Winter Grove Homes for Sale

5 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code

Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Discover the perfect blend of luxury, comfort, and convenience in this stunning Mahogany Grand home. Thoughtfully designed for both everyday living and entertaining, this exceptional two-story residence offers 5 bedrooms, 4 full bathrooms, a loft, and a spacious 3-car garage. The open-concept living area seamlessly connects the gourmet kitchen, café, and gathering room, creating an expansive and inviting space. Soaring ceilings and an elegant tray ceiling enhance the sense of openness, while a large pocket sliding glass door extends the living space onto the covered lanai, filling the home with natural light and creating the perfect blend of indoor and outdoor living. At the heart of the home, the gourmet kitchen showcases stacked soft-close cabinetry, quartz countertops, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and a refrigerator. Whether preparing everyday meals or hosting special gatherings, this kitchen is designed to impress. Privately situated in the back corner of the home, the spacious owner's suite offers a peaceful retreat and features an owner's suite extension, providing additional space for a sitting area, fitness nook, workspace, or whatever best suits your lifestyle. The spa-inspired en suite bath includes a walk-in closet, linen closet, walk-in shower with a rain shower head, and a private enclosed water closet. Three additional first-floor bedrooms and two bathrooms provide comfort and privacy for everyone. Upstairs, enjoy an additional 709 square feet of flexible living space, complete with a generous loft, private fifth bedroom, and full bathroom, making it ideal for a media room, guest suite, home office, or multigenerational living. Completing the home is a spacious 3-car garage with ample room for vehicles, storage, and hobbies. Don't miss the opportunity to tour this exceptional home and experience everything it has to offer.

285 Crystal Wood Drive, Winter Garden

$949,270

4 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Discover the perfect blend of luxury, comfort, and convenience in this stunning Mahogany Grand home. Thoughtfully designed for both everyday living and entertaining, this exceptional two-story residence offers 4 bedrooms, 3 full bathrooms, a convenient first-floor powder room, an enclosed flex room, and a spacious 3-car garage. The open-concept living area seamlessly connects the gourmet kitchen, café, and gathering room, creating an expansive and inviting space. Soaring ceilings and an elegant tray ceiling enhance the sense of openness, while a large pocket sliding glass door extends the living space onto the covered lanai, filling the home with natural light and creating the perfect blend of indoor and outdoor living. At the heart of the home, the gourmet kitchen showcases stacked soft-close cabinetry, quartz countertops, a decorative tile backsplash, farmhouse sink, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and 48-inch side-by-side refrigerator. Whether preparing everyday meals or hosting special gatherings, this kitchen is designed to impress. Privately situated in the back corner of the home, the spacious owner's suite offers a peaceful retreat and features an owner's suite extension, providing additional space for a sitting area, fitness nook, workspace, or whatever best suits your lifestyle. The spa-inspired en suite bath includes a walk-in closet, linen closet, walk-in shower with a rain shower head, and a private enclosed water closet. The enclosed flex room at the front of the home adds valuable versatility and can easily function as a home office, fitness room, playroom, or creative studio. Two additional first-floor bedrooms located in the opposite back corner of the owner’s suite provide comfort and privacy for everyone. A conveniently located powder room further enhances the home's thoughtful design. Upstairs, enjoy an additional 884 square feet of flexible living space, complete with a generous loft, private fourth bedroom, and full bathroom, making it ideal for a media room, guest suite, home office, or multigenerational living. Completing the home is a spacious 3-car garage with ample room for vehicles, storage, and hobbies. Don't miss the opportunity to tour this exceptional home and experience everything it has to offer.

