oak bluffs Homes with Shingle Style

Welcome to Oak Bluffs, a picturesque gem nestled in Dukes County, Massachusetts, on the enchanting island of Martha’s Vineyard. Known for its vibrant history and stunning coastal scenery, Oak Bluffs is a delightful blend of charming homes, beautiful beaches, and a rich cultural tapestry that makes it a sought-after destination for both residents and visitors alike.

One of the most captivating features of Oak Bluffs is its iconic Shingle Style architecture. These homes, characterized by their wooden shingles and sweeping rooflines, evoke a sense of timeless elegance and coastal charm. As you stroll through the tree-lined streets, you’ll be enchanted by the intricate details and unique designs of these homes, each telling its own story while harmonizing beautifully with the natural landscape.

Oak Bluffs is not just about stunning architecture; it boasts a lively community spirit. Enjoy the vibrant arts scene, with galleries and theaters showcasing local talent, or indulge in the culinary delights offered by a variety of restaurants, from casual seafood shacks to fine dining establishments. The town is also home to the famous Flying Horses Carousel, a historic landmark that adds a whimsical touch to the experience.

For those who appreciate outdoor activities, Oak Bluffs offers an array of options, from scenic bike rides along the coastline to sun-soaked days on the sandy beaches. With its welcoming atmosphere, rich history, and stunning Shingle Style homes, Oak Bluffs is truly a slice of paradise in Massachusetts. Whether you’re looking to buy a home or simply explore, Oak Bluffs invites you to discover its unique charm and beauty.

Newest oak bluffs Homes with Shingle Style

$625,000

2 Beds ⋅ 3 Baths ⋅ 73600575 MLS ⋅ ['Kings Way'] BLDG.

Natural light and peaceful surroundings welcome you to this inviting A-style Kings Way condominium. A charming brick walkway leads to the front entrance, where windows and sliders draw your eye toward the wooded backyard. The sun-filled eat-in kitchen overlooks the landscaped front entry and offers convenient access from the attached two-car garage. The formal dining room opens to a spacious living room with vaulted ceilings, a gas fireplace and sliders leading to a private deck with wooded views. Designed for comfortable one-floor living, the main level also features a primary ensuite with a walk-in closet and linen closet, a second bedroom, full bath and convenient laundry. The finished walkout lower level, with fresh paint & new carpeting, offers wonderful additional living space, including a family room with a bar, office, third full bathroom, walk-in closet and unfinished storage area. Sliders open directly to the backyard. Kings Way offers a wonderful lifestyle with an 18-hole executive golf course, swimming pool, tennis and pickleball courts, an on-site Italian restaurant & lounge, post office, and beautifully maintained grounds.

3 John Hall Cartway Unit 3, Yarmouth

$712,000

2 Beds ⋅ 2 Baths ⋅ 73598645 MLS ⋅ ['Wianno Knoll'] BLDG.

Welcome to the lovely Unit G2 at sought-after Wianno Knoll, and enjoy this beautifully appointed seaside village retreat ideally situated in the heart of Osterville Village. This gorgeous first floor condominium offers an inviting blend of comfort, style, and convenience. The bright, airy open concept floor plan features gleaming hardwood floors, a cozy fireplace and a welcoming great room for comfortable living. A gracious dining room with sliding glass doors leads to a sun-filled balcony, perfect for relaxing, overlooking the beautifully landscaped grounds. The thoughtfully designed custom kitchen with the latest appliances and ample storage is ready to inspire the family chef or host to create memorable holiday gatherings. A private primary en-suite bedroom and a lovely guest room, with easy access to a beautifully renovated full bath offer space for you and your guests. A full laundry and abundant storage including custom closets provide convenience and ease, and an additional large basement storage room has easy indoor access. Convenient parking is directly in front with additional spaces available for guests. Armstrong-Kelley Park, Dowses Beach, and the Village’s many restaurants and shops are steps away for your exploration and enjoyment. Come experience the best of the Cape Cod lifestyle!

