139

Homes for Sale near The Family School

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  • /18

    $259,000

    • 1 Bed
    • 1 Bath
    • 245 Sq Ft

    1975 State Hwy Unit 3, Eastham, MA 02642

    Own a charming cottage in South Eastham, gateway to the National Seashore. A perfect getaway with strong rental history, this cottage is located within the Cottage Grove association - situated on 2.69 acres of wooded property. This particular cottage is located toward the rear of the property, set back from the others in a quiet location - referred to as the ''honeymoon cottage''. Built in the

    Day - Logan Group Kinlin Grover Compass

    1975 State Hwy Unit 3, Eastham, MA 02642
  • /26

    $880,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,784 Sq Ft

    4 Wood Duck Ln, Eastham, MA 02642

    Charming Eastham ranch in a quiet cul-de-sac! This sun-filled 3-bed, 2.5-bath home with hardwood floors and a 2-car garage offers easy, single-level living. Enjoy a spacious living area, abundant natural light, and a beautiful primary suite with private bath. Stroll to the Windmill Green for concerts and festivals, then grab an ice cream or deli sandwich at the Superette. Just a five-minute walk

    Rebecca Archambeault Keller Williams Realty Signature Properties

    4 Wood Duck Ln, Eastham, MA 02642
  • /27

    $345,000

    • 1 Bed
    • 1 Bath
    • 579 Sq Ft

    82 Fletcher Ln Unit I, Brewster, MA 02631

    Step into this stunningly updated top-floor condo in the desirable Ocean Edge Resort community. This 1-bedroom, 1-bath home offers soaring cathedral ceilings and an airy, open layout drenched in natural light. Relax outside on your own private balcony, or enjoy the sleek, fully renovated kitchen featuring quartz counters, stainless steel appliances, contemporary cabinetry, and chic lighting. The

    Leighton Team Keller Williams Realty

    82 Fletcher Ln Unit I, Brewster, MA 02631
  • /53

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 2,064 Sq Ft

    53 Great Oak Rd, Orleans, MA 02653

    Tucked into one of East Orleans' most desirable spots, this 4 bed, 3 bath home offers both charm and convenience in equal measure. Inside, you'll find 2 bedrooms on the main level, 1 upstairs, & the 4th in the lower level walkout. Each floor has an updated full bath. Wood floors run throughout the main level. You'll notice thoughtful upgrades throughout, new patios and walkways, refreshed

    Jack Bohman Gibson Sotheby's International Realty

    53 Great Oak Rd, Orleans, MA 02653
  • /42

    $267,900

    • 1 Bed
    • 1 Bath
    • 579 Sq Ft

    60 Fletcher Ln Unit H, Brewster, MA 02631

    ***$4,000 sellers credit @ full price offer*** Live the Cape Cod dream at 60-H Fletcher Lane! This sunny 1-bedroom end unit in Ocean Edge is all about location and lifestyle—steps to pools, fitness, and golf. Enjoy morning coffee or sunset cocktails on your private garden-level patio overlooking the fairway. Inside, fresh paint, new stainless appliances, new kitchen counters, new carpet in

    Chelsea McLaughlin RE/MAX Legacy

    60 Fletcher Ln Unit H, Brewster, MA 02631
  • /14

    $295,000 Open Sat 11AM - 1PM

    • 1 Bed
    • 1 Bath
    • 579 Sq Ft

    61 Fletcher Ln Unit H, Brewster, MA 02631

    Settle in to the easy life at The Villages at Ocean Edge. 61-H offers first floor living with second floor privacy. Condo has an open concept flow with a fully applianced kitchen including a stackable washer and dryer. Living room stays bright with the newly upgraded large picture window and slider to the balcony which overlooks the Ocean Edge Golf Course. The built in Murphy bed creates

    Team Seaport Seaport Village Realty

    61 Fletcher Ln Unit H, Brewster, MA 02631
  • /42

    $1,250,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 3 Baths
    • 2,011 Sq Ft

