# 2247 Waukeenah Highway, Monticello, FL 32344 > **TL;DR:** 5bd/3ba single family, $695,000 ($197/sqft), built 1999, 3,536 sqft. > Fireplace, A/C. Est. $3,717/mo. Listed 77 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $695,000 | | Price/sqft | $197 | | Bedrooms | 5 | | Bathrooms | 3 full | | Square Feet | 3,536 | | Year Built | 1999 | | Lot Size | 455,202 sqft (10.45 acres) | | Stories | 2 | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 77 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $3,514 | | Estimated Insurance | $203 | | **Total** | **$3,717** | ## Nearby Schools - **Elementary:** Jefferson County K-12 School - **Middle:** Jefferson County K-12 School - **High:** Jefferson County K-12 School ## Key Amenities - Fireplace - A/C ## Property Highlights - Built in 1999 - 10.45 acre lot - 2 stories - Fireplace ## Description ### Agent Description Just 3 miles south of Monticello, FL and only 2.5 miles from I-10, this 10.45 acre working homestead has been thoughtfully set up for country living, livestock and extended family. The 3,536 sq. ft. home features 4 bedrooms/2 baths in the main house (with the set up for an additional bath upstairs) master is conveniently located downstairs with two walk-in closets, private access, plenty of lighting and a huge newly renovated bathroom, whirlpool tub in spare bath, high ceilings in the living area with a wood burning fireplace, bright beautiful kitchen with Corian counter tops, new dishwasher, new stovetop and French doors leading to the best views of the back of the property. This exceptional property also includes a private one bedroom, one bath mother in law suite with its own private entrance, connected to the main home by an enclosed breezeway (initially set up for a small hair salon business). The suite offers a large living area, new step in shower, new refrigerator, kitchen sink, microwave even their own back porch! Ideal for a parent, grown child, guests or simply someone who needs a little independence while staying close to family. Outside is where the property really earns the name farmstead. Six fenced paddocks (4 ft. high Bekaert high-tensile woven wire sheep and goat fencing) along with "no climb" fencing in the back yard for the dogs. Pines, crepe myrtles, beautiful live oaks line the back side of the house providing ample shade for livestock. There is a three bay pole barn (25x30), equipment shed/potting house (15x50), additional equipment barn (25x60), chicken coop (10x16), peach trees and blueberry bushes, plus plenty of room to continue growing, gardening and raising animals. New pitcher pump well provides access to water even when the power is out with the option to hook up to community water. Water is ran to EVERY pasture clear up to the main road! The property is gated with Ghost Controls, fenced and has excellent frontage on Waukeenah Highway. Best of all, there is no HOA and no deed restrictions to tell you how to use your own 10.45 acres. This isn't just a house with acreage. It's an established country homestead with the infrastructure already in place and close enough to town for conveniences. Most everything on the property is negotiable...including tractor with attachments, chickens, as well as other equipment and furnishings. ## Location - **Address:** 2247 Waukeenah Highway, Monticello, FL 32344 - **County:** Jefferson - **Coordinates:** 30.504133, -83.901953 - **Google Maps:** https://www.google.com/maps?q=30.504133,-83.901953 ## Listing Agent - **Name:** Alicia Radtke · **License:** 3526228 - **Brokerage:** All Realty Services - **Broker Phone:** (850) 933-6363 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/2247-Waukeenah-Hwy_Monticello_FL_32344_M61492-10654?f=listhub&s=TBRFL&m=403842&c=propsimple) ## Photos ![2247 Waukeenah Highway - Photo 1](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f718855251r.jpg) ![2247 Waukeenah Highway - Photo 2](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f518407825r.jpg) ![2247 Waukeenah Highway - Photo 3](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f3603798208r.jpg) ![2247 Waukeenah Highway - Photo 4](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1769334837r.jpg) ![2247 Waukeenah Highway - Photo 5](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2411073406r.jpg) ![2247 Waukeenah Highway - Photo 6](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2927990269r.jpg) ![2247 Waukeenah Highway - Photo 7](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1759527691r.jpg) ![2247 Waukeenah Highway - Photo 8](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f3738281333r.jpg) ![2247 Waukeenah Highway - Photo 9](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1523738543r.jpg) ![2247 Waukeenah Highway - Photo 10](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f582371061r.jpg) ![2247 Waukeenah Highway - Photo 11](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1118326651r.jpg) ![2247 Waukeenah Highway - Photo 