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233 W Main St, Milford
$599,999
4 Beds ⋅ 3 Baths ⋅ 24206306 MLS
Incredible Milford value! Welcome to 233 W Main St, a beautifully maintained 4-bedroom, 2.5-bath Cape offering turn-key living, thoughtful updates, and an unbeatable location just 0.5 miles from downtown Milford. The gorgeous updated kitchen features granite countertops, tile backsplash, stainless steel appliances, recessed lighting, and a spacious island with seating. The inviting living room showcases beautiful hardwood floors and abundant natural light. Two first-floor bedrooms offer convenience, while two spacious upstairs bedrooms provide flexible living space. Enjoy year-round comfort in the sunroom with heated floors. Outside, the beautifully landscaped, fully fenced yard features a spacious patio, pergola, lush lawn, outdoor sprinkler system, and fire pit area-perfect for entertaining. An oversized garage with workshop provides excellent storage and workspace. Additional amenities include an interior sound system, whole-house water filtration system, central air, and heated floors in the first floor full bath. Meticulously cared for and truly move-in ready, all just minutes from beaches, parks, restaurants, shops, the Green, and Metro-North with direct NYC service. An exceptional opportunity to own a beautifully updated home in one of Milford's most desirable locations-all that's left to do is unpack and move right in!

233 W Main St, Milford
555 Roses Mill Rd, Milford
$599,900
3 Beds ⋅ 2 Baths ⋅ 24205848 MLS
A wonderful opportunity to own a lovingly maintained home cherished by the same owner for 46 years & beautifully positioned on a picturesque .55-acre corner lot. The driveway is accessible from Lakeview Drive, a quiet, peaceful cul-de-sac, adding to the appeal of this special property. The sun-drenched interior offers tranquil views of Indian Lake from most rooms. The spacious kitchen features abundant maple cabinetry, honed granite countertops, tile flooring & backsplash, a pantry closet, & a generous dining area with built-in hutch. French doors from kitchen open to a Trex deck overlooking the level yard, creating a wonderful setting for morning coffee, outdoor dining, & entertaining. The gracious living room is highlighted by a pretty bay window & fireplace framed by custom moldings & marble, creating a warm & welcoming focal point. The king-sized primary bedroom boasts a remodeled full bath with marble tile & stall shower. Two additional bedrooms are served by a second full bath with tub/shower enclosure. The lower level provides even more living space with a comfortable family room featuring tile flooring, abundant windows, & a wood-burning stove, along with a storage/utility room & convenient walk-out access to the two-car garage. Additional amenities include low-maintenance vinyl siding, 200-amp electrical service, city water & sewer, central air, gas heat, and hardwood floors. Ideally located close to shopping, dining, everyday conveniences, I-95, & the Milford Train

555 Roses Mill Rd, Milford
370 Calf Pen Ln, Milford
$599,900
4 Beds ⋅ 3 Baths ⋅ 24214549 MLS
Embrace a premier coastal lifestyle in this expansive, well-maintained Historic Cape, perfectly sited on a manicured corner lot in Milford's sought-after Pond Point neighborhood. Just a short walk to the beach, this charming 4-bedroom, 3-full-bathroom home boasts nearly 3,000 square feet of finished living space. Originally built in 1938, the property merges thoughtful modern updates with timeless craftsmanship, highlighted by distinctive hand-milled white oak floors with walnut pegging. The versatile main level provides easy in-law potential, featuring a second kitchen, two full baths, a ground-level bedroom, and convenient laundry. Flexible adjoining spaces easily adapt into a home office, den, playroom, fitness room, or guest accommodations. Upstairs, a private primary suite, accessed via its own dedicated staircase, shares a semi-private en-suite bath with two generously sized bedrooms. Outdoor living shines with newer composite decking, multiple patios and entertaining areas, and a level backyard ready for a future pool. A detached garage and two storage sheds provide abundant space for hobbies, storage, a workshop, lawn equipment, or recreational gear. Buyers will value the brand-new roof (April 2026) backed by a 50-year transferable warranty. Ideally located near Milford's beaches, parks, downtown shops and restaurants, Metro-North rail service, and I-95, this special Pond Point home is ready for its next chapter.