    11 Juniper Cir, Brewster, MA 02631

    This spacious town home is located on Cape Cod Bay in a beautifully landscaped community with private beach, pool, and tennis courts. Three bedrooms and three full baths - along with a large living room with fireplace and cathedral ceiling - make this the perfect place to consider home. The kitchen has been refreshed with stainless steel appliances and granite countertops. The kitchen has a

    Falconio Jones Team Kinlin Grover Compass

    11 Juniper Cir, Brewster, MA 02631
  • /56

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 2,084 Sq Ft

    1437 Long Pond Rd, Brewster, MA 02631

    Welcome to this charming, well-maintained 3-bedroom, 2.5-bath home, situated on a peaceful lot set well back from the road. Built in 1985, this home combines timeless charm with modern updates. Step inside to discover a cozy living room with fireplace and gleaming hardwood floors that flow throughout the home. The updated eat-in kitchen is move-in ready with stainless appliances and granite

    Peg LoPresto William Raveis Real Estate & Home Services

    1437 Long Pond Rd, Brewster, MA 02631
  • /61

    $1,250,000

    • 3 Beds
    • 2 Baths
    • 1,829 Sq Ft

    75 Monument Rd, Orleans, MA 02653

    Thoreau would live here! Completely secluded yet in the heart of Orleans you will find this enchanting Cape retreat. Replete with cottage charm and in great condition, this year-round three bedroom home on a cultivated acre is surrounded by Orleans Conservation Trust land, ensuring the long-term privacy of this remarkable setting. Upon entering the generous parking area it becomes immediately

    Jeff Cusack Cove Road Real Estate

    75 Monument Rd, Orleans, MA 02653
  • /31

    $275,000

    • 1 Bed
    • 1 Bath
    • 579 Sq Ft

    60 Fletcher Ln Unit C, Brewster, MA 02631

    Welcome to 60-C Fletcher Lane—an inviting and open concept, updated one-bedroom condo located across the way from the Fletcher Pools and fitness center. Positioned on the garden level, this unit offers a private walkout patio—ideal for summer cookouts or unwinding after a day at the beach. Inside, the kitchen is finished with Quartz countertops and lightly used appliances from 2017. Laminate

    Leighton Team Keller Williams Realty

    60 Fletcher Ln Unit C, Brewster, MA 02631
  • /16

    $899,900

    • Land
    • 1.43 Acres
    • $629,301 per Acre

    110 Beach Rd, Orleans, MA 2653

    Don't miss this FABULOUS opportunity! Buildable One-Acre Lot Near Nauset Beach!Rare opportunity to build your dream home in East Orleans on this beautiful 1-acre lot, central to town and less than 1 mile from Nauset Beach! Enjoy gorgeous sunsets overlooking mature landscaping designed by Wilkinson Ecological. Seller has had perk tests successfully completed. Underground natural gas, electric

    Ashley Stucenski Orleans Village Properties, LLC

    110 Beach Rd, Orleans, MA 2653
  • /28

    $330,000

    • 1 Bed
    • 1 Bath
    • 579 Sq Ft

    62 Fletcher Ln Unit N, Brewster, MA 02631

    Move right into this beautifully renovated top-floor condo in the sought-after Ocean Edge Resort community. This 1-bedroom, 1-bath home features cathedral ceilings + an open-concept design that fills the space with natural light. Enjoy outdoor space on your private Balcony. Inside, enjoy a fully updated kitchen w/ sleek quartz countertops, stainless steel appliances, modern cabinetry, and

    Leighton Team Keller Williams Realty

    62 Fletcher Ln Unit N, Brewster, MA 02631
  • /47

    $1,199,000

    • 3 Beds
    • 2.5 Baths
    • 2,158 Sq Ft

    17 Crescent Ridge Way, Orleans, MA 02653

    Nestled off of a quiet cul-de-sac, this classic 3-bedroom, 2.5-bath Cape-style home offers the perfect blend of privacy and charm. Perched on a serene hilltop, the property is surrounded by nature, providing a peaceful retreat just minutes from all the Cape has to offer.Inside, enjoy a spacious layout with a bright and airy living room, a cozy fireplace, and a thoughtfully designed kitchen that

