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Explore Similar Homes Within 25 Miles of Milford, CT

  • /29

    $599,900

    • 2 Beds
    • 2.5 Baths
    • 1,820 Sq Ft

    36 Byrds Hill Rd, Pawling, NY 12564

    The Perfect Weekend Escape or Full-Time Country Home, just 90 minutes from NYC. Set on a quiet, scenic road in the prestigious Quaker Hill area, you’re a short drive to the Village of Pawling with shopping, restaurants, highways, and Metro-North access. From the outside, it’s a classic farmhouse with rolling green acreage and space to breathe. Step inside, and you’re met with modern, yet cozy

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    (845) 630-1049

    36 Byrds Hill Rd, Pawling, NY 12564
  • /48

    $785,000

    • 4 Beds
    • 3 Baths
    • 3,360 Sq Ft

    94 S Quaker Hill Rd, Pawling, NY 12564

    Welcome to Sunset View! Nestled on 3.24 acres of picturesque private land, this sprawling 4-bedroom split-level home offers a perfect blend of spacious living and expansive outdoor amenities including a 20 x 50 salt water inground pool. As you approach along the freshly paved driveway, you'll be welcomed into your very own private oasis. Upon entering through the front door, you’ll step into a

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 622-7595

    94 S Quaker Hill Rd, Pawling, NY 12564
  • /48

    $5,000,000

    • 4 Beds
    • 7 Baths
    • 6,824 Sq Ft

    151 Long Ridge Rd, Danbury, CT 06810

    ROADSIDE – A Storied 53-Acre Private Estate in Fairfield County, CTEscape to your own private nature retreat at ROADSIDE, an extraordinary 53.44-acre country estate blending historic charm and modern luxury, just 90 minutes from Manhattan and 1.5 miles from the Redding train station. This rare legacy property offers unparalleled privacy, provenance, and polish—ideal for equestrians,

    Chelsea Stinson Coldwell Banker Realty

    151 Long Ridge Rd, Danbury, CT 06810
  • /50

    $4,850,000

    • 4 Beds
    • 3.5 Baths
    • 3,920 Sq Ft

    8 Lost Pond Ln, North Salem, NY 10560

    Dappled Meadows Farm. Superb Equestrian homestead in highly sought after ‘Grant’s Farm.’ Located on North Salem’s coveted Lost Pond Lane, a stunning private gravel road - surrounded by over 1000 acres of preserved land with hiking and riding trails. Sited down a long gated driveway on over 9 pastoral acres of sprawling lawns, paddocks, mature plantings and specimen trees. Uber chic, designer

    William Stuart Berkshire Hathaway HS NE Prop

    8 Lost Pond Ln, North Salem, NY 10560
  • /50

    $2,995,000

    • 4 Beds
    • 7 Baths
    • 8,220 Sq Ft

    16 Reynwood Dr, Brewster, NY 10509

    An exquisite country estate nestled on over 15 acres of gated privacy with stunning mountain views. Just 60 miles from NYC, this property offers the ideal blend of tranquility and convenience. The professionally landscaped grounds feature an expansive stone patio with an outdoor kitchen and large decks with wrought iron railings that provide unobstructed panoramic views of Putnam, Westchester and

    Marcie Nolletti Coldwell Banker Realty

    16 Reynwood Dr, Brewster, NY 10509
  • /30

    $1,799,999

    • 2 Beds
    • 1 Bath
    • 1,600 Sq Ft

    165 Duell Hollow Rd, Wingdale, NY 12594

    Exceptional opportunity to acquire this contemporary masterpiece designed by renowned architect Allan Shope. Tucked away in the serene woods of Wingdale, this property spans 29.7 acres and boasts a substantial pond, once part of the historic Camp Sacajawea. The residence is positioned on a secluded, wooded parcel, offering breathtaking views of mountains and the tranquil pond making it an ideal

