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Central Florida Luxury

Homes for rent.

Luxury inventory across Dr. Phillips, Windermere, Winter Park, Lake Nona, Golden Oak, Bella Collina, and the Butler Chain. Live MLS data direct from Stellar MLS — search by community, price, or feature. For off-market and coming-soon access, join the VIP list.

Closed Sales Volume: $85M
Families Represented: 232
Years Licensed: 11
Zillow Rating: 5.0★

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914 listings found in kissimmee

3050 Pirates Retreat Ct #208, FL

ActiveCondominium360°

$1,800 /mo

3050 Pirates Retreat Ct #208

Kissimmee, FL 34747

2 bd · 2 ba · 1,445 sqft

Caribe Cove Condo Ph 2

MLS# S5149733

Photo coming soon

ActiveTownhouse

$2,350 /mo

1248 Wispy Cypress Dr

Kissimmee, FL 34746

4 bd · 3 ba · 1,868 sqft

Cypress Hammock Ph 1

MLS# S5150871

Photo coming soon

ActiveTownhouse

$3,300 /mo

8123 Coconut Pl

Kissimmee, FL 34747

4 bd · 3 ba · 1,712 sqft

Rolling Oaks Ph 7

MLS# O6410274

3069 Chromatic St, FL

ActiveTownhouse360°

$2,300 /mo

3069 Chromatic St

Kissimmee, FL 34758

3 bd · 3 ba · 1,873 sqft

Westview Pod A Ph 3

MLS# O6411632

3045 Chromatic St, FL

ActiveTownhouse360°

$2,300 /mo

3045 Chromatic St

Kissimmee, FL 34758

3 bd · 3 ba · 1,834 sqft

Westview Pod A Ph 3

MLS# O6411701

111 Cuautla Way #2, FL

ActiveSingle Family Residence360°

$1,199 /mo

111 Cuautla Way #2

Kissimmee, FL 34743

1 bd · 1 ba · 94 sqft

MLS# S5150730

2006 Maple Ln, FL

ActiveSingle Family Residence360°

$2,065 /mo

2006 Maple Ln

Kissimmee, FL 34759

4 bd · 2 ba · 1,886 sqft

Poinciana Nbrhd 02 Village 08

MLS# O6392444

295 Cobalt Dr, FL

ActiveHalf Duplex360°

$1,600 /mo

295 Cobalt Dr

Kissimmee, FL 34758

2 bd · 2 ba · 1,323 sqft

MLS# S5146551

567 Hummingbird Ct, FL

ActiveSingle Family Residence360°

$2,000 /mo

567 Hummingbird Ct

Kissimmee, FL 34759

4 bd · 3 ba · 2,113 sqft

Poinciana Nbrhd 05 North Village 03

MLS# S5150750

1895 Cassidy Knoll Dr, FL

ActiveSingle Family Residence360°

$2,650 /mo

1895 Cassidy Knoll Dr

Kissimmee, FL 34744

3 bd · 2 ba · 1,676 sqft

Kindred Ph 1e

MLS# O6404253

730 Siena Palm Dr #204, FL

ActiveTownhouse

$2,250 /mo

730 Siena Palm Dr #204

Kissimmee, FL 34747

2 bd · 1 ba · 1,390 sqft

Siena At Celebration Condo B

MLS# S5150734

2729 Amanda Kay Way, FL

ActiveSingle Family Residence360°

$2,200 /mo

2729 Amanda Kay Way

Kissimmee, FL 34744

3 bd · 2 ba · 1,866 sqft

Eagles Landing

MLS# S5150383

1736 Fulfillment Dr, FL

ActiveSingle Family Residence360°

$2,200 /mo

1736 Fulfillment Dr

Kissimmee, FL 34744

3 bd · 3 ba · 1,802 sqft

MLS# S5145718

3230 Stratton Cir, FL

ActiveSingle Family Residence360°

$2,600 /mo

3230 Stratton Cir

Kissimmee, FL 34744

4 bd · 2 ba · 2,121 sqft

South Pointe

MLS# S5150714

3001 Laurel Run Ln #301, FL

ActiveCondominium

$1,725 /mo

3001 Laurel Run Ln #301

Kissimmee, FL 34741

3 bd · 2 ba · 1,495 sqft

Flora Ridge Condo Ph 8 Bldg 11

MLS# S5142621

9035 Carlotta Way, FL

ActiveTownhouse360°

$2,000 /mo

9035 Carlotta Way

Kissimmee, FL 34747

3 bd · 3 ba · 1,674 sqft

Murano/Westside

MLS# S5144237

2281 Southbury Dr, FL

ActiveTownhouse

$2,550 /mo

2281 Southbury Dr

Kissimmee, FL 34744

4 bd · 3 ba · 1,770 sqft

MLS# O6402418

619 Reindeer Dr, FL

ActiveSingle Family Residence360°

$1,950 /mo

619 Reindeer Dr

Kissimmee, FL 34759

4 bd · 2 ba · 1,714 sqft

Poinciana Nbrhd 03 Village 03

MLS# O6406492

2728 Skyline Loop, FL

ActiveTownhouse360°

$2,000 /mo

2728 Skyline Loop

Kissimmee, FL 34758

3 bd · 3 ba · 1,834 sqft

Westview Pod A Ph 3

MLS# O6411801

2877 Oconnell Dr, FL

ActiveSingle Family Residence360°

$2,850 /mo

2877 Oconnell Dr

Kissimmee, FL 34741

4 bd · 2 ba · 2,287 sqft

Cypress Reserve Ph 2

MLS# S5150818

232 Cobalt Dr, FL

ActiveSingle Family Residence360°

$2,030 /mo

232 Cobalt Dr

Kissimmee, FL 34758

3 bd · 2 ba · 1,609 sqft

Poinciana Village 1 Nbhd 1 North

MLS# TB8513338

2338 Cordova Ct, FL

ActiveSingle Family Residence360°

$2,100 /mo

2338 Cordova Ct

Kissimmee, FL 34743

3 bd · 2 ba · 1,293 sqft

Monterey Vlg Ph1 Unit 1

MLS# S5150632

2421 Ashecroft Dr, FL

ActiveSingle Family Residence360°

$2,470 /mo

2421 Ashecroft Dr

Kissimmee, FL 34744

4 bd · 3 ba · 1,803 sqft

Remington Ph 2

MLS# O6410269

