Homes for sale in Winter Springs.

147 active listings in Winter Springs, FL — live Stellar MLS inventory.

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Communities in Winter Springs

60 subdivisions with active listings

Cypress Club6 Tuscany Place Ph 16 Heritage Park Twnhms5 Hickory Grove5 Deersong 24 Jesups Reserve Twnhms Rep4 Seville Chase4 Barrington Estates3 Seasons The3 Tuscawilla Unit 14b3 Wedgewood Tennis Villas3 Wildwood3 Barclay Reserve Twnhms2 Baytree Village2 Deer Run Unit 19a2 Greenbriar Sub Ph 22 Harbor Winds2 Highland Village 12 Highland Village 22 Highlands Sec 12 Highlands Sec 62 North Orlando2 North Orlando Ranches Sec 02a2 Oak Forest Unit 42 Seminole Crossing Twnhms2 Talmo Sub2 Tusca Oaks2 Avery Park1 Bahama Ranches1 Barclay Reserve Townhomes1 Bay Tree1 Bay Tree Sec 101 Chestnut Estates Ph 11 Chestnut Ridge1 Chestnut Ridge In Tuscawilla1 Citrus Oaks1 Davenport Glen1 Deer Run Unit 19b1 Deer Run Unit 201 Deersong1 Dougs Unit 11 Eagles Watch Ph 11 Fairway Oaks Unit 11 Fox Glen At Chelsea Parc Tuscawilla Ph 21 Foxmoor East1 Foxmoor Unit 21 Georgetowne Unit 11 Glen Eagle Unit 31 Greenspointe1 Heritage Commons1 Hickory Grove Twnhms1 Highland Patio Homes Amended Plat1 Highlands Glen1 Highlands Sec 41 Indian Ridge1 Jesups Landing1 Jesups Reserves Replat1 Mount Greenwood Unit 2 Of1 Mount Greenwood Unit 41 Mount Greenwood Unit 4 Of1

Listings in Winter Springs

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ActiveSingle Family Residence360°

$2,799,000

1447 Bird Rd

Winter Springs, FL 32708

6 bd · 6 ba · 6,132 sqft

Talis Crossing

MLS# O6388126

ActiveSingle Family Residence

$2,399,000

4910 E Lake Dr

Winter Springs, FL 32708

3 bd · 3 ba · 3,657 sqft

MLS# O6398929

ActiveSingle Family Residence360°

$1,249,000

120 E Bahama Rd

Winter Springs, FL 32708

4 bd · 3 ba · 4,464 sqft

Bahama Ranches

MLS# O6379165

ActiveSingle Family Residence360°

$1,200,000

1281 Natures Way

Winter Springs, FL 32708

5 bd · 4 ba · 3,212 sqft

Tuscawilla

MLS# O6404018

ActiveSingle Family Residence360°

$1,090,000

109 Cherry Creek Cir

Winter Springs, FL 32708

5 bd · 4 ba · 3,440 sqft

Reserve At Tuscawilla Ph 1 The

MLS# O6404923

ActiveSingle Family Residence360°

$999,000

1815 Seneca Blvd

Winter Springs, FL 32708

5 bd · 5 ba · 3,885 sqft

Tuscawilla Unit 14b

MLS# O6368232

ActiveSingle Family Residence

$899,900

702 Golfpoint Dr

Winter Springs, FL 32708

5 bd · 5 ba · 3,660 sqft

Glen Eagle Unit 3

MLS# O6397566

ActiveSingle Family Residence360°

$850,000

1160 Citrus Oaks Run

Winter Springs, FL 32708

5 bd · 4 ba · 3,118 sqft

Citrus Oaks

MLS# O6408959

ActiveQuadruplex360°

$850,000

100 Cory Ln

Winter Springs, FL 32708

8 bd · 8 ba · 3,752 sqft

Dougs Unit 1

MLS# O6410025

ActiveSingle Family Residence360°

$838,500

1444 Bird Rd

Winter Springs, FL 32708

4 bd · 2 ba · 2,350 sqft

Watts Farms

MLS# O6344113

ActiveSingle Family Residence360°

$824,900

226 Chestnut Ridge St

Winter Springs, FL 32708

4 bd · 3 ba · 2,902 sqft

Chestnut Ridge

MLS# O6398877

ActiveSingle Family Residence360°

$820,000

330 Hayes Rd

Winter Springs, FL 32708

4 bd · 2 ba · 2,252 sqft

North Orlando Ranches Sec 04

MLS# O6404598

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 1:33 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