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316-West Main St Unit 1, Milford
$3,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24214355 MLS
Beautifully renovated 3-bedroom 2 bathrooms apartment at 316 W Main St in Milford! Featuring fresh paint, updated interiors, and a clean, modern feel throughout. Conveniently located near downtown Milford, the Metro-North train station, shopping, restaurants, and local parks. Enjoy easy access to everyday essentials and nearby green spaces, all in a convenient location. Don't miss the opportunity to make this beautifully updated apartment your new home!

316-West Main St Unit 1, Milford
60 Round Hill Ter, Milford
$529,500
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24214644 MLS
Your Vision, Your Dream Home! Discover an exceptional opportunity to customize this 3-bedroom, 2.5-bath ranch on a quiet cul-de-sac in a sought-after North Milford neighborhood. Set on a spacious .58-acre level lot, this home needs updates and offers the space, setting, and potential to make it your own. The main level features an entertainment-sized living room with a wood-burning fireplace and a generous eat-in kitchen ready to be reimagined into the kitchen you've always wanted. Three comfortably sized bedrooms include a primary bedroom with a private half bath. Hardwood flooring throughout the main level provides a beautiful starting point for your updates. The lower level expands your living space with a large family room, wet bar/kitchenette, separate office, and full bath. This versatile layout offers room to entertain, work from home, or explore a possible in-law suite. Outside, the expansive level yard offers plenty of space for gardening, outdoor gatherings, and a potential pool. Enjoy a convenient location just a short ride from the Metro-North train with service to New York City, vibrant downtown Milford's shops and restaurants, Silver Sands State Park, and Milford's local beaches. Bring your ideas and imagine the possibilities-this North Milford blank slate is ready for its next chapter! Schedule your private showing today.

60 Round Hill Ter, Milford
252 Oronoque Rd, Milford
$699,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24212973 MLS
A Rare North Milford Find! Newly renovated and impeccably presented, this 5-bedroom, 3-bath Colonial features a separate one-bedroom main-level in-law/accessory dwelling unit, offering exceptional flexibility for multigenerational living or potential supplemental income. Set on a beautiful .88 picturesque lot in quiet North Milford. This home combines modern updates, generous living spaces, and a convenient Milford location. An inviting enclosed porch welcomes you into the main home, where a spacious, entertainment-friendly living room and beautiful hardwood flooring in most rooms create a warm, welcoming atmosphere. The bright eat-in kitchen features white cabinetry, stainless steel appliances, and an adjoining pantry/laundry room. A main-level bedroom and new full bath offer everyday convenience, while three generously sized upstairs bedrooms and a newer full bath complete the main residence. The beautifully updated in-law enjoys its own entrance for added privacy. Its modern, open layout includes a kitchen with stainless steel appliances, a dining area, and an airy living area with a cathedral ceiling, skylights, and sliders. A separate bedroom, newer full bath with a custom shower, stackable washer/dryer, and new vinyl flooring throughout. Additional highlights include a newer roof, 400-amp electrical service, newer plumbing, and a new on-demand water heater. A short ride to Metro North/New York City train, vibrant downtown Milford, Silver Sands State Park, and highways.

252 Oronoque Rd, Milford
40-42 Golden Hill St, Milford
$899,900
4 Beds ⋅ 6 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24211892 MLS
Attention Owner-Occupants and Savvy Investors! Presenting an exceptional opportunity to own a 2009-built townhouse-style duplex, thoughtfully constructed by one of the area's most reputable and experienced builders. This modern and meticulously maintained property offers the rare combination of quality craftsmanship, generous square footage, and flexible living options-ideal for both investment and personal residence. Purchase this and have nothing to fix, repair or remodel, including all mechanicals. Each side of this side-by-side duplex lives like an individual home, offering privacy and comfort. Features include inviting covered front porches, private rear decking over the garages, and designated parking. Inside, you'll find spacious rooms, abundant closet storage, and high-efficiency heating and cooling systems, including tankless gas water heaters for each unit. These two units have 2 bedrooms both ensuite, plus a main level half bath. Perfectly situated just at the "Greens End" Downtown Milford. Enjoy the nearby amenities of the many great restaurants, pubs, coffee shops, crafts and festivals, and Milford's Harbor/Marina-with access to public boat launches and available slips for boating enthusiasts. This is a wonderful area to walk, jog, bike and explore the many events and activities of busy Milford Downtown living. Whether you're looking to offset your mortgage with rental income or expand your investment portfolio with a high-performing asset. A must see!

