Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Save search

Map layers

Safety

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Rentals Under $2,000/mo in Winter Garden, FL
Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Residential
  • Commercial

24 listings
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save search
3 bedsHousesWith a pool

Rentals Under $2,000/mo for Rent in Winter Garden, FL

Rentals Under $2,000/mo for Rent in Winter Garden, FL

Hide Map
24 Listings
Map

Rentals Under $2,000/mo for Rent in Winter Garden, FL

24 Listings

  1. 417 Southern Pecan Cir #208 — photoNew40Active

    $1,825/mo

    2 bd · 2 ba · 1,264 sqft

    417 Southern Pecan Cir #208, Winter Garden, FL

    Vicky Ramos · ALL COUNTY CFL PROPERTY MGMT

  2. 170 Windtree Ln #U — photo20Active

    $1,750/mo

    2 bd · 2 ba · 918 sqft

    170 Windtree Ln #U, Winter Garden, FL

    Romina Cabanas · LA ROSA REALTY LLC

  3. 634 Foster Ave — photo20Active

    $1,550/mo

    2 bd · 1 ba · 696 sqft

    634 Foster Ave, Winter Garden, FL

    Anthony O'Reilly Brookes · WINTER GARDEN REAL ESTATE

  4. 405 Southern Pecan Cir #108 — photo21Active

    $1,950/mo

    2 bd · 2 ba · 1,152 sqft

    405 Southern Pecan Cir #108, Winter Garden, FL

    Francisco Orchilles · LAKESIDE REALTY WINDERMERE INC

  5. 955 Butterfly Blvd — photo11Active

    $1,850/mo

    3 bd · 2 ba · 1,216 sqft

    955 Butterfly Blvd, Winter Garden, FL

    Suzanne Seenandan · PREFERRED RE BROKERS III

  6. 509 Varsity St — photo8Active

    $1,750/mo

    2 bd · 1 ba · 780 sqft

    509 Varsity St, Winter Garden, FL

    Angela Chapman · CAPITAL REALTY GROUP FLORIDA

  7. 502 Dunbar Ave — photoPrice Reduced13Active

    $1,399/mo

    2 bd · 1 ba · 816 sqft

    502 Dunbar Ave, Winter Garden, FL

    Nancy Guadagnino · SPECIALIZED PROPERTY MANAGEMENT

  8. 430 Southern Pecan Cir #106 — photo29Active

    $1,695/mo

    1 bd · 1 ba · 838 sqft

    430 Southern Pecan Cir #106, Winter Garden, FL

    Seyed Azimi · AFT PROPERTY LLC

  9. 200 Southern Pecan Cir #206 — photoPrice Reduced53Active

    $1,800/mo

    2 bd · 2 ba · 1,276 sqft

    200 Southern Pecan Cir #206, Winter Garden, FL

    Nicole Howell · FANNIE HILLMAN & ASSOCIATES

  10. 1007 Carol Anderson Dr — photoPrice Reduced10Active

    $2,000/mo

    4 bd · 2 ba · 1,300 sqft

    1007 Carol Anderson Dr, Winter Garden, FL

    Charles Maligaya · LA REALTY SERVICES LLC

  11. 92 Windtree Ln #L — photo10Active

    $1,650/mo

    2 bd · 2 ba · 918 sqft

    92 Windtree Ln #L, Winter Garden, FL

    Maria Perez · ROMAN'S PRO REALTY LLC

  12. 15347 Gilligan Ct — photo9Active

    $1,600/mo

    1 bd · 1 ba · 620 sqft

    15347 Gilligan Ct, Winter Garden, FL

    Andrea Munoz · MOSAIC PARTNERS GROUP

  13. 341 Southern Pecan Cir #201 — photoPrice Reduced23Active

    $1,575/mo

    1 bd · 1 ba · 738 sqft

    341 Southern Pecan Cir #201, Winter Garden, FL

    Elizabeth Rodriguez Bello · LA ROSA REALTY LLC

