38 Woldbrook Drive, Windham, ME 04062
OFF MARKET

38 Woldbrook Drive
Windham, ME 04062

  • 3 Beds
  • 3 Baths
  • 4,907 sqft (on 1.77 acres)

$1,366,900

Trulia Estimate
as of May 18, 2026
Est. Refi. Payment $8,017/mo*
Refinance Your Home

$1,366,900

Trulia Estimate
as of May 18, 2026
Est. Refi. Payment $8,017/mo*
Refinance Your Home
3 Beds
3 Baths
4,907 sqft
(on 1.77 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination
Last check for updates: about 2 hours ago
Listed by Portside Real Estate Group
Bought with: Portside Real Estate Group
Source: Maine Listings, MLS#1560047

Description

Welcome to 38 Woldbrook Drive, located in one of Windham's most sought after neighborhoods on Sebago Lake! A meandering drive passes manicured lawns, stone walls and lush landscaping and ends atop a hill where this beautiful 4,907+/-SF custom colonial has been thoughtfully placed. You approach the home through terraced stone walls w/ granite steps and gardens, and enter the meticulous home in the 2-story foyer. An open floor plan is highlighted w/ an exposed wood center stairway, and polished wood columns throughout define the cozy living areas. A dining area accommodates seating for 12 and is framed with 12 custom wood transom windows and wood floors. Custom cherry cabinets and Corian counters outline the chef's kitchen w/ center island that is complimented with Thermadore and JennAir appliances, large pantry, tiled floors, and a half bath off it. A home office is off the foyer w/ built-in cherry cabinets and bookcase. A master suite on the upper level has a wood burning fireplace, walk-in closet, an oversized master bath w/ glass walk-in tiled shower, and a Jacuzzi tub. There are 2 additional bedrooms, a full bath, laundry room with utility sink, an exercise/study room, and walk-in access to 600+/-SF of current attic space with full dormer, power, and development potential.
You will love entertaining in the 1,400+/- lower level w/ a media room, billiard room, full oak bar with sink and fridge, half bath w/ urinal, and a bunk room.
The large custom terraced deck provides 468+/- SF of outdoor space and enjoys views of the grounds and hillside w/ an abundance of wildlife. The 1.77+/- private lot has an 11-station irrigation system, quaint fire pit w/ large boulder landscaping, and a vegetable garden. Take your golf cart for a short & leisurely ride through the neighborhood to 3 beaches w/ over 700'+/- on Sebago Lake. The amenities of ''Windemere on Sebago'' are the finest w/ tennis & basketball courts, volleyball, horseshoe, kayak/canoe racks, & a 20 slip marina
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from January 15, 2025

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Deck
A/C
Heating & Cooling
HOA
$160/Monthly
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 38 Woldbrook Drive

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Interior Entry,Daylight,Finished,FullNumber of Rooms: 11Types of Rooms: Bedroom 1, Bedroom 2, Bedroom 3, Dining Room, Family Room, Kitchen, Laundry, Living Room, Office, Other Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 2Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 4907 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Dryer, Microwave, Gas Range, Refrigerator, Wall Oven, WasherDishwasherDryerLaundry: Built-Ins,SinkMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,ZonedHas CoolingHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Door: Storm Door(s)Flooring: Carpet, Tile, Wood
Levels, Entrance, & Accessibility
Floors: Carpet, Tile, Wood
Security
Security: Air Radon Mitigation System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck, PorchNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Paved,5 - 10 Spaces,On Site,Off Street,Garage Door Opener,Storage
Frontage
WaterfrontRoad Frontage: Private RoadRoad Surface Type: PavedOn Waterfront
Water & Sewer
Sewer: Septic Design AvailableWater Body: Sebago Lake
Farm & Range
Frontage Length: Waterfrontage: 700, Waterfrontage Shared: 700
Finished Area
Finished Area (above surface): 3499 Square FeetFinished Area (below surface): 1408 Square Feet

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Wood Frame, Wood Siding

Price & Status

Price
List Price: $1,249,900
Status Change & Dates
Off Market Date: Thu Jun 22 2023

Media

Location

Direction & Address
City: WindhamCommunity: Windemere Homeowners Association
School Information
High School District: RSU 14

Building

Building Area
Building Area: 4907 Square Feet

HOA

Has an HOAHOA Fee: $160/Monthly

Lot Information

Lot Area: 1.77 Acres

Energy

Energy Efficiency Features: Ceiling Fans

Miscellaneous

BasementMls Number: 1560047Above Grade Unfinished Area: 3499

Price History for 38 Woldbrook Drive

DatePriceEventSource
07/28/2023$1,150,000Sold
Maine Listings #1560047
06/22/2023$1,249,900PendingMaine Listings #1560047
06/21/2023$1,249,900PriceChange
Maine Listings #1560047
06/03/2023$1,395,000Listed For SaleMaine Listings #1560047
10/27/2017$514,000Sold
Maine Listings #1314281
06/24/2017$539,900Listed For SaleAgent Provided
12/01/2016$529,000ListingRemovedAgent Provided
07/29/2016$529,000Listed For SaleAgent Provided
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2024
Tax$12,390
Assessment$1,080,200
Home facts updated by county records

