Homes for Sale Under $300K in Wildwood, FL

This page tracks every Wildwood listing with an asking price under $300,000, by community, with live counts and asking prices. Prices are asking prices from the MLS, not values, and the list changes with every refresh.

106 homes listed under $300,000 are for sale or pending in Wildwood, FL today across 46 communities. The median asking price is $221,950, from $60,000 to $299,990. Listings in Wildwood without that feature have a median of $377,377. Most listings right now: Tillman Oaks (10), Woodland Crossings (9), Continental Country Club (8). Updated October 2, 2026 from the MLS.

First-time buyers: what Wildwood costs at the entry level

48 active single-family homes, townhomes and condos at or below $300,000 — median $265,990, about $1,673/mo principal & interest at 6.95% with 5% down. Live from the MLS, refreshed nightly.

Newest homes under $300K in Wildwood

9699 County Road 121, starter home for sale in Wildwood
$275,000 New
3 bd · 2 ba · 1,392 sq ft · built 2007
9699 County Road 121, 34785
Listing courtesy of LAKE PROPERTY STARS
601 Kilgore Street, starter home for sale in Wildwood
$235,000 New
1 ba · 2,430 sq ft · built 1959
601 Kilgore Street, 34785
Listing courtesy of WEMERT GROUP REALTY LLC
8801 Pine Bark Way, starter home for sale in Wildwood
$257,990 New
3 bd · 2 ba · 1,250 sq ft · built 2026
8801 Pine Bark Way, 34785
Tillman Oaks
Listing courtesy of HOLIDAY BUILDERS GULF COAST
8796 Pine Bark Way, starter home for sale in Wildwood
$265,990 New
3 bd · 2 ba · 1,525 sq ft · built 2026
8796 Pine Bark Way, 34785
Tillman Oaks
Listing courtesy of HOLIDAY BUILDERS GULF COAST
8902 Wildflower Field Lane, starter home for sale in Wildwood
$283,990 New
4 bd · 2.5 ba · 1,895 sq ft · built 2027
8902 Wildflower Field Lane, 34785
Woodland Crossings
Listing courtesy of MALTBIE REALTY GROUP
8785 Pine Bark Way, starter home for sale in Wildwood
$286,990 New
4 bd · 2 ba · 1,802 sq ft · built 2026
8785 Pine Bark Way, 34785
Tillman Oaks
Listing courtesy of HOLIDAY BUILDERS GULF COAST
8782 Triumph Circle, starter home for sale in Wildwood
$294,295 New
3 bd · 2 ba · 1,672 sq ft · built 2026
8782 Triumph Circle, 34785
Triumph South
Listing courtesy of DR HORTON REALTY OF WEST CENTRAL FLORIDA
608 Masters Avenue, starter home for sale in Wildwood
$295,000 New
3 bd · 2 ba · 1,689 sq ft · built 2019
608 Masters Avenue, 34785
Listing courtesy of WORLD CLASS REALTY GROUP LLC
13103 Sandalwood Drive #13-103, starter home for sale in Wildwood
$115,000 New
2 bd · 1 ba · 1,032 sq ft · built 1980
13103 Sandalwood Drive #13-103, 34785
Listing courtesy of REALTY EXECUTIVES IN THE VILLAGES
5238 Dragonfly Drive, starter home for sale in Wildwood
$265,000 New
3 bd · 2.5 ba · 1,812 sq ft · built 2023
5238 Dragonfly Drive, 34785
Beaumont
Listing courtesy of LPT REALTY, LLC
7974 Penrose Place, starter home for sale in Wildwood
$294,900
3 bd · 2 ba · 1,844 sq ft · built 2023
7974 Penrose Place, 34785
Listing courtesy of RE/MAX PREMIER REALTY HWY 200
8765 Triumph Circle, starter home for sale in Wildwood
$292,990
3 bd · 2 ba · 1,672 sq ft · built 2026
8765 Triumph Circle, 34785
Triumph South
Listing courtesy of DR HORTON REALTY OF WEST CENTRAL FLORIDA
705 5Th Street, starter home for sale in Wildwood
$227,000
3 bd · 2 ba · 1,261 sq ft · built 2017
705 5Th Street, 34785
Listing courtesy of OPENDOOR BROKERAGE LLC
5365 Pinecone Court, starter home for sale in Wildwood
$229,000
3 bd · 2.5 ba · 1,688 sq ft · built 2021
5365 Pinecone Court, 34785
