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151 Oakland Street, Wellesley MA 02481

Wellesley, MA 02481 • Wellesley Hills
$4,650,000
Est. $26,914/month
6
Beds
5
Baths
6,990
Sq Ft
$665
Price/Sq Ft
1.15
Acres
1748
Year Built
46
Days on Market
Active Price Drop -$300,000 Listed Jan 16, 2026 • MLS# 73469127 Copied!

About this home

A rare Wellesley gem set on 1.15 acres, overlooking the 15th hole & 16th tee of Wellesley Country Club with sweeping scenic golf course views. Fully renovated in 2022, this distinguished home blends historic character with refined luxury, featuring wide pine floors, 6 fireplaces, and walls of windows overlooking the greens. Gracious living spaces include an inviting great room, sophisticated library, elegant dining room, private home office with separate entrance (or 6th bedroom). The second floor features a vaulted primary suite and 4 additional bedrooms, while a flexible third-floor game room adds versatility. The finished lower level includes a billiards/family room, gym, workshop & storage. Outdoors, a bluestone patio and wraparound deck capture panoramic views, spectacular sunrises and sunsets, fruit trees and a 19th-century barn w/2 horse stalls and fenced paddock. Abutting conservation land with a two-car garage, this is a rare opportunity to own a piece of Wellesley history.

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Public Records

Current Owner

Owner Todd, Gary O, Trustee
Mailing Address 151 Oakland Street, Wellesley, MA, 02481

Land Use

Use Code 101
Description Single Family
Style Colonial

Tax Information

Assessed Value $3,573,000
Tax Rate $10.14 per $1,000
Base Tax $36,230
CPA Surcharge 1.5% ($528)
Estimated Annual Tax $36,758

Assessment History

Year Land Building Total Change
FY2025 $2,249,000 $1,309,000 $3,573,000

Sale History

Date Price Book/Page
Apr 28, 2022 $10 40498/62

Municipal Context: WELLESLEY

Median Home Value $1,575,000
Avg SF Tax Bill $15,970
Residential Tax Rate $10.14/1000
CPA Surcharge 1.5%
County Norfolk

Property Data Comparison

Discrepancies found between MLS and assessor records.

Field Assessor MLS Match
Sqft 4,797 6,990
Year built 1,748 1,748
Match: address_exact (85.0% confidence) · Data as of Feb 27, 2026

Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1748
Bedrooms
6
Full Bathrooms
5
Living Area
6,990 sq ft
Total Rooms
15

Facts & Features

2 Car Garage
Central AC

Home Facts

Type Residential
Style Single Family Residence
Year Built 1748
Living Area 6,990 sq ft
Lot Size 1.15 acres
Bedrooms 6
Full Baths 5
Total Rooms 15

Interior

Heating Forced Air, Natural Gas, Hydro Air
Cooling Central Air
Flooring Tile, Carpet, Hardwood, Pine
Appliances Gas Water Heater, Range, Oven, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer
Fireplace Dining Room, Family Room, Living Room
Fireplaces 6
Basement Full, Finished, Interior Entry, Garage Access, Concrete
Laundry Electric Dryer Hookup, Washer Hookup
Features Library, Sun Room, Home Office-separate Entry, Exercise Room, Office, Wet Bar, Walk-up Attic

Exterior

Construction Frame
Architecture Colonial, Antique
Roof Shingle
Features Deck, Patio, Storage, Barn/stable, Paddock, Professional Landscaping, Sprinkler System, Fenced Yard, Fruit Trees, Garden, Horses Permitted, Stone Wall
Pool None
Spa None
Fencing Fenced/enclosed, Fenced
Patio/Porch Deck, Patio

Parking

Garage Spaces 2
Has Garage Yes
Features Attached, Under, Garage Door Opener, Storage, Driveway, Paved
Total Spaces 6

Utilities

Electric Circuit Breakers
Water Public
Sewer Public Sewer
Gas None
Other For Gas Range, For Electric Oven, For Electric Dryer, Washer Hookup

Financial

Annual Tax $38,412
Assessed Value $3,777,000

Interior Features

Flooring: Tile, Carpet, Hardwood, Pine
Appliances: Gas Water Heater, Range, Oven, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer
Interior Features: Library, Sun Room, Home Office-Separate Entry, Exercise Room, Office, Wet Bar, Walk-up Attic
Windows:
Basement: Full, Finished, Interior Entry, Garage Access, Concrete
Laundry: Electric Dryer Hookup, Washer Hookup
Security:

Construction & Materials

Style: Colonial, Antique
Year Built: 1748
Structure Type:
Exterior Materials: Frame
Roof: Shingle
Foundation: Concrete Perimeter, Brick/Mortar