12](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f4210821724r.jpg) ![2247 Waukeenah Highway - Photo 13](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f280246251r.jpg) ![2247 Waukeenah Highway - Photo 14](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1893744428r.jpg) ![2247 Waukeenah Highway - Photo 15](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2457480994r.jpg) ![2247 Waukeenah Highway - Photo 16](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f3238254315r.jpg) ![2247 Waukeenah Highway - Photo 17](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f496173379r.jpg) ![2247 Waukeenah Highway - Photo 18](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f266057887r.jpg) ![2247 Waukeenah Highway - Photo 19](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f866761525r.jpg) ![2247 Waukeenah Highway - Photo 20](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1371528355r.jpg) ![2247 Waukeenah Highway - Photo 21](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2633593762r.jpg) ![2247 Waukeenah Highway - Photo 22](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1415011418r.jpg) ![2247 Waukeenah Highway - Photo 23](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f3118958312r.jpg) ![2247 Waukeenah Highway - Photo 24](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f3300903270r.jpg) ![2247 Waukeenah Highway - Photo 25](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f3775239908r.jpg) ![2247 Waukeenah Highway - Photo 26](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2204502300r.jpg) ![2247 Waukeenah Highway - Photo 27](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2830109840r.jpg) ![2247 Waukeenah Highway - Photo 28](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1946551347r.jpg) ![2247 Waukeenah Highway - Photo 29](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2216629244r.jpg) ![2247 Waukeenah Highway - Photo 30](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1579211549r.jpg) ![2247 Waukeenah Highway - Photo 31](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f579164151r.jpg) ![2247 Waukeenah Highway - Photo 32](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f3689421246r.jpg) ![2247 Waukeenah Highway - Photo 33](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1316663054r.jpg) ![2247 Waukeenah Highway - Photo 34](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f3789770259r.jpg) ![2247 Waukeenah Highway - Photo 35](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f974094711r.jpg) ![2247 Waukeenah Highway - Photo 36](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f991157906r.jpg) ![2247 Waukeenah Highway - Photo 37](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1169752254r.jpg) ![2247 Waukeenah Highway - Photo 38](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1274365891r.jpg) ![2247 Waukeenah Highway - Photo 39](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f3621319508r.jpg) ![2247 Waukeenah Highway - Photo 40](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2388139505r.jpg) ![2247 Waukeenah Highway - Photo 41](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f901755017r.jpg) ![2247 Waukeenah Highway - Photo 42](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2711200086r.jpg) ![2247 Waukeenah Highway - Photo 43](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2665844254r.jpg) ![2247 Waukeenah Highway - Photo 44](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f521399277r.jpg) ![2247 Waukeenah Highway - Photo 45](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1815519028r.jpg) ![2247 Waukeenah Highway - Photo 46](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1417148306r.jpg) ![2247 Waukeenah Highway - Photo 47](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2879964385r.jpg) ![2247 Waukeenah Highway - Photo 48](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f245228739r.jpg) ![2247 Waukeenah Highway - Photo 49](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2836615037r.jpg) ![2247 Waukeenah Highway - Photo 50](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f569782281r.jpg) ![2247 Waukeenah Highway - Photo 51](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f922394289r.jpg) ![2247 Waukeenah Highway - Photo 52](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f3629545053r.jpg) ![2247 Waukeenah Highway - Photo 53](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2885420352r.jpg) ![2247 Waukeenah Highway - Photo 54](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f951595604r.jpg) ![2247 Waukeenah Highway - Photo 55](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f946553366r.jpg) ![2247 Waukeenah Highway - Photo 56](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2496153850r.jpg) ![2247 Waukeenah Highway - Photo 57](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1371441378r.jpg) ![2247 Waukeenah Highway - Photo 58](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1367634417r.jpg) ![2247 