21 Check Point Drive, Raymond, ME 04071
Property image
Property image
OFF MARKET

21 Check Point Drive
Raymond, ME 04071

  • 5 Beds
  • 3.5 Baths
  • 3,890 sqft (on 2.70 acres)

$1,604,100

Trulia Estimate
as of Jul 20, 2026

$1,604,100

Trulia Estimate
as of Jul 20, 2026
5 Beds
3.5 Baths
3,890 sqft
(on 2.70 acres)

Local Information

  • Map ViewExplore the area around 21 Check Point Drive.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination
Last check for updates: about 3 hours ago
Listed by Maine Real Estate Pros
Bought with: EXP Realty
Source: Maine Listings, MLS#1566972

Description

280 feet of waterfront on Big Sebago Lake. 2.7 acres of land with a beautiful Main house AND Guest House. Extremely private setting with wonderful water views from your deck. Enjoy the campfire right in front of the water. Property sits in a cove offering great swimming, skiing, etc. Water too cold then enjoy your heated in-ground pool!!! Both homes are gorgeous and very well maintained. Both offer great water views. 2 Car garage and lots of additional parking. All new paving being done on the 5th of September 2023. The main home has 4 bedrooms and two and a half baths and a 6 month old furnace. Guest house has one bedroom, a full bath, and a large living room topped off with a 2 month old roof!!
Enjoy whole days out on Big Sebago Lake. Raymond is positioned nicely between the towns of Windham and Naples where there are activities galore such as shopping and restaurants. A 30 minute ride to our largest city Portland with numerous ski mountain resorts within an hour away.
21 Check Point Drive, Raymond, ME 04071 is a 5 bedroom, 4 bathroom, 3,890 sqft single-family home built in 1979. It last sold for $1,365,000 on Nov 27, 2023 (13% below the $1,575,000 asking price). More recently, it was listed as a rental in February 2026 with an asking price of $5,000 per month. That rental listing was removed on March 9, 2026. It is currently off market. The Trulia Estimate is $1,604,100, with a rent estimate of $5,067/month.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
$21/Monthly
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 21 Check Point Drive

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Interior EntryNumber of Rooms: 11Types of Rooms: Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3890 Square Feet
Heating & Cooling
Heating: Baseboard,Hot WaterHas CoolingHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Gas & Electric
Electric: On Site, Circuit Breakers, Generator HookupHas Electric on Property
Windows, Doors, Floors & Walls
Flooring: Carpet, Tile
Levels, Entrance, & Accessibility
Floors: Carpet, Tile

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: DeckNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageParking Spaces: 2Parking: Garage
Frontage
WaterfrontOn Waterfront
Water & Sewer
Sewer: Septic TankWater Body: Sebago Lake
Farm & Range
Frontage Length: Waterfrontage: 280, Waterfrontage Owned: 280
Finished Area
Finished Area (above surface): 2340 Square FeetFinished Area (below surface): 1550 Square Feet

Property Information

Year Built
Year Built: 1979
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch

Price & Status

Price
List Price: $1,575,000
Status Change & Dates
Off Market Date: Thu Sep 21 2023

Media

Location

Direction & Address
City: Raymond

Building

Building Area
Building Area: 3890 Square Feet

HOA

Has an HOAHOA Fee: $250/Annually

Lot Information

Lot Area: 2.7 Acres

Miscellaneous

BasementMls Number: 1566972Above Grade Unfinished Area: 2340

Price History for 21 Check Point Drive

DatePriceEventSource
03/09/2026$5,000ListingRemovedZillow Rentals
02/08/2026$5,000Listed For RentZillow Rentals
02/20/2025$5,000ListingRemovedZillow Rentals
02/11/2025$5,000PriceChange
Zillow Rentals
01/27/2025$2,500PriceChange
Zillow Rentals
01/15/2025$2,800Listed For RentZillow Rentals
11/23/2024$3,000ListingRemovedZillow Rentals
11/04/2024$3,000Listed For RentZillow Rentals
08/18/2024ListingRemovedZillow Rentals
07/31/2024$3,500PriceChange
Zillow Rentals
07/16/2024$4,000Listed For RentZillow Rentals
11/27/2023$1,365,000Sold
Maine Listings #1566972
09/23/2023$1,575,000PendingMaine Listings #1566972
09/06/2023$1,575,000PriceChange
Maine Listings #1566972
07/28/2023$1,650,000Listed For SaleMaine Listings #1566972

