370 Main Street South
Dennis, MA, 02660
$1,569,000
5 Beds
4.5 Baths
2,617 SqFt
0.88 Acres
Add
MLS #22602581 image #0MLS #22602581 image #1MLS #22602581 image #2MLS #22602581 image #3MLS #22602581 image #4MLS #22602581 image #5MLS #22602581 image #6MLS #22602581 image #7MLS #22602581 image #8MLS #22602581 image #9MLS #22602581 image #10MLS #22602581 image #11MLS #22602581 image #12MLS #22602581 image #13MLS #22602581 image #14MLS #22602581 image #15MLS #22602581 image #16MLS #22602581 image #17MLS #22602581 image #18MLS #22602581 image #19MLS #22602581 image #20MLS #22602581 image #21MLS #22602581 image #22MLS #22602581 image #23MLS #22602581 image #24MLS #22602581 image #25MLS #22602581 image #26MLS #22602581 image #27MLS #22602581 image #28MLS #22602581 image #29MLS #22602581 image #30MLS #22602581 image #31MLS #22602581 image #32MLS #22602581 image #33MLS #22602581 image #34MLS #22602581 image #35MLS #22602581 image #36MLS #22602581 image #37MLS #22602581 image #38MLS #22602581 image #39MLS #22602581 image #40MLS #22602581 image #41MLS #22602581 image #42MLS #22602581 image #43MLS #22602581 image #44MLS #22602581 image #45MLS #22602581 image #46MLS #22602581 image #47MLS #22602581 image #48MLS #22602581 image #49MLS #22602581 image #50MLS #22602581 image #51MLS #22602581 image #52MLS #22602581 image #53MLS #22602581 image #54MLS #22602581 image #55MLS #22602581 image #56MLS #22602581 image #57MLS #22602581 image #58MLS #22602581 image #59MLS #22602581 image #60MLS #22602581 image #61MLS #22602581 image #62MLS #22602581 image #63MLS #22602581 image #64MLS #22602581 image #65MLS #22602581 image #66MLS #22602581 image #67MLS #22602581 image #68MLS #22602581 image #69MLS #22602581 image #70MLS #22602581 image #71MLS #22602581 image #72MLS #22602581 image #73MLS #22602581 image #74MLS #22602581 image #75MLS #22602581 image #76MLS #22602581 image #77MLS #22602581 image #78MLS #22602581 image #79MLS #22602581 image #80MLS #22602581 image #81MLS #22602581 image #82MLS #22602581 image #83MLS #22602581 image #84MLS #22602581 image #85MLS #22602581 image #86MLS #22602581 image #87MLS #22602581 image #88MLS #22602581 image #89MLS #22602581 image #90MLS #22602581 image #91MLS #22602581 image #92
Meticulously restored circa-1840 Sea Captain’s home in the heart of the South Dennis Historic District.This landmark property offers 5 BRs and 4.5 BAs, including 2 first-floor en suite BRs that provide exceptional flexibility & convenience. The versatile floor plan is equally well suited for a private residence, multigenerational living, seasonal retreat, or hospitality use. Extensively renovated & improved over the past 2 decades, the home features a luxury chef’s kitchen w/ premium appliances & custom cabinetry, updated baths, modernized systems, mini-split heating & cooling, new roof, restored interiors, & exceptional craftsmanship throughout.Historic details including wide-board floors, exposed beams, fireplaces, built-ins, & an antique brick oven blend seamlessly w/ modern comforts.Beautifully landscaped grounds feature a covered porch, brick terrace, mature gardens, & a distinctive seashell driveway.For nearly 20 years, the property was operated as a successful bed & breakfast w/ an international clientele, & remains an actively licensed B&B property.Prime location near Bass River, beaches, marinas, golf, dining, shopping, conservation & the Cape Cod Rail Trail. The spacious chef’s kitchen has been recently & extensively renovated with upscale finishes, top line appliances, crisp white cabinetry, and thoughtful planning (including two sinks!)

This is a home designed for gathering — the kind of place where large families, grandchildren, and summer visitors naturally come together. There is room for everyone, yet the home still feels warm, intimate, and welcoming.

Outdoors, life slows down. The covered side porch overlooks a brick terrace, perennial gardens, & the wooded beauty of its shady hollow. Whether enjoying morning coffee, hosting summer gatherings, or simply listening to birdsong drifting through the trees, the setting feels remarkably peaceful & private.