    Bianca D'Alesandro Serhant LLC

    165 Duell Hollow Rd, Wingdale, NY 12594
  • /4

    $175,000

    • Land
    • 0.73 Acre
    • $239,726 per Acre

    0 Walnut St, Pawling, NY 12564

    Great opportunity to build a home in the beautiful Village of Pawling! This property is on municipal water and sewer! Thousands will be saved - no expense incurred on a drilled well or septic system! .73-acre lot offers a lovely western view. Walk to the picturesque Village center with its shops, bakeries, restaurants, library, so much more! Metro-North Train Station, Harlem Line, is located in

    Lisa Liffland McGrath Realty Inc

    0 Walnut St, Pawling, NY 12564
  • /50

    $498,000

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    57 Panorama Dr, Patterson, NY 12563

    Swimming, skiing, snowboarding, kayaking in the Patterson Great Swamp, walking or biking the nearby rail trail or Wonder Lake State Park, just minutes to the quaint Village of Pawling, shopping, dining, highway and train...these are just a few of the perks that living at 57 Panorama Dr. has to offer. This desirable neighborhood with its incredible views and convenient location boasting Carmel

    Karyne Aabel Briante Realty Group, LLC

    57 Panorama Dr, Patterson, NY 12563
  • /37

    $699,000

    • 4 Beds
    • 5 Baths
    • 4,018 Sq Ft

    175 Old Quaker Hill Rd, Pawling, NY 12564

    A Stately Cape Cod Estate with Exceptional Potential awaits. Set on an expansive, flat parcel of land surrounded by farms, rolling hills, and mountain views, this once grand and elegant residence offers a rare opportunity to restore and reimagine a home of timeless distinction. A property of this caliber, featuring grand proportions, architectural charm, and breathtaking grounds, is a true gem

    Tom Consaga RE/MAX Ace Realty

    175 Old Quaker Hill Rd, Pawling, NY 12564
  • /46

    $724,900

    • 4 Beds
    • 4.5 Baths
    • 4,938 Sq Ft

    172 Cornwall Hill Rd, Patterson, NY 12563

    Set on a quiet and scenic lot in Patterson, NY, this expansive 4-bedroom, 3.5-bathroom home offers exceptional space, architectural charm, and incredible potential. With a thoughtful layout, grand living spaces, and picturesque views, this is an ideal opportunity for buyers seeking a large home they can truly make their own.The standout feature of this property is the dramatic two-story great

    Robert Villone RE/MAX Classic Realty

    172 Cornwall Hill Rd, Patterson, NY 12563
  • /22

    $585,000

    • 4 Beds
    • 3.5 Baths
    • 2,502 Sq Ft

    8 Newburgh Rd, Patterson, NY 12563

    Pre-Construction Opportunity: Select Your Custom 3–4 Bedroom Smart Home with Private Lake Access This listing offers the opportunity to build a 3–4 bedroom home on one of two available 10,000 sq ft parcels in a peaceful, well-connected neighborhood. Located just a few feet from public transportation and a 10-minute drive to the MTA, the property combines convenience with privacy. Buyers can

    Jonathan Minerick HomeCoin.com

    8 Newburgh Rd, Patterson, NY 12563
  • /47

    $1,250,000

    • 4 Beds
    • 6 Baths
    • 3,012 Sq Ft

    16 Anderson Rd, Pawling, NY 12564

    Welcome to 16 Anderson Road — a beautifully crafted modern home perched atop the prestigious Quaker Hill in Pawling. Built in 2023, construction completed in 2024, this thoughtfully designed residence blends contemporary elegance with exceptional functionality, offering over 3,000 square feet of refined living space. From the moment you arrive, the home's charm is undeniable — lush landscaping

    Ryan Arket Compass Greater NY, LLC

    16 Anderson Rd, Pawling, NY 12564
  • /33

    $749,999

    • 3 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    444 Haviland Hollow Rd, Patterson, NY 12563

    Tucked away in picturesque Haviland’s Hollow lies this beautiful Colonial home on 14.7 bucolic acres of serenity. Enjoy mornings on the covered front porch and evenings on the large 600 square foot deck. Updated kitchen with quartz countertops, new appliances, and storage galore. All new LVP flooring on the main level makes for easy maintenance. Hardwood floors throughout rest of house. Spacious

    Gabriella DeMarco-Piciulli Giner Real Estate Inc.

