Caleb Stephens

Monticello FL

Silo Hill Properties

59 Closed Sales

$17.9M Total Value

$73K - $1.5M Price Range

$303.1K Average Price

Prior 5 years

About Caleb

I'm an expert real estate agent with Waypoint Properties in Crawfordville, FL and the nearby area, providing home-buyers and sellers with professional, responsive and attentive real estate services. Want an agent who'll really listen to what you want in a home? Need an agent who knows how to effectively market your home so it sells? Give me a call! I'm eager to help and would love to talk to you.

Home Types: House, Manufactured, Lot/Land, Townhouse, Commercial

Years of Experience: 6

Transaction History

1 Year
2 Year
5 Year

Seller Deals

Total Deals

Total Value

$2,443,600

Average Sale Price

$222,145

Price Range

$73K - $465K

Buyer Deals

Total Deals

Neighborhoods Caleb is Experienced In

Caleb's Active Listings

$369,000
- 5 Beds
- 3 Baths
- 2,700 Sq Ft
240 Smokehouse Way

Greenville, FL
Uncover this stunning 5-bedroom, 3-bath home spanning 2,700 sqft, nestled on 5 acres of private land and all it has to offer. Enjoy the tranquility of a beautiful man-made pond filled with fish and perfect for swimming and relaxing. Highlights include: Modern updates throughout. Fun hidden bookshelf doors and secret floor storage for a touch of adventure. Spacious, powered barn ideal for projects

Caleb Stephens Silo Hill Properties

$249,000
- 3 Beds
- 2 Baths
- 1,553 Sq Ft
1822 Wales Dr

Tallahassee, FL
Discover your new home with this charming 3-bedroom, 2-bath brick residence located just minutes from town. Featuring a spacious layout with modern updates, including an updated bathroom and stylish vinyl plank floors throughout. The two-car garage provides plenty of parking and storage space. Perfect for families or anyone looking for comfort and convenience! Key Features: 3 Bedrooms 2 Bathrooms

Caleb Stephens Silo Hill Properties

$550,000
- 6,024 Sq Ft
535 Hagan St

Monticello, FL
Rare Investor Opportunity: 7-Unit Residential Complex for Sale Don't miss this fantastic investment opportunity! This well-maintained 7-unit complex features: Six 3-bedroom, 1-bathroom units One 2-bedroom, 1-bathroom unit Walking distance to downtown – perfect for tenants seeking convenience Corner lot location with excellent visibility Designated parking spots for each unit 2023 Roof Whether

Caleb Stephens Silo Hill Properties

$625,000
- 4 Beds
- 3 Baths
- 2,716 Sq Ft
140 Shumard Ct

Monticello, FL
Discover this stunning 2,600+ sqft home built in 2021, offering the perfect blend of quiet country living and modern convenience. Adjoinging additional lot can also be purchased! Features include: 4 spacious bedrooms and 3 full bathrooms 2 master bedrooms located downstairs Dedicated office/bonus room – ideal for work or hobbies Modern kitchen and open living spaces Attached 2-car garage Just

Caleb Stephens Silo Hill Properties

$1,540,000
- 6 Beds
- 4.5 Baths
- 4,843 Sq Ft
174 Decey Wallace Ln

Crawfordville, FL
This stunning 6-bedroom, 5-bathroom residence is thoughtfully designed with both luxury and functionality in mind. From the moment you step inside, you’ll be captivated by the soaring 25-ft oakwood coffered ceilings in the living room, complemented by a dramatic upstairs catwalk that overlooks the main living space. The home features rich hardwood floors throughout, solid oak stair treads, and

Caleb Stephens Silo Hill Properties

$199,900
- 3 Beds
- 1.5 Baths
- 1,150 Sq Ft
4008 Sonnet Dr

Tallahassee, FL
Seller to offer $5,000 in concessions with acceptable offer. This charming property offers a perfect blend of comfort and convenience. Featuring spacious living areas, some modern updates, and a welcoming atmosphere. Enjoy a well-maintained yard, and easy access to local amenities, schools, shopping and parks. Don't miss the opportunity to make this beautiful house your new home!