Beaumont
Listing courtesy of RE/MAX SELECT PARTNERS
8890 Wildflower Field Lane, starter home for sale in Wildwood
$279,990
4 bd · 2 ba · 1,722 sq ft · built 2027
8890 Wildflower Field Lane, 34785
Woodland Crossings
Listing courtesy of MALTBIE REALTY GROUP
8878 Wildflower Field Lane, starter home for sale in Wildwood
$249,990
3 bd · 2 ba · 1,302 sq ft · built 2027
8878 Wildflower Field Lane, 34785
Woodland Crossings
Listing courtesy of MALTBIE REALTY GROUP
8884 Wildflower Field Lane, starter home for sale in Wildwood
$259,990
3 bd · 2 ba · 1,452 sq ft · built 2027
8884 Wildflower Field Lane, 34785
Woodland Crossings
Listing courtesy of MALTBIE REALTY GROUP
8896 Wildflower Field Lane, starter home for sale in Wildwood
$299,990
4 bd · 2.5 ba · 2,240 sq ft · built 2027
8896 Wildflower Field Lane, 34785
Woodland Crossings
Listing courtesy of MALTBIE REALTY GROUP
8391 Clearway Drive, starter home for sale in Wildwood
$289,990
3 bd · 2 ba · 1,672 sq ft · built 2026
8391 Clearway Drive, 34785
Triumph South
Listing courtesy of DR HORTON REALTY OF WEST CENTRAL FLORIDA
8740 Wildflower Field Lane, starter home for sale in Wildwood
$279,900
3 bd · 2 ba · 1,545 sq ft · built 2026
8740 Wildflower Field Lane, 34785
Woodland Crossings
Listing courtesy of CAMBRIDGE REALTY OF CENTRAL FL
5395 Sunshine Drive, starter home for sale in Wildwood
$289,500
2 bd · 2 ba · 1,614 sq ft · built 2020
5395 Sunshine Drive, 34785
Beaumont
Listing courtesy of ORCHARD BROKERAGE, LLC
5311 Dragonfly Drive, starter home for sale in Wildwood
$216,000
3 bd · 2.5 ba · 1,812 sq ft · built 2022
5311 Dragonfly Drive, 34785
Beaumont
Listing courtesy of RE/MAX SELECT PARTNERS
8806 Pine Bark Way, starter home for sale in Wildwood
$257,990
3 bd · 2 ba · 1,250 sq ft · built 2026
8806 Pine Bark Way, 34785
Tillman Oaks
Listing courtesy of HOLIDAY BUILDERS GULF COAST
8818 Pine Bark Way, starter home for sale in Wildwood
$246,990
3 bd · 2 ba · 1,525 sq ft · built 2026
8818 Pine Bark Way, 34785
Tillman Oaks
Listing courtesy of HOLIDAY BUILDERS GULF COAST
8399 Clearway Drive, starter home for sale in Wildwood
$299,990
4 bd · 2 ba · 1,828 sq ft · built 2026
8399 Clearway Drive, 34785
Triumph South
Listing courtesy of DR HORTON REALTY OF WEST CENTRAL FLORIDA
3554 County Road 230C, starter home for sale in Wildwood
$199,000
2 bd · 2 ba · 1,218 sq ft · built 2005
3554 County Road 230C, 34785
Listing courtesy of CONNIE MAHAN REAL ESTATE GROUP
5254 Dragonfly Drive, starter home for sale in Wildwood
$202,000
3 bd · 2.5 ba · 1,688 sq ft · built 2023
5254 Dragonfly Drive, 34785
Beaumont
Listing courtesy of RE/MAX SELECT PARTNERS
8668 Wildflower Field Lane, starter home for sale in Wildwood
$268,900
3 bd · 2 ba · 1,486 sq ft · built 2026
8668 Wildflower Field Lane, 34785
Woodland Crossings
Listing courtesy of CAMBRIDGE REALTY OF CENTRAL FL
7889 Penrose Place, starter home for sale in Wildwood
$299,000
3 bd · 2 ba · 1,844 sq ft · built 2023
7889 Penrose Place, 34785
Listing courtesy of RE/MAX PREMIER REALTY
8669 Triumph Circle, starter home for sale in Wildwood
$290,000
4 bd · 2 ba · 1,816 sq ft · built 2022
8669 Triumph Circle, 34785
Triumph South
Listing courtesy of WORTH CLARK REALTY

What the payment looks like

Purchase priceP&I at 6.95%, 5% downP&I, 20% downCash to close at 5% down (est.)
$150,000$943$794$12,000
$200,000$1,258$1,059$16,000
$250,000$1,572$1,324$20,000
$300,000$1,887$1,589$24,000

Estimates only; taxes, insurance, HOA and mortgage insurance are on top. Closing costs assumed at 3%.

