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299 W Main St, Milford
$545,000
3 Beds ⋅ 3 Baths ⋅ 24195357 MLS
Location, Location, Location! Timeless charm meets modern updates in this beautifully renovated 3-bedroom, 2.5-bath Colonial, just 0.7 miles from vibrant downtown Milford, the Green, restaurants, shops, and Metro-North with direct service to NYC. From the moment you enter, you'll appreciate the beautiful hardwood floors, detailed woodwork, and craftsmanship rarely found in today's construction. The spacious living room with fireplace and formal dining room offer warmth and character while blending seamlessly with today's updates. The beautifully designed kitchen features quartz countertops, stainless steel appliances, abundant cabinetry, and a convenient half bath nearby. Upstairs are three generously sized bedrooms and two full baths, including a spacious primary suite with a beautifully tiled private bath and custom-organized walk-in closet. Both additional bedrooms offer impressive walk-in closets, providing exceptional storage. The full basement includes a washer/dryer combination, ample storage, and updated propane-fueled mechanicals. Outside, the expansive front porch adds to the home's classic appeal and is the perfect place to relax. With a roof less than two years old, thoughtful renovations throughout, and beautiful original character preserved, this home truly offers the best of old-world charm and modern-day living, all in an exceptional Milford location.

299 W Main St, 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.

19 Chetwood St, Milford

33 Acorn Ln, Milford
$629,900
3 Beds ⋅ 3 Baths ⋅ 24192026 MLS
BACK ON MARKET-NEW OPPORTUNITY IN DESIRABLE LEXINGTON GREEN WEST! Contract terminated due solely to buyer financing. No inspection or appraisal issues. Welcome to Lexington Green West, a private community where neighbors become friends & pride of ownership shines throughout. Whether you're enjoying evening strolls along quiet streets, or relaxing on your own backyard deck, you'll love calling this special neighborhood home. This charming 3/4 bedroom, 2 1/2 bath Colonial offers 1,528 sq. ft. plus an additional 475 sq. ft. of finished lower-level living space. The inviting floor plan features a dining room for memorable gatherings and a beautifully remodeled kitchen with granite countertops, stainless steel appliances, tile backsplash, and a slider opening to a generous 15' x 20' deck, perfect for summer barbecues and outdoor entertaining. The cozy living room is enhanced by a gas fireplace, creating a warm and welcoming space year-round. Upstairs, you'll find 3 bedrooms, including the primary suite with a cathedral ceiling, deep walk-in closet, and direct access to the shared full bath. The finished lower level expands your options with a FR/playroom, a 2nd full bath, and a versatile room perfect for a guest bedroom, home office, gym, or hobby space. Recent updates include a newer roof, debris free gutters, washer/dryer, toliets, full bath vanity & gas fireplace. Living Room & Primary BR Virtually Stage

33 Acorn Ln, Milford

843 North St Unit N3, Milford
$499,000
2 Beds ⋅ 2 Baths ⋅ 24192988 MLS ⋅ Windsor Place Townhouses-Verify In Process! BLDG.
Welcome to Windsor Place Townhomes, a collection of 44 newly constructed residences offering a serene, private community in one of Milford's most sought after locations. Windsor Place delivers a maintenance free, lock and leave lifestyle. Professionally designed by House of Huck and built by Anastasia Home Builders, renowned for custom luxury homes along Connecticut's Gold Coast. Each thoughtfully crafted three story townhome offers approximately 1,200 square feet of living space with two bedrooms and 1.5 baths. This residence offers buyers the rare opportunity to personalize their home by selecting from the builder's professionally curated, pre-approved designer finishes and textiles, creating a space that reflects their individual style without compromising the community's cohesive luxury aesthetic. The ground level features an attached garage, in-unit laundry, dedicated storage, and electric vehicle charging capability. The main living level showcases an open concept floor plan filled with natural light, featuring a beautifully appointed kitchen and living area and finally powder room, perfect for everyday living and entertaining. Upstairs, two generously sized bedrooms share a full bath.

