255 Jack Boot Way, Monument, CO 80132
Property image
Property image
SOLD
JUN 17, 2026

255 Jack Boot Way
Monument, CO 80132

  • 5 Beds
  • 3 Baths
  • 4,179 sqft (on 0.70 acres)

$835,000

Last Sold: Jun 17, 2026
2% below list $850K
$200/sqft
Est. Refi. Payment $4,553/mo*
Refinance Your Home

$835,000

Last Sold: Jun 17, 2026
2% below list $850K
$200/sqft
Est. Refi. Payment $4,553/mo*
Refinance Your Home
5 Beds
3 Baths
4,179 sqft
(on 0.70 acres)

Local Information

  • Map ViewExplore the area around 255 Jack Boot Way.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Tucked among the trees in the heart of Woodmoor, this custom Tudor-style two-story is a true showstopper. This home blends timeless character with thoughtfully curated, design-forward living. Step inside to the elevated foyer, striking wood staircase, and classic wainscoting that sets a warm and inviting tone. The family room features rich herringbone floors, exposed beams, and a cozy wood-burning fireplace framed by a bay window overlooking the backyard. High-quality finishes shine throughout, including solid wood windows and doors, a statement stone feature wall, and designer paint selections. The kitchen pairs style and function with a Zellige tile backsplash, granite countertops, butler’s pantry, and upgraded appliances, including a 750-degree convection pizza oven. Updated lighting, dimmers, and hardwired sconces further enhance the home’s ambiance. Upstairs, the primary suite offers a custom walk-in closet, four-piece ensuite, and private deck. Three additional bedrooms (new carpet coming soon) and a full bath complete the level. The partially finished walk-out basement is ready for your vision, offering flexibility and future value, while a new furnace adds peace of mind. Outside, the experience continues. Fresh exterior paint, two composite decks, spacious paver patio with solid stone steps and winding pathways create a seamless extension of the home. A fully fenced backyard, a stunning gas firepit with seating wall, and thoughtfully placed string lights and uplighting set the stage for unforgettable evenings. A greenhouse with automated ventilation, vibrant seasonal landscaping, auto irrigation, and low-maintenance, pet-friendly turf complete the setting, all enhanced by dusk-to-dawn lighting. Layered, soulful, and truly one-of-a-kind, this is not your average Woodmoor home. If you’ve been waiting for something with personality and warmth, this is it. Call to schedule your private tour today.
255 Jack Boot Way, Monument, CO 80132 is a 5 bedroom, 4 bathroom, 4,179 sqft single-family home built in 1988. It last sold for $835,000 on Jun 17, 2026 (2% below the $850,000 asking price). It is currently off market. The Trulia Estimate is $835,000, with a rent estimate of $4,076/month.

Home Highlights

Parking
2 Car Garage
Outdoor
Yes
A/C
Heating & Cooling
HOA
$26/Monthly
Price/Sqft
$200/sqft
Listed
93 days ago

Home Details for 255 Jack Boot Way

Interior Features

Interior Details
Basement: Full,Partially FinishedNumber of Rooms: 1
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 2Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 4179 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Natural Gas ConnectedAppliances: 220v in Kitchen, Dishwasher, Disposal, Dryer, Microwave, Oven, Refrigerator, WasherDishwasherDisposalDryerLaundry: Electric Hook-up,Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Ceiling Fan(s)Has HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: OneHas a Fireplace
Gas & Electric
Electric: 220 Volts in GarageHas Electric on Property
Windows, Doors, Floors & Walls
Window: Window CoveringsFlooring: Carpet, Tile, Vinyl/Linoleum, Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Carpet, Tile, Vinyl Linoleum, Wood

Exterior Features

Exterior Home Features
Roof: Composite ShinglePatio / Porch: Composite, Other, See Prop Desc RemarksFencing: Back YardOther Structures: GreenhouseFoundation: Walk Out
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached,Garage Door Opener,Oversized,Concrete Driveway,RV Access/Parking
Finished Area
Finished Area (above surface): 2723 Square FeetFinished Area (below surface): 1456 Square Feet

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Brick, Stucco, Wood Siding, Framed on Lot, FrameNot a New ConstructionNot Attached Property
Property Information
Condition: Existing Home

Price & Status

Price
List Price: $850,000Price Per Sqft: $200/sqft
Status Change & Dates
Off Market Date: Sun May 24 2026