Comparable Sales for 38 Woldbrook Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
18 Woldbrook Drive, Windham, ME
0.17
Single-Family Home
$1,385,000
09/29/25
5
4.5
4,463
11 Oxford Road, Windham, ME
0.19
Single-Family Home
$915,000
11/13/25
4
2.5
4,520
8 Henderson Court, Windham, ME
0.25
Single-Family Home
$1,550,000
09/26/25
5
3.5
5,856
101 Whites Bridge Road, Windham, ME
0.25
Single-Family Home
$525,000
07/10/25
3
2
1,829
136 Mineral Spring Road, Windham, ME
0.33
Single-Family Home
$560,000
11/04/25
3
1.5
1,884
57 Keeps Way, Windham, ME
0.56
Single-Family Home
$789,900
10/24/25
4
2
2,512
44 BASIN Road, Windham, ME
1.20
Single-Family Home
$1,498,700
07/01/25
3
3.5
3,146
81 Whites Point Road, Standish, ME
0.85
Single-Family Home
$1,700,000
09/26/25
3
2.5
1,850
27 Lake Avenue, Windham, ME
1.05
Single-Family Home
$800,000
07/31/25
3
2.5
2,580

Assigned Schools

These are the assigned schools for 38 Woldbrook Drive.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Windham

At least 40 Trulia users voted on each feature.

  • 96 % Say car is needed

  • 91 % Say parking is easy

  • 85 % Say yards are well-kept

  • 80 % Say there's wildlife

  • 79 % Say there's holiday spirit

  • 78 % Say people would walk alone at night

  • 67 % Say it's quiet

  • 67 % Say they plan to stay for at least 5 years

  • 67 % Say it's dog friendly

  • 66 % Say neighbors are friendly

  • 66 % Say kids play outside

  • 31 % Say there are community events

  • 28 % Say there are sidewalks

  • 28 % Say it's walkable to restaurants

  • 17 % Say streets are well-lit

  • 13 % Say it's walkable to grocery stores

Learn more about our methodology.
  • Charliestandishjr
    "There are lots of dogs in the neighborhood . Everyone’s welcome and pets are always welcomed here. And everyone picks up their dogs pop"
    0
    Flag
  • Charliestandishjr
    "It’s a good place to live . I feel safe in my neighborhood. My neighbors are all friendly .They’re is enough stores in town that I don’t have to go to Portland "
    0
    Flag
  • Charliestandishjr
    "I love living here. It’s safe and nice to look at.Dead end street no through traffic. "
    0
    Flag
  • Geri Post
    "My wonderful neighbors very helpful. Look out for each other and consider ourselves family quiet neighborhood and nice area surrounding trees and a pool"
    0
    Flag
  • Jeannine M.
    "Great area for kids and easy to get to Portland for nightlife or the Mountains for skiing. There's farmer's markets and maple sugar farms, and many deer. If you have kids this is a great place to live where they can ride bikes or play in the lake. "
    1
    Flag
  • Jess I.
    "Many of the people in my neighborhood enjoy the outdoors. We live on the Presumscot River so we have all kinds of wildlife, many enjoy water sports like kayaking, paddle boarding, boating, fishing, and you see them out and about. We also have close access to the Mt. Division trail which is great for everyone, including Fido, as long as they are on a leash. There are farmers markets, lots of shopping, restaurants and sea coast fun park. Just go 5miles up the road. Or the Highschool has sports fields, an outdoor track, a rock climbing wall inside through adult Ed I think? Windham is a great place to be."
    0
    Flag
  • Katie
    "no public transport. good areas and bad. dog friendly. side roads do not get taking care of well in winter months . nice trails for walking. not a very well known going out town most people still travel to portland for drinks with friends dancing ect. "
    13
    Flag
  • Lizmc200
    "I love everything about Windham. The people are great and the town has everything you need in it. "
    0
    Flag
  • Laura C.
    "One way in and one way out. Not a lot of traffic or random drive throughs. Quiet, nice neighborhood with lots of friendly faces."
    2
    Flag
  • Jennilee M.
    "Quiet and friendly, I love this neighborhood. There are Lots of kids around with pets in the area. Everyone looks out for one another "
    1
    Flag
  • zmbailey
    "If you don't have a car, do not move here. Air is relatively clean though."
    0
    Flag
  • Julie L. D.
    "I live two streets from Carmichael and love living so close to the lakes and less than twenty minutes to Portland! The schools are within a 5-7 minute drive and shopping is less than three miles down the road. You can avoid the traffic by taking the backroads, that lead into outer Washington Ave or travel down the road to enter the Maine Turnpike just down the street in Gray. I love listening to the loons on the lake, early Spring into the Fall, and it is always fun to watch the fireworks show on the lake July 4th, put on by neighbors all around the lake! With the snowmobile trails so close by, I can hop on my sled, ice fishing, ice skate, or boat all outside my front door! This is a great area to retire, or raise a family"
    0
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Homes for sale near 38 Woldbrook Drive

Skip to last item
Skip to first item
Listing data is derived in whole or in part from Maine Real Estate Information System, Inc. (d/b/a Maine Listings) and is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved. Equal Housing Opportunity.
Zillow Inc. 415 Congress St #202 Portland, ME 04101 206-424-8443

Homes for rent near 38 Woldbrook Drive

Skip to last item
  • Results are loading
Skip to first item

Off Market Homes Near 38 Woldbrook Drive

Skip to last item
Skip to first item

Explore by feature

38 Woldbrook Drive, Windham, ME 04062 is a 3 bedroom, 4 bathroom, 4,907 sqft single-family home built in 1996. This property is not currently available for sale. 38 Woldbrook Drive was last sold on Jul 28, 2023 for $1,150,000 (8% lower than the asking price of $1,249,900). The current Trulia Estimate for 38 Woldbrook Drive is $1,366,900.