76 Overlook Rd, Windham, ME 04062
OFF MARKET

76 Overlook Rd
Windham, ME 04062

  • 3 Beds
  • 2 Baths
  • 1,664 sqft

$720,900

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $4,324/mo*
Refinance Your Home

$720,900

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $4,324/mo*
Refinance Your Home
3 Beds
2 Baths
1,664 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

*Available for 30 day or more rental January 1st 2025 - April 31st 2026*

Welcome to Windham Wind Down, your peaceful getaway in Windham, Maine! As you step into this charming lake house, you'll be greeted by beautiful views and the fresh scent of the surrounding pines. Whether you're here for adventure or relaxation, this home provides everything you need for an unforgettable stay including private lake access. Forget your worries in this spacious and serene space.

 15 Min Seacoast Adventure Park
 20 Min to Portland, ME
 20 Min to Maine Wildlife Park
 25 Min to Portland's Old Port
 25 Min to Portland International Jetport
 40 Min to Portland Head Light

 Sleeps 6. 3 Bedrooms. 1 King. 1 Queen. 4 twin bunk beds
 2 Full Bathrooms with Shower/Tub Combo
 Private Dock (mid-May to mid-October)
 Modern, Well-Equipped Kitchen
 WiFi with 2 Smart TV's & Streaming Services
 Fire Pit with Adirondack Chairs
 Kayaks, Paddle boards & Fishing Rods Provided
 Life Vests Available for Adults & Children
 Private Deck with Outdoor Seating & Grill
 Board Games and Books
 Beautiful Lake Views

 BEDROOMS

This gorgeous retreat accommodates 6 guests in 3 bedrooms all located on the 2nd level. The primary bedroom is fitted with a king-size bed and beautiful lake views. The 2nd bedroom, also boasting amazing lake views, is outfitted with a queen bed and all the comforts of home. The 3rd bedroom is perfect for kids or friends as it sleeps 4 in 4 bunk beds. All rooms offer air conditioning in the summer months, plush bedding and ample storage to make your stay as comfortable as possible.

 BATHROOMS

There are two full bathrooms, each of them stocked with all the essentials you need for the duration of your stay.

The 1st floor hosts a full bathroom with a shower-tub combination. It is located just off of the main living area near the kitchen and is easily accessible for all guests on the 1st floor.. The full bathroom on the 2nd level boasts a combination shower and tub. Worry about nothing with these thoughtfully stocked bathrooms that provide everything you need and more.

 KITCHEN & LIVING AREA

The bright and airy kitchen is fully equipped with all the appliances, utensils and cookware you need to feel at home. This thoughtfully-designed home provides an eat-In kitchen option with the dining seating 6 guests at the gorgeous wooden table.

The first living area is situated on the main level of the home and is kitted with an HDTV with a Roku entertainment system and XBox, allowing full access to your favorite streaming services. Not interested in TV? The living area hosts a comfy seating area where you can enjoy your favorite book or watch out the window as guests enjoy the lake.

OUTSIDE SPACE

The exterior area of this home boasts gorgeous views and ample privacy. The front deck overlooks HIghland Lake, allowing you to appreciate the breathtaking views from this exclusive retreat while you prepare a meal on the BBQ. The back deck leads guests directly to the cozy fire pit for all to enjoy. Enjoy your days on the lake with complimentary access to kayaks and paddle boards. Bringing your boat? Access to Windham Wind Down's private dock is an amenity that is hard to beat!

Guests staying at Windham Wind Down have exclusive access to numerous amenities. Take time to enjoy the gorgeous views from the private viewing deck as you sip morning coffee or your favorite glass of wine. There are 2 HDTVs in the home, along with an entertainment system powered by Roku. You are welcome to use the laundry area at your convenience. Windham Wind Down is fitted with a smart door lock and free parking for vehicles is available on the premises.

Please feel free to use the gas grill. Grills need to stay 5-10 feet from the home. Please clean the grill after each use. If you run out of propane, please check for the backup tank.We appreciate a notice if you finish a tank so we can replace it between guests, or if you refill a tank at a local establishment please send us the receipt and we will happily refund the cost of the propane.

The host pays all utilities up to $550 each month. Guests will be asked to pay an additional fee for utility bills beyond $550 each month.

*Driveway parking

*Available for 30 day or more rental January 1st 2025 - April 31st 2026*

*No smoking or vaping of any product or substance is permitted.

*Unit inspection is required once a month with 24-hour notice. You may request cleaning service during your stay at an additional cost

*We collect the first and last month's rent once the booking is confirmed (for 60+ days bookings)

*We ask all guests, upon confirmation of the booking, to acknowledge and sign the Short Rental Agreement. These requirements are important for the smooth operation of our property and to ensure a pleasant stay for all guests

Note: Listed price doesn't include taxes and fees yet.

Owner pays all utilities up to $550/month. The renter is responsible for all utility bills that exceed $550 each month.
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 30, 2026

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 76 Overlook Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Window UnitHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood
Room & Shared Space
Shared space is furnished

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 6 Month

Price History for 76 Overlook Rd

DatePriceEventSource
01/31/2026$4,000ListingRemovedZillow Rentals
09/11/2025$4,000Listed For RentZillow Rentals
10/28/2021ListingRemovedZillow Rental Manager
10/22/2021$3,150Listed For RentZillow Rental Manager
12/20/2019$393,000Sold
Maine Listings #1432897
11/16/2019$409,000PendingAgent Provided
10/30/2019$409,000PriceChange
Agent Provided
09/13/2019$430,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2024
Tax$8,481
Assessment$739,400
Home facts updated by county records

Comparable Sales for 76 Overlook Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
139 Vista Drive, Windham, ME
0.10
Single-Family Home
$726,300
08/05/25
3
2
1,532
12 Pilgrim Lane, Windham, ME
0.25
Single-Family Home
$415,000
05/30/25
2
1.5
1,464
6 Weeks Lane, Windham, ME
0.28
Single-Family Home
$780,000
09/18/25
3
2
2,028
37 Swan Road, Windham, ME
0.32
Single-Family Home
$400,000
01/07/26
3
1
1,938
22 Candlewyck Road, Windham, ME
0.22
Single-Family Home
$410,000
08/29/25
4
1
1,258
50 Overlook Road, Windham, ME
0.11
Single-Family Home
$365,000
02/06/26
2
1
972
19 Moss Road, Windham, ME
0.39
Single-Family Home
$502,500
01/29/26
4
3
2,170
44 Brentwood Rd, Windham, ME
0.46
Single-Family Home
$545,000
08/12/25
2
3
1,903
8 Overlook Road, Windham, ME
0.40
Single-Family Home
$742,000
11/17/25
3
2.5
2,208
14 Anthoine Road, Windham, ME
0.71
Single-Family Home
$550,000
07/08/25
3
1.5
1,512

Nearby homes

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Assigned Schools

These are the assigned schools for 76 Overlook Rd.
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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

Sourced by Trulia users. 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
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  • 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
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  • Charliestandishjr
    "I love living here. It’s safe and nice to look at.Dead end street no through traffic. "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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"
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76 Overlook Rd, Windham, ME 04062 is a 3 bedroom, 2 bathroom, 1,664 sqft single-family home. This property is not currently available for sale. 76 Overlook Rd was last sold on Dec 20, 2019 for $393,000 (9,725% higher than the asking price of $4,000). The current Trulia Estimate for 76 Overlook Rd is $720,900.