  14. 502 Varsity St — photoPrice Reduced5Active

    $1,675/mo

    2 bd · 1 ba · 780 sqft

    502 Varsity St, Winter Garden, FL

    Angela Chapman · CAPITAL REALTY GROUP FLORIDA

  15. 508 Varsity St — photoPrice Reduced10Active

    $1,675/mo

    2 bd · 1 ba · 780 sqft

    508 Varsity St, Winter Garden, FL

    Angela Chapman · CAPITAL REALTY GROUP FLORIDA

  16. 1105 Lincoln Ter — photoPrice Reduced22Active

    $1,950/mo

    3 bd · 1 ba · 814 sqft

    1105 Lincoln Ter, Winter Garden, FL

    Simone Pinto de Almeida Santos · NOVA REAL ESTATE SERVICES INC

  17. 407 Douglas Way #66 — photoPrice Reduced15Active

    $1,795/mo

    2 bd · 2 ba · 930 sqft

    407 Douglas Way #66, Winter Garden, FL

    Justin LaManna · HOMEVEST REALTY

  18. 1301 Eastern Pecan Pl #208 — photoPrice Reduced33Active

    $1,900/mo

    2 bd · 2 ba · 1,264 sqft

    1301 Eastern Pecan Pl #208, Winter Garden, FL

    Neyla Alvarez · EXP REALTY LLC

  19. 417 Southern Pecan Cir #204 — photo14Active

    $1,950/mo

    2 bd · 2 ba · 1,264 sqft

    417 Southern Pecan Cir #204, Winter Garden, FL

    Alejandro Hernandez · HP PROPERTY SOLUTIONS, LLC

  20. 1432 Broken Oak Dr #31a — photo20Active

    $1,900/mo

    2 bd · 2 ba · 1,216 sqft

    1432 Broken Oak Dr #31a, Winter Garden, FL

    Dan Thompson · OPTIMA ONE REALTY, INC.

  21. 430 Southern Pecan Cir #203 — photoPrice Reduced11Active

    $1,500/mo

    1 bd · 1 ba · 942 sqft

    430 Southern Pecan Cir #203, Winter Garden, FL

    Nick Horton · BANNER INT'L REAL ESTATE

  22. 200 Southern Pecan Cir #203 — photoPrice Reduced30Active

    $1,830/mo

    2 bd · 2 ba · 1,276 sqft

    200 Southern Pecan Cir #203, Winter Garden, FL

    Hans Tank · FLORIDA SCANDI REALTY LLC

  23. 14978 Lebeau Loop — photoPrice Reduced18Active

    $1,510/mo

    1 bd · 1 ba · 700 sqft

    14978 Lebeau Loop, Winter Garden, FL

    Christian Dell Olio · AGENT TRUST REALTY CORPORATION

  24. 15000 Stratus Loop #a2 — photoPrice Reduced23Active

    $1,850/mo

    1 bd · 1 ba · 873 sqft

    15000 Stratus Loop #a2, Winter Garden, FL

    AJ Rebhan · THE APARTMENT BROTHERS LLC

Explore Winter Garden rentals

By price

  • Rentals Under $2,000/mo
  • Rentals Under $3,000/mo
  • Rentals Under $4,000/mo

By bedrooms

  • 2 Bedroom Rentals
  • 3 Bedroom Rentals
  • 4 Bedroom Rentals
  • 5 Bedroom Rentals

By type

  • Single-Family Rentals
  • Townhome Rentals
  • Condo Rentals

By feature

  • Rentals with a Pool
Realty.com

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

Equal Housing OpportunityEqual Housing Lender

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

© 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

Listing data & MLS disclosures

Stellar MLS
Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Garden, FL community profile

Population
50,261
Median income
$102,195
Housing units
18,962
People per sq. mi.
562.2
Area
89.4 sq. mi.

Source: HJN community data