727 Main St Unit G2, Barnstable

$599,000

3 Beds ⋅ 2 Baths ⋅ 73597386 MLS

Set back from Route 28A on a private acre in Cataumet, this 3-bedroom, 1.5-bath home offers one-floor living with an open floor plan connecting the living, kitchen, and dining areas. A two-car attached garage and large barn/shed provide additional storage for vehicles or boats. Three spacious bedrooms offer flexibility for family, guests, or a home office, while the full unfinished basement provides even more storage and potential for future use. The interior is a work in progress waiting for the buyer to finish with their personal touches. The home needs floors, paint and other finish details. The large yard enjoys a deck in the backyard which is partially fenced. Drive off the busy road way back to this oasis and come see for yourself. Roll up your sleeves and bring your imagination and make this Cataumet property home. Priced to sell and being offered as-is, this home is ready for its next chapter.

26 Route 28 A, Bourne

$2,950,000

4 Beds ⋅ 4 Baths ⋅ 22605525 MLS

NEW HOME TO BE BUILT CLOSE TO THE BEACH AND MARINIA.THE PROPERTY IS ALSO APPROVED FOR A ONE-BEDROOM ACCESSARY DWELLING UNIT.THIS IS A GREAT PROPERTY FOR A LARGE FAMILY WITH THE POTENTIAL FOR AN IN-LAW APARTMENT OR AS AN ADDITIONAL RENTAL UNIT.

43-49 South Street, Dennis

$825,000

2 Beds ⋅ 4 Baths ⋅ 73595938 MLS ⋅ ["Pinehills - Winslowe's View"] BLDG.

Welcome to refined living in Winslowe’s View, one of The Pinehills’ most desirable neighborhoods. Set in a peaceful, private setting with picturesque golf course views, this beautifully maintained 2+ bedroom (which really lives like a 3 bedroom), 3.5-bath home offers three finished levels of living space, quality upgrades, and exceptional indoor-outdoor living. The main level features hardwood floors, soaring vaulted ceilings, recessed lighting, plantation shutters, and upgraded window treatments. The spacious, light-filled great room flows into a well-appointed kitchen with granite countertops and premium Bosch appliances. A separate den with a fireplace and slider opens to the private courtyard, creating a comfortable space to relax or entertain. The primary suite features a dramatic soaring ceiling, generous closet space, and a private bath with linen storage. Upstairs, a versatile loft provides space for a home office or reading area, complemented by a bedroom and full bath. The beautifully finished lower level adds even more flexibility, with plush carpeting, recessed lighting, a full bath, ample storage, and a large walk-in cedar closet. Outdoor living is a standout feature, with a mahogany deck and motorized retractable awning, two patios, a private courtyard, and mature landscaping with established perennial gardens. Stairs connect the upper outdoor living area and the secluded backyard, creating multiple spaces to enjoy the peaceful surroundings and golf course views. Additional highlights include three heating and cooling zones, a water heater replaced in 2023, and a 2-car garage with painted flooring. The home has also benefited from extensive exterior improvements, with the siding, trim, vapor barrier, gutters, roof, sliders and front storm door recently replaced. Enjoy the privacy of a setting with no immediate neighbors directly in front or behind, along with the resort-style amenities and community events that make The Pinehills such a special place to call home.

11 Pelham Walk Unit 11, Plymouth

$539,900

2 Beds ⋅ 2 Baths ⋅ 73595904 MLS

WATERVIEW!! Welcome to 2 Wind Rose Lane! Whether you’re buying your first home, simplifying your lifestyle, or looking for a relaxing getaway, this property is full of possibilities! This charming 2-bed,1.5-bath cape offers a peaceful setting with pond views of Wall Pond. The inviting first floor offers a comfortable open feel with hardwood flooring, a spacious living room with views of the pond, a dining area with fireplace, and a well-appointed kitchen with updated cabinetry, countertops, gas cooking stove and new appliances. A convenient first-floor office or 3rd bedroom along with brand new full bathroom add functionality. Upstairs, the primary bedroom, half bath, and additional bedroom provide comfortable private space. 2026 Improvements include a new first-floor bathroom, where sophisticated design meets exquisite tile, new roof, exterior paint, new oil and propane tanks, new septic system, new high-efficiency washer/dryer and appliances. Additional highlights include a high-efficiency exhaust fan, LED/Bluetooth/anti-fog bathroom mirror and Wi-Fi whole-home security/intercom system. The full walk-out basement offers additional potential and storage. Conveniently located in South Plymouth with easy access to Plymouth amenities and Cape Cod. Wall Pond Association with rights to Big Sandy Pond.