40-42 Golden Hill St, Milford
275 Wheelers Farms Rd, Milford
$699,500
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24211322 MLS
Enjoy easy one-level living in this well-maintained Ranch set on .60 acres, featuring a bright, open-concept layout, vaulted ceilings, and abundant natural light. The main level offers 3 bedrooms, including a primary suite with en-suite bath, an additional full bath, and 2 fireplaces. A slider from the family room opens to a deck overlooking the private backyard, while a brand-new A/C system (August 2026) and attached 2-car garage add comfort and convenience. The finished walk-out lower level adds 1,240 sq. ft. of versatile living space with a bedroom, full bath, fireplace, and direct backyard access-ideal for multi-generational living, guests, recreation, or a home office. Ideally situated for commuters, with convenient access to I-95 and the Merritt Parkway, as well as Milford's train station for travel to and from NYC. Just minutes from the Downtown Green, restaurants, shops, and Milford beaches, this home offers space, flexibility, and the convenience of Milford's coastal location.

275 Wheelers Farms Rd, Milford
51 Meadow Park Dr, Milford
$409,000
3 Beds ⋅ 1 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24211067 MLS
Welcome to 51 Meadow Park Drive. This 3-bedroom, 1-bath ranch offers approximately 1,100 square feet of comfortable one-level living, plus a partially finished, heated basement providing approximately 500 square feet of additional space. The lower level offers plenty of possibilities and is ready to be refreshed to suit your needs and style. An attached one-car garage adds everyday convenience, while several important improvements have already been completed. Updates include a new roof, a newer boiler, a newer central air conditioning unit, a new sump pump, upgraded electrical, and thermopane windows. Enjoy a neighborhood setting that's well-suited for getting outside and taking a walk, while still enjoying all that Milford has to offer. With a practical ranch-style layout, additional heated lower-level space, an attached garage, and numerous major improvements, 51 Meadow Park Drive is ready for its next chapter. Conveniently located in Milford's 06461 area near the Boston Post Road corridor. Schedule your showing and discover the possibilities at 51 Meadow Park Drive.

51 Meadow Park Dr, Milford
63 Golden Hill St, Milford
$459,900
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24209490 MLS
Discover the charm of historic Milford at 63 Golden Hill Street, a beautifully updated home offering timeless character, modern improvements, and an exceptional walkable location. Built in 1900, this distinctive home has been thoughtfully renovated while preserving its original charm. Refinished hardwood floors and four original fireplaces add warmth and character throughout. Recent updates include a new gas furnace, new hot water heater, upgraded electrical service, and a new exterior rear door. The first floor offers a flexible layout with multiple living spaces and an upgraded kitchen, ideal for entertaining, working from home, or everyday living. Upstairs are two bedrooms and a full bathroom with a tub. Walk to historic Downtown Milford, the Milford Green, restaurants, shops, seasonal fairs, community events, and the Milford train station. Milford's beaches, shoreline, additional shopping and dining, I-95, and the Merritt Parkway are all just a short drive away. A rare opportunity to enjoy classic New England charm in the heart of Milford.