Market trends in Raymond

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
37
7MoM
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Property Tax and Assessment

Year2024
Tax$10,783
Assessment$626,900
Home facts updated by county records

Comparable Sales for 21 Check Point Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
30 Turtle Cove Road, Raymond, ME
0.17
Single-Family Home
$549,900
10/14/25
3
2.5
2,200
7 Casselton Road, Raymond, ME
0.50
Single-Family Home
$900,000
04/30/26
4
2.5
3,473
22 Jewett Road, Raymond, ME
0.24
Single-Family Home
$594,600
12/01/25
3
2
1,692
99 Deep Cove Road, Raymond, ME
0.60
Single-Family Home
$475,000
05/18/26
3
3
2,144
18 SHEEHANS ISLAND Road, Raymond, ME
0.56
Single-Family Home
$5,195,000
08/27/25
4
5
5,474
1569 Roosevelt Trail, Raymond, ME
1.00
Single-Family Home
$540,000
04/10/26
4
4
3,534
2 Oakledge Hills Road, Raymond, ME
0.98
Single-Family Home
$490,000
10/30/25
3
3
2,858
32 Hidden Cove Road, Raymond, ME
1.02
Single-Family Home
$650,000
07/23/25
3
2.5
2,096
1525 Roosevelt Trail, Raymond, ME
0.94
Single-Family Home
$522,000
05/22/26
3
2
2,372

Nearby homes

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Assigned Schools

These are the assigned schools for 21 Check Point Drive.

What Locals Say about Raymond

At least 8 Trulia users voted on each feature.

  • 100 % Say yards are well-kept

  • 92 % Say they plan to stay for at least 5 years

  • 92 % Say car is needed

  • 91 % Say it's dog friendly

  • 89 % Say parking is easy

  • 88 % Say there's holiday spirit

  • 85 % Say there's wildlife

  • 82 % Say it's quiet

  • 77 % Say kids play outside

  • 66 % Say neighbors are friendly

  • 55 % Say people would walk alone at night

  • 27 % Say there are community events

  • 18 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Jcornish08
    "Very family friendly, has all the benefits of the lakes region but just 10 mins away from Windham where you have all of your essentials for stores and amenities. Perfect place to raise a family and enjoy lake life in a quiet and rural environment. Love every moment here raising my family. "
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  • Jcornish08
    "Very safe town and Main Street shuts down for Halloween. Everything you need and plenty of parks to play in"
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  • Jessica Brum
    "They are shutting the middle school down in 2027 and building a giant mega middle school in Windham for all Windham and Raymond students. So Raymond children will have a 1 hour or more bus ride one way each day. Unfortunately the town select board doesn’t stand up for the people of the town. "
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  • Jess S.
    "The middle school in Raymond will be shut down in 2027. The children in Raymond will have to travel to windham for middle and high school. The elementary school is great. It’s unfortunate that the children will end up at a middle school with 1200 other students with a bus ride 60+ minutes away. "
    1
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  • Jcornish08
    "I’ve been here for 5 years now and we love it here. Friendly neighborhood and the town is wonderful. Only 10 mins away from everything we need but have nice quiet space that we live in with land and privacy. We absolutely love it here. "
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  • Irislynn.roberts
    "Love the Raymond, ME area. Lakes all around. I can hear the loons in the morning having my coffee on the front porch. Very quiet area and your neighbors are close enough but not too close. Plenty of town and shopping in any direction from my house."
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  • Iris
    "Raymond is a bustling little town in the summer with all the lakes surrounding us. It is wonderful for kayaking! And the lakes a gorgeous. Overall is is a great little town."
    1
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  • Tiffany A.
    "Neighbors are very kind and neighborly. The community library is very nice. Schools are great! Trick-or-treating every year is wonderful and safe here. "
    1
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  • jhdscot6
    "A beautiful safe area with good schools and friendly neighbors. Winters can be challenging but not as severe as the rumors would tell you. The Midwest has it much worse and Mainers are prepared for it. Summers are incredible."
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  • jhdscot6
    "As the second largest lake in Maine, Sebago offers many opportunities for water sports in the summer and winter activities in the winter. Fall and Spring are truly spectacular. Overall a beautiful and safe place to live. The local residents are particularly friendly."
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Apartments for Rent

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Homes for sale near 21 Check Point Drive

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Off Market Homes Near 21 Check Point Drive

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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.
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