Homes In Orlando For Sale Search

This page tracks what homes in Winding Hollow actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 13 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated August 2026.

What homes sold for in Winding Hollow

$588,300Median sale price
$238.72Median per square foot
6 daysMedian days to contract
13Homes sold in 12 months

Sale prices ran from $510,000 to $749,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

By size

Home sizeSalesMedian priceMedian $/sq ftMedian days
2,000 to 3,000 sq ft11$588,300$241.906 days

Larger homes usually show a lower price per square foot. That is normal and it is why a price per foot taken from the whole neighborhood should never be applied straight to one house.

Homes priced right sold far faster

Median days to go under contract. Shorter is better.

Never reduced 7 sales, closed at 100.0% of asking4 days
Reduced at least once 6 sales, closed at 99.0% of the reduced price92 days

Sellers who priced correctly and held their number went under contract in a median 4 days. Sellers who had to reduce took 92 days and still closed at 99.0% of their already reduced price, after a typical cut of $17,000. Opening high costs time and money, in that order.

Seller concessions

46%Of sales included a seller credit
$8,912Typical credit when there was one
6 of 13Sales carrying a credit

A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.

How buyers paid

Conventional 9 sales69%
Cash 2 sales15%
FHA 1 sales8%
VA 1 sales8%

Cash was 15% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

What is around Winding Hollow

Drive times below are measured on the road network from the center of Winding Hollow, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving toTimeMiles
Downtown Orlando30 min23.0
Orlando International Airport33 min28.9
Winter Park28 min12.1
Heathrow and Lake Mary offices28 min11.2
Schools nearby
  • Winter Springs High School 1.0 mi
  • Layer Elementary School 1.1 mi
  • Indian Trails Middle School 1.1 mi
  • Keeth Elementary School 1.3 mi
Parks and recreation
  • Winding Hollow Park 0.3 mi
  • Oak Hollow Park 0.4 mi
  • Central Winds Park 1.0 mi
  • Mount Greenwood Park 1.1 mi
Groceries and errands
  • ALDI 1.0 mi
  • Publix Super Market at Winter Springs Town Center 1.0 mi
  • Winn-Dixie 2.6 mi
  • Key Food Supermarkets 2.9 mi

Nearest is not the same as zoned. The schools above are the closest ones to Winding Hollow by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Seminole County Public Schools before it matters to a decision.

Places and drive times from Google, checked 30 August 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

Homes for sale in Winding Hollow right now

Current listings appear below and update automatically as homes come on and off the market. If nothing is showing, there is nothing available in Winding Hollow today, which happens in a neighborhood this size.

About this data. Source is the Stellar MLS feed for Winding Hollow in Winter Springs, Seminole County, covering closed sales from 4 September 2025 through 30 August 2026, refreshed monthly and current as of August 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. 0 records were excluded as off-market transfers rather than open market sales. Condition is inferred from listing descriptions. Data believed accurate but not guaranteed; listings and closings change daily.

Questions about a specific home in Winding Hollow, or want to know what yours would sell for? Call or text Brenden Rendo at 407-616-9019 or send a message.

$649,900
4 Beds ⋅ 3 Baths ⋅ Winding Hollow Unit 2 SubDv. ⋅ 32708 Zip Code
MAJOR PRICE IMPROVEMENT!! Pride of ownership is evident throughout this beautifully updated, MOVE-IN PERFECT, one-owner home located in the highly sought-after WINDING HOLLOW community of Winter Springs. This ideal two-story floor plan offers 4 BEDROOMS, 3 FULL BATHS, BONUS ROOM, 3-CAR GARAGE, and a LARGE SCREENED LANAI, showcasing timeless style, thoughtful updates, and versatility with TILE FLOORING throughout the first floor and LAMINATE WOOD FLOORING upstairs. The bright, OPEN-CONCEPT floor plan offers exceptional flow and is perfect for entertaining, featuring spacious formal living and dining rooms with soaring ceilings that create an inviting sense of space. The heart of the home is the beautifully designed ISLAND KITCHEN, perfectly positioned between the breakfast nook and impressive family room with 18-FOOT CEILINGS and dramatic upper windows that flood the home with natural light. The kitchen features GRANITE COUNTERTOPS, ABUNDANT WOOD CABINETRY with PULL-OUT DRAWERS, STAINLESS STEEL APPLIANCES, PANTRY, and convenient access to the garage and laundry room with additional storage. The spacious FIRST-FLOOR PRIMARY SUITE offers a sitting area, TWO WALK-IN CLOSETS, and an updated spa-inspired bath featuring a SOAKING TUB, GLASS SHOWER, and DUAL QUARTZ VANITIES, creating the perfect private retreat. A SPLIT FIRST-FLOOR GUEST SUITE with a full bath provides ideal accommodations for visitors or MULTI-GENERATIONAL LIVING. Upstairs you’ll find BEDROOMS 3 & 4, a full hallway bath, and a versatile BONUS ROOM/FLEX SPACE with a walk-in closet overlooking the family room below. Easily used as a 5TH BEDROOM, MEDIA ROOM, PLAYROOM, HOME OFFICE, or HOME GYM, this flexible space adapts to your family’s needs. Enjoy Florida living year-round from the expansive TILED SCREENED LANAI, accessible from the formal living room, family room, and primary suite while overlooking the PRIVATE, LUSHLY TREED BACKYARD. Additional highlights include PLANTATION SHUTTERS THROUGHOUT, a spacious 3-CAR GARAGE with overhead storage, an EXPANDED BRICK-PAVER DRIVEWAY, 2018 ROOF, TWO ZONED A/C SYSTEMS (2022 & 2019), 2019 WATER HEATER, and COMPLETE PLUMBING REPIPE (2025). Ideally located WITHIN WALKING DISTANCE TO THE CROSS SEMINOLE TRAIL & CENTRAL WINDS PARK, and just minutes from TOP-RATED WINTER SPRINGS SCHOOLS, shopping, dining, SR 417, and US 17-92, this exceptional home truly offers the perfect combination of LOCATION, LIFESTYLE, AND VALUE. WELCOME HOME!

525 Saddlewood Lane, Winter Springs
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