370 Calf Pen Ln, Milford
12 Naugatuck Ave Unit B1, Milford
$599,900
2 Beds ⋅ 2 Baths ⋅ 24212102 MLS ⋅ Island Sands BLDG.
Some homes are about the house, others are about the lifestyle-and here you get both. Wake up near the shoreline and enjoy beautiful water views from home, all while living in Milford's sought-after Walnut Beach area. Start your mornings with coffee overlooking the water, take an afternoon walk along the beach, and end the day watching the shoreline change with the seasons. Step inside this spacious 2-bedroom, 1.5-bath home offering approximately 1,461 square feet and hardwood floors. The living space offers an easy flow for entertaining or simply relaxing at home, with the water view providing the perfect backdrop. When Connecticut temperatures drop, turn on the gas fireplace and enjoy cozy winter nights without giving up the coastal scenery outside. Two bedrooms provide flexibility for everyday living, overnight guests, or a home office, while in-unit laundry keeps daily life convenient. A detached garage means no scraping snow off the car during those New England winters. And when summer returns, the beach and everything that makes Milford shoreline living special are right outside your door. Water views, coastal living, and the convenience of calling Walnut Beach home-this is a lifestyle meant to be enjoyed through all four seasons.

12 Naugatuck Ave Unit B1, Milford
136 Oxford Rd, Milford
$599,900
3 Beds ⋅ 3 Baths ⋅ 24209182 MLS
VETERANS: ASSUMABLE 2.25% LOAN, A RARE OPPORTUNITY! Stunning 3-bed, 2.5-bath Milford home built for comfortable living and smart investing. Updated kitchen flows into the dining and living areas, ideal for daily life and entertaining. Newly refinished hardwood floors, adjustable recessed lighting, and Samsung smart appliances. Primary suite has an updated private bath. Finished lower level offers a family room, flexible office/guest space, half bath, and laundry. Hardwired Ethernet in the living room, bedroom, and lower level supports work, streaming, and gaming. Solar panels eliminated the electric bill for 11 months, and 2023 insulation upgrades (loose-fill) keep costs down year-round. Outdoors, enjoy a sparkling pool, hot tub, and expansive deck. Extended driveway parking fits guests, plus a gravel area for a boat or RV. Recent upgrades include city sewer conversion and epoxy garage flooring. ADU potential: Milford's expanded accessory dwelling rules permits a detached garage apartment on this lot, subject to city approval, for a great income opportunity. Close to shopping, dining, parks, and commuter routes. Move-in ready with indoor luxury and an outdoor paradise. Eligible veterans can assume the 2.25% loan for exceptional value - Inquire with listing agent.

136 Oxford Rd, Milford
766 E Broadway, Milford
$599,900
2 Beds ⋅ 1 Baths ⋅ 24208602 MLS
Welcome to coastal living in Milford's sought-after Silver Sands Beach community! Located directly across from the beach, this beautifully reimagined 2-bedroom, 1-bath coastal cottage with a bonus bunk room comfortably sleeps up to 10 and offers three incredible opportunities: 1. LIVE THE COASTAL LIFESTYLE:Make this charming beach cottage your personal seaside retreat, enjoying beach days, coastal breezes and everything Silver Sands has to offer. 2. TURNKEY INCOME-PRODUCING INVESTMENT: Step into an established, successful short-term rental with a 5-year Superhost history, year-round bookings and strong repeat guest demand. Offered fully furnished and equipped with everything guests need, including beach chairs, wagon, umbrella, towels, toys and paddle boards. The private backyard features a fire pit, new outdoor shower and market lights. An established rental business ready for its next owner! 3. REIMAGINE THE POSSIBILITIES:Explore the opportunity to expand, raise or rebuild the existing cottage, with architectural plans available for review, subject to necessary approvals. Whether you're seeking a personal beach escape, an established income-producing investment or the opportunity to create your dream coastal home, this property delivers endless possibilities. Fully furnished. Turnkey. Steps to the beach. Your coastal lifestyle starts here!

