261 Chessman Dr, Four Seasons, MO 65049
OFF MARKET

$235,400

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,250 sqft

261 Chessman Dr, Four Seasons, MO 65049

Est. Refi. Payment $1,444/mo*
Refinance Your Home

Home Value

Trulia Estimate
$235K
Since last month
Decreased$20K (-7.9%)
Since last year
Decreased$1K (-0.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +85% in the last 10 years
MonthEstimated value
2026
September 2026$235K
August 2026$233K
July 2026$256K
June 2026$257K
May 2026$235K
April 2026$258K
March 2026$222K
February 2026$230K
January 2026$221K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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
5844 Horseshoe Bend Pkwy, Lake Ozark, MO
0.34
Single-Family Home
-
08/14/26
3
2
1,470
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
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
105 Yonkers Ct, Lake Ozark, MO
0.74
Single-Family Home
-
08/28/26
3
2
1,625

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
38 Chessman Dr, Lake Ozark, MO 65049
0.05
$10,000
-
-
-
For Sale
Lot 895 Scarsdale Cir, Lake Ozark, MO 65049
0.11
-
-
-
-
Recently Sold
422 Scarsdale Cir, Lake Ozark, MO 65049
0.14
-
4
3
3,325
Recently Sold
458 Albany Dr, Lake Ozark, MO 65049
0.18
$618,200
3
3
3,300
Off Market
70 Bloomington Dr, Lake Ozark, MO 65049
0.18
-
-
-
-
Recently Sold
71 & 72 Bloomington Dr, Lake Ozark, MO 65049
0.19
$59,900
-
-
-
For Sale
404 Albany Dr, Lake Ozark, MO 65049
0.21
$489,700
4
3
2,937
Off Market
7 Chessman Dr, Lake Ozark, MO 65049
0.17
-
-
-
-
Off Market
425 Albany Dr, Lake Ozark, MO 65049
0.21
$5,000
-
-
-
For Sale
175 Albany Dr, Lake Ozark, MO 65049
0.23
$3,000
-
-
-
For Sale
53 Horseshoe Bend Pkwy, Lake Ozark, MO 65049
0.20
-
-
-
-
Off Market
416 Bloomington Dr, Lake Ozark, MO 65049
0.24
$358,700
3
2
1,470
Off Market

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

Single-Family Home
Built in 1985
1,250 sqft
$188/sqft

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $235,400, with a rent estimate of $2,001/month.

Home Details for 261 Chessman Dr

Property Information

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

Price and Tax history

DateEventPrice
Jun 17, 2010
Source: Agent Provided
ListingRemoved
$99,000
Oct 1, 2009
Source: Agent Provided
Listed For Sale
$99,000

Market trends in Village of Four Seasons

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
166
7MoM

Around this home

What Locals Say about Village of Four Seasons

At least 28 Trulia users voted on each feature.

  • 95 % Say car is needed

  • 93 % Say it's dog friendly

  • 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

  • 66 % 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.
  • Trulia User
    "We have the beautiful Lake of the Ozarks surrounding us and yet this particular area is like a small town next to a big city with all the big stores. "
    0
    Flag
  • 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

Frequently asked questions about 261 Chessman Dr

  • What is 261 Chessman Dr estimated to be worth?
    Trulia's estimated value for 261 Chessman Dr in Four Seasons, MO is $235,400.
  • Is Four Seasons a buyer's or seller's market?
    Four Seasons is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Four Seasons?
    Residents describe Four Seasons, MO as dog-friendly, easy to park in, and quiet. Most residents say you need a car. See recently sold homes in Four Seasons, MO.
  • What are the closest schools to 261 Chessman Dr?
    The closest schools to 261 Chessman Dr in Four Seasons, MO are Leland O. Mills Elementary School, Osage High School (rated 7/10), Osage Middle School (rated 9/10).

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