C
Seller's Agent in 2025
Callan Cassidy
Waypoint Brokers Collective
(207) 210-0781
4 in this area
117 Total Sales
18 Woldbrook Dr Windham, ME 04062
5
Beds
4.5
Baths
4,463
Sq Ft
1.51
Acres
Highlights
- 700 Feet of Waterfront
- Tennis Courts
- Viking Appliances
- Beach Access
- 1.51 Acre Lot
- Deck
About This Home
As of September 2025Lakeside luxury meets everyday comfort in this custom-built home designed for living, relaxing, and entertaining—all just a stone's throw (or golf cart ride) from Sebago Lake.
Set in one of the area's premier communities, this spacious 5-bedroom, 4.5-bath home offers a perfect blend of elegance and practicality, with a layout that flows beautifully from one inviting space to the next.
The grand entry opens to cathedral ceilings, a formal living area with fireplace, and a bright, open kitchen featuring Viking appliances, a wine cooler, and beautiful views of the lake. A cozy den provides the perfect spot to unwind, while the sun-drenched dining area is made for memorable meals with family and friends.
The newly renovated primary suite is a true retreat: radiant heated floors, a dual-head walk-in shower, air jet soaking tub, and custom walk-in closet deliver spa-like comfort. The first-floor full bath and laundry/mudroom have also been stylishly renovated for everyday ease.
Remote work is a breeze with not one, but two home office options—choose between the elegant rotunda office or a more private lower-level workspace with its own sauna. Downstairs also features a full bar with granite countertops, sink, dishwasher, and keg fridge—plus direct access to a private patio, ideal for game day gatherings or evening cocktails.
Additional highlights include mini-splits for efficient heating and cooling, updated lighting throughout, an irrigation system, invisible fence, and race deck flooring in the garage.
Step outside onto the expansive composite deck with plexiglass railings—perfect for soaking in the sunshine and lake views. And when you're ready to explore, enjoy three association beaches, tennis courts, a boat launch, and a mooring included with the marina!
Only 2 minutes to the town center and Richardson's Marina, 40 minutes to Pleasant Mountain, and a straightforward commute to Portland—this is more than a home, it's a lifestyle by the lake
Last Agent to Sell the Property
Waypoint Brokers Collective Brokerage Email: callan@waypointbrokers.com Listed on: 06/16/2025
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $11,311
Year Built
- Built in 1989
Lot Details
- 1.51 Acre Lot
- 700 Feet of Waterfront
- Property fronts a private road
- Landscaped
- Level Lot
- Open Lot
- Irrigation
- Wooded Lot
HOA Fees
- $160 Monthly HOA Fees
Parking
- 2 Car Direct Access Garage
- Parking Storage or Cabinetry
- Automatic Garage Door Opener
- Driveway
Property Views
- Water
- Scenic Vista
Home Design
- Contemporary Architecture
- Ranch Style House
- Concrete Foundation
- Wood Frame Construction
- Shingle Roof
- Wood Siding
- Radon Mitigation System
- Concrete Perimeter Foundation
Interior Spaces
- Central Vacuum
- Built-In Features
- Coffered Ceiling
- Cathedral Ceiling
- Skylights
- Wood Burning Fireplace
- Gas Fireplace
- Mud Room
- Family Room with Fireplace
- 2 Fireplaces
- Living Room
- Dining Room
- Home Office
- Sink in Utility Room
Kitchen
- Eat-In Kitchen
- Built-In Oven
- Electric Range
- Microwave
- Dishwasher
- Viking Appliances
- Kitchen Island
- Granite Countertops
- Trash Compactor
- Disposal
Flooring
- Wood
- Laminate
- Tile
Bedrooms and Bathrooms
- 5 Bedrooms
- Primary bedroom located on second floor
- En-Suite Primary Bedroom
- En-Suite Bathroom
- Walk-In Closet
- Bedroom Suite
- Dual Vanity Sinks in Primary Bathroom
- Jetted Tub and Shower Combination in Primary Bathroom
- Secondary Bathroom Jetted Tub
- Soaking Tub
- Separate Shower
Laundry
- Laundry Room
- Laundry on main level
- Dryer
- Washer
Finished Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
- Interior Basement Entry
- Natural lighting in basement
Outdoor Features
- Beach Access
- Nearby Water Access
- Tennis Courts
- Deck
- Patio
Utilities
- Cooling Available
- Zoned Heating
- Heating System Uses Gas
- Heating System Uses Propane
- Heat Pump System
- Baseboard Heating
- Hot Water Heating System
- Generator Hookup
- Water Heater
- Septic System
- Septic Design Available
- Private Sewer
Listing and Financial Details
- Tax Lot 8
- Assessor Parcel Number WINM-000074A-000000-000008
Community Details
Overview
- Windemere Subdivision
- The community has rules related to deed restrictions
Amenities
- Community Storage Space