8825 Grand Palms Cir #B, FL

ActiveCondominium360°

$1,700 /mo

8825 Grand Palms Cir #B

Kissimmee, FL 34747

3 bd · 2 ba · 1,222 sqft

Grand Palms Condo 4 Ph 4

MLS# O6409004

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Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information 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.

Based on information submitted to the MLS GRID as of May 29, 2026 at 2:15 PM ET. 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.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA

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Browse by area

The neighborhoods we cover.

Welcome to Dr. Phillips, Florida — area entry sign on Sand Lake Road

Neighborhood

Dr. Phillips

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American flag-painted horse statue in front of the Town of Windermere town hall, FL

Neighborhood

Windermere

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Butler Chain of Lakes — Central Florida lakefront aerial near Windermere and Dr. Phillips

Neighborhood

Butler Chain of Lakes

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Isleworth Country Club's white Mediterranean-style clubhouse with palm-lined drive, Windermere, FL

Neighborhood

Isleworth

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Aerial view of Lake Nona master-planned community, southeast Orlando

Neighborhood

Lake Nona

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Historic Park Avenue in Winter Park, Florida

Neighborhood

Winter Park

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Spanish Colonial estate on the water inside Golden Oak at Walt Disney World

Neighborhood

Golden Oak

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Tuscan hilltop village overlooking blue water — the Italian inspiration behind Bella Collina

Neighborhood

Bella Collina

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Live oak canopy road — the defining image of Gotha, FL

Neighborhood

Gotha

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Wadeview Park — a neighborhood green space in Orlando's SODO district

Neighborhood

SODO

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Lake Eola fountain and Downtown Orlando skyline's Lake Eola condos

Neighborhood

Downtown Orlando Condos

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Lake Eola fountain and Orlando skyline at dusk

Neighborhood

Lake Eola Heights

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Florida waterway with private docks — the lakefront lifestyle of the Conway Chain of Lakes

Neighborhood

Conway Chain of Lakes

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Florida Mediterranean home exterior with palm trees, representative of Stoneybrook East

Neighborhood

Stoneybrook East

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Stoneybrook West community entrance with fountain, monument sign, and championship golf course, Winter Garden FL

Neighborhood

Stoneybrook West

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Lake Lily Park in Maitland, Florida — peaceful lakeside fountain and green parkland

Neighborhood

Maitland

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Cranes Roost Park lake at dusk in Altamonte Springs, Florida

Neighborhood

Altamonte Springs

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Dramatic sunset over Lake Jesup from a boat in Oviedo, Florida

Neighborhood

Oviedo

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Aerial view of Lake Howell in Casselberry, Florida surrounded by residential neighborhoods

Neighborhood

Casselberry

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Boardwalk trail through Senator Park nature preserve in Longwood, Florida

Neighborhood

Longwood

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Lake Apopka north shore — the natural waterfront of Apopka's growing residential market

Neighborhood

Apopka

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Celebration town center and lakefront

Neighborhood

Celebration

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Winter Garden master-planned community — aerial view of clubhouse, resort pool, and tennis courts

Neighborhood

Winter Garden

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Baldwin Park village center and Lake Baldwin