843 North St Unit N3, Milford

370 Calf Pen Ln, Milford
$619,900
4 Beds ⋅ 3 Baths ⋅ 24192670 MLS
Walk to the beach in minutes with 4 beds, 3 full baths and easy in-law potential in this expansive, charming, well-maintained Historic Cape on a manicured corner lot in the Pond Point neighborhood. Originally built in 1938, this distinctive home showcases hand-milled white oak floors with walnut pegging, blending timeless craftsmanship with thoughtful updates throughout its nearly 3,000 square feet of finished living space. The main level features convenient laundry, a potential in-law setup with a second kitchen, two full baths, a ground-level bedroom, and versatile spaces ideal for a home office, den, playroom, fitness room, or guest accommodations. Upstairs, the private primary suite is accessed by its own staircase and shares a semi-private en-suite bath with two generously sized bedrooms. Character and charm resonate throughout. Outdoor living shines with newer composite decking, multiple patio 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. A brand new roof installed in April 2026 includes a transferable 50-year warranty. Ideally located near Milford's beaches, parks, downtown shops and restaurants, Metro-North rail service, and I-95, this exceptional Pond Point home offers the rare combination of history, craftsmanship, modern updates, and coastal lifestyle. A truly special property ready for its next chapter.

370 Calf Pen Ln, Milford

498 Naugatuck Ave Unit C, Milford
$299,000
2 Beds ⋅ 2 Baths ⋅ 24191969 MLS ⋅ Parker Court BLDG.
Investor opportunity! This well-maintained 2-bedroom, 1.5-bath townhouse-style condominium is ideally located on the outskirts of Devon, just minutes from shopping, restaurants, and beautiful Walnut Beach. The home has been thoughtfully updated with an eat-in kitchen featuring granite countertops, soft-close cabinetry, and stainless steel appliances. Sliding glass doors lead to a private patio, creating an inviting outdoor space for tenants to enjoy. The updated half bath on the main level and renovated full bath upstairs add to the home's appeal, while the partially finished basement offers approximately 400 square feet of additional living space along with a dedicated laundry area. Currently tenant-occupied by outstanding tenants with a lease in place till next year, this property offers immediate rental income and a seamless investment opportunity. With its desirable location, modern updates, and strong rental appeal, this is an excellent addition to any investment portfolio.

498 Naugatuck Ave Unit C, Milford

169 Yale Ave, Milford
$489,900
2 Beds ⋅ 1 Baths ⋅ 24191771 MLS
HIGHEST & BEST BY 5:00 PM, TUESDAY JULY 21ST Move right in and enjoy the best of Milford living in this beautifully renovated 2+ Bedroom Ranch, perfectly sited on a large, level fenced lot just a short walk to the water, neighborhood restaurants, shops, playground, and pickleball courts. The open-concept floor plan is designed for today's lifestyle and effortless entertaining. A spacious Living Room flows seamlessly into the stunning renovated Kitchen featuring quartzite countertops, stainless steel appliances, a center island with breakfast bar, and leads to an expansive deck-perfect for summer barbecues and indoor/outdoor living. Two comfortable Bedrooms with ceiling fans and a beautifully updated Full Bath complete the main level. Gleaming hardwood floors, newer windows, central air conditioning, updated plumbing, and tasteful finishes throughout add to the home's move-in-ready appeal. The finished lower level provides extra living space with a spacious Family Room with wood burning stove and a private Office-ideal for working from home, a playroom, or guest accommodations. Step outside to a picturesque, fully fenced backyard with plenty of room for a pool, gardens, pets and entertaining. Enjoy the coastal lifestyle w/beaches, waterfront walks, local dining, & everyday conveniences just moments away. A quick drive brings you to Milford's vibrant downtown, Metro-North/New York City train station, & major highways.

169 Yale Ave, Milford

44 Wood Ave, Milford
$460,000
2 Beds ⋅ 2 Baths ⋅ 24186458 MLS
Coastal cottage charm with NO FLOOD INSURANCE awaits it's new steward! Welcome to this sweet beachy bungalow, nestled in one of Milford's most sought after coastal communities - Walnut & Windermere Beach. Enter through the open living & dining area, accented with custom built-in dry bar. This flows to the sunny kitchen with granite countertops, the most perfect breakfast nook, and full tile bathroom with incredible natural light. Just off the kitchen your invited to the charming, fully fenced in backyard. Imagine the enjoyment here on the freshly painted, expansive deck with bench seating, pergola and a coveted outdoor shower! The second level is a reprieve with two lovely bedrooms, and a fantastic full bath with sun beaming through the sky light to the jacuzzi tub, double sink & tile shower. Off street parking and stone driveway complete this special home. Just a few short minutes to the beach, guest parking lot, playground, Walnut Beach Creamery, restaurants, and so much more. Experience the best of Connecticut shoreline living with out the waterfront maintenance!

