Last Sold Price
4 beds2,902 sqft$276/sqft
106 Upland Rd, Winthrop, MA 02152

Description

HERE IS A MUST SEE......THIS AMAZING TWO FAMILY HAS NATURAL BEAUTY INSIDE AND OUT, Beautiful wood decking and flower gardens greet you upon entering. Both units have been freshly painted with a clean and bright look allowing for a fresh canvas to add your own personal touches. Each unit has two bedrooms and two baths and heated sunporch rooms with sweeping ocean views! The first floor has a good working kitchen with lots of cabinets, S/S appliances and sliders to a private deck and garden area.The...HERE IS A MUST SEE......THIS AMAZING TWO FAMILY HAS NATURAL BEAUTY INSIDE AND OUT, Beautiful wood decking and flower gardens greet you upon entering. Both units have been freshly painted with a clean and bright look allowing for a fresh canvas to add your own personal touches. Each unit has two bedrooms and two baths and heated sunporch rooms with sweeping ocean views! The first floor has a good working kitchen with lots of cabinets, S/S appliances and sliders to a private deck and garden area.The second floor open floor plan has a huge kitchen (3 yrs)/dining/living room combo with cathedral ceilings open to the sunporch room, full of windows offering ocean views and tons of natural light. The master suite has an A/C split system and French doors to a dressing room, 3/4 bath and laundry area. Gleaming hardwood floors, recessed lighting and lots of updates make this a home to enjoy with the ocean & sunrises from the front and city views and sunsets from the back!
LISTING CLOSED: 09/23/2021 12:00 AM

Listing Agents

  1. Sharon Tallent

    Sharon Tallent

    Listing Agent

    Compass

    P: (617) 953-4460

    M: (617) 953-4460

  2. David Tallent

    David Tallent

    Alternative Listing Agent

    Compass

    P: (617) 694-1629

    M: (617) 694-1629

Property Details for 106 Upland Road

Status
MLS #
72883656
Days on Market
21
Taxes
$6,557 / year
HOA Fees
-
Property Type
MLS Type
Multi-family / 2 Family
Year Built
1885
Buyer's Agent Compensation
2%
Town
Winthrop
MLS Area
Winthrop Highlands
Area
MA-Winthrop
Style
Garden
Garage Spaces
0
Open Parking Spaces
3.00
Parking Spaces Total
3