Neighborhood

Baldwin Park

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College Park Edgewater Drive streetscape with Craftsman bungalows and oak canopy

Neighborhood

College Park

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Horizon West community streetscape West Orange County Florida

Neighborhood

Horizon West

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Aerial view of the Cocoa Beach shoreline along the Atlantic Ocean

Neighborhood

Cocoa Beach

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Aerial view of the Satellite Beach oceanfront and Atlantic shoreline

Neighborhood

Satellite Beach

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Aerial view of Indian Harbour Beach with Banana River frontage

Neighborhood

Indian Harbour Beach

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Melbourne Beach Atlantic shoreline from the air

Neighborhood

Melbourne Beach

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View of Indialantic from the Melbourne Causeway

Neighborhood

Indialantic

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Lake Washington from the air — Melbourne's largest freshwater lake

Neighborhood

Melbourne

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Aerial view of NE Palm Bay residential neighborhoods

Neighborhood

Palm Bay

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Aerial view of Grant-Valkaria rural acreage in South Brevard

Neighborhood

Grant-Valkaria

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Aerial view of mainland Cocoa, FL

Neighborhood

Cocoa

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Aerial view of Rockledge, FL — Central Brevard's oldest city

Neighborhood

Rockledge

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Aerial view of Merritt Island waterfront residential

Neighborhood

Merritt Island

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Aerial view of Viera, FL — Brevard's master-planned community

Neighborhood

Viera

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Aerial view of Vero Beach at night from the air — CC BY-SA 4.0 by Kiran891

Neighborhood

Vero Beach

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Aerial view of Cape Canaveral and the Atlantic shoreline

Neighborhood

Cape Canaveral

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Aerial view of Port St. John residential community

Neighborhood

Port St. John

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Rural acreage home on large lot in Mims, far north Brevard County, Florida

Neighborhood

Mims & Scottsmoor

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Indian River and Titusville waterfront view

Neighborhood

Titusville

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Sunrise at New Smyrna Beach (photo: Rae K. Hauck, CC BY-SA 3.0)

Neighborhood

New Smyrna Beach

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Balmoral community entrance sign, Windermere, FL

Neighborhood

Balmoral

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Cypress Landing community entrance sign, Dr. Phillips, Orlando, FL

Neighborhood

Cypress Landing

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The Estates at Cypress Landing community entrance sign, Dr. Phillips, Orlando, FL

Neighborhood

The Estates at Cypress Landing

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Harbor Isle community entrance sign, Windermere, FL

Neighborhood

Harbor Isle

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Havencrest community entrance sign, Orlando, FL

Neighborhood

Havencrest

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Lake Down Crest community entrance sign, Windermere, FL

Neighborhood

Lake Down Crest

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Lake Down Village community entrance sign, Windermere, FL

Neighborhood

Lake Down Village

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Marbella community entrance sign, Dr. Phillips, Orlando, FL

Neighborhood

Marbella

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Willow Wood community entrance sign, Dr. Phillips, Orlando, FL

Neighborhood

Willow Wood

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Windsor Hill luxury community entrance sign, Windermere, FL

Neighborhood

Windsor Hill

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Wingrove Estates community entrance sign, Dr. Phillips, Orlando, FL

Neighborhood

Wingrove Estates

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Sunrise over Lake Tohopekaliga with fishing boats in Kissimmee, FL

Neighborhood

Kissimmee

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St. Cloud lakefront park on Lake Tohopekaliga with pavilions and boat docks

Neighborhood

St. Cloud

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Historic First Street in downtown Sanford FL with brick storefronts and restaurants

Neighborhood

Sanford

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Heathrow Country Club golf course in Lake Mary FL with custom homes in background

Neighborhood

Lake Mary

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Cross Seminole Trail paved path through Winter Springs FL with cyclists and trees

Neighborhood

Winter Springs

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Boardwalk over crystal-clear springs at Gemini Springs State Park in DeBary, FL

Neighborhood

DeBary

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Tree-lined residential street in Deltona FL with mature oaks and single-family homes

Neighborhood

Deltona

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Historic Woodland Boulevard in downtown DeLand FL with 1920s commercial buildings and pedestrians

Neighborhood

DeLand

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Neighborhood

Clermont

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Neighborhood

Mount Dora

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Neighborhood

Tavares

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Neighborhood

Leesburg

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Eustis

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Neighborhood

Haines City

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Auburndale

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Winter Haven

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Neighborhood

Lakeland

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Neighborhood

Daytona Beach

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Aerial view of ChampionsGate golf course and resort community near Davenport, Florida

Neighborhood

ChampionsGate

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Aerial view of Solivita golf course and resort-style amenity campus in Poinciana, Florida

Neighborhood

Solivita

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Storey Lake Resort clubhouse with lazy river and waterslide in Kissimmee, Florida

