261 Chessman Dr, Four Seasons, MO 65049
OFF MARKET

261 Chessman Dr
Four Seasons, MO 65049

  • 3 Beds
  • 2 Baths
  • 1,250 sqft

$255,000

Trulia Estimate
as of Aug 4, 2026
Est. Refi. Payment $1,506/mo*
Refinance Your Home

$255,000

Trulia Estimate
as of Aug 4, 2026
Est. Refi. Payment $1,506/mo*
Refinance Your Home
3 Beds
2 Baths
1,250 sqft

Local Information

  • Map ViewExplore the area around 261 Chessman Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1985
Living Area
1,250 sqft
Price/Sqft
$204

About this House

Enjoy the peace and serentiy of Four Season's Largest Interior Lake from your covered porch. That is the wonderful setting for this 3BR/2BA home still owned by original owner that had it custom built. Very nice open floorplan with vaulted ceilings, fireplace, and kitchen w/ breakfast bar. Enjoy the view and fishing on what feels like your own private lake! Lots of potential for first time homebuyer or retiree.....check it out today!
261 Chessman Dr, Four Seasons, MO 65049 is a 3 bedroom, 2 bathroom, 1,250 sqft single-family home built in 1985. It is currently off market. The Trulia Estimate is $255,000, with a rent estimate of $1,958/month.

Home Details for 261 Chessman Dr

Property Information

Year Built
Year Built: 1985
Property Type / Style
Property Type: Single Family Home

Price History for 261 Chessman Dr

DatePriceEventSource
06/17/2010$99,000ListingRemovedAgent Provided
10/01/2009$99,000Listed For SaleAgent Provided

Market trends in Village of Four Seasons

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
154
8MoM
Skip to last item
  • Results are loading
Skip to first item

Comparable Sales for 261 Chessman Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
284 Bloomington Dr, Four Seasons, MO
0.29
Single-Family Home
-
03/13/26
3
2
1,365
264 Bloomington Dr, Four Seasons, MO
0.29
Single-Family Home
-
09/15/25
3
2
1,550
5592 Horseshoe Bend Pkwy, Lake Ozark, MO
0.23
Single-Family Home
-
11/21/25
4
3
2,256
422 Scarsdale Cir, Lake Ozark, MO
0.14
Single-Family Home
-
11/21/25
4
3
3,325
404 Albany Dr, Lake Ozark, MO
0.21
Single-Family Home
-
10/10/25
4
3
2,937
326 Bloomington Dr, Lake Ozark, MO
0.30
Single-Family Home
-
08/21/25
4
3
2,276
147 Cambridge Dr, Lake Ozark, MO
0.68
Single-Family Home
-
12/09/25
3
2
1,320
141 Oriole Dr, Lake Ozark, MO
0.65
Single-Family Home
-
11/07/25
3
2
1,568
328 Albany Dr, Lake Ozark, MO
0.27
Single-Family Home
-
01/09/26
4
3
3,300
310 Palisades Dr, Lake Ozark, MO
0.45
Single-Family Home
-
05/15/26
3
3
2,741

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 261 Chessman Dr.
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 Village of Four Seasons

At least 28 Trulia users voted on each feature.

  • 95 % Say it's dog friendly

  • 95 % Say car is needed

  • 88 % Say there's wildlife

  • 87 % Say parking is easy

  • 82 % Say there's holiday spirit

  • 80 % Say it's quiet

  • 71 % Say yards are well-kept

  • 68 % Say people would walk alone at night

  • 65 % Say they plan to stay for at least 5 years

  • 58 % Say neighbors are friendly

  • 53 % Say streets are well-lit

  • 50 % Say kids play outside

  • 39 % Say there are sidewalks

  • 26 % Say there are community events

  • 16 % Say it's walkable to restaurants

  • 16 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Shae K.
    "Garage sale by home owners Our community is very safe for our children and children's children!! There is a large amount of neighbor's that are all animal livers with dog's walking them with the whole family. which isn't seen that many places these days. There ismt many places you seen multiple families walking , laughing, smiling, together. Most people are in tremendously great shape for their ages!! "
    0
    Flag
  • Becca H.
    "Sidewalks everywhere. Dog park close by. Leash law. Other people out with dogs so you know it’s a dog friendly area "
    0
    Flag
  • Nancyhogland
    "There are standards that, while sometimes get irritating, protect property values. We also have great pools and parks."
    0
    Flag
  • Lindarsandbothe
    "Well protcted.Pride of ownership shows in FOUR SEASONS.GREAT VILLAGE BOARD OF DIRECTORS! ESPECIALLY THE PRESIDING TRUSTEE!"
    0
    Flag
  • Lkusterdavis
    "There are a lot of community events... due to work have not attended. Grandkids went to Easter egg hunt and really enjoyed it!"
    0
    Flag
  • Amschlicher
    "Most folks keep their homes pretty nice. There is a small convenience store with gas right down the street and several community pools. "
    3
    Flag
  • Mike S.
    "Great retirement location, but there is a lack of activities in the winter months. Wish there were more businesses with off season offerings."
    0
    Flag
  • Susan
    "I live and have worked in the Four Seasons area for over twenty years, Each year I have seen improvements to the amenities without substantial increases in assessment. Check out the walking trails, the new Bark Park, playground and improvements to the community pools. Can't wait for Spring to kick off the season and welcome our lake visitors."
    1
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Air Conditioning

9 rentals with air conditioning in Four Seasons, MO

Explore by feature - Pool

8 rentals with a pool in Four Seasons, MO

Explore by feature - Washer/dryer

8 rentals with a washer/dryer in Four Seasons, MO

Homes for sale near 261 Chessman Dr

Skip to last item
Skip to first item

Off Market Homes Near 261 Chessman Dr

Skip to last item
Skip to first item