Caleb Stephens Silo Hill Properties

Co-Listing Agent

$650,000
- Land
- 56 Acres
- $11,562 per Acre
0 Kemp Rd

Havana, FL
Stunning 56-acre property featuring a beautiful pond, abundant of wildlife including deer and turkeys, open pasture and the perfect setting for your future homesite. The property is already improved with a recently drilled well and power. Enjoy the privacy and flexibility of this property while still being very conveniently located. 25 minutes from Bannerman crossing, and other popular

Caleb Stephens Silo Hill Properties

$349,000
- 3 Beds
- 2 Baths
- 1,502 Sq Ft
406 Robin Rd

Monticello, FL
This charming 3-bedroom, 2-bath residence offers spacious living with vaulted ceilings, all nestled on five acres of private land. The property features a new roof for peace of mind, and the large deck is perfect for outdoor entertaining.This home also has a large unfinished basement to fit many of needs. The acreage is divided into 4 lots, providing plenty of space and potential. Located on a

Caleb Stephens Silo Hill Properties

Recently Sold

$175,000 Sold Apr 6, 2026
- 3 Beds
- 1.5 Baths
- 910 Sq Ft
4501 Hickory Forest Cir

Tallahassee, FL
- $192/SF
- 3 Days On Market
- Current Est. Value $187K
Caleb Stephens Silo Hill Properties

$465,000 Sold Apr 1, 2026
- 3 Beds
- 2 Baths
- 2,268 Sq Ft
308 Cherry Tree Rd

Monticello, FL
- 2% Below List
- $205/SF
- Current Est. Value $473K
Caleb Stephens Silo Hill Properties

$117,500 Sold Feb 13, 2026
- 2 Beds
- 1 Bath
- 912 Sq Ft
3725 Sutor Ct

Tallahassee, FL
- $129/SF
- 0 Days On Market
- Current Est. Value $125K
Caleb Stephens Silo Hill Properties

$117,500 Sold Feb 13, 2026
- 2 Beds
- 1 Bath
- 920 Sq Ft
3729 Sutor Ct

Tallahassee, FL
- $128/SF
- 0 Days On Market
- Current Est. Value $124K
Caleb Stephens Silo Hill Properties

$389,500 Sold Jan 12, 2026
- 3 Beds
- 2 Baths
- 1,865 Sq Ft
173 Deerfield Ln

Monticello, FL
- 9% Below List
- $209/SF
- 110 Days On Market
Caleb Stephens Silo Hill Properties

$168,100 Sold Nov 17, 2025
- 3 Beds
- 2 Baths
- 1,716 Sq Ft
375 Maple St

Monticello, FL
- 11% Below List
- $98/SF
- 70 Days On Market
- Current Est. Value $170K
Caleb Stephens Silo Hill Properties

$73,000 Sold Aug 25, 2025
- Land
- 5.58 Acre Lot
XXX Kelly Farm Rd

Havana, FL
- 3% Below List
- 5 Days On Market
Caleb Stephens Silo Hill Properties

$225,000 Sold Aug 15, 2025
- 3 Beds
- 2 Baths
- 1,824 Sq Ft
2168 Pineland Dr

Tallahassee, FL
- $123/SF
- 15 Days On Market
Caleb Stephens Silo Hill Properties

$179,000 Sold Jul 11, 2025
- 3 Beds
- 2 Baths
- 1,620 Sq Ft
120 E 1st Place

Greenville, FL
- 10% Below List
- $110/SF
- 360 Days On Market
Caleb Stephens Silo Hill Properties

Agent License: Florida 3464391

Caleb Stephens

(850) 518-7370

Silo Hill Properties

(850) 518-7370

Homes for Sale by City

Caleb Stephens

About Caleb

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Caleb is Experienced In

Caleb's Listings and Deals

Caleb's Active Listings

Recently Sold