    Kimberley Vitale William Raveis Real Estate & Home Services

    17 Crescent Ridge Way, Orleans, MA 02653
  • /54

    $6,000,000

    • 20 Beds
    • 7.5 Baths
    • 6,657 Sq Ft

    150 Old State Hwy Unit Compound, Eastham, MA 02642

    This rare offering includes all seven cottages in the Collins Cottages Historic District - a historic and nostalgic waterfront enclave on Town Cove in Eastham, now zoned for year-round living and being converted to condominiums. In addition to the cottages, this sweeping property includes a waterfront boathouse, 4 car detached garage, and 13 dock slips. With 400 feet of waterfront with

    Sarah Keith eXp Realty, LLC

    150 Old State Hwy Unit Compound, Eastham, MA 02642
  • /61

    $924,900

    • 2 Beds
    • 2 Baths
    • 1,567 Sq Ft

    10 Center Place Unit 16, Orleans, MA 02653

    Orleans Village Perfection - Renovated Townhome with Custom Finishes. Rare luxury townhome in the heart of Orleans! World-class beaches, boutique shopping, fine dining & everything Orleans has to offer. This move-in-ready residence offers a maintenance-free lifestyle with brand new ducted central heat/AC, two fully renovated baths, custom closets, updated lighting and flooring, plus a private

    Michael Letourneau Orleans Village Properties, LLC

    10 Center Place Unit 16, Orleans, MA 02653
  • /26

    $6,950,000

    • 8 Beds
    • 4 Baths
    • 5,506 Sq Ft

    2079 Head of The Bay Rd, Harwich, MA 02645

    Nestled on 1.85 acres along the pristine shores of Pleasant Bay, this extraordinary waterfront estate offers an elegant blend of craftsmanship, comfort, and sweeping water views. Thoughtfully updated and expanded over the years, the home showcases a stunning post-and-beam addition with soaring cathedral ceilings, exposed trusses, and walls of windows that frame captivating views of the bay and

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    2079 Head of The Bay Rd, Harwich, MA 02645
  • /3

    $200,000

    • Land
    • 0.92 Acre
    • $217,391 per Acre

    0 S Orleans Rd, Harwich, MA 02645

    Undevelopable Land per the Town of Harwich. Property could be sub-divided into 4 10,000 s.f. increments for bedroom credits as part of the Nitrogen Loading Credits program so an additional bedroom can be added to another property in Harwich.

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    0 S Orleans Rd, Harwich, MA 02645
  • /34

    $899,000 Open Sun 10:30AM - 12PM

    • 2 Beds
    • 3 Baths
    • 2,000 Sq Ft

    510 Hay Rd, Eastham, MA 02642

    Bayside Eastham gem, updated & beautifully maintained in desirable South Eastham is in close proximity to Boat Meadow Beach. This light filled, open floor plan Cape has gleaming refinished hardwood floors throughout, a freshly painted interior & is ready to move into. The main level features a cathedral-ceiling kitchen with skylight, a spacious living room and dining area with French doors

    Dolores Alberti Gibson Sotheby's International Realty

    510 Hay Rd, Eastham, MA 02642
  • /14

    $475,000

    • 2 Beds
    • 1 Bath
    • 1,008 Sq Ft

    48 Long Pond Dr, Harwich, MA 02645

    If you are looking for sweat equity, this is a great spot for it. Just 3/10 mile to either the bike path (at beautiful Pleasant Lake General Store) or deeded beach on Long Pond. This 2 bedroom ranch does have a fireplace, wood floors and full stairs to a walk-up attic, full basement and garage under. Plus a 24x24 detached 2 car garage with great 2nd floor space for workshop or make into an

    Paul Welch Sesuit Harbor Real Estate

    48 Long Pond Dr, Harwich, MA 02645
  • /3

    $314,900

    • Land
    • 0.44 Acre
    • $715,682 per Acre

    0 Pine Grove Rd Unit 22503517, Brewster, MA 02631

    This is a rare opportunity to own a fully approved, buildable lot on the border of Brewster & Orleans. This lot has had all engineering done to it, including approval for a 1560 sqft single family ranch style home--no delays, no hassles, just close and start building. Located in a peaceful, well-established neighborhood, this lot offers the perfect blend of convenience and tranquility. A mile

