Tuskawilla Rd, FL Homes for Sale

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  /27

  $299,000

  • 2 Beds
  • 2.5 Baths
  • 1,275 Sq Ft

  167 Constitution Way, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. ROOF & ELECTRICAL UPDATED (2023) – this well-maintained townhome in the gated Heritage Park community of Winter Springs offers peace of mind along with stylish, LOW MAINTENANCE LIVING in one of Seminole County’s most convenient locations! Thoughtfully designed with TILE & LUXURY VINYL PLANK FLOORING throughout, this home feels light, bright, and

  Jennifer Wemert WEMERT GROUP REALTY LLC

  167 Constitution Way, Winter Springs, FL 32708
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  /24

  $280,000

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  600 Northern Way Unit 1608, Winter Springs, FL 32708

  Very motivated sellers! Condo in Tuskawilla’s Tuscany Place •Discover comfort and convenience in Winter Springs’ Tuskawilla neighborhood. Tuscany Place is a gated community with a private pool, near Trotwood Park, Cross Seminole Trail, and top-rated schools. •Double Balcony (length of condo) •Corner unit with pool view •Updated kitchen w/stainless steel appliances •New water heater (2023) •New

  Kelly Boulton WORTH CLARK REALTY

  600 Northern Way Unit 1608, Winter Springs, FL 32708
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  /44

  $485,000

  • 3 Beds
  • 2.5 Baths
  • 1,988 Sq Ft

  348 Michael Blake Blvd, Winter Springs, FL 32708

  Move-in ready home in highly desirable Winter Springs Village with over $75,000 in recent improvements. Features include updated kitchen with modern cabinetry, countertops, and stainless steel appliances, plus luxury vinyl plank flooring throughout. Energy-efficient solar system designed to help reduce utility costs. Additional upgrades include fresh exterior paint, updated landscaping, and

  Shahram Sondi SHAHRAM SONDI + CO.

  348 Michael Blake Blvd, Winter Springs, FL 32708
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  /38

  $795,000

  • 5 Beds
  • 4 Baths
  • 3,001 Sq Ft

  5130 Morning Dew Loop, Oviedo, FL 32765

  One or more photo(s) has been virtually staged. This multigenerational property sits on over 1⁄2 ACRE with NO HOA. Nestled beneath mature oak trees, this single-story home offers 5 bedrooms and 4 bathrooms, blending traditional character with modern, resort-style features. Inside, you’ll find 12-foot ceilings, spacious light-filled living areas, and a split floor plan that provides both comfort

  Jason Asa LPT REALTY, LLC

  5130 Morning Dew Loop, Oviedo, FL 32765
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  /15

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft

  1083 Cherokee Village Trail, Winter Springs, FL 32708

  This Triple Wide Home features a welcoming front porch to enter a 1772 sq.ft. Beautiful Home.. Has large Living- Dining Area and Large Bonus room with back door to patio area to accent the overall space for entertaining. Master Bath has extra large walk-in shower, garden tub, dual sinks. Two Car Garage offers so much storage space. Home is on City Sewer and Lot rent of $835. per month includes

  Todd Newby NEWBY REALTY INC

  1083 Cherokee Village Trail, Winter Springs, FL 32708
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  /36

  $470,000

  • 4 Beds
  • 2 Baths
  • 2,066 Sq Ft

  1126 Trotwood Blvd, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Top-Rated Schools! Beautiful and well-maintained 4-bedroom, 2-bath home located in desirable Winter Springs. This home features ceramic tile flooring throughout for easy maintenance and a spacious layout perfect for comfortable living. Enjoy a huge patio—ideal for family gatherings and entertaining guests. Brand new roof (2025) provides peace of

  Joyce Tang JOY ESTATE ENTERPRISE INC

  1126 Trotwood Blvd, Winter Springs, FL 32708
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  /11

  $569,000

  • 4 Beds
  • 2.5 Baths
  • 2,674 Sq Ft

  30 Sable Ct, Winter Springs, FL 32708

  REDUCED! Beautiful Executive 4 bedroom POOL home in Tuscawilla Country Club Golf Community! NO HOA! Mediterranean feel with wrought iron accents and courtyard. Huge Kitchen with island in the middle. All appliances. Hot water heater 2017. Lots of cabinet space. Spacious eat-in area beside kitchen. Formal Dining and Living rooms. Large bedrooms. Big Owners bedroom with walk-in closet and updated

