$3M - $5M

22 Paddock Road Oak Bluffs MA 02557

Oak Bluffs, MA22 Paddock Road

Price$4,995,000

Est. Mortgage: $/month

MLS Number 38557

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 6.5
  • Acreage 1.867

THIS IS THE ONLY LOT AVAILABLE in the PRESERVE at The WOODLANDS! COMING SOON...TO BE BUILT...by SHAWN CHAPPS...UNDER EARLY STAGES OF DESIGN and STILL TIME to CUSTOMIZE with YOUR OWN PERSONAL TOUCHES! Sophisticated Sprawling Contemporary Barn Style Residence with Clean Classic Lines, Natural Timber Beams, Field Stone Fireplace and Soaring Ceilings. This Spacious Airy Open Floor Plan will have no shortage of living areas with multiple intimate gathering spaces surrounded by lots of glass that displays an unobstructed panorama of the lush landscaped backyard and 20x 40 Gunite Pool and Spa. The Decked Out Chefs Kitchen will be a fusion of modern design, rustic accents and State of the Art Appliances. Boasting 6 en suite luxury bedrooms and unmatched bathrooms, with deep soaking tubs, artistic tiled showers, custom vanities, walk-in closets, and sitting areas all designed for convenience and comfort. A generous walk-out finished basement, containing over 2000 square feet, will include additional living areas along with a custom home bar, gym/media room and or wine cellar. Other Rare feature is the "Show Stopping Two Story Vaulted Stairway" This Unparalleled design with exceptional visuals highlighted by exquisitely detailed finishes will be SUPER DELUXE; So Be prepared for the "WOW FACTOR " Don't Wait...Call Today to Secure this RARE OFFERING in the POSH PRESERVE Oak Bluffs' Newest Luxury En Clave abutting conservation land and trails for hiking, walking and biking!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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53 Wequobsque Road Chilmark MA 02535

Chilmark, MA53 Wequobsque Road

Price$4,900,000

Est. Mortgage: $/month

MLS Number 39258

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 6.4

This magnificent waterfront home sited on 6.4 acres sits atop the dramatic Wequobsque cliffs. On Chilmark's coveted South Shore, this home boasts ownership of over 350 feet of private beach with access from your staircase in the backyard. The home has a 5-bedroom and 4-bath wing. Attached by a screened-in porch, is the large gathering kitchen with ceiling beams, tall columns and an open, airy design. Enjoy meals in the dining area with ocean views. Dine on the large outdoor deck facing the Ocean. On the west side of the property sits the barn with a half bath and a loft that can be used as an office or extra sleeping area. There is a wet bar, ping-pong table, large screen TV and sofa. There's space to install a wood stove. The home has a new full basement and HVAC system. A very large one car garage below the barn completes the property. This is your opportunity to own your dream home on the waterfront on Chilmark's South Shore.

Listed by Grace Hagerty Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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137 Massasoit Avenue Vineyard Haven MA 02568

Vineyard Haven, MA137 Massasoit Avenue

Price$4,750,000

Est. Mortgage: $/month

MLS Number 39426

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3.5
  • Acreage 0.87

VIEWS galore from this spacious West Chop House loved and enjoyed by the same family for many decades. Start your day off viewing the magnificent sunrises from the huge, sun-dappled porch on this family-friendly house, set within the West Chop “loop” in Vineyard Haven. It is the perfect spot to relax and watch the ferries sailing back and forth to Martha’s Vineyard. Just inside, the soaring great room with its vaulted ceiling, exposed beams, hardwood floors, expansive windows, and views out to Nantucket Sound – offers a warm and welcoming gathering space. Five bedrooms, three-and-a-half bathrooms, a spacious eat-in country kitchen with adjacent dining room, and plenty of sitting areas throughout allow this much-loved home to accommodate a swell of visiting family and friends with room to spare. A perfect place to work from home with privacy and separation. The bright and airy master suite upstairs has magnificent northeast views over the water, with a cathedral ceiling, comfortable sitting area, dressing room, and full bath. As a bonus, enjoy a walk-through study and den/bedroom, another full bath, and a light-filled bedroom. There are two spacious bedrooms downstairs, together with a third full bath and a half bathroom. Built in 1988 and renovated in 2002, the house has mini-splits, a gas furnace, irrigation, and an outdoor shower, comfortable for year-round living and well-suited for holiday gatherings. Tucked away from Main Street atop a beautiful, grassy slope overlooking the water, and the Sound beyond. The house is set on .87 acres of quiet woodland and open lawn bordered by a stone wall and flowering meadow plantings. It’s a rare offering in this location, right across the street from the West Chop Club’s Middle Pier and swimming beach. Close by are the West Chop Club, Vineyard Haven Yacht Club, Mink Meadows Golf Club, the 83-acre West Chop Woods nature preserve, and the classic 1891 West Chop lighthouse. Sailing, tennis, walking and running trails, biking fishing, children’s activities, and more are close at hand. Please note that 125 Massasoit, an abutting property, is also for sale at $3.1M offering a spectacular compound in the heart of West Chop. Rarely do you find homes with these magnificent views in West Chop, it is an opportunity not to be missed. easy to show!