Active Status

MLS Status: Sold

Location

Direction & Address
City: Monument
School Information
Elementary School: Bear CreekElementary School District: Lewis-Palmer-38Jr High / Middle School: Lewis PalmerJr High / Middle School District: Lewis-Palmer-38High School: Lewis PalmerHigh School District: Lewis-Palmer-38

Building

Building Area
Building Area: 4179 Square Feet

HOA

HOA Fee Includes: Covenant Enforcement, Management, Snow RemovalHas an HOAHOA Fee: $309/Annually

Lot Information

Lot Area: 0.70 acres

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Miscellaneous

BasementMls Number: 7381478Attribution Contact: 719-216-3266Above Grade Unfinished Area: 2723
Last check for updates: about 3 hours ago
Listed by Kara Baretich ABR GRI MRP PSA RENE SRS , (719) 216-3266
Structure Real Estate Group, LLC
Bought with: Stacey Lehner ABR AIC C2EX LHC MRP SRES , (719) 684-3457, Your Neighborhood Realty, Inc.
Source: elevateMLS, MLS#7381478

Price History for 255 Jack Boot Way

DatePriceEventSource
06/17/2026$835,000Sold
elevateMLS #7381478
05/25/2026$850,000PendingREcolorado as distributed by MLS GRID #2015956
05/25/2026$850,000ContingentelevateMLS #7381478
05/20/2026$850,000PendingToActiveelevateMLS #7381478
05/17/2026$850,000PendingREcolorado as distributed by MLS GRID #2015956
05/16/2026$850,000ContingentelevateMLS #7381478
05/11/2026$850,000PriceChange
elevateMLS #7381478
05/01/2026$875,000PriceChange
elevateMLS #7381478
04/20/2026$885,000PriceChange
elevateMLS #7381478
04/08/2026$900,000Listed For SaleelevateMLS #7381478
05/04/2023$669,000Sold
N/A
01/24/2023$699,900ContingentelevateMLS #1058665
11/04/2022$699,900PriceChange
elevateMLS #1058665
09/23/2022$719,999Listed For SaleelevateMLS #1058665

Market trends in Monument

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$707K
$20.83KMoM
Sale-to-List Price
98.8%
0.6%MoM
Price per sq ft
$220
$4MoM
Available listings
254
7MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2024
Tax$2,773
Assessment$710,774
Home facts updated by county records

Comparable Sales for 255 Jack Boot Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
270 Lodgepole Way, Monument, CO
0.05
Single-Family Home
$845,000
01/28/26
5
3
3,438
265 Lodgepole Way, Monument, CO
0.09
Single-Family Home
$870,000
12/19/25
5
3.5
5,057
17430 Lamplight Dr, Monument, CO
0.14
Single-Family Home
$950,000
12/30/25
4
3.5
3,944
17815 Fairplay Way, Monument, CO
0.25
Single-Family Home
$675,000
11/11/25
5
3
3,952
220 Cobblestone Way, Monument, CO
0.27
Single-Family Home
$730,000
02/09/26
5
3.5
3,463
17395 Caribou Dr E, Monument, CO
0.29
Single-Family Home
$840,000
03/31/26
4
2.5
2,692
17365 Caribou Dr E, Monument, CO
0.24
Single-Family Home
$730,000
10/06/25
4
3
3,098
17805 Fairplay Way, Monument, CO
0.27
Single-Family Home
$745,000
07/02/26
4
3.5
3,198

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 255 Jack Boot Way.
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 Monument

At least 131 Trulia users voted on each feature.