Recent comparable sales

Median sold price

$895,000

Avg days on market

30

Sale-to-list ratio

98.4%

Winthrop, MA

9 comparable properties found

$930,000 | 68-70 Floyd Street, Winthrop, MA 02152
1/33
1

$930,000

Sold 08/22/25

4
Bedrooms
3,432
Square Feet
0.21
Acres
a view of a terrace
1/41
2

$895,000

Sold 03/07/25

4
Bedrooms
3,331
Square Feet
0.19
Acres
a view of a table and chairs in patio with a swimming pool
1/26
3

$880,000

Sold 09/26/25

4
Bedrooms
2,764
Square Feet
0.12
Acres
$1,278,000 | 242 Main Street, Winthrop, MA 02152
1/22
4

$1,278,000

Sold 04/07/25

5
Bedrooms
2,717
Square Feet
0.11
Acres
$855,000 | 18-20 Fairview Street, Winthrop, MA 02152
1/43
5

$855,000

Sold 08/10/26

5
Bedrooms
3,035
Square Feet
0.24
Acres
a front view of a house with a yard
1/40
6

$875,000

Sold 11/18/25

4
Bedrooms
2,972
Square Feet
0.13
Acres
a front view of a house with a garden
1/25
7

$825,000

Sold 10/11/24

4
Bedrooms
3,922
Square Feet
0.07
Acres
$900,000 | 5 Charles Street, Winthrop, MA 02152
1/40
8

$900,000

Sold 02/14/25

5
Bedrooms
2,157
Square Feet
0.11
Acres
a front view of a house with garden
1/31
9

$950,000

Sold 11/21/25

5
Bedrooms
2,550
Square Feet
0.08
Acres

Location

Sold By Lantern Residential, Nicole Bettano

Add your commute

Building Information for 106 Upland Road

Stories3Residences2Year Built1885Building Size-Lot Size0.10 AC / 4,411 SF

Payment Calculator

$4,613 per month

30 year fixed, 6.55% Interest

Principal and Interest

$4,066

Property Taxes

$546

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 106 Upland Road

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Walk/Jog Trails, Golf Course, Conservation Area, Sidewalks
  • Current Financing: Cash
  • Living Area: 2902.0
  • Total Units: 2
  • Waterfront: No
  • Water View: Yes
  • Year Built Details: Approximate
  • Year Built Source: Public Records
Features
Interior Features
  • Appliances: Other, Unit 1(Range, Dishwasher, Refrigerator, Washer, Dryer), Unit 2(Range, Gas Water Heater, Utility Connections for Gas Range, Utility Connections for Electric Range
  • Basement Features: Full, Walk Out, Sump Pump
  • Num of Baths: 4.0
  • Num of Full Baths: 4
  • Num of Half Baths: 0
  • Bathrooms Total Decimal: 4.00
  • Bathrooms Total Integer: 4
  • DoorFeatures: Insulated Doors
  • FireplaceYN: No
  • Fireplaces: 0
  • Flooring: Hardwood, Unit 1(undefined), Unit 2(Hardwood Floors)
  • Interior Features: Other (See Remarks), Unit 1(Ceiling Fans, Bathroom With Tub & Shower), Unit 2(Ceiling Fans, Cathedral/Vaulted Ceilings, Stone/Granite/Solid Counters, Unit 1 Rooms(Living Room, Kitchen, Office/Den, Sunroom), Unit 2 Rooms(Kitchen, Living RM/Dining RM Combo
  • Interior Features: Other (See Remarks), Other(See Remarks)
  • Laundry Features: Unit 2 Laundry Room
  • Window Features: Insulated Windows
Exterior Features
  • Construction: Frame
  • Exterior Features: Professional Landscaping, Garden, Balcony/Deck, Unit 1 Balcony/Deck
  • Exterior Features: City View(s), Fenced Yard, Professional Landscaping, Garden Area, Deck, Patio
  • Fencing: Fenced
  • Patio And Porch Features: Deck, Patio
  • Roof Material: Shingle
  • View: City View(s), Scenic View(s), City
  • View: Yes
  • Waterfront Features: Beach Front, Ocean, 0 to 1/10 Mile To Beach, Beach Ownership(Public)
  • Waterview Features: Marsh, Ocean
Parking Features
  • Covered Spaces: .00
  • Garage: No
  • Garage Parking: Paved Drive, Off-Street, Paved Driveway
  • Open Parking: Yes
  • Parking Features: Paved Drive, Off-Street, Paved Driveway
  • Parking Features: Off-Street, Paved Driveway
Utilities
  • Cooling: Other (See Remarks), Unit 1(Ductless Mini-Split System, Other (See Remarks)), Unit 2(Ductless Mini-Split System)
  • Cooling: Yes
  • Electric: Circuit Breakers
  • Heating: Other, Unit 1(Steam, Gas), Unit 2(Steam
  • Heating: Yes
  • Sewage District: MWRA
  • Sewer: City/Town Sewer
  • Utility Connections: for Gas Range, for Electric Range
  • Water: Public
Property Information
Property Info
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • Lot Size Units: Acres
  • Road Frontage Type: Public
  • Road Responsibility: Public Maintained Road
  • Disclosures: On file,Procuring cause guidelines adhered to for compensation. All data is as of listing date and subject to change. Buyer agent to verify and update all necessary information for their client. Property to be delivered vacant,free and clear of all tenants. Roof,3-4 Yrs. H/W tanks 2 & 3 yrs.old
Tax Information
  • Tax ID: 1425094
  • Assessments: $517,100
  • Book: 19139
  • Tax Year: 2021
  • Zoning: RES.
Building / Association Information
Living Characteristics
  • Beds Total: 4
  • Total Living Levels: 3
Other Building Characteristics
  • Foundation: Stone
  • Cooling Units: 1
  • Cooling Zones: 1
  • Heat Units: 2
  • Heat Zones: 2
Unit Information
Unit 1 Description
  • Floor U1: 1
  • Lease U1: N
  • Levels U1: 1
Unit 2 Description
  • Floor U2: 2
  • Lease U2: N
  • Levels U2: 2
Rental Info
Rental Info
  • Total Actual Rent: $.00
Market and Agent Information
Sale Info
  • Buyer Broker Comp: 2.0
  • Other Agent Compensation: 1.0

Property History for 106 Upland Road

DateEvent & SourcePriceAppreciation
Sep 23, 2021

Sold

MLS PIN #72883656

$800,000
Aug 24, 2021

Contingent

MLS PIN #72883656

Aug 18, 2021

Listed (Active)

MLS PIN #72883656

$845,000
DateEvent & SourcePrice
09/23/2021

Sold

MLS PIN #72883656

$800,000
08/24/2021

Contingent

MLS PIN #72883656

08/18/2021

Listed (Active)

MLS PIN #72883656

$845,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 106 Upland Road

Taxable ValueLand$404,700Additions$409,600Total$814,300
Tax Record2025$8,404 ($700 / month)
Home Facts
Baths2Total Finished SqFt3,014 SqFtAbove Grade Finished SqFt3,014 SqFtStories2Lot Size4,411 SqFtStyleDuplexYear Built1895CountySUFFOLKAPNWINT M:072 L:039

Schools near 106 Upland Road

This home is within Winthrop School District.
Rating
School
Type
Grades
Distance
Public - PK to 2
Public - 3 to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Arthur T. Cummings Elementary School
Public3 to 5

Winthrop Middle School
Public6 to 8

Winthrop Sr High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 106 Upland Road, Winthrop, MA 02152
$800,000
4
2,902
4,411
$262,000
3
1,424
3,920
$405,000
3
1,742
2,933
4,197
$460,000
4
1,704
3,736
$100,000
2
1
1,449
4,279

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.