Photo 1 at 96 Winterhoff Trail, Brewster, MA 02631

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Map location of 96 Winterhoff Trail, Brewster, MA 02631

$3,670,000

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96 Winterhoff Trail, Brewster, MA 02631

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4 Beds

6 Baths

5,874 Sq Ft

RARE BAYSIDE COMPOUND, splendidly sited to maximimize sweeping views of Cape Cod Bay while minimizing erosion. Airy main house plus new free-standing guest quarters. Grounds enhanced by mature landscaping & profuse native beach plum. 4 Bedroom (4500 sq. ft) Main house sports open floor plan dressed in walls of glass. Easy flow for entertaining encouraged by generous kitchen, multiple fireplaces & sprawling decks. Stroll barefoot to your sandy beach. 1st Fl Master offers two baths appointed w whirlpool, stall shower, bidet, generous dressing room & deck access. 2nd story loft. Beach level houses family room, addl bedrooms & baths. Separate entry suite above garage PLUS a charming 1372 sf 2 bedroom guest house. Invite the whole crowd! [See MLS# 21409508 for details on the guest house, only sold in tandem w main house] $3,670,000 for both.

Listing By: Hardman-Liberles Team - oldCape Sotheby's International Realty maccia Realty.com

MLS# 21409144
Date Listed09/30/2014
Bedrooms 4
Bathrooms 5 Full baths, 1 Half baths
Lot Size 1.1 acres (47,916 sq. ft)
Property Type Single Family
County Barnstable
Year Built 1986
Water Public
Square Feet 5,874 sq. ft
Price Per Sq. Ft $624.79

Interior Features

Flooring Wood, Carpet, Tile
Cooling Central Air
Heating Hot Water, Other

Exterior / Lot Features

Exterior Outdoor Shower, Other, Outbuilding
Roof Asphalt
Lot Size Acres 1.10
Lot Size SQFT 47,916.00
Lot Features On Golf Course, Near Golf Course, Level, Waterfront

Directions

From 6A, take Point of Rocks Road. Left onto Pilgrim Pine. Right onto Winterhoff Trail to #96 on your right.

Financial Considerations

Tax Amount $17,459
Terms Cash, Conventional, FHA, VA Loan

1.5 mi

Distance

Sales & Tax History

Source: Public Records

Street Address	Beds	Baths	Sold Date	List Price	Valuation Date	Valuation Price
253 Point Of Rocks Road	3	2	Oct 24, 2025	$689,000	Dec 10, 2025	-
187 Breakwater Road \| Listing	4	2	Oct 25, 2025	$850,000	Mar 15, 2024	$1,149,000
83 Williams Drive	4	3	Oct 25, 2025	$599,000	Dec 10, 2025	-
24 Old North Road	2	1	Oct 25, 2025	$549,900	Dec 10, 2025	-
30 Bog Pond Road \| Listing	5	3	Oct 25, 2025	$840,000	Mar 21, 2024	$1,605,285
25 Bog Pond Road \| Listing	3	3	Oct 25, 2025	$825,000	Mar 21, 2024	$1,461,497
195 Cathedral Road \| Listing	4	4	Oct 25, 2025	$1,749,000	Mar 21, 2024	$1,931,209
48 Foster Road \| Listing	4	2	Oct 25, 2025	$750,000	Sep 25, 2024	$852,080
237 Crocker Lane	4	4	Oct 24, 2025	$3,675,000	Dec 10, 2025	-
94 Clipper Way \| Listing	3	2	Oct 25, 2025	$749,000	Mar 21, 2024	$904,074

Population & Environment

Source: Sperling's Best Places

	Zip	City	County	National
Population	11,132	11,274	224,793	335,858,263
Population Density	503	493	571	95
People per Household	2.2	2.2	2.2	2.6
Median Age	56.6	56.5	52.5	39.1
Median Income	$80,637	$80,570	$78,548	$66,222
Average Income	$49,898	$49,891	$47,040	$35,475
Cost of Living Index	101	101	101	100

	Zip	City	County	National
January Avg. High Temp	24°F	24°F	21.2°F	22.6°F
July Avg. High Temp	74.6°F	74.6°F	77.8°F	86.2°F
Annual Precipitation	46.71"	46.71"	43.03"	38"

...

Walkability in MA / 02631

Source: Walkscore

13/100

Car-Dependent

Walk Score ®

20/100

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: 0/100, Bike Score: 25/100.

Property Change History

25 Oct 2025

Property Lot Features updated

View Changes

Previous Value:

Sloped, On Golf Course, Near Golf Course, Gentle Sloping, Views, Level, Waterfront

Updated Value:

On Golf Course, Near Golf Course, Level, Waterfront

Points of Interest near 96 Winterhoff Trail, Brewster, MA 02631

Myricks Pond, Brewster, MA, USA

Natural • Recreation

0.29 mi

Distance

Point of Rocks Landing Beach, Brewster, MA, USA

Natural • Recreation

0.34 mi

Distance

Paine Lot, Brewster, MA, USA

Recreation

0.41 mi

Distance

Priest Lot, Brewster, MA, USA

Recreation

0.46 mi

Distance

Price Lot, Brewster, MA, USA

Recreation

0.48 mi

Distance

Labrecque Cr, Brewster, MA, USA

Recreation

0.5 mi

Distance

Stonehedge, Brewster, MA, USA

Recreation

0.63 mi

Distance

Shaw Lot, Brewster, MA, USA

Recreation

0.68 mi

Distance

Brewster Coffee Shop, Brewster, MA, USA

Food • Retail • Nightlife

0.49 mi

Distance

Brewster Fish House, Brewster, MA, USA

Food • Retail • Nightlife

0.54 mi

Distance

The Island Blue Crab, Brewster, MA, USA

Food • Retail • Nightlife • Professional

0.62 mi

Distance

Myricks Pond, Brewster, MA, USA

Natural • Recreation

0.29 mi

Distance

Point of Rocks Landing Beach, Brewster, MA, USA

Natural • Recreation

0.34 mi

Distance

Brewster Coffee Shop, Brewster, MA, USA

Food • Retail • Nightlife

0.49 mi

Distance

Brewster Fish House, Brewster, MA, USA

Food • Retail • Nightlife

0.54 mi

Distance

The Island Blue Crab, Brewster, MA, USA

Food • Retail • Nightlife • Professional

0.62 mi

Distance

Brewster Coffee Shop, Brewster, MA, USA

Food • Retail • Nightlife

0.49 mi

Distance

Brewster Fish House, Brewster, MA, USA

Food • Retail • Nightlife

0.54 mi

Distance

The Island Blue Crab, Brewster, MA, USA

Food • Retail • Nightlife • Professional

0.62 mi

Distance

Mobil, Brewster, MA, USA

Transport • Professional

0.51 mi

Distance

The Island Blue Crab, Brewster, MA, USA

Food • Retail • Nightlife • Professional

0.62 mi

Distance

Mobil, Brewster, MA, USA

Transport • Professional

0.51 mi

Distance

Drummer Boy Museum, Brewster, MA, USA

Education • Entertainment

0.61 mi

Distance

Drummer Boy Museum, Brewster, MA, USA

Education • Entertainment

0.61 mi

Distance

Brewster Town Hall, Brewster, MA, USA

Government

0.64 mi

Distance

Point Of Rocks Beach, Brewster, MA, USA

0.34 mi

Distance

Breakwater Beach, Brewster, MA, USA

0.43 mi

Distance

Town Hall Fields, Brewster, MA, USA

0.54 mi

Distance

Breakwater Landing, Brewster, MA, USA

0.57 mi

Distance

Foster Cemetery, Brewster, MA, USA

0.6 mi

Distance

Community Center, Brewster, MA, USA

0.64 mi

Distance

Frequently Asked Questions for 96 Winterhoff Trail

Source: Realty.com

96 Winterhoff Trail, Brewster, MA 02631 is a Single Family 5,874 sq. ft. home listed for sale. Realty.com has 34 photos available of this 4 bed, 6 bath house, listed at $3,670,000. View sales and tax history, use our mortgage calculator and more on Realty.com

Realty.com has 34 photos of 96 Winterhoff Trail.

Our records indicate that 96 Winterhoff Trail was built in 1986.

The full address for this home is 96 Winterhoff Trail, Brewster, MA 02631.

96 Winterhoff Trail has been listed on Realty.com since Tue September 30, 2014

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: 0/100, Bike Score: 25/100.

There are 3 schools assigned to this home. Check out the schools near 96 Winterhoff Trail. Stony Brook Elementary School (Grades: PK - 2), Eddy Elementary School (Grades: 3 - 5), Cape Cod Region Vocational Technical (Grades: 9 - 12)

Listing provided courtesy of: oldCape Sotheby's International Realty (tel: 5082556000)
Listing agent: Whitaker Group Cape Cod (#T31)

This content last refreshed on 2025-12-10 12:00:46. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

Export listing data of 96 Winterhoff Trail, Brewster, MA 02631 : MLS# 21409144

96 Winterhoff Trail, Brewster, MA 02631

Interior Features

Exterior / Lot Features

Directions

Financial Considerations

Nearby Schools

1.22 mi

1.22 mi

6.13 mi

1.22 mi

1.22 mi

6.53 mi

7.04 mi

8.22 mi

6.13 mi

1.5 mi

Sales & Tax History

Population & Environment

Walkability in MA / 02631

Car-Dependent

Bikable

Overview

Walkability averages in the surrounding area

Previous Value:

Updated Value:

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