Neighborhood

Storey Lake

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Aerial view of Poinciana planned community in Osceola and Polk counties, Florida

Neighborhood

Poinciana

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Lake Buck and walking trail in Harmony master-planned community, St. Cloud, Florida

Neighborhood

Harmony

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Tree-lined entry to Weslyn Park at Sunbridge, St. Cloud, Florida

Neighborhood

Weslyn Park

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Guard-gated entrance to Heathrow community in Lake Mary, Florida

Neighborhood

Heathrow

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Guard-gated entrance to Lake Forest community in Sanford, Florida

Neighborhood

Lake Forest

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Canopy of mature oaks arching over Markham Woods Road in Seminole County, Florida

Neighborhood

Markham Woods Corridor

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Tuscawilla Country Club golf course in Winter Springs, Florida at dusk

Neighborhood

Tuscawilla

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Timacuan Golf Club fairway in Lake Mary, Florida, lined with mature trees

Neighborhood

Timacuan

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Historic First Street in Sanford, Florida with restored Victorian commercial buildings

Neighborhood

Historic Sanford

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Victoria Park town center with front-porch homes and tree-lined streetscape, DeLand FL

Neighborhood

Victoria Park

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Trails of DeLand gated entrance with mature oak trees lining the entry road

Neighborhood

Trails of DeLand

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Deltona Lakes neighborhood with mature tree canopy lining a residential street, Deltona FL

Neighborhood

Deltona Lakes

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Pelican Bay guard gate entrance with manicured landscaping, Daytona Beach FL

Neighborhood

Pelican Bay

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LPGA International championship golf course fairway with water features, Daytona Beach FL

Neighborhood

LPGA International

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DeBary SunRail commuter rail station with the emerging Town Center District surrounding area

Neighborhood

DeBary Town Center District

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Aerial view of Lakeview Preserve community in Clermont, Florida with resort pool and tree-lined streets

Neighborhood

Lakeview Preserve

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Highland Ranch community entrance in Clermont, Florida on the US-27 corridor

Neighborhood

Highland Ranch

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Central Florida skyline near Clermont and the greater Orlando area

Neighborhood

Wellness Ridge

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Gated entrance to Serenoa community in Clermont, Florida on the US-27 south corridor

Neighborhood

Serenoa

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Guard-gated entrance to Country Club of Mount Dora, Florida

Neighborhood

Country Club of Mount Dora

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Aerial view of Royal Harbor 55+ community waterfront and boat slips on Lake Harris in Tavares, Florida

Neighborhood

Royal Harbor

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Golf course and amenity center at Royal Highlands 55+ community in Leesburg, Florida

Neighborhood

Royal Highlands

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Aerial view of Plantation at Leesburg 55+ community showing golf courses and activity centers in Leesburg, Florida

Neighborhood

Plantation at Leesburg

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Aerial view of Southern Dunes Golf & Country Club fairways in Haines City, Florida

Neighborhood

Southern Dunes

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Entrance to Highland Reserve gated community in Haines City, Florida

Neighborhood

Highland Reserve

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Traditions clubhouse and resort pool on Lake Ruby in Winter Haven, Florida

Neighborhood

Traditions

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Lakefront homes on Lake Shipp in Winter Haven, Florida at sunset

Neighborhood

Lake Shipp Heights

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Grasslands Golf & Country Club fairway and custom homes in northwest Lakeland, Florida

Neighborhood

Grasslands Golf & Country Club

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Tree-canopied residential street in Cleveland Heights neighborhood, Lakeland, Florida

Neighborhood

Cleveland Heights

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Lake Hollingsworth waterfront and residential streets in south-central Lakeland, Florida

Neighborhood

South Lakeland / Lake Hollingsworth

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Craftsman bungalow homes on a shaded street in Lakeland's Dixieland Historic District

Neighborhood

Dixieland Historic District

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Neighborhood

Suntree

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Heritage Isle

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Baytree National

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Indian River Colony Club

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Trasona

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Lansing Island

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Eau Gallie

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Bayside Lakes

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The Compound

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Capron Ridge

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Rockledge Country Club

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Historic Cocoa Village

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Tortoise Island

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South Patrick Shores

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Riomar

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Aquarina Beach & Country Club

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Neighborhood

Snug Harbor

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Harbor Heights

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La Cita Country Club

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Windover Farms

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Forest City neighborhood in Altamonte Springs, Seminole County

Neighborhood

Forest City

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Sweetwater Club private golf course along the Little Wekiva River in Longwood

Neighborhood

Sweetwater Club

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Lake shoreline in the Apopka and Seminole County area near Bear Lake, Central Florida

Neighborhood

Bear Lake

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Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · All information deemed reliable but not guaranteed · Equal Housing Opportunity · MLS data courtesy of Stellar MLS · Full disclaimer