44 Wood Ave, Milford

153 Chapel St, Milford
$599,000
4 Beds ⋅ 2 Baths ⋅ 24187952 MLS
Welcome to 153 Chapel Street, where timeless character meets modern updates in this beautifully renovated 4-bedroom, 2-full-bath Colonial just minutes from Milford's beaches. This move-in ready home blends classic charm with today's conveniences, featuring hardwood floors throughout, a sun-filled living room, and an updated kitchen. A bright four-season sunroom provides additional living space and easy access to the deck overlooking the private, fully fenced backyard. The new large patio is perfect for relaxing and entertaining on beautiful summer nights. The upper levels offer four generously sized bedrooms, including a flexible additional room on the 3rd floor. Additional highlights include a detached one-car garage, inviting front porch, and an unbeatable location just a short stroll to beaches, parks, shopping, restaurants, and all that Milford has to offer.

153 Chapel St, Milford

25 Fowler Ter, Milford
$524,900
3 Beds ⋅ 2 Baths ⋅ 24188482 MLS
Welcome to this bright and airy, move-in ready raised ranch where style meets modern comfort! This beautifully updated home offers 3 bedrooms, 2 full baths, and gleaming hardwood floors throughout the main level. The heart of the home is the stunning renovated kitchen, featuring white shaker cabinetry, quartz countertops, a center island, stainless steel appliances, and a classic subway tile backsplash. The finished lower level provides versatile living space, perfect for a family room, home office, gym, or recreation area. An attached 2-car garage adds convenience and ample storage. Ideally located just minutes from beaches, downtown Milford, shopping, dining, Metro-North, and major commuter routes, this exceptional home offers the perfect blend of sophistication and everyday living. Don't miss this opportunity-schedule your private showing today! Be sure to click the virtual tour link to experience the immersive 3D tour!

25 Fowler Ter, Milford

67 Wilbar Ave, Milford
$649,999
4 Beds ⋅ 2 Baths ⋅ 24182228 MLS
Nestled in right off of the desirable Gulf Street, this charming Colonial offers the perfect blend of coastal beauty and timeless character. Featuring 4 spacious bedrooms and 1.5 baths, this inviting home boasts picturesque views of the harbor and Spencer's Marina, creating a waterfront backdrop that can be enjoyed year-round. Step outside to the patio where you can relax and entertain while enjoying refreshing Long Island Sound breezes. Watch sailboats and passing ships glide through the harbor as you take in the serene water views from your front porch. An exceptional opportunity to enjoy harbor-side living in one of the area's most sought-after locations, just moments from Gulf Beach, waterfront amenities, downtown dining, and recreation. Don't miss out, schedule your viewing today!

67 Wilbar Ave, Milford

292 Naugatuck Ave, Milford
$475,000
3 Beds ⋅ 2 Baths ⋅ 24180296 MLS
Step out of the ordinary and into this amazing Mediterranean-style Ranch, featuring a bright, sunny open floor plan with gleaming hardwood floors and a cozy fireplace. The remodeled eat-in kitchen offers granite counters, stainless steel appliances including a top of the line, Wolf gas stove and Thermador dishwasher, the sliders lead to a covered backyard patio-perfect for relaxing or entertaining. This inviting home includes 3 spacious bedrooms, 2 renovated full baths, and a newer HVAC system for year-round comfort and peace of mind. The partially finished lower level offers great potential and is ready for your finishing touches. Enjoy an exceptional location just minutes from Milford's beautiful beaches, scenic boardwalk, and fishing pier. Vibrant downtown Milford, marinas, restaurants, parks, the train station, and convenient access to major highways are all nearby, making it easy to enjoy everything this charming shoreline community has to offer. Whether you're a first-time buyer, downsizing, or seeking a home near the water, this is a wonderful opportunity to embrace Milford's highly desirable coastal lifestyle.

292 Naugatuck Ave, Milford

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