  • 98 % Say it's dog friendly

  • 94 % Say car is needed

  • 92 % Say parking is easy

  • 85 % Say there's wildlife

  • 80 % Say there's holiday spirit

  • 80 % Say yards are well-kept

  • 79 % Say people would walk alone at night

  • 78 % Say it's quiet

  • 73 % Say kids play outside

  • 60 % Say neighbors are friendly

  • 56 % Say they plan to stay for at least 5 years

  • 47 % Say there are sidewalks

  • 33 % Say streets are well-lit

  • 33 % Say there are community events

  • 30 % Say it's walkable to restaurants

  • 28 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Lwmanus
    "We’ve lived in Monument Colorado for 25 years and love, love, love it. Small town with all the conveniences. "
    0
    Flag
  • Lwmanus
    "When I did commute it’s wasn’t a trouble since the interstate is very close and there are alternate routes as well. "
    0
    Flag
  • John Patrick
    "Most dog owners have in ground wireless fences Its dog friendl with people keeping track of pets.. "
    0
    Flag
  • J Hyland
    "Dog owners walk their dog’s frequently in this area, and they are welcome. Good area for shops and business , houses and walkable living. The town is open and friendly to all. Groceries , pharmacies, coffee are all available."
    0
    Flag
  • Jtomal4az
    "Lots of parks, green space, and walking paths. Owners are very responsible for their pets and keep the areas clean. "
    0
    Flag
  • Justin.paul.piasecki
    "Commute is entirely by car but always reliable school bus routes and safe pick up points when it comes to the kids."
    0
    Flag
  • Brittany B.
    "Woodmoor garage sale event is great. Fireworks in Palmer lake for the Fourth of July. Parade in downtown monument for the 4th of July "
    0
    Flag
  • Pierceja61
    "There is lot space and trails to walk dogs and go walking and jogging. Also good for riding bikes and owners are good at picking up after their dogs. Most keep track of lost dogs. The next door app is good to look for lost/found dogs "
    0
    Flag
  • Matt M.
    "Quiet and easy going. neighborhood street parking makes streets tight but people are patient. quick access to major roads "
    0
    Flag
  • Brendajsrk
    "Very friendly & private I can get anywhere in Colorado Springs easily, ask neighbors for help and found the home of my dreams"
    0
    Flag
  • Paula
    "Monument is a wonderful area to live, but rapid changes in development are transforming this community."
    0
    Flag
  • Druselle M.
    "parks and good schools. neighborhood block parties and neighborhood outreach. good HOA and more than anything, good parks for dogs"
    0
    Flag
  • Andi B
    "Town concerts, art festivals, farmers market and many more fun events happening all the time. Food is great!"
    1
    Flag
  • Sher M.
    "Easy access to the highway for smooth commute to Colorado springs or Denver. Park and ride is minutes away if you prefer public transportation. "
    0
    Flag
  • p
    "Nice small town feel have felt safe and love living here. Easy to get to all shopping and entertainment."
    0
    Flag
  • pmh1415
    "There is such a community of dog owners here. All kinds of services, classes, parks. It truly is a huge part of most of our lives....great vets with access to CSU vet school. Bunches of rescues to include National Mill Dog Rescue is here. "
    6
    Flag
  • John
    "A nice neighborhood with well maintained homes, trails and parks with an excellent grade school. "
    0
    Flag
  • Pameladiamond0620
    "Great place to live and have a family. People are friendly and the school district are great. Great shops and restaurants for breakfast, lunch, and dinner. Monument lake is beautiful, lots of trails to walk. "
    2
    Flag
  • Husband
    "It’s worth it. I commute to DTC. I leave early, around 6:30 am and miss the heavy traffic. It’s a beautiful drive for most of the way, often see wildlife."
    0
    Flag
  • Kathleencmiller
    "This is a quiet, country life neighborhood. There are great schools and easy access to cities. Good restaurants. Small town feel. "
    0
    Flag
  • Armasreynoso
    "I just work here during the night and it is a safe place. If I were able to live I am not sure because I like the city"
    0
    Flag
  • Minsuehall
    "I love this neighborhood because it feels like a small town but big cities are only 15 minutes away, North or South. "
    0
    Flag
  • Carol
    "Nice area. Close to town but not too close. No HOA. Few covenants (no chickens or goats)."
    0
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

11 pet-friendly rentals in Monument, CO

Explore by feature - Garage

25 rentals with a garage in Monument, CO

Explore by feature - Air Conditioning

25 rentals with air conditioning in Monument, CO

Explore by feature - Pool

Explore by feature - Washer/dryer

31 rentals with a washer/dryer in Monument, CO

Explore by feature - Outdoor Space

8 rentals with an outdoor space in Monument, CO

Homes for sale near 255 Jack Boot Way

Skip to last item
Skip to first item

Off Market Homes Near 255 Jack Boot Way

Skip to last item
Skip to first item
The real estate listing information and related content displayed on this site is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This information and related content is deemed reliable but is not guaranteed accurate by the Pikes Peak REALTOR® Services Corp d/b/a elevateMLS.