Listed by Viewpoints

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 Pondmark Chilmark MA 02535

Chilmark, MA1 Pondmark

Price$4,700,000

Est. Mortgage: $/month

MLS Number 38183

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 4.7

Turn onto country lane and make first turn to right. Drive past Norwegian Pine and many mature plantings and follow stately stone walls up past an open field overlooking the pond. The gentle slope takes you past the garden to a parking area. The white cottage sits on top of the knoll with sweeping views looking out over Keith farm and beyond to the ocean. From the living room the light brightens the large room with vaulted ceilings and a fireplace with a copper chimney hood.You can walk out on the deck for breakfast and watch the cows, geese, horses or the calming motion of the sea. You can lay in bed and take it all in from the king size bed and wall of windows facing south. There is room for a guest house or barn in this private setting. There are walking trails on Old North Road or a trail to Menemsha Crossroads. Go back in time to a slower way of life in this old style Chilmark retreat.

Listed by Gay Head Realty

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$
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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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77 North Neck Road Edgartown MA 02539

Edgartown, MA77 North Neck Road

Price$4,695,000

Est. Mortgage: $/month

Active With Contract

MLS Number 37573

  • Land
  • Village Chappy
  • Acreage 5.85
  • Bedrooms 4
  • Bathroom 4

CHAPPY WATERFRONT WITH BOAT HOUSE AND DOCK. Set on Chappaquiddick's North Neck, this private multi-acre waterfront property features a gentle rolling landscape that stretches to meet the water's edge.The superlative, unobstructed views expand to Edgartown Harbor and Nantucket Sound -- and the westerly exposure is the perfect for spectacular evening sunsets. A pathway leads the way to the nearly 200-foot beach with private dock, where there is also a small shingled building that can be used as a beach cabana or boathouse. There is an approved septic design for up to nine (9) bedrooms, which is expired however can be updated with a new application and proposed home design. This is an unparalleled opportunity to build your signature waterfront home in this most magical setting on Chappaquiddick.

Listed by Compass | Point B

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$
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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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11 Peter Williamson Boulevard Oak Bluffs MA 02557
Pending

MLS Number 39271

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 4.5
  • Acreage 1.37

NEW CONSTRUCTION WITH A POOL & SPA, OAK BLUFFS Built in 2019 by a well-known Island contractor and designer, this sweet hidden pearl is elegant, private and relaxing. Conveniently located 3 miles from the triangle in Edgartown and 4 miles from downtown Oak Bluffs with bike paths in both directions, situated off a main road in a very quiet dead-end neighborhood with plenty of opportunities for biking in the woods and walking around neighborhood ponds. The 4,200 square feet contemporary house has a main floor with an open cathedral ceiling great room that overlooks the heated pool. Sliding glass doors lead to beautifully Zen landscaped exterior living space with areas for dining under an umbrella, sitting on the couch next to the pool, playing bean bag toss, grilling a steak, or sitting in the hot tub. Outdoor lighting allows for ultimate enjoyment of this magical oasis. Simple monolithic building shapes create minimalistic, peaceful respite for ultimate year-round escapes. Remarkably, this is not only an amazing place to gather, it is an amazing place to find reflection. Recharge, have adventures, inspire.