766 E Broadway, Milford
357 Plains Rd, Milford
$599,900
3 Beds ⋅ 3 Baths ⋅ 24196674 MLS
Spacious split-level home offering approximately 2,200 square feet of living space on a .25-acre lot. The main level features a living room with vaulted ceiling, hardwood floors and fireplace, along with an eat-in kitchen offering a breakfast bar, vaulted ceiling and skylight. The upper level includes the primary bedroom and two additional bedrooms. A lower-level family room with a second fireplace provides additional living space. The finished basement offers a potential fourth bedroom, full bath and flexible space that may be suitable for a potential in-law setup, guest area, home office or recreation room. Additional highlights include a newer roof, new furnace, central air, storage shed, garden area and apple trees.

357 Plains Rd, Milford
33 Central Ave, Milford
$599,000
3 Beds ⋅ 2 Baths ⋅ 24205374 MLS
Excellent investment opportunity in Milford's desirable Green area, ideal for both investors and owner-occupants looking to offset their monthly housing expenses with rental income. A short walk to downtown with ever-expanding shops, restaurants, and entertainment. Both units have very attractive floorplans, newer appliances, and recent cosmetic updates. Unit 1 has an open concept kitchen/living room with granite countertops and room for a small office off the living room. Unit 2 has a beautiful deck overlooking the backyard and second bedroom/office space off the living room. Both Units have washer/dryer in unit. 2 driveways on each side of the house offer multiple off street parking spots for tenants.

33 Central Ave, Milford
75 Robert Treat Pkwy, Milford
$599,000
2 Beds ⋅ 1 Baths ⋅ 24205315 MLS
This is a classic Colonial-style single-family home situated in an established residential neighborhood in Milford. The property offers a traditional two-story layout, which typically includes a formal living room, a separate dining room, and a family room or den on the main level. The home sits on a level, landscaped lot. A notable feature of this property is the in-ground swimming pool located in the rear yard. The pool is accompanied by a surrounding patio or deck area, providing space for outdoor seating. The yard is enclosed, offering a degree of privacy. The exterior of the home reflects standard Colonial architecture, characterized by a symmetrical facade, gabled roof, and central entryway. WALKING Distance to Milford Train Station, Beach, Downtown Restaurants and Shopping! Great School Systems and Safe Neighborhood! FULL 2nd Bathroom in Basement

75 Robert Treat Pkwy, Milford
19 Chetwood St, Milford
$599,000
3 Beds ⋅ 2 Baths ⋅ 24195409 MLS
Welcome to 19 Chetwood St. in Milfords Silver Beach neighborhood, a move-in ready, completely renovated, elevated coastal home where you can have the perfect year round residence, conveniently located weekend retreat or investment property. The sun-filled main level, features 9-foot ceilings, rich hardwood floors, a cozy gas fireplace, and an open concept layout for quiet evenings or entertaining friends after a day at the beach. The beautifully updated kitchen is the heart of the home, complete with granite countertops, abundant cabinetry and generous center island where everyone gathers! Sliding doors open to a spacious Trex deck with stairs to brick patio below. Upstairs, hardwood floors continue throughout all 3 bedrooms. The primary bedroom features a custom California Closet. Its updated bath includes a full-sized stacked washer and dryer and energy efficient Navien on-demand hot water system. Unlike many, 19 Chetwood offers the convenience of both a private driveway and a full-sized garage, providing both valuable parking as well as storage! You're just steps to the Beach, Silver Sands State Park, its scenic boardwalk, downtown restaurants, shopping, Metro-North station, and major highways for easy access to both New York & Boston! If you're searching for a weekend getaway from the City, a full-time coastal residence or a property with excellent rental potential, 19 Chetwood St offers that rare authentic beach lifestyle without sacrificing convenience.OwnerAgent