Lovingly restored and extensively improved over the past two decades, the property combines historic integrity with modern comfort. Significant recent updates include a beautifully renovated kitchen, new roof, comprehensive interior & exterior painting, updated systems, mini-split heating and cooling, renovated interior spaces, new porches, exterior improvements, & artistic landscaping.

Just minutes from beaches, boating, the bike trail, restaurants, shops, & conservation land, this exceptional South Dennis property offers the very best of Cape Cod living. Located above the flood zone and close to Bass River, Nantucket Sound beaches, Cape Cod Bay beaches, bike trail, dining, shopping, and marinas, this is a rare opportunity to own one of South Dennis Village’s landmark properties.

Property Details

Price:
$1,569,000
MLS #:
22602581
Status:
Active
Beds:
5
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Jun 1, 2026
Finished Sq Ft:
2,617
Total Sq Ft:
2,617
Lot Size:
38,333 sqft / 0.88 acres (approx)
Year Built:
1840
AntiqueWoodedOutbuildingDennis-yarmouth

Ask a Question

See this Listing

Send
  

Schools

School District:
Dennis-Yarmouth

Interior

Appliances
Dishwasher, Washer, Wall/Oven Cook Top, Range Hood, Refrigerator, Gas Range, Microwave, Freezer, Gas Dryer, Gas Water Heater
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Fireplaces Total
2
Flooring
Wood
Heating
Hot Water
Interior Features
Pantry, Mud Room, Linen Closet
Laundry Features
Laundry Room, Sink, Built-Ins, First Floor
Main Level Bathrooms
3

Exterior

Architectural Style
Antique
Construction Materials
Clapboard, Shingle Siding
Exterior Features
Outdoor Shower, Garden
Fencing
Partial
Lot Features
Bike Path, Medical Facility, Major Highway, Cape Cod Rail Trail, Public Tennis, Marina, In Town Location, Conservation Area, Wooded, North of Route 28
Open Parking YN
1
Other Structures
Outbuilding
Parking Features
Shell
Parking Spots
8
Parking Total
8
Patio And Porch Features
Patio, Porch
Roof
Asphalt, Shingle, Pitched
Stories
3

Financial

Tax Year
2026
Taxes
$3,678

Map

Community

Market Summary

Current real estate data for Single Family in Dennis as of Jun 15, 2026
107
Single Family Listed
68
Avg DOM
714
Avg $ / SqFt
$1,355,765
Avg List Price

Property Summary

    370 Main Street South Dennis MA is a Single Family for sale in Dennis, MA, 02660. It is listed for $1,569,000 and features 5 beds, 5 baths, and has approximately 2,617 square feet of living space, and was originally constructed in 1840. The current price per square foot is $600. The average price per square foot for Single Family listings in Dennis is $714. The average listing price for Single Family in Dennis is $1,355,765. To schedule a showing of MLS#22602581 at 370 Main Street South in Dennis, MA, contact your Pleasant Bay Realty agent at (774) 209-1428.

Similar Listings Nearby

broker reciprocity
MLS# 22602817broker reciprocity
15 Beach Pine Road Port
Dennis, MA

$1,999,000

2.4 miles away

broker reciprocity
MLS# 22601933broker reciprocity
2 Ernst Way Port
Harwich, MA

$1,995,000

3.0 miles away

broker reciprocity
MLS# 22601406broker reciprocity
11 Joyce Circle East
Dennis, MA

$1,960,000

4.8 miles away

broker reciprocity
MLS# 22601825broker reciprocity
1014 Route 6A Port
Yarmouth, MA

$1,895,000

3.4 miles away

broker reciprocity
MLS# 22601963broker reciprocity
127 Uncle Barneys Road West
Dennis, MA

$1,825,000

2.2 miles away

broker reciprocity
MLS# 22601714broker reciprocity
194 Center Street Port
Yarmouth, MA

$1,800,000

4.5 miles away

broker reciprocity
MLS# 22601362broker reciprocity
946 Main Street
Dennis, MA

$1,799,000

4.6 miles away

broker reciprocity
MLS# 22600349broker reciprocity
29 Parkers Neck Road South
Yarmouth, MA

$1,795,000

4.3 miles away

broker reciprocity
MLS# 22602812broker reciprocity
19 Coveview Drive South
Yarmouth, MA

$1,700,000

0.9 miles away

broker reciprocity
MLS# 22601729broker reciprocity
68 Loring Avenue West
Dennis, MA

$1,699,000

2.0 miles away

370 Main Street South
Dennis, MA