Listed by C McManus Realty Group

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$
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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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87 Bellevue Avenue & 0 Howard Street Vineyard Haven MA 02568

MLS Number 39481

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3
  • Acreage 2.96

Sited on a bluff with expansive views overlooking the beautiful Lagoon Pond is this uniquely classic Victorian style cottage. The property is comprised of 2 adjacent parcels totaling 3 acres, a beautiful landscaped lawn, lush gardens, and mature plantings. Also featured is 270 feet of beachfront on Lagoon Pond. Built in the 1870's, this extraordinary home was once a part of the Innisfall Inn, which was a summer resort for actors, opera singers, and musicians. With many renovations and updates over the years, the original Victorian details have been thoughtfully preserved and the details of the new construction have been carefully matched. There is a charming detached bedroom/guest cottage, complete with water views, that has an attached storage shed. The location of the property affords one to easily access downtown Vineyard Haven by foot, bike, or boat . The private 270 waterfront beach is perfect for sailing, swimming, kayaking, paddling, etc. The property upon which the house is located is 1.57 acres, with a 5 bedroom septic system. The adjacent parcel is 1.39 acres, and has a 4 bedroom septic system installed to facilitate the permitting of a second home. Many options exist for this truly "one of a kind" property.

Listed by Match Point Properties

$
$
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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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24 Crocker Drive Edgartown MA 02539

Edgartown, MA24 Crocker Drive

Price$4,295,000

Est. Mortgage: $/month

MLS Number 38647

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 3.5
  • Acreage 0.6438

CHIC MODERN COASTAL RETREAT IN KATAMA. Construction is nearing completion for this modern and sophisticated coastal retreat on Crocker Drive, one of the premier streets in Katama -- near The Field Club and surrounded by luxurious homes such as the 2015 HGTV Dream Home. This architect-designed home features classic New England architecture with a fresh, modern vibe -- including a coastal-inspired interior with shiplap paneling, driftwood, and bleached wood accents, plus chic modern hardware and lighting fixtures throughout. The open-designed floor plan is perfectly designed for indoor-outdoor living with a full wall of sliding glass doors that open out to an expansive stone terrace with pergola, outdoor gas fireplace, and surrounded by a beautifully landscaped and private backyard. There is also room to round-out the outdoor living space by adding a 16x32-foot gunite saltwater pool (pool is not included in the offering, however the Seller has a pool permit in-hand). The sun-filled gourmet cook's kitchen will feature high-end stainless appliances, stone countertops and a large center island with counter seating. There are three spacious bedrooms, all with en suite baths -- including a beautifully designed first-floor Primary Suite with French doors that open out to the terrace and pool, a walk-in closet and a luxurious spa-like bath. Other extras include an in-home office, Den/TV Area, wet bar area off the pool entrance, two laundry areas, and an unfinished basement level with 9-foot ceilings. This superlative property is located equidistant to Edgartown Village and South Beach and offers a wonderful opportunity to create your very own island retreat in this highly sought-after Katama location. Floor plans are attached; building specifications available upon request. NOTE: Target completion date is June, 2022 -- just in time for Summer!

Listed by Compass | Point B

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$
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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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26 North Summer Street Edgartown MA 02539

Edgartown, MA26 North Summer Street

Price$4,250,000

Est. Mortgage: $/month

MLS Number 39565

  • Residential
  • Mls Status Active
  • Bedrooms 8
  • Bathroom 5.5
  • Acreage 0.33

Located in the heart of historic downtown Edgartown on a prime commercial street lies this beautiful 1820’s Colonial building on nearly 15,000 sq. ft. of property. Patrick Ahearn’s office was retained to permit for renovations to the main residence and guest house, as well as a new pool and pool house. This property offers the rare opportunity to create a substantial in-town compound with matter of right permitting. Alternatively, this property has tremendous potential to offer the many usages allowed in the Edgartown B1 district and could provide a wonderful mix of retail, office and residential uses. There is substantial frontage on North Summer Street just a half block from Main Street. In addition, the rear of the property fronts the entire rear length of the town parking area that also offers entrances to a number of commercial businesses, including Espresso Love, 19 Raw / 19 Prime, Juniper and the Edgartown Cinemas. Please call to preview this unique opportunity.