Ownership History
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Jun 16, 2025
Closed on
Sep 29, 2025
Sold by
Rock John and Rock Hannah
Bought by
Reagan Lisa and Reagan Thomas
Seller's Agent
Callan Cassidy
Waypoint Brokers Collective
Buyer's Agent
Belinda Desmond
Keller Williams Realty
List Price
$1,495,000
Sold Price
$1,385,000
Premium/Discount to List
-$110,000
-7.36%
Views
83
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
-20.75%
Purchase Details
Listed on
Oct 28, 2022
Closed on
Dec 6, 2022
Sold by
Davis Laura P and Davis Christopher T
Bought by
Rock Hannah and Rock John
Seller's Agent
Laura Davis
Portside Real Estate Group
Buyer's Agent
Callan Kilroy
Bean Group
List Price
$989,000
Sold Price
$1,000,000
Premium/Discount to List
$11,000
1.11%
Views
7
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
12.24%
Original Mortgage
$400,000
Interest Rate
5.88%
Mortgage Type
Purchase Money Mortgage
Purchase Details
Listed on
May 12, 2016
Closed on
Jun 28, 2016
Sold by
Hanson Jana A and Merrill Jana A
Bought by
Davis Christopher T and Davis Laura P
Seller's Agent
Payson Swan
Swan Real Estate
Buyer's Agent
Carrie Scoville Amy Foley
The Maine Real Estate Network
List Price
$449,900
Sold Price
$431,438
Premium/Discount to List
-$18,462
-4.1%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
13.92%
Original Mortgage
$345,149
Interest Rate
3.57%
Mortgage Type
New Conventional
Purchase Details
Closed on
Jun 12, 2014
Sold by
Daggett 2Nd Richard M and Daggett Carrie L
Bought by
Merrill Jana A
Purchase Details
Closed on
Dec 6, 2013
Sold by
Sbs Investment Group Llc
Bought by
Oscta Ents Llc
Purchase Details
Closed on
Jul 17, 2013
Sold by
White Eugene E and White Shirley A
Bought by
Merrill Jana A
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area
Home Values in the Area
Average Home Value in this Area
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $1,385,000 | -- | |
| Warranty Deed | $1,000,000 | None Available | |
| Warranty Deed | -- | -- | |
| Warranty Deed | -- | -- | |
| Warranty Deed | -- | -- | |
| Interfamily Deed Transfer | -- | -- | |
| Interfamily Deed Transfer | -- | -- | |
| Warranty Deed | -- | -- | |
| Warranty Deed | -- | -- |
Source: Public Records
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $400,000 | Purchase Money Mortgage | |
| Previous Owner | $345,149 | New Conventional | |
| Previous Owner | $240,000 | Unknown |
Source: Public Records
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 09/29/2025 09/29/25 | Sold | $1,385,000 | -1.1% | $310 / Sq Ft | |
| 08/28/2025 08/28/25 | Pending | -- | -- | -- | |
| 07/12/2025 07/12/25 | Price Changed | $1,400,000 | -6.4% | $314 / Sq Ft | |
| 06/16/2025 06/16/25 | For Sale | $1,495,000 | +49.5% | $335 / Sq Ft | |
| 12/06/2022 12/06/22 | Sold | $1,000,000 | +1.1% | $224 / Sq Ft | View Prior Sale |
| 10/30/2022 10/30/22 | Pending | -- | -- | -- | |
| 10/28/2022 10/28/22 | For Sale | $989,000 | +129.2% | $222 / Sq Ft | |
| 06/27/2016 06/27/16 | Sold | $431,438 | -4.1% | $97 / Sq Ft | View Prior Sale |
| 05/16/2016 05/16/16 | Pending | -- | -- | -- | |
| 05/12/2016 05/12/16 | For Sale | $449,900 | -- | $101 / Sq Ft |
Source: Maine Listings
Tax History Compared to Growth
Tax History
| 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 |
|---|---|---|---|---|
| 2024 | $11,311 | $986,100 | $289,900 | $696,200 |
| 2023 | $9,211 | $822,400 | $269,700 | $552,700 |
| 2022 | $8,440 | $727,000 | $239,500 | $487,500 |
| 2021 | $6,868 | $545,100 | $121,300 | $423,800 |
| 2020 | $7,233 | $482,200 | $100,400 | $381,800 |
| 2019 | $7,059 | $482,200 | $100,400 | $381,800 |
| 2018 | $6,781 | $446,700 | $93,000 | $353,700 |
| 2017 | $6,855 | $417,200 | $84,900 | $332,300 |
| 2016 | $5,743 | $365,800 | $84,900 | $280,900 |
| 2015 | $5,542 | $365,800 | $84,900 | $280,900 |
| 2014 | $5,220 | $365,800 | $84,900 | $280,900 |
| 2013 | -- | $365,800 | $84,900 | $280,900 |
Source: Public Records
Agents Affiliated with this Home
-
Callan Cassidy
-
Belinda Desmond
Buyer's Agent in 2025
Belinda Desmond
Keller Williams Realty
(617) 462-9826
3 in this area
61 Total Sales
-
Laura Davis
Seller's Agent in 2022
Laura Davis
Portside Real Estate Group
(207) 329-9744
17 in this area
99 Total Sales
-
C
Buyer's Agent in 2022
Callan Kilroy
Bean Group
-
Payson Swan
Seller's Agent in 2016
Payson Swan
Swan Real Estate
(207) 415-8140
13 in this area
57 Total Sales
-
C
Buyer's Agent in 2016
Carrie Scoville Amy Foley
The Maine Real Estate Network
Map
Source: Maine Listings
MLS Number: 1626801
APN: WINM-000074A-000000-000008
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