2099 Roland Dr, Bailey, CO 80421
Property image
Property image
OFF MARKET

2099 Roland Dr
Bailey, CO 80421

  • 3 Beds
  • 2 Baths
  • 1,230 sqft (on 0.90 acres)

$474,900

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $2,594/mo*
Refinance Your Home

$474,900

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $2,594/mo*
Refinance Your Home
3 Beds
2 Baths
1,230 sqft
(on 0.90 acres)

Local Information

  • Map ViewExplore the area around 2099 Roland Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Welcome home to this charming 3 bedroom, 2 bath home situated on nearly an acre. Escape from your day on the expansive wrap around deck or on the private balcony off the upstairs bedroom. New interior paint and carpet make this home move in ready with additional opportunities to update and make it your own. Upstairs bathroom and kitchen have been updated. Options abound for the massive workshop/outbuilding at the back of the the property with a roll up garage door, insulation and electric.
2099 Roland Dr, Bailey, CO 80421 is a 3 bedroom, 2 bathroom, 1,230 sqft single-family home built in 1977. It last sold for $425,000 on Aug 4, 2021. It is currently off market. The Trulia Estimate is $474,900, with a rent estimate of $2,410/month.

Home Highlights

Parking
Garage
Outdoor
Deck
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 2099 Roland Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1.5
Interior Details
Number of Rooms: 5

Exterior Features

Exterior Home Features
Roof: CompositionDeckExterior: WoodFoundation Type: Concrete
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1977
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.90 acres

Price History for 2099 Roland Dr

DatePriceEventSource
08/04/2021$425,000Sold
N/A
07/12/2021$425,000PendingRE/MAX International #2596989
07/01/2021$425,000Listed For SaleRE/MAX International #2596989
11/13/2008$115,000Sold
N/A
06/06/2008$175,900ListingRemovedAgent Provided
03/15/2008$175,900PriceChange
Agent Provided
03/09/2008$0Listed For SaleAgent Provided

Market trends in Bailey

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
100
2MoM
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Property Tax and Assessment

Year2025
Tax$1,851
Assessment$439,655
Home facts updated by county records

Comparable Sales for 2099 Roland Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2137 Roland Drive, Bailey, CO
0.03
Single-Family Home
$500,000
09/29/25
3
2
1,852
1999 Roland Drive, Bailey, CO
0.08
Single-Family Home
$350,000
01/29/26
3
2.5
1,848
1534 Roland Drive, Bailey, CO
0.18
Single-Family Home
$380,000
06/05/26
3
2
2,168
303 Kudu Trail, Bailey, CO
0.24
Single-Family Home
$539,000
03/02/26
3
2
1,702
1269 Roland Drive, Bailey, CO
0.10
Single-Family Home
$460,000
04/01/26
3
2
1,976
261 Impala Trail, Bailey, CO
0.40
Single-Family Home
$495,000
05/29/26
3
2
1,653
294 Kudu Trail, Bailey, CO
0.30
Single-Family Home
$565,000
01/22/26
3
2.5
2,296
195 Doe Circle, Bailey, CO
0.96
Single-Family Home
$505,000
04/23/26
3
2
1,344
1242 Roland Drive, Bailey, CO
0.19
Single-Family Home
$337,000
10/09/25
1
1
600
20 Long Ridge Drive, Bailey, CO
0.81
Single-Family Home
$565,000
07/02/26
3
2
2,182

Nearby homes

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Assigned Schools

These are the assigned schools for 2099 Roland 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 Bailey

At least 24 Trulia users voted on each feature.

  • 100 % Say there's wildlife

  • 94 % Say car is needed

  • 94 % Say parking is easy

  • 83 % Say it's dog friendly

  • 79 % Say it's quiet

  • 77 % Say there's holiday spirit

  • 67 % Say neighbors are friendly

  • 65 % Say yards are well-kept

  • 63 % Say they plan to stay for at least 5 years

  • 59 % Say kids play outside

  • 42 % Say people would walk alone at night

  • 34 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Jesstwyford
    "It’s not too bad. Summer Fridays is usually pretty busy going up the hill with all the campers and Sunday mornings is crazy with campers heading home. "
    0
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  • Jim.tyler2009
    "Dog owners should love this area. So many hiking areas. Lots of dogs. Parks recreation areas and dog friendly people. The wildlife can be of serious concern to dog owners so it’s a place to be on constant guard of your pets. Mountain Lions, Bear and coyote have all been seen in the area. There does not seem to be any cats here. Just dogs. Probably best that small dogs be watched at a high level. "
    1
    Flag
  • Elk.martin
    "this is a great place to live. the people are very friendly and there is abundant wildlife in the area."
    0
    Flag
  • Decker903
    "Wildlife, and calmness of the mountains mixed with the feeling is a close nit community. There is a learning curve for people coming from a city atmosphere."
    0
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  • Nick W.
    "A mountain town if there ever was one! Gorgeous place to live, just be ready to commute for most things. Definitely need a car that handles well in the snow."
    4
    Flag
  • Susan B.
    "absolutely gorgeous mountain living with wildlife on properties only 35 minutes from Denver"
    0
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  • jtdayusa
    "Incredible views with a sky full of stars at night. Great energy here."
    0
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  • sam s.
    "Great area for work at home people, also a opportunity for mechanic, cabinet maker or any one who wants privacy and a bif insulated shop to make a living and only have a 100 ft commute. The roads are maintained all year so when you do need to get into town there is no problems. If you are into hiking, biking, wildlife or just peace and quiet all you have to do is walk out your front door. the community has three stocked fishing lakes and a community center with a park for the little ones. "
    0
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Off Market Homes Near 2099 Roland Dr

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