  Julie Bailey HOME SOLD NETWORK LLC

  30 Sable Ct, Winter Springs, FL 32708
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  /42

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  600 Northern Way Unit 201, Winter Springs, FL 32708

  Welcome home to this maintained 3-bedroom, 2-bathroom ground-floor condominium offering 1,425 square feet of comfortable, low-maintenance living in a desirable gated community in the heart of Tuscawilla — perfect for investors or those seeking a primary residence. Step inside to an inviting open floor plan highlighted by tile flooring throughout the main living areas, creating a seamless space

  Veronica Figueroa EXP REALTY LLC

  600 Northern Way Unit 201, Winter Springs, FL 32708
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  /10

  $247,000

  • 2 Beds
  • 1.5 Baths
  • 1,156 Sq Ft

  1305 Park Villa Place, Winter Springs, FL 32708

  Outstanding 2 BD 1.5 BT! Open-concept, two-story home with a lot of natural light Move-in Ready. New AC (4 Years New), Roof is 4 years new & Newer Appliances. Great Schools! Community Pool. 2 parking Spaces. Walk to Trotwood & Trail. Hurry! Won't last!

  Caroline Moffitt-Lawton KELLER WILLIAMS HERITAGE REALTY

  1305 Park Villa Place, Winter Springs, FL 32708
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  /77

  $1,850,000

  • 5 Beds
  • 4.5 Baths
  • 4,288 Sq Ft

  4469 Old Bear Run, Winter Park, FL 32792

  Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom residence offers a rare combination of privacy, scale, and true Florida waterfront lifestyle. A circular driveway behind a private gate welcomes you to a thoughtfully renovated home designed to capture sweeping lake views. Bear Gully

  Keigan Lewis LPT REALTY, LLC

  4469 Old Bear Run, Winter Park, FL 32792
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  /60

  $599,900

  • 4 Beds
  • 3 Baths
  • 2,531 Sq Ft

  203 Wise Owl Way, Casselberry, FL 32708

  HUGE PRICE DROP! SELLERS NEED TO SELL! WALK ON IN AND CALL IT HOME! Welcome to this stunning 4-bedroom, 3-bathroom home nestled in the highly sought-after Tuskawilla Crossings community of Winter Springs. From the moment you step inside, you’ll be greeted by a tastefully decorated foyer that opens up into a spacious living room and a beautifully designed open kitchen, perfect for entertaining and

  Lindsay Kaye Voss VOSS REALTY INC

  203 Wise Owl Way, Casselberry, FL 32708
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  /63

  $489,975

  • 4 Beds
  • 3.5 Baths
  • 2,353 Sq Ft

  1262 Spotted Sandpiper Loop, Winter Springs, FL 32708

  "VA ASSUMABLE LOAN" Imagine a home that doesn't just house your life but elevates every chapter of it. At this stunning tri-level townhouse, the story begins the moment you step across the covered front porch and through the front door.Your day begins on the third level, where light pours through the expansive windows of your primary retreat. You wake up in a sanctuary defined by a sense of

  Mark Anthony Buot ROI AVE LLC

  1262 Spotted Sandpiper Loop, Winter Springs, FL 32708
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  /38

  $469,900 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,501 Sq Ft

  903 Torrey Pine Dr, Winter Springs, FL 32708

  **NEW ROOF TO BE INSTALLED IN APRIL!!** Paradise found in Tuscawilla! Come fall in love with this idyllic low maintenance waterfront villa on over 1/3 acre with lawn care and community pool included. Walk out the back door of this beautiful 3 bedroom home to your “high and dry” oasis backing up to serene Howell Creek. Inside the home, you will be greeted by a cozy yet open floor plan with

  Colleen Kahl RE/MAX TOWN & COUNTRY REALTY

  903 Torrey Pine Dr, Winter Springs, FL 32708
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  /39

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,665 Sq Ft

  3032 Pilot House Place, Oviedo, FL 32765

  Welcome to maintenance-free living in the heart of Oviedo. Next to the Cross Seminole Trail and halfway between Oviedo on the Park and Park Ave Winter Park. TESLA CHARGER already installed and comes with the home. Nestled behind the gates of one of the newest private enclave townhome communities, Tuskawilla Commons, this beautifully designed 3-bedroom, 2.5-bath townhome with a 1-car garage offers