63 Golden Hill St, Milford
193 Clark St, Milford
$460,000
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24208587 MLS
Located close to the train station and vibrant downtown Milford, this beautifully remodeled Cape Cod home delivers move-in ready comfort in an exceptionally convenient location. Inside, you'll find an open floor plan filled with light, accented by hardwood floors throughout. The heart of the home is the expansive, newly renovated kitchen complete with rich cherry cabinets, granite countertops, and modern pendant lighting, flowing effortlessly alongside a fully updated bathroom. A finished basement offers two additional rooms, ideal for a home office, gym, or guest space. Major updates provide complete peace of mind, including a new roof (2012), siding (2012), windows (2012), screened gutters (2026), and a 50-gallon water heater (2026). Outside, the unusually huge, private backyard creates the ultimate setup for outdoor entertaining, gardening, and summer gatherings. Enjoy close proximity to local dining, shops, and Metro-North commuting. This home isn't just updated. It's your opportunity to live the central Milford lifestyle with modern comfort and rare backyard space just moments from downtown.

193 Clark St, Milford
1412 Windward Rd Unit 1412, Milford
$450,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24208257 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
357 Plains Rd, Milford
$599,900
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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
145 Lexington Way N, Milford
$1,000,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24195257 MLS
Beautiful, well maintained, 4-bedroom, 3.5-bath colonial in a desirable, well-managed community - situated on the main loop with lovely views overlooking the central green/park. This home features large bedrooms, laundry/mud room and very large finished walk-out, lower level, great for multipurpose use. Modern conveniences including central air, central vacuum, and an automatic lawn sprinkler system. Private and picturesque, yet conveniently close to town, shopping, and major routes. A perfect blend of comfort, space, and location.

145 Lexington Way N, Milford
40 Lexington Way N, Milford
$729,900
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24173863 MLS
Back on the market as of August 19 due to the buyer inability to secure financing. Agent to review the agent remarks to better understand the home. Welcome to Lexington Green. This 11 Room, 5 Bedroom, 3.5 bathroom colonial style home has many unique property features including an In-law in the lower level ( 847 square feet ), Primary Bedroom ( 421 square feet ) with a walk in closet and full Bathroom, Deck ( 154 square feet ), Attached 2 Car Garage ( 399 square feet ). The open expansive floor plan is ideal for entertaining and welcomes you with a dramatic two story foyer and features Living Room with fireplace, Dining Room, Eat-in kitchen with a center island, Family Room, Laundry/Mud Room, Powder Room, Deck. 4 Bedrooms on the upper level and In-Law in the lower level. You are within a few minutes drive to everything including 0.9 miles to Boston Post road ( RT 1 ), 1.1 miles to shopping & restaurants, 1.7 miles to the Merritt Parkway, 1.9 miles to I-95 North & South ramps, 2.1 miles to Milford train station, 8.4 miles to Route 34, 10.6 miles to Yale New Haven Hospital, 7.1 miles to Woodmont Beach.

40 Lexington Way N, Milford
231 W River St, Milford
$775,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24174394 MLS
ATTENTION SMALL BUSINESS OWNERS! UNLOCK THE ULTIMATE LIVE-WORK OPPORTUNITY! For the first time in over 50 years, the iconic Almond Building is available-perfect for entrepreneurs seeking the ideal blend of business and lifestyle. This is your chance to own not only a charming 1920s Cape Cod residence in the prestigious Duck Pond neighborhood, but also a highly visible commercial warehouse with office space and a tandem garage, right on bustling Boston Post Rd. Enjoy unmatched exposure for your business while living just steps away from your workplace! This unique offering includes both 231 W. River and 233 W. River for a combined price of $840,000 (see MLS 24174397). The home boasts classic curb appeal, a welcoming front porch, and a flexible layout with a living room, dining room, kitchen, bedroom, and full bath on the main floor, plus two additional bedrooms and a half bath upstairs. The attached one-car garage connects seamlessly to the commercial building-a former barn with a fun loft and over 4,000 sq. ft. of versatile workspace, including office areas and a tandem garage. The original barn has a crawl space beneath it, while the office space, garages, and some of the storage areas are on concrete slabs. Don't miss your chance to secure a rare property that gives you the best of both worlds: the prestige and tranquility of a historic neighborhood and the convenience and visibility your business deserves! Schedule your tour today and envision your best future here.

231 W River St, Milford

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