    Matthew Medeiros Millennium Realty Firm LLC

    0 Pine Grove Rd Unit 22503517, Brewster, MA 02631
  • /6

    $725,000

    • Land
    • 0.97 Acre
    • $747,423 per Acre

    2 Carolines Way, Orleans, MA 2653

    This is a rare opportunity to purchase a 0.97 acre lot on Cape Cod in the quintessential town of Orleans. Whether you are looking to build your family's next home, your dream retirement oasis, or your summer retreat this corner lot is the perfect spot. This vacant lot is only a 1/2 mile from the Portanimicut Town Landing with a boat launch, dock, and mooring field so you can enjoy all your

    Kate Nadolski Elliott Griffin Realty Group

    2 Carolines Way, Orleans, MA 2653
  • /38

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 2,440 Sq Ft

    958 Long Pond Rd, Brewster, MA 02631

    Three Lots Totaling 3+ Acres in Brewster!An exceptional opportunity awaits with this unique offering of three adjoining lots totaling over 3 acres. A spacious 2440 SF Cape is situated on a pastoral 2+ acre lot, featuring 4 bedrooms, 3 full bathrooms, including a large first-floor primary suite with a walk-in closet & private bath. Main living areas are generous sized. Heat is by natural gas &

    Dee Higgins Gibson Sotheby's International Realty

    958 Long Pond Rd, Brewster, MA 02631
  • /69

    $775,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 4 Baths
    • 2,353 Sq Ft

    1875 State Hwy, Eastham, MA 02642

    This custom-built home on a .9 acre lot is nicely set back from the street with a circular stone driveway, irrigated front lawn, and soaring poplars, cedars and evergreens for privacy. It offers a unique blend of antique touches and contemporary flair. Built in 1924, the home was taken back the studs and rebuilt with dormers and a bay window for more light, new granite kitchen, new interior

    Reita Donaldson Kinlin Grover Compass

    1875 State Hwy, Eastham, MA 02642
  • /9

    $649,997

    • Land
    • 1.29 Acres
    • $503,874 per Acre

    320 State Hwy, Eastham, MA 02642

    Builder Package available to create your oceanfront dream home. Current plans can be customized. This lot is SHOVEL READY. The building permit and ALL approvals are IN PLACE, including architectural plans for a five-bedroom home and two car garage. Dock and moorings are currently pending approval, adding even more potential to this waterfront retreat. This is your chance to own a truly

    Derek Greene The Greene Realty Group

    320 State Hwy, Eastham, MA 02642
  • /50

    $1,249,000

    • 3 Beds
    • 2.5 Baths
    • 1,795 Sq Ft

    12 Skaket Way, Brewster, MA 02631

    A rare offering tucked well within Brewster's coveted Seaview neighborhood and wrapped in conservation is 12 Skaket Way. Perched on an impossibly quiet and well-spaced tree lined street, 12 Skaket is a five-minute stroll to association tennis as well as the Cape Cod Rail Trail and convenient to beaches, shops and amenities offered in both Brewster and Orleans. The handful of over/under photos

    Jon Clark Nauset Management

    12 Skaket Way, Brewster, MA 02631
  • /16

    $185,000

    • Land
    • 0.34 Acre
    • $544,118 per Acre

    0 Underpass, Brewster, MA 02631

    Rare, commercially-zoned, .34 acre lot. The setting offers great visibility on a main road for your business. (It abuts 195 Underpass Rd. which is under contract, scheduled to close 8/27/25.) Check with the Town to see what is possible. Buyers/agents to confirm all details.