  Dan Teston EXP REALTY LLC

  3032 Pilot House Place, Oviedo, FL 32765
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  /25

  $325,000

  • 3 Beds
  • 2.5 Baths
  • 1,468 Sq Ft

  116 Philadelphia Way, Winter Springs, FL 32708

  Well-appointed 3-bedroom, 2.5-bath townhome for sale in a gated community, offering a great combination of functionality, privacy, and location. Designed for comfortable living, this home includes energy-efficient double-pane windows that enhance interior comfort and help reduce outside noise. The primary suite features a spacious walk-in closet with natural light, creating a bright and welcoming

  Isabel Sirizzotti SUNNY 365 REALTY GROUP

  116 Philadelphia Way, Winter Springs, FL 32708
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  /29

  $412,000

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  1411 Borg Ln, Winter Springs, FL 32708

  Price Reduced!! Your wait is over! Welcome to your new home! This beautiful 3 bedroom, 2 bath home delivers 1,368 sq. ft. of peaceful living area in a quiet corner lot. Located in the gorgeous Tuskawilla Country Club community, this home features luxury vinyl flooring throughout the house. Entertain effortlessly with a spacious kitchen featuring stainless steel appliances, recessed lighting, and

  Trevor Laug. Realtor SOLID OAK REAL ESTATE LLC

  1411 Borg Ln, Winter Springs, FL 32708
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  /27

  $299,999

  • 3 Beds
  • 3 Baths
  • 1,609 Sq Ft

  600 Northern Way Unit 906, Winter Springs, FL 32708

  Turnkey townhouse in the newest phase of Tuscany Place and ready for immediate move-in. Exceptional open floor plan at over 1,600 square feet truly sets this home apart as does the flexibility for multi-generation living. This beautiful home has three en-suites with one of the bedrooms on the ground level, so it’s perfect for a mother-in-law suite. Large sized rooms, updated bathrooms, and all

  John Vincent JR REALTY GROUP LLC

  600 Northern Way Unit 906, Winter Springs, FL 32708
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  /47

  $280,000

  • 2 Beds
  • 2.5 Baths
  • 1,306 Sq Ft

  3825 Black Spruce Ln, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. This beautifully updated 2 large bedroom and 2 1/2 bath townhouse is move-in ready! New carpet and luxury vinyl floor coverings, as well as brand new appliances: dishwasher, range, hood, microwave just installed in 2026. Newer AC and refrigerator ( 2 yrs.) complete this well-maintained townhouse overlooking the back patio and pond. The home boasts

  Iris Bolt Malishewsky ABSOLUTE REALTY GROUP, LLC

  3825 Black Spruce Ln, Winter Springs, FL 32708
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  /29

  $500,000

  • 4 Beds
  • 2 Baths
  • 1,979 Sq Ft

  1201 Wolverine Trail, Winter Springs, FL 32708

  Welcome to this charming 4-bedroom, 2-bath home tucked away in a quiet, tree-lined neighborhood in desirable Winter Springs. Surrounded by mature trees, this property offers a peaceful atmosphere and a spacious backyard, ideal for entertaining, relaxing, or enjoying Florida outdoor living. Inside, you’ll find a warm and inviting layout highlighted by an original masonry fireplace, adding timeless

  Nairobi Rondon LPT REALTY, LLC

  1201 Wolverine Trail, Winter Springs, FL 32708
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  /56

  $498,900

  • 4 Beds
  • 2 Baths
  • 1,864 Sq Ft

  986 Turkey Hollow Cir, Winter Springs, FL 32708

  986 Turkey Hollow Circle—where comfort, style, and Florida living come together beautifully. Nestled in one of Winter Springs’ most desirable neighborhoods, this 4-bedroom, 2-bath pool home offers the perfect blend of warmth, functionality, and thoughtful updates—just minutes from Tuskawilla Road, SR-434, shopping, dining, and top-rated schools. Step inside to an open, light-filled great room

  Christopher Dunlop CALL IT CLOSED INTL REALTY

  986 Turkey Hollow Cir, Winter Springs, FL 32708
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  /36

  $700,000

  • 4 Beds
  • 3 Baths
  • 2,562 Sq Ft

  4951 Courtland Loop, Winter Springs, FL 32708

  This beautifully updated home blends timeless character with modern comfort, offering an inviting layout designed for both everyday living and entertaining. The light-filled interior showcases a stunning, renovated kitchen with new quartz extended countertops, a butcher block island, recessed lighting, and a full suite of high-end appliances including a JennAir refrigerator, KitchenAid pull-out