2 Wind Rose Lane, Plymouth

$2,875,000

4 Beds ⋅ 5 Baths ⋅ 73594795 MLS

Set on 4.9 acres surrounded by the natural beauty of Chappaquiddick, this residence offers approximately 2,900 square feet of living space, quality craftsmanship, and a private setting. The home features three bedrooms, including a first-floor primary suite with a private bath. Upstairs, two additional bedrooms each have ensuite baths. The living room features soaring cathedral ceilings finished in tongue-and-groove wood and a wood-burning fireplace. Custom interior doors and detailed woodwork are found throughout, while the kitchen is appointed with high-end appliances and custom Neff cabinetry.The enclosed, year-round porch features tongue-and-groove ceilings, slate flooring, and a wood-burning fireplace, providing additional living space in every season. A mahogany deck overlooks the surrounding property. Above the detached garage is an additional bedroom and full bath, offering flexibility for guests, a home office, or studio. A new Mitsubishi inverter-technology heating and cooling system, installed in 2026, features six independently controlled zones, with heating and cooling extending to the basement and enclosed porch. Owned solar panels provide a net $100.00 per month positive utility bill. There is an 8 bedroom septic system and so expansion opportunities are plenty. Approximately one acre of the property is located across Litchfield Road, offering potential for a future guest house or accessory dwelling unit (ADU), subject to applicable approvals. Located on Chappaquiddick, the property offers convenient access to beaches, conservation trails, and the natural surroundings that define Chappy, all just a short ferry ride from downtown Edgartown.

91 Litchfield Rd, Edgartown

$1,395,000

3 Beds ⋅ 3 Baths ⋅ 73594346 MLS

Premier South Shore Builder Eric Pontiff offering The Cottages at Old Oaken Bucket, 24 new standalone single family style homes within a condo community. This homesite offers a walkout basement w/slider in a peaceful private setting. Relax in Scituate’s newest neighborhood convenient to all amenities including Greenbush commuter rail, shopping, schools, beaches. Traditional New England architecture combines with a modern open concept for easy living and appeal to all ages. The welcoming front porch opens to a spacious kitchen and living/dining area with gas fireplace plus the 1st floor Master suite all overlooking the privacy of the backyard. All homes feature 9 FT 1st Floor Ceilings, Crown Molding, Shiplap and a great Bonus room above garage alongside the 2 - 2nd floor bedrooms. We work with you to design your perfect space with numerous choices. Reserve 8 Grace Way currently under construction in time to make your own interior design choices.

8 Grace Way Unit 8, Scituate

$1,500,000

3 Beds ⋅ 3 Baths ⋅ 22605330 MLS

Set in an extraordinary 3.11-acre setting on Little Hog Pond, this architecturally designed residence offers an exceptional blend of craftsmanship, privacy, and relaxed Cape Cod living. Ideally positioned between The Ridge Club and Holly Ridge, it is a true golfer's paradise, surrounded by some of the area's most coveted amenities. Thoughtfully designed and constructed by respected local builder Peter Poretti, the home reflects a commitment to quality and enduring detail. The inviting interior features 3 bedrooms plus a home office, while the kitchen flows into a family room anchored by a fireplace and custom built-ins. Walls of windows bring the surrounding landscape indoors, while a screened porch and open deck provide the perfect vantage points from which to savor the serene pond views, lush landscaping, and changing seasons. A green house accessed from the home would please any gardener. For the hobbyist, collector, or auto enthusiast, an extraordinary detached second garage adds another dimension to this unique property. Heated and A/C on 2 floors, the spacious structure can accommodate up to four vehicles while offering exceptional room for a workshop, studio, or ADU. Second Detached Garage accommodates 4 or more autos! Ideal for the hobbyist or collector.