    Amy Harbeck Kinlin Grover Compass

    0 Underpass, Brewster, MA 02631
  • /6

    $925,000

    • Land
    • 0.88 Acre
    • $1,051,136 per Acre

    60 Gibson Rd, Orleans, MA 2653

    Set along the shoreline of Town Cove, 60 Gibson Road presents a rare opportunity to build a custom waterfront home in one of Orleans' most desirable locations. This 3-bedroom buildable lot offers direct access to the water, the potential for a mooring with harbormaster approval, and beautiful views that reflect the natural charm of Cape Cod.The property includes a barn with electricity--ideal for

    Dawn Lee Gibson Sotheby's International Realty

    60 Gibson Rd, Orleans, MA 2653
  • /25

    $325,000 Open Fri 11AM - 1PM

    • 1 Bed
    • 1 Bath
    • 579 Sq Ft

    81 Fletcher Ln Unit I, Brewster, MA 02631

    Enjoy one level living and move right into this beautifully renovated, first-floor condo in the sought-after Ocean Edge Resort without any stairs to navigate. This 1-bedroom, 1-bath home features an open-concept layout filled with natural light.The kitchen has been fully updated with quartz countertops, stainless steel appliances, modern cabinetry, and stylish lighting. The bathroom has also been

    Leighton Team Keller Williams Realty

    81 Fletcher Ln Unit I, Brewster, MA 02631
  • /50

    $2,100,000

    • 3 Beds
    • 2.5 Baths
    • 1,956 Sq Ft

    63 Briar Spring Rd, Orleans, MA 02653

    With a front row view of Pochet Inlet, Pochet Island and the Atlantic just beyond the outer beach, 63 Briar Spring offers three levels of thoughtfully designed living space over its nearly 2000 square feet. Level one features 3 bedrooms to include two water-facing walkouts, one of which is a master, as well as an additional full bath. The main living level has an open concept amplified by a

    Jon Clark Nauset Management

    63 Briar Spring Rd, Orleans, MA 02653
  • /42

    $697,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 1 Bath
    • 809 Sq Ft

    137 Rock Harbor Rd Unit 4, Orleans, MA 02653

    Welcome to the Captain Carlson house at Rock Harbor Condominiums! This is a year-round, two bedroom cottage showcasing incredible artwork and craftsmanship. Nautical tile, marine pottery, shells, sea glass and thousands of rocks and pebbles hand collected from Nauset Beach, all coupled together to create a mozaic depiction of natures coastal marine life. Stained glass windows, antique door knobs,

    Matthew Burger Kinlin Grover Compass

    137 Rock Harbor Rd Unit 4, Orleans, MA 02653
  • /14

    $1,225,000

    • 4 Beds
    • 2 Baths
    • 2,149 Sq Ft

    2 Shell Ln, Orleans, MA 02653

    LOCATION, LOCATION, LOCATION! This home is a 4 bedroom 2 bath home that has been in the family for many years. The field card says 3 bedrooms but will be updated in December ,by the town, to reflect the 4th bedroom. The Engineering for the septic is almost completed for the 4 bedroom system. It is close to Rock Harbor and the center of Orleans but hidden away for lots of privacy. The large

    Eileen Loranger Bayside Realty Consultants

    2 Shell Ln, Orleans, MA 02653
  • /2

    $314,900

    • Land
    • 0.44 Acre
    • $715,682 per Acre

    0 Pine Grove Rd Unit 73397945, Brewster, MA 02631

    This is a rare opportunity to own a fully approved, buildable lot on the border of Brewster & Orleans. This lot has had all engineering done to it, including approval for a 1560 sqft single family ranch style home—no delays, no hassles, just close and start building. Located in a peaceful, well-established neighborhood, this lot offers the perfect blend of convenience and tranquility. A mile

    Matthew Medeiros Millennium Realty Firm, LLC

    0 Pine Grove Rd Unit 73397945, Brewster, MA 02631
  • /67

    $729,000

    • 5 Beds
    • 2 Baths
    • 1,344 Sq Ft

    26 Newport Rd, Brewster, MA 02631

    Five bedrooms and deeded rights to Sheep Pond combine for an excellent income opportunity! Enjoy living through the beautiful off season on the Cape while reaping the benefits of the rental season. Gather friends and family at your summer home, or settle into your year round Cape Cod home. Reimagine one or two bedrooms as a home office, den, playroom or whatever unique use your imagination

    Christine Briscoe SeasCape Realty, Inc.