289 Crystal Wood Drive, Winter Garden

$1,600,000

5 Beds ⋅ 5 Baths ⋅ Winter Grv SubDv. ⋅ 34787 Zip Code

Welcome to Winter Grove in the charming city of Winter Garden. Ideally located just 1.2 miles from Winter Garden Village and approximately 2.8 miles from Historic Downtown Winter Garden, this intimate gated community offers the perfect blend of luxury, convenience, and privacy. Featuring spacious homesites and no CDD, residents enjoy easy access to premier shopping, dining, entertainment, and everything that makes this one of Central Florida’s most sought-after locations. Introducing the stunning Roseland model, a beautifully designed 5-bedroom, 5-bathroom residence with a 3-car garage, offering an exceptional balance of elegance, functionality, and thoughtfully curated finishes throughout. As you step through the impressive double glass entry doors, you are welcomed by a dramatic two-story foyer that immediately creates a grand first impression. Just off the entrance, an enclosed flex room provides endless possibilities—ideal as a home office, fitness room or additional living space—while the formal dining room creates the perfect setting for entertaining. Continuing through the home, a striking staircase featuring engineered hardwood plank treads and wrought iron balusters enhances the sophisticated design. Tucked beneath the staircase is a wine lover’s dream: a stylish wine cave complete with built-in cabinetry, quartz countertops, and designer tile backsplash. At the heart of the home, the open-concept kitchen is designed to impress, featuring built-in KitchenAid stainless steel appliances, including a gas-cooktop, oven, and beverage cooler. Beautiful two-tone soft-close cabinetry is paired with elegant quartz countertops, creating a timeless and refined aesthetic, while a spacious walk-in pantry provides abundant storage. The seamless flow between the kitchen, café, and gathering room creates an inviting and light-filled space, ideal for both everyday living and entertaining. Sliding doors lead to the covered lanai, which has already been pre-plumbed and pre-wired for a future outdoor kitchen, including electric, water, sewer, and natural gas connections—allowing the future owner to easily create their dream outdoor living space. Also located on the first floor is a spacious Multi-Gen Suite, perfect for guests or multigenerational living, complete with a walk-in closet and private bathroom. Upstairs, the luxurious owner’s suite occupies its own private wing, creating a peaceful retreat. An additional sitting area provides the perfect place to unwind or enjoy quiet moments. The spa-inspired owner’s bath showcases a freestanding soaking tub, oversized frameless glass shower and generous dual walk-in closets. The second floor also features additional well-appointed bedrooms, including two connected by a Jack-and-Jill bathroom and another with its own private en-suite bath, offering both comfort and privacy for family and guests. The upstairs laundry room, complete with cabinetry and a utility sink with quartz finishes, adds everyday convenience. Residents of Winter Grove also enjoy access to community amenities including a beautiful pond with walking trails. With an intelligently designed floor plan, carefully selected finishes, and a highly desirable location, this exceptional home offers the perfect blend of luxury, comfort, and lifestyle. Schedule your private tour today and experience this extraordinary home has to offer.

325 Crystal Wood Drive, Winter Garden

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Orange County › Winter Garden › Winter Grove

Winter Grove, Winter Garden

Winter Grove is a 2020s neighborhood in south Winter Garden, in the 34787 zip code. Homes are block and stucco. Most homes fall between about 2,600 and 4,400 square feet under air, and the median lot is roughly a fifth of an acre.

Homes here carry an HOA, billed monthly, typically around $240. Confirm the figure on a specific parcel before relying on it.

What the homes are

Built Essentially all built in the 2020s.
Construction Block and stucco. Shingle roofs are near universal.
Size Most homes fall between about 2,600 and 4,400 square feet under air.
Bedrooms Five bedrooms is the most common plan, then four.
Lot The median lot is roughly a fifth of an acre.
HOA Billed monthly, typically around $240. Confirm on a specific parcel before relying on it.

Where Winter Grove is

Winter Grove, centered at 28.532895, -81.586742. Drag to explore.

Street level, inside the neighborhood. Drag to look around.

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

Driving to	Time	Miles
Downtown Orlando	27 min	17.0
Walt Disney World	25 min	19.0
Orlando International Airport	32 min	25.3
Universal Orlando	26 min	15.9

Public schools nearby

SunRidge Elementary School 12 min, 4.4 mi
West Orange High School 6 min, 1.7 mi
Maxey Elementary School 8 min, 2.5 mi
Lake Whitney Elementary School 9 min, 3.4 mi

Private schools nearby

StarChild Academy Winter Garden 4 min, 1.0 mi
Winter Garden Christian Academy 4 min, 1.4 mi
ESTEEM Academy 6 min, 2.1 mi

Parks and recreation

North Edge Park 6 min, 2.0 mi
Tildenville Park 10 min, 3.7 mi
West Orange Dog Park 6 min, 2.3 mi
Warrior Park 6 min, 2.4 mi

Groceries and errands

Target Grocery 6 min, 1.7 mi
Publix Super Market at West Point Commons 4 min, 1.5 mi
A&E Grocery Store 10 min, 3.7 mi
ALDI 6 min, 1.9 mi

Useful local links

Nearest is not the same as zoned. The schools above are the closest ones to Winter Grove 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 Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Winter Grove actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 9 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 November 2026.

What homes sold for in Winter Grove

$879,520Median sale price

$267Median per square foot

36 daysMedian days to contract

9Homes sold in 12 months

Sale prices ran from $810,000 to $1,488,360, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

By size

Home size	Sales	Median price	Median $/sq ft	Median days
3,000 sq ft and up	8	$929,290	$264	44 days

A price per foot taken from the whole neighborhood should never be applied straight to one house.

Price cuts and time to contract

Median days to go under contract. Shorter is better.

Never reduced 6 sales, closed at 100% of asking22 days

Reduced at least once 3 sales, closed at 94.1% of the reduced price52 days

Sellers who held their number went under contract in a median 22 days. Sellers who had to reduce took 52 days and still closed at 94.1% of their already reduced price, after a typical cut of $15,610.

Seller concessions

89%Of sales included a seller credit

$15,000Typical credit when there was one

8 of 9Sales 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

Private 5 sales56%

Cash 2 sales22%

Conventional 2 sales22%

Cash was 22% 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.

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

About this data. Source is the Stellar MLS feed for Winter Grove in Winter Garden, Orange County, covering closed sales from 8 November 2025 through 3 November 2026, refreshed monthly and current as of November 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. 3 records were excluded as off-market transfers rather than open market sales. Data believed accurate but not guaranteed; listings and closings change daily.