  Carolina Taborda MOMENTUM REALTY

  4951 Courtland Loop, Winter Springs, FL 32708
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  /57

  $719,000

  • 5 Beds
  • 3 Baths
  • 3,287 Sq Ft

  1503 Graceful Doe Loop, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. This stunning 5-bedroom, 3-bathroom home with a three-car garage offers a perfect blend of style, comfort, and functionality. As you step inside, you are greeted by a spacious floor plan. One bedroom and a full bathroom are conveniently located downstairs, providing privacy and flexibility for guests.The main level features an open and versatile

  Gabriel Andrada FLORIDA SPIRIT HOMES

  1503 Graceful Doe Loop, Winter Springs, FL 32708
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  /22

  $299,000

  • 3 Beds
  • 2.5 Baths
  • 1,468 Sq Ft

  476 Tradition Ln, Winter Springs, FL 32708

  Welcome to this beautiful townhome in the heart of desirable Winter Springs! This townhome sits on a quiet street an established community. Roof was replaced in 2023! Featuring a split floor plan, vaulted ceilings, and a large primary suite with walk-in closet, the layout provides comfort and flexibility. The screened-in lanai overlooks backyard with a community walk, perfect for relaxing or

  Shadi Tamimi SET HOMES REALTY LLC

  476 Tradition Ln, Winter Springs, FL 32708
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  /30

  $524,900

  • 4 Beds
  • 2.5 Baths
  • 2,058 Sq Ft

  4190 Bear Gully Rd, Winter Park, FL 32792

  Spacious Winter Park home on over a half acre with no rear neighbors!. In Bear Gully Forest community and has over 2,000 s/f- with a Living Room, Dining Room, Eat-in Kitchen and more. The home's fully-equipped kitchen has excellent cabinet space and appliances that include a stove, microwave, and dishwasher. An inside laundry room has a washer/dryer combination for your convenience. Bedroom with

  Craig Swetnam ADVANCE REALTY & MANAGEMENT LLC

  4190 Bear Gully Rd, Winter Park, FL 32792
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  /30

  $340,000

  • 3 Beds
  • 2.5 Baths
  • 1,502 Sq Ft

  2833 Shady Willow Ln, Oviedo, FL 32765

  Welcome home to Clayton Crossing, one of Oviedo’s most desirable gated townhome communities. This beautifully designed 3-bedroom, 2.5-bath home with a 1-car garage offers a perfect blend of comfort, style, and convenience. Step inside to an open-concept layout featuring upgraded 18-inch tile and a bright modern kitchen with stainless steel appliances overlooking the dining and family room ideal

  Liza Figueroa EXP REALTY LLC

  2833 Shady Willow Ln, Oviedo, FL 32765
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  /27

  $440,000

  • 4 Beds
  • 3 Baths
  • 1,769 Sq Ft

  4701 New Orleans Cove, Oviedo, FL 32765

  THIS HOME QUALIFIES FOR NO MONEY DOWN FINANCING! A rare opportunity in Oviedo! This exceptional END-UNIT townhome built in 2023 offers 4 spacious bedrooms and 3 full bathrooms, including a highly desirable bedroom and full bath on the main floor—perfect for guests, multi-generational living, or a dedicated home office. Step inside to a bright, open layout featuring a generous living space and a

  Irina Paul FUTURE HOME REALTY INC

  4701 New Orleans Cove, Oviedo, FL 32765
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  /39

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,377 Sq Ft

  600 Northern Way Unit 1403, Winter Springs, FL 32708

  A Beautiful, Well-Appointed Condo in Tuscany Place Condominiums ~ Upon Entering this Beautiful Unit You will find High Ceilings and Upscale Wood Laminate Flooring throughout the first floor ~ The Owner's Suite is on the First Floor with Large Closets with Built-in Shelving. The Kitchen has Wood Cabinetry with High-end Features, Back Splash, Granite Counters, Stainless Appliances, Under Cabinet

  Elizabeth Larsen JULIE B REALTY, INC

  600 Northern Way Unit 1403, Winter Springs, FL 32708
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  /57

  $579,000

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft

  1675 Thornhill Cir, Oviedo, FL 32765

  Motivated seller !!! NEW ROOF 2025 ,NEW PLUMBING 2025 , NEW FLOORS 2026 ,NEW PAINT 2026 !!! This 4-bedroom, 2.5 -bathroom 2 car garage home is ready for a new family , 2023 water heater, 2021 A/C, NEW Roof 2025 . Seminole County School District is one of the best in Florida. Designed with a spacious split floor plan, the home features formal living and dining rooms, vaulted ceilings, and a cozy

