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$6,350,000

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345 Windswept Way, Osterville, MA 02655

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5 Beds

8 Baths

6,104 Sq Ft

A rare opportunity to own one of the most elegantly appointed, custom built homes on Oyster Harbors. This 5+ bedroom, 8 bath residence is sure to impress with its state-of-the art Savant systems, its outstanding craftsmanship and the high quality materials used. On entering the front foyer, you are struck by its spaciousness and the grandeur of the finish work. The living room with its 10' ceilings, handsome gas fireplace and French doors opening onto the bluestone patio is elegant and inviting. The gleaming quarter sawn oak floors take you through the formal dining room and into the Great room and Chef's kitchen. The stone and tile work are superb and the appliances are top rated. The primary bedroom, en suite bathroom, dressing area and Endless indoor pool are in another wing of the home. Adjacent is a lovely en suite guest room. There is a handsome wood paneled library/study with custom features and a gas fireplace. Upstairs are 3 large en suite bedrooms. The sunroom facing the pool and cabana is another appealing feature. The home is adjacent to the club golf course and is surrounded by expansive lawns and specimen plantings, providing a lush privacy. Deeded beach rights.

Listing By: Maureen C Carven - Kinlin Grover Compass maccia Realty.com

MLS# 22205083
Date Listed09/23/2022
Bedrooms 5
Bathrooms 6 Full baths, 2 Half baths
Lot Size 1.69 acres (73,616 sq. ft)
Sewer Private Sewer
Subdivision Oyster Harbors
Property Type Single Family
County Barnstable
Year Built 2012
Water Private, Well
Square Feet 6,104 sq. ft
Price Per Sq. Ft $1040.3

Interior Features

Appliances Tankless Water Heater
Flooring Hardwood, Tile
Cooling Central Air
Heating Forced Air

Exterior / Lot Features

Exterior Garden, Outdoor Shower, Pool House, Outbuilding
Roof Wood
Lot Size Acres 1.69
Lot Size SQFT 73,616.00
Lot Features On Golf Course, Near Golf Course, Level

Directions

Stop at gate to Oyster Harbors. Go straight, then bear right, pass in front of Club. Take rt on Windswept Way. Take first right into driveway

Financial Considerations

HOA Fee $4,000 Annually
Tax Amount $28,728
Terms Cash, Conventional, FHA, VA Loan

Nearby Schools

Source: School Digger

Enoch Cobb Early Learning Center

Public • PK - PK • Serves this home

8.19 mi

Distance

Barnstable United Elementary School

Public • 4 - 5 • Serves this home

5.02 mi

Distance

Barnstable High School

Public • 8 - 12 • Serves this home

8.19 mi

Distance

Enoch Cobb Early Learning Center

Public • PK - PK • Serves this home

8.19 mi

Distance

Barnstable United Elementary School

Public • 4 - 5 • Serves this home

5.02 mi

Distance

Barnstable Intermediate School

Public • 6 - 7

8.67 mi

Distance

Barnstable High School

Public • 8 - 12 • Serves this home

8.19 mi

Distance

Sales & Tax History

Source: Public Records

Year	Total Assessments
2023	$45,000
2020	$46,100
2019	$50,100
2018	$52,200
2017	$54,200
2015	$58,100
2014	$60,100

Date	Event	Price
12/16/2022	Sold	$5,850,000.00 7.87%
10/14/2022	Pending	$6,350,000.00
09/23/2022	Active	$6,350,000.00

Street Address	Beds	Baths	Sold Date	List Price	Valuation Date	Valuation Price
1326 Main Street \| Listing	5	3	Oct 25, 2025	$1,395,000	Mar 21, 2024	$1,830,088
307 Ocean View Avenue	6	6	Oct 25, 2025	$6,195,000	Dec 09, 2025	-
473 Grand Island Drive \| Listing	5	6	Oct 24, 2025	$3,495,000	Dec 09, 2025	-
41 Keela Road	4	2	Oct 25, 2025	$819,000	Dec 09, 2025	-
1160 Main Street \| Listing	3	3	Oct 25, 2025	$1,050,000	Jan 24, 2024	$1,576,124
1000 Main Street \| Listing	3	4	Oct 25, 2025	$2,695,000	Mar 21, 2024	$3,398,293
72 Oceanview Avenue \| Listing	5	5	Oct 25, 2025	$2,475,000	Mar 21, 2024	$3,117,873
292 Grand Island Drive \| Listing	6	6	Oct 25, 2025	$3,400,000	Feb 23, 2024	$3,326,352
10,20,21 Scallop Path \| Listing	9	9	Oct 25, 2025	$19,800,000	Dec 09, 2025	-
186 Windswept Way \| Listing	8	8	Oct 24, 2025	$15,495,000	Dec 09, 2025	-

Population & Environment

Source: Sperling's Best Places

	Zip	City	County	National
Population	3,538	3,538	224,793	335,858,263
Population Density	548	548	571	95
People per Household	2.1	2.1	2.2	2.6
Median Age	55.1	55.1	52.5	39.1
Median Income	$94,261	$94,261	$78,548	$66,222
Average Income	$73,021	$73,021	$47,040	$35,475
Cost of Living Index	100	100	101	100

	Zip	City	County	National
January Avg. High Temp	21.2°F	21.2°F	21.2°F	22.6°F
July Avg. High Temp	77.8°F	77.8°F	77.8°F	86.2°F
Annual Precipitation	43.03"	43.03"	43.03"	38"

...

