NOT LISTED FOR SALE

Estimated Value: $3,061,231

5 Beds
7 Baths
7,803 Sq Ft
$392/Sq Ft Est. Value

Sale Details

Date Sold: May 8, 2026

Last sale price $3,100,000 $397 Per Sq Ft

Est. 1% decrease in value since last sale

Current estimated payment $19,819 / mo

81 Days on Market

Highlights

  • 2.15 Acre Lot
  • Wooded Lot
  • 5 Car Direct Access Garage
  • Colonial Architecture
  • Radiant Floor
  • Fireplace

About This Home

As of May 2026

Step into timeless elegance at 39 Overton Road—a residence where sophistication, craftsmanship, and comfort converge across 7,803 finished square feet of extraordinary living space. Perfectly sited on over 2 acres in one of Windham’s most coveted neighborhoods, this 5-bed, 7-bath estate captures the essence of refined living. A stately stone façade, manicured grounds, and grand entry set the tone for the quality found within. Inside, radiant floor heating, rich hardwood flooring, and custom millwork accent spacious, light-filled rooms designed for both grand entertaining and everyday comfort. The gourmet kitchen serves as the heart of the home, complemented by formal and casual gathering areas and four fireplaces, adding warmth & charm. A richly appointed office provides an inspiring workspace with timeless appeal. The opulent primary suite is a true retreat with a spa-inspired bath, dual walk-in closets, and serene views. Upstairs bedrooms each feature private or en-suite baths, ensuring comfort for family and guests. The walkout lower level expands the living space with areas for recreation or fitness, complete with a convenient 3⁄4 bath. A walk-up third floor provides endless potential for future expansion or storage. Outdoors, enjoy your own private oasis with an in-ground pool, expansive patio, and lush landscaped grounds ideal for entertaining. This remarkable home defines luxury, elegance, and timeless design in Windham.

Last Agent to Sell the Property

Shannon DiPietro

DiPietro Group Real Estate License #049965 Listed on: 10/24/2025

Last Buyer's Agent

Shannon DiPietro

DiPietro Group Real Estate License #049965 Listed on: 10/24/2025

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Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $26,403

Year Built

  • Built in 2005

Lot Details

  • 2.15 Acre Lot
  • Property fronts a private road
  • Landscaped
  • Level Lot
  • Wooded Lot
  • Property is zoned RD

Parking

  • 5 Car Direct Access Garage
  • Heated Garage

Home Design

  • Colonial Architecture
  • Wood Frame Construction
  • Asphalt Shingled Roof

Interior Spaces

  • Property has 2 Levels
  • Fireplace
  • Radiant Floor

Bedrooms and Bathrooms

  • 5 Bedrooms

Partially Finished Basement

  • Walk-Out Basement
  • Basement Fills Entire Space Under The House

Utilities

  • Forced Air Heating and Cooling System
  • Heating System Uses Oil
  • Heating System Uses Propane
  • Propane
  • Private Water Source
  • Private Sewer

Listing and Financial Details

  • Legal Lot and Block 748 / A
  • Assessor Parcel Number 7

Home Details

Home Type

Single Family

Est. Annual Taxes

$26,403

Year Built

Built in 2005

Lot Details

2.15 Acres

Parking

5

Listing Details

  • Seasonal: No
  • Property Type: Residential
  • Year Built: 2005
  • Display On Internet: High Speed Intrnt Avail
  • Architectural Style: Colonial
  • ResoLotFeatures: Landscaped, Level, Wooded
  • Road Frontage Type: Paved, Public Maintained Road, Public
  • PropertySubType: Single Family Residence
  • MLS Status: (20) Closed - Closed
  • Above Grade Finished Sq Ft: 5894.0
  • Unit Levels: Two
  • ResoPropertyCondition: Existing
  • Flood_Zone: No
  • Foreclosed_Or_Bank_Owned_Or_REO: No
  • Mobile_Home: No
  • Pre_Construction: No
  • Timeshare_Or_Fract_Ownrshp: No
  • Basement_Access_Type: Walkout
  • Total_Finished_Area: 7803
  • Total_Area: 8440
  • Above_Grade_Unfinished_Area: 0
  • Above_Grade_Unfinished_Area_Source: Public Records
  • Below_Grade_Unfinished_Area: 637
  • Below_Grade_Unfinished_Area_Source: Public Records
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 5
  • Basement: Full, Partially Finished, Walkout
  • Basement YN: Yes
  • Full Bathrooms: 5
  • Half Bathrooms: 2
  • Below Grade Sq Ft: 1909.0

Exterior Features

  • Driveway: Paved
  • Roof: Asphalt Shingle
  • Easements: Yes
  • Construction Type: Wood Frame
  • Foundation Details: Poured Concrete

Garage/Parking

  • Garage Spaces: 5.0
  • Attached Garage: Yes
  • Parking Features: Attached, Detached, Direct Access, Heated Garage

Utilities

  • Electric: Circuit Breakers
  • Sewer: Private Sewer
  • Heating: Propane, Oil, Forced Air, Radiant Floor
  • Cooling: Central Air
  • Utilities: Propane, Other
  • Water Source: Private

Lot Info

  • Surveyed: Unknown
  • Zoning: RD
  • Lot Size Acres: 2.15
  • Lot Size Sq Ft: 93654.0

Tax Info

  • Tax Year: 2024
  • Tax Annual Amount: 26403.0
  • Tax Block: A
  • Tax Lot: 748
  • Tax Map Number: 7

Ownership History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Name Owned For Owner Type

Purchase Details

Listed on
Oct 24, 2025
Closed on
May 8, 2026
Sold by
Bought by
Seller's Agent
Shannon DiPietro
DiPietro Group Real Estate
Buyer's Agent
Shannon DiPietro
DiPietro Group Real Estate
List Price
$3,295,000
Sold Price
$3,100,000
Premium/Discount to List
-$195,000
-5.92%
Views
239
Current Estimated Value
$3,061,231

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
-$38,769
Avg. Annual Appreciation
-5.11%

Purchase Details

Closed on
May 21, 2020
Sold by
Bought by

Purchase Details

Closed on
May 7, 2004
Sold by
Bought by
Source: Public Records

Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

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Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Buyer Sale Price Title Company
$1,100,000 --
-- None Available
$230,000 --
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Borrower Loan Amount
Previous Owner $895,000
Closed $620,000
Closed $1,092,000
Previous Owner $107,980
Previous Owner $150,000
Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft
05/08/2026 05/08/26 Sold $3,100,000 -5.9% $397 / Sq Ft
10/24/2025 10/24/25 For Sale $3,295,000 -- $422 / Sq Ft
Source: PrimeMLS

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $35,927 $2,539,000 $401,800 $2,137,200
2024 $26,403 $1,166,200 $248,000 $918,200
2023 $24,957 $1,166,200 $248,000 $918,200
2022 $22,965 $1,162,200 $248,000 $914,200
2021 $21,640 $1,162,200 $248,000 $914,200
2020 $22,233 $1,162,200 $248,000 $914,200
2019 $20,322 $901,200 $202,400 $698,800
2018 $21,639 $929,100 $202,400 $726,700
2017 $18,768 $929,100 $202,400 $726,700
2016 $20,273 $929,100 $202,400 $726,700
2015 $20,363 $937,500 $202,400 $735,100
2014 $19,625 $817,700 $195,000 $622,700
2013 $19,505 $826,500 $195,000 $631,500
Source: Public Records

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Map

Source: PrimeMLS

MLS Number: 5067107

PrimeMLS

APN: 7 A 748

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