  Steve Wermager REAL BROKER, LLC

  1675 Thornhill Cir, Oviedo, FL 32765
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  /22

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  724 Barrington Cir, Winter Springs, FL 32708

  Very well maintained home in Tuskawilla! Updated kitchen with Granite countertops, Elegant mirrored wall, Ceramic Tile throughout. Double sinks in beautiful master bathroom with garden shower tub! Owners have access to the neighborhood clubhouse and Community pool, HOA takes care of front yard lawn maintenance. Two parks and a nature trail are walking distance from the home. Walk to Trotwood Park

  Ramon Ortiz Cruz DIAMOND 2000 REALTY, INC

  724 Barrington Cir, Winter Springs, FL 32708
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  /77

  $750,000

  • 4 Beds
  • 2.5 Baths
  • 3,334 Sq Ft

  1204 Swan St, Winter Springs, FL 32708

  Great location, No HOA..69 acres , 4 bedrooms,2 bathrooms, one half bathroom out door shower, kitchen, living room, family room, huge Florida room, huge enclosed pool, 2 car garage, enclosed out door kitchen, game room, storage. Close to major Roads, sipping centers, , schools, hospitals, 17 minutes to Sanford Airport, 11 minutes to Oviedo mall, 20 minutes to UCF. 20 minutes to Orlando Health

  Rosa Rodriguez STIRLING INTERNATIONAL REAL ES

  1204 Swan St, Winter Springs, FL 32708
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  /47

  $279,999

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  600 Northern Way Unit 502, Winter Springs, FL 32708

  Location! Location! Location! This pristine condo nestled in the heart of Tuscawilla offers an incredible opportunity for low maintenance living in a serene and gated community. Enjoy summer days by the beautiful community pool and relax in the cabana. Across the way you will find access to Trotwood Park, with its picturesque settings ideal for picnics and recreational activities. Featuring a

  Robert Bretz, PA EXP REALTY LLC

  600 Northern Way Unit 502, Winter Springs, FL 32708
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  /18

  $484,940 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,704 Sq Ft

  161 Bear Springs Dr, Winter Springs, FL 32708

  With an open concept ground floor and spacious living areas, the Sofia is ideal for entertaining and everyday life. Dedicated as an end unit, this floorplan features 3 bedrooms, 2.5 bathrooms and a rear-loading 2-car garage. The 2nd floor features a loft, abundant storage, and laundry space. Located on the 1st floor, the owner's suite that has it all - a spacious walk-in closet, great natural

  Mattamy Homes Builder

  161 Bear Springs Dr, Winter Springs, FL 32708
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  /18

  $484,940 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,704 Sq Ft

  173 Bear Springs Dr, Winter Springs, FL 32708

  With an open concept ground floor and spacious living areas, the Sofia is ideal for entertaining and everyday life. Dedicated as an end unit, this floorplan features 3 bedrooms, 2.5 bathrooms and a rear-loading 2-car garage. The 2nd floor features a loft, abundant storage, and laundry space. Located on the 1st floor, the owner's suite that has it all - a spacious walk-in closet, great natural

  Mattamy Homes Builder

  173 Bear Springs Dr, Winter Springs, FL 32708
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  /18

  $384,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,476 Sq Ft

  165 Bear Springs Dr, Winter Springs, FL 32708

  As you step inside the Aurora, you are greeted by an inviting open-concept gathering room, seamlessly connecting the dining room and kitchen. The flowing layout creates an expansive and airy atmosphere, perfect for both entertaining guests and enjoying everyday life. The owner's suite is a true retreat, offering a sanctuary of relaxation and tranquility. The spacious bedroom is complemented by a

  Mattamy Homes Builder

  165 Bear Springs Dr, Winter Springs, FL 32708
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  /43

  $585,000 Pre-Foreclosure

  • 4 Beds
  • 2 Baths
  • 2,608 Sq Ft

  805 Leopard Trail, Winter Springs, FL 32708

  Welcome to this beautifully updated 4-bedroom, 2-bath custom home located in the desirable Tuskawilla community—known for its top-rated schools and family-friendly charm. Set on a nearly half-acre lot, this 2,608 sq ft residence offers the perfect mix of comfort, character, and everyday convenience. Step inside and you’ll immediately notice the inviting warmth of the engineered hardwood floors

  Miguel Anastacio COLDWELL BANKER REALTY

  805 Leopard Trail, Winter Springs, FL 32708

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