Heating, Cooling & Utilities

Heating: Forced Air, Natural Gas, Hydro Air
Cooling: Central Air
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features: Deck, Patio, Storage, Barn/Stable, Paddock, Professional Landscaping, Sprinkler System, Fenced Yard, Fruit Trees, Garden, Horses Permitted, Stone Wall
Patio & Porch: Deck, Patio
Fencing: Fenced/Enclosed, Fenced
Other Structures: Barn/Stable
Lot Features: Corner Lot
Road Frontage: 229.00 ft
Road Surface: Paved

Parking & Garage

Garage Spaces: 2
Garage Type: Attached
Total Parking Spaces: 6
Parking Features: Attached, Under, Garage Door Opener, Storage, Driveway, Paved

Special Features

Fireplaces: 6
Fireplace Type: Dining Room, Family Room, Living Room
View: Yes
View Type: Scenic View(s)
Community Amenities: Shopping, Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Conservation Area, Highway Access, House of Worship, Private School, Public School, University

Location

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Neighborhood

Wellesley Hills

151 Oakland Street, Wellesley MA 02481

Wellesley, MA 02481

Walkability

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Nearby Schools

School District
Wellesley School District local
A+
🎓 Where Graduates Go Class of 2021
81% attend college
78% 4-Year 3% 2-Year 56% Out of State 2% Working
School Safety 2024-25
0.3% Low
0.3% Suspensions 0.5% In-School
5.2% below state avg
E

Elementary Schools

10 schools
St. John the Evangelist School
1.2 mi
Grades PK-06
Star Academy Boston (Wellesley Campus)
1.5 mi
Grades PK-12
Tenacre Country Day School
1.9 mi
Grades PK-06
Preschool at Wellesley Schools
0.7 mi
87 students Diverse
Diverse Student Body
Grades PK
A+
Joseph E Fiske School
0.7 mi | #32 of 824 | Score: 63.6
Improved 28 spots from last year
+5.4 above state avg
278 students Diverse
Rising School Diverse Student Body Strong Attendance
Grades K-05
A
Schofield School
1.0 mi | #141 of 824 | Score: 57.4
Dropped 77 spots from last year
-0.9 below state avg
291 students Diverse
Strong Attendance
Grades K-05
A
Hunnewell School
1.7 mi | #162 of 824 | Score: 56.6
Dropped 73 spots from last year
-1.6 below state avg
294 students Moderate
Strong Attendance
Grades K-05
A
Sprague Elementary School
1.9 mi | #165 of 824 | Score: 56.3
Dropped 129 spots from last year
-1.9 below state avg
289 students Diverse
Diverse Student Body
Grades K-05
A
Katharine Lee Bates School
2.4 mi | #119 of 824 | Score: 58.1
Dropped 114 spots from last year
-0.2 below state avg
286 students Moderate
Strong Attendance
Grades K-05
A+
John D Hardy School
2.5 mi | #51 of 824 | Score: 62.2
Dropped 23 spots from last year
+4 above state avg
280 students Diverse
Diverse Student Body Strong Attendance
Grades K-05
M

Middle Schools

1 school
A+
Wellesley Middle School
1.5 mi | #7 of 352 | Score: 64.5
Same rank as last year
+6.3 above state avg
919 students Diverse
Strong Attendance
Grades 06-08
H

High Schools

3 schools
Dana Hall School
1.8 mi
Grades 06-12
A+
Wellesley Sr High School
1.0 mi | #28 of 346 | Score: 71.3
Improved 63 spots from last year
+13.1 above state avg
1,262 students Diverse
20 sports • 2,762 athletes
Strong AP Program High Graduation Rate Rising School Strong Athletics
Grades 09-12
North American Hockey Academy
2.9 mi
Grades 09-12
Learn about these ratings

Monthly Payment Calculator

Monthly Payment
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Principal, interest, taxes & insurance
Loan Amount
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After down payment
Total Interest
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Over life of loan
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Including down payment
%
Down: $0
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $3,201
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

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Current Rate
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+0.5% Rate
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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Property History

Market Insights

1
Price Changes
6.1%
Price Range

Property Timeline

Price Reduced
Feb 27, 2026
$4,650,000 $300,000 (-6.06%)
From $4,950,000 to $4,650,000 (-6.1%)
🏠
Listed for Sale
Jan 16, 2026
$4,950,000
Original listing
Agent: Beth Dickerson Office: Gibson Sotheby's International Realty

Price & Status History

Date Event Price Change
Feb 27, 2026 Price Changed $4,650,000 -$300,000
Jan 16, 2026 New Listing Added $4,950,000

Market Statistics

Days on Market
46 days
Price per Sq Ft
$665
Total Price Drop
-$300,000

Tax History

Year Taxes Assessment
2026 $38,412 $3,777,000

Financial Details

Annual Property Tax
$38,412
Tax Year 2026
Assessed Value
$3,777,000

Listing Information

Listing Agent Beth Dickerson
Listing Office Gibson Sotheby's International Realty
Agent MLS ID BB904055
Office MLS ID BB5919
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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Market Analytics for Wellesley, MA

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