122 Country Club Road, Sandwich

$3,950,000

5 Beds ⋅ 5 Baths ⋅ 73592553 MLS

Welcome home to this meticulously renovated Martha's Vineyard property, where coastal elegance meets effortless indoor-outdoor living. Offered fully furnished, "turn-key" ready and spanning over 4,200 square feet of beautiful living space, this property offers a total of 5 bedrooms and 4.5 baths between the main house and detached 1 bedroom guest suite. In the main house, the spacious great room boasts cathedral ceilings, wood-burning fireplace, and glass doors that seamlessly connect the interior to the outdoors. The custom kitchen is outfitted with an expansive granite center island, stainless steel appliances and a generous dining area. The private primary retreat includes a custom walk-in closet and en suite bath, featuring a double sink vanity and a walk-in shower with dual shower heads. 3 private guest rooms and 2 additional full baths, located on a separate floor, ensure plenty of privacy for everyone. The finished basement offers approximately 670 square feet of additional living space to the main house and is perfect for entertaining, complete with a custom bar, built-in cabinetry, and a half bath. The detached 1 bedroom and 1 bath guest suite is located above the oversize 2-bay garage and is ideal for extended family and friends. This beautifully appointed space features an open floor plan, high-end materials throughout and a large private deck. From the moment you arrive, the professionally landscaped grounds invite you to enjoy everything this property has to offer. With dedicated outdoor entertaining areas, multiple decks, outdoor tv, firepit and hot tub, the space is perfectly designed for both grand hosting and quiet relaxation. This exceptional property checks off all the boxes for the perfect Vineyard home.

6 Hollow Way, Edgartown

$2,250,000

5 Beds ⋅ 2 Baths ⋅ 22605333 MLS

Set high on a bluff in the heart of Falmouth Heights, this bright and inviting five-bedroom ocean view retreat captures extraordinary 180-degree views across Vineyard Sound toward Martha's Vineyard and Nantucket Sound. Walls of glass frame the water from throughout the home, while multiple porch and deck areas create wonderful places to relax, dine, and take in the ever-changing coastal scenery. Designed for effortless family living and entertaining, the two-story home features two kitchens, generous gathering spaces, central air conditioning, and a flexible layout ideal for hosting family and friends. Step outside and the best of Falmouth Heights is right at your doorstep, with the beach just moments away, nearby restaurants within easy reach, and expansive green space behind the property offering access to ball fields, soccer, basketball, and other recreational amenities. The location is especially memorable during two of Falmouth's signature summer traditions. The town's spectacular Fourth of July fireworks are launched from a barge directly offshore, offering a remarkable front-row view from the property, while the world-renowned Falmouth Road Race passes by.

331 Grand Avenue, Falmouth

$3,249,000

3 Beds ⋅ 4 Baths ⋅ 22605318 MLS

Pool days, outdoor dinners, and evenings by the fire—this West End home brings it all together, tucked behind a front yard of lush, mature plantings. The backyard centers on a heated saltwater pool with hot tub and cold plunge and a granite dining table with fire feature. Inside, vaulted ceilings, new hardwood floors, and designed lighting frame an expansive living area, with a wall of glass opening to the outdoors. The reimagined kitchen offers dramatically veined natural stone counters, luxury appliances, and an oversized island, with a nearby office. Three bedrooms and 3.5 baths include two primary suites, each with a steam shower. The main-level suite opens to the yard; a guest bedroom, half bath, and mudroom complete the floor. Upstairs, the larger primary suite adds a den and private deck. The finished ground floor offers a full bath, gym, guest overflow, and ample storage. From a quiet morning by the pool to a full house for dinner, there's room here to enjoy Provincetown.

75 Franklin Street, Provincetown

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oak bluffs Homes with Shingle Style

Newest oak bluffs Homes with Shingle Style

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