Waukeenah Highway - Photo 59](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1669863042r.jpg) ![2247 Waukeenah Highway - Photo 60](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f557870614r.jpg) ![2247 Waukeenah Highway - Photo 61](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2311428400r.jpg) ![2247 Waukeenah Highway - Photo 62](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2538392170r.jpg) ![2247 Waukeenah Highway - Photo 63](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2699536592r.jpg) ![2247 Waukeenah Highway - Photo 64](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2380030547r.jpg) ![2247 Waukeenah Highway - Photo 65](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f620240419r.jpg) ![2247 Waukeenah Highway - Photo 66](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2382693946r.jpg) ![2247 Waukeenah Highway - Photo 67](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2471596773r.jpg) ![2247 Waukeenah Highway - Photo 68](http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f54275526r.jpg) --- **MLS#:** 403842 | **Updated:** 2026-11-01 **Source:** listhub *Copyright © 2026 Tallahassee Board of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://staging.propertysimple.ai/listing/2247-waukeenah-highway-monticello-fl-32344-df2acf49246a466e81701be2661e1439) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/2247-waukeenah-highway-monticello-fl-32344-df2acf49246a466e81701be2661e1439#listing", "url": "https://staging.propertysimple.ai/listing/2247-waukeenah-highway-monticello-fl-32344-df2acf49246a466e81701be2661e1439", "name": "2247 Waukeenah Highway, Monticello, FL 32344", "description": "Just 3 miles south of Monticello, FL and only 2.5 miles from I-10, this 10.45 acre working homestead has been thoughtfully set up for country living, livestock and extended family. The 3,536 sq. ft. home features 4 bedrooms/2 baths in the main house (with the set up for an additional bath upstairs) master is conveniently located downstairs with two walk-in closets, private access, plenty of lighting and a huge newly renovated bathroom, whirlpool tub in spare bath, high ceilings in the living area with a wood burning fireplace, bright beautiful kitchen with Corian counter tops, new dishwasher, new stovetop and French doors leading to the best views of the back of the property. This exceptional property also includes a private one bedroom, one bath mother in law suite with its own private entrance, connected to the main home by an enclosed breezeway (initially set up for a small hair salon business). The suite offers a large living area, new step in shower, new refrigerator, kitchen sink, microwave even their own back porch! Ideal for a parent, grown child, guests or simply someone who needs a little independence while staying close to family. Outside is where the property really earns the name farmstead. Six fenced paddocks (4 ft. high Bekaert high-tensile woven wire sheep and goat fencing) along with \"no climb\" fencing in the back yard for the dogs. Pines, crepe myrtles, beautiful live oaks line the back side of the house providing ample shade for livestock. There is a three bay pole barn (25x30), equipment shed/potting house (15x50), additional equipment barn (25x60), chicken coop (10x16), peach trees and blueberry bushes, plus plenty of room to continue growing, gardening and raising animals. New pitcher pump well provides access to water even when the power is out with the option to hook up to community water. Water is ran to EVERY pasture clear up to the main road! The property is gated with Ghost Controls, fenced and has excellent frontage on Waukeenah Highway. Best of all, there is no HOA and no deed restrictions to tell you how to use your own 10.45 acres. This isn't just a house with acreage. It's an established country homestead with the infrastructure already in place and close enough to town for conveniences. Most everything on the property is negotiable...including tractor with attachments, chickens, as well as other equipment and furnishings.", "image": [ "http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f718855251r.jpg", "http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f518407825r.jpg", "http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f3603798208r.jpg", "http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1769334837r.jpg", "http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2411073406r.jpg", "http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f2927990269r.jpg", "http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1759527691r.jpg", "http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f3738281333r.jpg", "http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1523738543r.jpg", "http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f582371061r.jpg", "http://lh.rdcpix.com/8f6703560c4bd58363bd892a158d57dfl-f1118326651r.jpg", 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