Listed by Landvest MV

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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72 Chappaquiddick Avenue Edgartown MA 02539

Edgartown, MA72 Chappaquiddick Avenue

Price$4,200,000

Est. Mortgage: $/month

MLS Number 39511

  • Residential
  • Mls Status Active
  • Bedrooms 8
  • Bathroom 7.5
  • Acreage 3

WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a YOGA BARN, a POOL, a VOLLEY BALL COURT and a TENNIS COURT with a BASKETBALL COURT, all set upon three acres of private, expansive land with distant WATER VIEWS! The estate is spectacularly located on Sampson Hill, being the highest elevation on Chappaquiddick. The location is convenient to the Chappy ferry, the Chappy Community Center, Slip Away Farm, the hiking trails on Land Bank properties and the beaches. A true gem of a location! This Chappy Compound has been meticulously grown and maintained over the years through architectural design, professional decorating and professional landscaping. The Yoga Barn was recently constructed in 2022. It has a light airy feeling with its cathedral ceiling, light colored wood and abundance of natural light streaming into its interior space. An interior barn door separates the space into two work out areas. The architecturally designed Guest House was constructed in 2018 with year round living as an option. It was designed with an open floor plan and an abundance of outdoor living spaces to make this Guest House live large. The fun Pool House sports a wooden beamed cathedral ceiling with a large open lounge area, kitchenette and bath, overlooking the Pool and Yoga Barn. The interplay between the Yoga Barn, Pool House, Pool and abutting Tennis Court makes this Chappy Compound fun and playful!

Listed by Vineyard Village Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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26 Morse Street Edgartown MA 02539

Edgartown, MA26 Morse Street

Price$4,200,000

Est. Mortgage: $/month

MLS Number 38332

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.1774

Beautifully restored 4 bedrooms 3.5 bath 1840 In Town Edgartown Home... Pease Simpson House. In the Historic District. Original wood floors. One first floor bedroom with private bath. Second floor Master with ensuite bath with standing tub and two additional bedrooms and full bath. This home was gutted and renovated in 2016 both inside and out. All new electrical, plumbing, double paned windows with wood sashes, roof (35 year) shingles, *siding, *shutters, bathrooms, plaster and mechanicals. Lovely fir deck accessed from dining room and upscale kitchen with pantry, laundry room and half bath. Outdoor shower (cedar). Irrigation. Central Air. All fireplaces are relined. Separate shed and outdoor shower in yard. Lovely gardens with stone border with a little room to be creative. Propane FHW and FHA systems.

Listed by Martha's Vineyard Seacoast Properties

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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42 Road to the Plains Edgartown MA 02539

Edgartown, MA42 Road to the Plains

Price$4,195,000

Est. Mortgage: $/month

MLS Number 39591

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 4.5
  • Acreage 0.5

NEW CONSTRUCTION. Currently in-progress 6 bedroom home in Katama with 14 by 36 pool. Located ideally in Katama, with easy access to South Beach, downtown Edgartown, Morning Glory Farm, Vineyard Golf Club and more, this custom home built by Hess Construction & Renovation is designed with two primary suites, an additional four large bedrooms, and dramatic common areas that lend naturally to indoor/outdoor and comfortable year-round living. The huge open kitchen with island features extensive cabinetry, stainless steel Thermador appliances, quartz counters, and more. Jutting out toward the private south-facing backyard/pool area is a 24’ by 20’ great room with beamed cathedral ceiling, and huge windows/glass doors. Wood floors throughout are 8” knotty white oak. All bathrooms will be luxuriously fitted with tile floors, marble counters, and spa-like fixtures. Professional landscaping will include propane heated pool with bluestone edging, irrigated lawn and garden beds, peastone driveway, and more. Room for pool house or garage/carriage house. Partially finished basement includes utilities, storage and finished rec. room. Some images are renderings, finish samples or in-progress construction photos (subject to change). Some finish and landscape choices may be modified prior to delivery - estimated completion by July 2022.

Listed by Compass | MV Team

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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"Based on information submitted to MA_LINKMV as of May 22, 2022 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing."