421 Main St
Osterville, MA 02655
Osterville
9 Beds
10 Baths
11,578 sqft (on 5.46 acres)
9 Beds
10 Baths
11,578 sqft
(on 5.46 acres)
Local Information
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Description
Overlooking the beautiful waters of East Bay and Nantucket Sound sits this sophisticated yet intimate waterfront estate. The current owners completely renovated the 11,578sf home from stem to stern with the highest grade materials and exceptional craftsmanship. Interior spaces are bathed in natural light with beautifully balanced living areas all oriented toward the water. You'll find a welcoming foyer with original wood floors, living and dining rooms with custom fireplaces, a spacious, well-equipped kitchen and a handsome library with hand pegged wood. Casual spaces for family and friends include a family room, sunroom and enclosed porch. The second level offers 2 master suites and 7 additional bedrooms. An expansive lawn, in-ground pool and scores of privacy trees dress the 5.46 acre site. A custom beach house enhances the private dock. The property offers a detached 5 car garage with a gorgeous 3 bedroom, 1,875sf carriage house above for guests and extended family.Information herein is not guaranteed or warranted and should be verified by any person who is looking at this property to purchase. Square footage, bedrooms and bathrooms do not include 1,875 sq ft guest cottage with three bedrooms and two full bathrooms.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
No Info
Outdoor
No Info
A/C
Cooling only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 421 Main St
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|---|
Levels, Entrance, & Accessibility Stories: 2 |
Interior Details Number of Rooms: 20 |
Heating & Cooling Air Conditioning |
Fireplace & Spa Fireplace |
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|---|
Year Built Year Built: 1928 |
Property Type / Style Property Type: Single Family Home |
|
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Exterior Home Features Exterior: Shingles |
Parking & Garage Parking Spaces: 5 |
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Lot Area: 5.46 acres |
Price History for 421 Main St
| Date | Price | Event | Source |
|---|---|---|---|
| 08/19/2019 | $9,950,000 | Sold | CCIMLS #21607681 |
| 07/12/2019 | $9,950,000 | Pending | Agent Provided |
| 04/08/2019 | $9,950,000 | PriceChange | Agent Provided |
| 04/06/2018 | $11,500,000 | PriceChange | Agent Provided |
| 03/03/2017 | $13,900,000 | PriceChange | Agent Provided |
| 09/26/2016 | $14,900,000 | Listed For Sale | Agent Provided |
| 01/10/1997 | $2,800,000 | Sold | N/A |
Market trends in Barnstable
Last updated April 2026
Avg. sale price
$680K $5.83KMoM
Sale-to-List Price
98.3% 0.6%MoM
Price per sq ft
$418 $3MoM
Available listings
322 87MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $97,413 |
| Assessment | $12,041,200 |
Home facts updated by county records
Comparable Sales for 421 Main St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.98 | Single-Family Home | $6,500,000 | 06/12/25 | 10 | 7 | 8,834 | |
0.98 | Single-Family Home | $6,500,000 | 06/12/25 | 10 | 7 | 8,834 | |
1.12 | Single-Family Home | $4,650,000 | 05/28/26 | 7 | 8 | 8,345 | |
0.54 | Single-Family Home | $4,200,000 | 08/08/25 | 7 | 5.5 | 4,375 | |
0.56 | Single-Family Home | $4,200,000 | 08/08/25 | 7 | 5.5 | 4,375 | |
1.29 | Single-Family Home | $10,500,000 | 12/16/25 | 6 | 5.5 | 6,830 | |
1.29 | Single-Family Home | $10,500,000 | 12/16/25 | 6 | 5.5 | 6,830 | |
1.39 | Single-Family Home | $5,600,000 | 09/02/25 | 6 | 7.5 | 6,565 | |
1.39 | Single-Family Home | $5,600,000 | 09/02/25 | 6 | 7.5 | 6,565 | |
0.88 | Single-Family Home | $3,995,000 | 06/01/26 | 5 | 4.5 | 6,239 |
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Assigned Schools
These are the assigned schools for 421 Main St.
- Barnstable High School
- 8-12
- Public
- 1581 Students
3/10GreatSchools RatingParent Rating AverageBarnstable High School has been fabulous for our son! He was at Sturgis Charter for one year and it really turned him off to school as the teachers did not make him feel welcome and were not supportive. What a difference at Barnstable! The teachers were supportive and gave him the structure he needed to succeed. Also, the variety of sports and other activities at BHS is amazing. He loved being part of various sports teams and other activities. We cannot be more thrilled with the combination of academic rigor, supportive teachers, counselors and administrators and extracurricular activities. We're glad he's a BHS Red Raider. This is the best high school on Cape Cod.Parent Review11y ago - Barnstable Intermediate School
- 6-7
- Public
- 581 Students
4/10GreatSchools RatingParent Rating AverageDecent-food isn't great, as sometimes/often hair found in it. absolutely amazing advanced academics, most teachers i've had don't remind you to turn in assignments/ didn't notify me on failed assignments. Teachers aren't great at updating grades till the last minute, admin has to announce everyday that they need to post attendance. They don't usually resolve conflicts very well.Student Review3y ago - West Villages Elementary School
- K-3
- Public
- 397 Students
8/10GreatSchools RatingParent Rating Average
No reviews available for this school. - Barnstable United Elementary School
- 4-5
- Public
- 723 Students
3/10GreatSchools RatingParent Rating AverageNo reviews available for this school. 
Check out schools near 421 Main St.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
What Locals Say about Osterville
At least 22 Trulia users voted on each feature.
91 % Say car is needed
83 % Say parking is easy
78 % Say there's wildlife
76 % Say yards are well-kept
73 % Say it's quiet
71 % Say it's dog friendly
63 % Say neighbors are friendly
63 % Say there's holiday spirit
59 % Say they plan to stay for at least 5 years
57 % Say people would walk alone at night
50 % Say kids play outside
49 % Say it's walkable to restaurants
40 % Say there are community events
38 % Say it's walkable to grocery stores
27 % Say there are sidewalks
25 % Say streets are well-lit
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
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421 Main St, Osterville, MA 02655 is a 9 bedroom, 11 bathroom, 11,578 sqft single-family home built in 1928. 421 Main St is located in Osterville, Osterville. This property is not currently available for sale. 421 Main St was last sold on Aug 19, 2019 for $9,950,000. The current Trulia Estimate for 421 Main St is $16,239,200.