    26 Newport Rd, Brewster, MA 02631
  • /42

    $1,995,000

    • 3 Beds
    • 3 Baths
    • 2,471 Sq Ft

    410 Blueberry Pond Dr, Brewster, MA 02631

    Completed in 2023, this newly built, fully electric home blends elevated design, sustainability, and timeless Cape Cod charm. Privately sited on 1.15 acres across two parcels and surrounded by conservation, the property offers gated access to Blueberry Pond and 2,400 sq ft of living across three levels. Designed with a primary suite on each main level, the layout supports multigenerational living

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    410 Blueberry Pond Dr, Brewster, MA 02631
  • /50

    $895,000

    • 3 Beds
    • 2 Baths
    • 1,867 Sq Ft

    126 Bittersweet Dr, Brewster, MA 02631

    3BR, 2BA Cape located at the end of a quiet cul-de-sac near Cape Cod Bay beaches, the CC Bike Trail, shops, and restaurants. Lovingly maintained by one family since 1985, this 2-story home offers easy first-floor living with a spacious kitchen featuring granite counters, center island, laundry, and a dining area with slider to a private deck. The bright and airy living room has a bay window and

    Dee Higgins Gibson Sotheby's International Realty

    126 Bittersweet Dr, Brewster, MA 02631
  • /88

    $2,450,000

    • 4 Beds
    • 3 Baths
    • 2,615 Sq Ft

    136 Monument Rd, Orleans, MA 02653

    This classic Cape just 300 feet from the sandy beach at beloved Crystal Lake has been completely transformed by JC Donald Custom Building and Design. From its elevated setting this light-filled home overlooks a cranberry bog and offers peeks of Crystal Lake and Lonnie's Pond. There is nothing to do but move in and enjoy the lake or the new inground swimming pool and its expansive patio areas.

    Jeff Cusack Cove Road Real Estate

    136 Monument Rd, Orleans, MA 02653
  • /56

    $1,199,000 Open Sun 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,877 Sq Ft

    43 Owl Pond Rd, Brewster, MA 02631

    Welcome to a home that truly has it all--space, style, and a setting that makes every day feel like a getaway. This residence, originally built by its owner, has been lovingly updated and offers a layout designed for both gathering and privacy. With three separate family rooms, there's room for everyone to spread out or come together. Outside, discover your private retreat: an expansive yard with

    Leona Bicker Gibson Sotheby's International Realty

    43 Owl Pond Rd, Brewster, MA 02631
  • /60

    $1,960,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 2,565 Sq Ft

    142 Monument Rd, Orleans, MA 02653

    Orleans Jewel with Private tennis court- This lovingly restored, meticulously maintained 1820 property sits perfectly located between two fresh water ponds and a saltwater inlet. Capturing filtered views of Pilgrim Lake, this property captures authentic charm with renovated beauty . As you move from room to room, you will admire all the thoughtful period details, beautiful floors, fantastic

    Robin Thayer Gibson Sotheby's International Realty

    142 Monument Rd, Orleans, MA 02653
  • /45

    $1,075,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 2 Baths
    • 2,184 Sq Ft

    18 Juniper Cir, Brewster, MA 02631

    Coastal luxury in Brewster's coveted Sears Point. Welcome to 18 Juniper Circle, a spacious and elegant two-bedroom condominium offering over 2,100 square feet of living in the prestigious Sears Point Association. This exclusive enclave of just 64 residences is set on more than 30 wooded acres north of Route 6A and features outstanding amenities including a stunning private beach on Cape Cod Bay,

    Paul McCormick Gibson Sotheby's International Realty

    18 Juniper Cir, Brewster, MA 02631
  • /25

    $335,000

    • 1 Bed
    • 1 Bath
    • 579 Sq Ft

    81 Fletcher Ln Unit C, Brewster, MA 02631

    Move right into this beautifully renovated, first-floor condo in the sought-after Ocean Edge Resort without any stairs to navigate. This 1-bedroom, 1-bath home features an open-concept layout filled with natural light and a private patio overlooking the Nicklaus Design Golf Course. The kitchen has been fully updated with quartz countertops, stainless steel appliances, modern cabinetry, and

    Leighton Team Keller Williams Realty

    81 Fletcher Ln Unit C, Brewster, MA 02631

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