Walkability in MA / 02655

Source: Walkscore

5/100

Car-Dependent

Walk Score ®

26/100

Bikable

Bike Score ®

Overview

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 11/100, Transit Score: 3/100, Bike Score: 24/100.

Property Change History

24 Oct 2025

Property Interior Features updated

View Changes

Previous Value:

Walk-In Closet(s), Sound System, Sauna, Recessed Lighting, Pantry

Updated Value:

Sound System, Recessed Lighting, Pantry, Walk-In Closet(s)

Points of Interest near 345 Windswept Way, Osterville, MA 02655

Oyster Harbors Club, Barnstable Town, MA, USA

Recreation • Entertainment

0.41 mi

Distance

Rokeby Farms, Barnstable Town, MA, USA

Recreation

0.47 mi

Distance

Cr #30, Barnstable Town, MA, USA

Recreation

0.48 mi

Distance

Sampsons Island Sanctuary, Barnstable Town, MA, USA

Recreation

0.56 mi

Distance

Oyster Harbors Beach, Barnstable County, MA, USA

Natural • Recreation

0.63 mi

Distance

Sampsons Island, Barnstable Town, MA, USA

Recreation

0.68 mi

Distance

Ropes Beach, Barnstable Town, MA, USA

Natural • Recreation

0.8 mi

Distance

Oyster Harbors Beach, Barnstable County, MA, USA

Natural • Recreation

0.63 mi

Distance

Ropes Beach, Barnstable Town, MA, USA

Natural • Recreation

0.8 mi

Distance

Oyster Harbors Club, Barnstable Town, MA, USA

Recreation • Entertainment

0.41 mi

Distance

Oyster Harbors Clubhouse, Barnstable Town, MA, USA

Professional

0.43 mi

Distance

Parsonage of Cotuit Federated Church, Barnstable Town, MA, USA

Religion

0.86 mi

Distance

Noisy Point, Barnstable Town, MA, USA

0.39 mi

Distance

Cotuit Bay, Barnstable Town, MA, USA

0.47 mi

Distance

Tims Point, Barnstable Town, MA, USA

0.52 mi

Distance

Tims Cove, Barnstable Town, MA, USA

0.53 mi

Distance

Bluff Point, Barnstable Town, MA, USA

0.63 mi

Distance

Handy Point, Barnstable Town, MA, USA

0.64 mi

Distance

Cotuit Town Dock, Barnstable Town, MA, USA

0.78 mi

Distance

Little River, Barnstable Town, MA, USA

0.78 mi

Distance

Oyster Lane Road Landing, Barnstable Town, MA, USA

0.78 mi

Distance

Guest House, Barnstable Town, MA, USA

0.81 mi

Distance

CMYC Pier (private), Barnstable Town, MA, USA

0.85 mi

Distance

Frequently Asked Questions for 345 Windswept Way

Source: Realty.com

345 Windswept Way, Osterville, MA 02655 is a Single Family 6,104 sq. ft. home listed for sale. Realty.com has 66 photos available of this 5 bed, 8 bath house, listed at $6,350,000. View sales and tax history, use our mortgage calculator and more on Realty.com

Realty.com has 66 photos of 345 Windswept Way.

Our records indicate that 345 Windswept Way was built in 2012.

The full address for this home is 345 Windswept Way, Osterville, MA 02655.

345 Windswept Way has been listed on Realty.com since Fri September 23, 2022

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 11/100, Transit Score: 3/100, Bike Score: 24/100.

There are 3 schools assigned to this home. Check out the schools near 345 Windswept Way. Enoch Cobb Early Learning Center (Grades: PK - PK), Barnstable United Elementary School (Grades: 4 - 5), Barnstable High School (Grades: 8 - 12)

Listing provided courtesy of: Kinlin Grover Compass (tel: 508-420-1130)
Listing agent: Maureen Carven (tel: 781-249-2188) (#U5289)

This content last refreshed on 2025-12-09 04:55:23. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

Export listing data of 345 Windswept Way, Osterville, MA 02655 : MLS# 22205083

345 Windswept Way, Osterville, MA 02655

Interior Features

Exterior / Lot Features

Directions

Financial Considerations

Nearby Schools

8.19 mi

5.02 mi

8.19 mi

8.19 mi

5.02 mi

8.67 mi

8.19 mi

Sales & Tax History

Population & Environment

Walkability in MA / 02655

Car-Dependent

Bikable

Overview

Walkability averages in the surrounding area

Previous Value:

Updated Value:

Nearby Properties

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