to the beach! This spacious home features two balconies, a deck off of the kitchen, central air, natural gas heating, a wood-burning fireplace, and a walk-up attic for additional storage. An extra room in the lower level that can be used as an office or a gym. Includes a 1-car garage. This unit is move in ready.

22 Seabreeze Ave Unit C, Milford
$410,000
3 Beds ⋅ 1 Baths ⋅ 24199072 MLS
Welcome to this charming, exceptionally well-kept beach cottage in Milford's sought-after Bay View Beach Association. Bay View Beach is a private neighborhood beach available to homeowners within the association boundaries, offering a relaxed shoreline setting, seasonal lifeguard coverage, boat-rack availability, and an active community calendar of summer gatherings and activities. The town lists the home as three bedrooms, with one currently used as a dining room-offering flexible space for entertaining, a home office, or conversion back to a bedroom. Thoughtful features include central air, a wood-burning fireplace, a new hot water heater, and recently replaced, low-cost solar panels. A newer heated sunroom, an inviting space not included in the recorded square footage, extends the home's enjoyment through every season. Outside, the beautiful backyard is enhanced by attractive plantings and provides a peaceful setting for morning coffee, summer entertaining, or unwinding after the beach. Enjoy the best of the Milford lifestyle, from its coastal setting and city beaches to Silver Sands State Park, Milford Harbor, and a vibrant, walkable downtown with restaurants, boutiques, the historic Milford Green, community events, and Metro-North rail service.

103 Orland St, Milford
$400,000
2 Beds ⋅ 1 Baths ⋅ 24205088 MLS
This one is all about location, lifestyle and potential! Located in the heart of the beloved Bayview Beach community, this charming cottage offers an exciting opportunity to create something special just steps from the water. Bayview is known for its private association beach, strong neighborhood feel and the kind of coastal community people simply love to call home. The current footprint offers an enclosed front porch leading into the living and dining area, with the kitchen and laundry located toward the rear of the home. A small covered back porch opens to a brick patio and private backyard. Upstairs, you'll find two bedrooms and a full bath. 24 Milesfield is ready for its next chapter and a buyer with vision, whether that means reimagining the existing home or exploring the possibilities for something new. With public water and sewer, bring your ideas and come see why people love Bayview!

24 Milesfield Ave, Milford

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