19 Chetwood St, Milford
29 Dawes St, Milford
$575,000
4 Beds ⋅ 2 Baths ⋅ 24204263 MLS
You'll be delighted by this classic Cape Cod-style home nestled in a sought-after neighborhood within the desirable Orchard Hills School District! Offering 4 bedrooms and 2 full baths, this charming home combines character with many recent updates that will give you peace of mind for years to come! The updated kitchen features a convenient door leading directly to the deck, creating an ideal flow for outdoor dining and entertaining, overlooking the huge, level backyard. The hardwood floors throughout add warmth to the home and the beautiful bow window in the living room accentuates the lovely new fireplace insert, ready for a cozy winter. The extensive list of improvements is sure to impress, including a new AC unit, new chimney and fireplace insert, vinyl fencing around the huge backyard, vinyl siding, Thermopane windows, and a 50-year roof-all completed within the past two years! The spacious, fenced backyard provides plenty of room for recreation, gardening, pets, play or even a pool! With its classic Cape Cod charm, thoughtful updates, generous outdoor space, and prime location in the Orchard Hills School District, this home is a wonderful opportunity to enjoy comfort, convenience, and character in a highly desirable neighborhood.

29 Dawes St, Milford
36 Kenwood Rd, Milford
$569,999
3 Beds ⋅ 3 Baths ⋅ 24174928 MLS
Charming, expansive Cape, a mile from the beach!! . The solar panels will help with your electric bill, no escalation clause! The home offers just under a half acre of perfectly flat outdoor space with a fire pit and a big deck. There is central air/oil heat and hot water and a two car garage. The location is wonderful, with the beach, parks, tennis, pickle ball and basketball courts all within a miles walk.

36 Kenwood Rd, Milford
18 Willow St, Milford
$565,000
3 Beds ⋅ 2 Baths ⋅ 24216006 MLS
Welcome to 18 Willow Street, a beautifully maintained three-bedroom, two-full-bath New England beach house within walking distance of Fort Trumbull and Silver Sands beaches and just minutes from downtown Milford. Nicely updated inside and out, this charming home captures the ease of coastal living with inviting spaces and an abundance of natural light. Inside, hardwood floors bring warmth and character, while an updated kitchen and two updated full bathrooms offer modern comfort. Large windows brighten many of the rooms, including a beautiful bay window in the dining area overlooking the backyard-an inviting backdrop for morning coffee, weekend brunch, or gathering with friends. Here, the lifestyle extends well beyond home. Begin your morning with a walk along the shore, spend an afternoon at the beach, then head downtown for dinner at a favorite local restaurant or an evening stroll by the harbor. Milford's charming boutiques, waterfront dining, picturesque Green, and seasonal community events bring something to enjoy throughout the year. With convenient access to Metro-North, shopping, and major commuter routes, you can embrace the relaxed rhythm of a beach town while staying connected to everyday essentials. Whether you're seeking a full-time residence or a shoreline retreat, 18 Willow Street is a welcoming place to settle in and enjoy life by the coast. Schedule your private showing today. (Professional interior photos coming soon.)

18 Willow St, Milford
69 Fairview St, Milford
$564,999
4 Beds ⋅ 2 Baths ⋅ 24200760 MLS
Coastal living meets expansive space! Fully renovated in 2026, this 4-bedroom, 2-bathroom Colonial offers a welcoming neighborhood setting just a short stroll to Dockside Brewery, local marinas, and Milford's beautiful beaches. The heart of the home is a bright, wide-open kitchen/living area designed for gathering and entertaining. The chef's kitchen is anchored by an oversized quartz island, custom white Shaker cabinetry, and premium stainless appliances over refinished hardwood floors with an adjacent formal dining room. Both full bathrooms are custom luxury retreats, showcasing natural marble, designer tilework, rainfall showers, and warm brass accents. Unlike typical coastal homes, this property boasts exceptionally large bedrooms. The versatile layout features a convenient main-level bedroom (or office) and three bedrooms upstairs with brand-new, ultra-plush carpeting. Need even more room? The partially finished lower level adds ~400 square feet of extra space, perfect for a family room, home gym, or playroom. This space is in addition to the 1,696 square feet listed in public tax records. Outside, enjoy a professionally landscaped backyard with freshly planted garden beds, functional storage shed, and an expansive lawn built for summer cookouts. A large driveway and ample street parking provide plenty of space for vehicles, or even a boat. Impeccably updated and entirely turn-key. Homeowner is a licensed real estate agent in Connecticut.

69 Fairview St, Milford

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