    444 Haviland Hollow Rd, Patterson, NY 12563
  • /50

    $7,999,000

    • 10 Beds
    • 11 Baths
    • 10,700 Sq Ft

    422 Hardscrabble Rd, North Salem, NY 10560

    Iconic Darlington Hall estate. Set on over 83 pristine acres in the heart of Westchester’s horse country. A true architectural masterpiece - replicating Sir Edward Lutyen’s ‘Salutation’ in England. Captivating half mile meandering drive through hayfields and woodlands. The property features an indoor swimming pool with underground tunnel, an 11 stall horse barn with groom’s quarters, a jumping

    William Stuart Berkshire Hathaway HS NE Prop

    422 Hardscrabble Rd, North Salem, NY 10560
  • /48

    $799,900

    • 4 Beds
    • 2.5 Baths
    • 3,350 Sq Ft

    134 Old Pawling Rd, Pawling, NY 12564

    Beautiful Colonial home, Well Maintained level land W/Meadow view, for the first time on the market .This beautiful home offer 4 bedroom and 2 full bathroom and half Den room on the first floor, Bonus Room on the second floor, Formal living room and formal dining room, 1,25 acres .Gorgeous Oak eating kitchen with sliding door to the deck outside, family room and half bath. Second floor offer 4

    Drita Shala Howard Hanna Rand Realty

    134 Old Pawling Rd, Pawling, NY 12564
  • /3

    $89,900

    • Land
    • 5 Acres
    • $17,767 per Acre

    0 Sheldon Rd Unit KEY832601, Dover, NY 12594

    Sheldon Rd is peaceful and quiet, not a through road. The road is town maintained. Residential use only, Off-the-Grid homes are acceptable. Upward sloping property is lightly wooded with a pretty seasonal view.

    Lisa Liffland McGrath Realty Inc

    0 Sheldon Rd Unit KEY832601, Dover, NY 12594
  • /36

    $14,995,000

    • 4 Beds
    • 3.5 Baths
    • 3,942 Sq Ft

    15 Kirby Hill Rd, Pawling, NY 12564

    Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, Grand Prix polo field, over 100 acres of fenced property, and 150 acres of riding trails

    Brian McGrath McGrath Realty Inc

    15 Kirby Hill Rd, Pawling, NY 12564
  • /36

    $5,500,000

    • 17 Beds
    • 13 Baths
    • 15,000 Sq Ft

    618 Quaker Hill Rd, Pawling, NY 12564

    25.5-acre equestrian estate with a 43-room Elizabethan Style manor house, two caretaker homes, a carriage house with groom’s quarters, a yoga studio, a 12,000 sq. ft. stable, greenhouse and more. Situated on the crest of Quaker Hill, Elmwood Farm has stunning views and endless possibilities. The 3-story, 17-bedroom (7 of which are in the nursery wing and the caretakers' wing) 9-bath (plus 4

    Harriet Norris Douglas Elliman Real Estate

    618 Quaker Hill Rd, Pawling, NY 12564

Home Trends in Milford, CT

Housing Trends

Median Sale Price
$267,000
Median Single Family Sale Price
$795,000
Median Townhouse Sale Price
$412,500
Median 2 Bedroom Sale Price
$432,300
Median 1 Bedroom Sale Price
$258,600
Average Price Per Sq Ft
$330
Number of Homes for Sale
6
Last 12 months Home Sales
119
Months of Supply
0.60
Median List Price
$314,950
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
-23%
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