Down-payment assistance in Sumter County · First-time buyer guide

Wildwood homes under $300K by community

Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.

CommunityHomes Under $300KNew buildMedian listFrom
Tillman Oaks1010$265,990$246,990
Woodland Crossings99$279,990$249,990
Continental Country Club80$169,700$124,500
Timberwoods Estates80$126,700$79,900
Beaumont Ph 170$227,500$202,000
Beaumont Ph 2 & 350$267,900$249,500
Triumph South44$293,642$289,990
Continental Camper Resorts Uni40$135,000$134,900
Highfield At Twisted Oaks33$295,450$295,360
Heritage Wood N Lakes Estates30$219,900$170,000
Sandalwood Condo30$125,000$115,000
Highfield At Twisted Oaks Ph 222$298,065$296,690
Triumph South Ph 120$287,500$285,000
Beaumont Ph I20$240,500$216,000
Wildwood Ranch20$137,500$99,500
Moreland Park20$129,500$60,000
Sunny Dell Sub Un 210$295,000$295,000
Rolling Hills Manor10$275,000$275,000
Wildwood Ranches10$275,000$275,000
Gray Porter Sub10$254,900$254,900
Barwicks Add/Wildwood10$247,900$247,900
Poinsetta Park10$240,000$240,000
Barwicks Add Wildwood10$235,000$235,000
Meadovista10$229,900$229,900
Block F Meadowlawn Add10$227,000$227,000
Lake Miona Heights10$224,700$224,700
Continental Cntry Club Inc Residence10$219,600$219,600
Continental Country Club Inc10$219,000$219,000
Bridges11$212,500$212,500
Bridges Sub To Wildwood10$185,000$185,000
Hearty Host Lake Resort10$185,000$185,000
Bridges Sub11$184,996$184,996
Pettys Add10$179,900$179,900
Continental Cc Inc Resorts10$179,500$179,500
Timberwood Estates10$179,000$179,000
Coleman Oaks10$169,900$169,900
Continental Camper Resort10$165,000$165,000
Continental Campers Resorts10$162,500$162,500
Continental Country Club - Timberwoods10$159,900$159,900
Continental Camper Ress Incorp10$159,000$159,000
Continental Ctry Club Comm10$149,000$149,000
Continental Camper Resorts Inc10$147,000$147,000
Sandalwood Condminium10$115,000$115,000
Water Wheel Adult Mobile Home10$114,000$114,000
Continental Campers Resort10$106,500$106,500
Moreland Park Sub10$104,900$104,900

What under $300,000 buys and what to check

In this price band the differences between listings are usually age, size and condition rather than location alone, so read each listing’s year built, square footage and property type (a condo or manufactured home and a single-family home can sit at the same price with very different monthly costs). Budget the full monthly number, not the price: taxes, insurance, and HOA or CDD fees are all on each listing page, and our true cost of ownership calculator puts them into one figure. Insurance quotes on older roofs and older electrical can change which of two similar homes is actually cheaper.

Questions to ask about any listing in this band

How old is the roof, and will insurers write it? Is there a four-point inspection on file? What did the seller pay for insurance last year? In a condo, what are the dues, is there a special assessment or milestone inspection pending, and what do the reserves look like? Is the price a recent reduction, and how long has it been listed? A local agent who works the area will know which communities in this band have the fewest surprises at inspection.

Common questions

How many homes listed under $300,000 are for sale in Wildwood?
As of October 2, 2026, 106 Wildwood, FL listings whose MLS record reports an asking price under $300,000 are active or pending, across 46 communities. The count updates with every MLS refresh.
What do homes under $300K cost in Wildwood?
The median asking price today is $221,950, with listings from $60,000 to $299,990. Wildwood listings without that feature have a median of $377,377.
Which Wildwood community has the most homes under $300K for sale?
Tillman Oaks has the most right now (10), followed by Woodland Crossings (9), Continental Country Club (8), Timberwoods Estates (8).
What is the monthly payment on a home under $300,000?
At today’s rates with 20% down, principal and interest on a $300,000 purchase runs in the $1,500–$1,700 a month range before taxes, insurance and any HOA; each listing page shows the property tax and fees for that home, and the true-cost calculator linked above turns them into one monthly number.

Keep exploring Wildwood

Homes Under $300K in nearby Sumter County cities

Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Wildwood, FL whose MLS record reports an asking price under $300,000. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.

Listings courtesy of Stellar MLS as distributed by MLS GRID.

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