Rivendell Homes for Sale in Osprey - 6 homes

Remarks: Discover one of Osprey's best-kept secrets-The Cottages of Rivendell. Tucked away within The Woodlands of Rivendell, offers a lifestyle that is becoming increasingly rare. Towering oak trees create a tranquil, park-like setting, while charming front porches, white picket fences, and classic Old Florida architecture give the neighborhood its unmistakable character. This beautifully maintained 3/2 home welcomes you with an expansive great room featuring an elegant tray ceiling, creating a wonderful sense of openness. Enjoy peace of mind with numerous recent updates, including a new roof (2022), HVAC system (2025), water heater (2026), exterior paint (2026), a separate AC system for the garage, and a generator for the house. Residents enjoy exclusive access to a private community pool and clubhouse, while the Association provides landscape maintenance, allowing you to embrace a carefree, low-maintenance lifestyle. What truly sets The Cottages of Rivendell apart is its warm sense of community. Neighbors know one another, friendships flourish, and life's special moments are celebrated together, making this a truly exceptional place to call home. Ideally located just a short walk from the nationally recognized Pine View School, one of Florida's top-rated schools for the gifted, and only 5.5 miles from Nokomis Beach.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)

Listing Agent: Zita Bowers (941-465-5819)

Remarks: Completely renovated St. Charles floor plan in the highly desirable Woodlands community of Rivendell. You must see to believe the upgrades! Just half a block to the community pool and less than five minutes to the renowned Pine View School for the intellectually gifted.Enjoy stunning brand-new granite countertops in the kitchen and bathrooms, plus beautiful ceramic tile flooring throughout the entire home for easy durability and maintenance. Gain total peace of mind with a new tile roof installed in 2023 and a new air conditioning system from 2024, making this home truly move-in ready. Located just minutes from world-famous Gulf beaches, shopping, and entertainment, this property features low HOA fees and an unbeatable location.

Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)

Listing Agent: Curtis Andrews (941-914-3253)

Remarks: Under contract-accepting backup offers. Set within Rivendell's 400 acres of lakes, preserves, and open spaces, this Osprey pool home checks the boxes buyers rarely find together: a quiet, established neighborhood, a long list of owner-completed upgrades, and no CDD fees. If you're looking for a move-in-ready foundation you can personalize over time, this one deserves a look. Major upgrades include: • NEW ROOF and GARAGE DOOR (2023) • NEW A/C (2021) • New dishwasher and garbage disposal (2020) • New pool pump (2017) • Irrigation well deepened (2016) • New pool cage (2015) • Replumbed (2012) Additional features include a portable generator that conveys with the sale. Inside, high ceilings and abundant natural light create an airy atmosphere throughout. Granite countertops in the kitchen and all bathrooms. The split floor plan separates the primary suite from guest bedrooms, while the main living areas open through sliding glass doors to the covered lanai and private pool, an ideal setup for entertaining or everyday Florida living. The generous 3-car garage adds flexibility for storage, hobbies, or workspace. Rivendell is known for its scenic preserve setting, walking trails, heated community pool, and peaceful park-like atmosphere. Residents enjoy convenient access to the Legacy Trail, Oscar Scherer State Park, Nokomis Beach, Siesta Key Beach, shopping, dining, and everyday conveniences along US-41. Approximately 1 mile from Pine View School, consistently ranked among the top public schools in the nation. Low HOA fees, no CDD fees, and a location close to beaches, nature, and everyday conveniences make this a rare find in one of Osprey's most established communities.

Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)

Listing Agent: Katrin Pfitzenreiter (917-543-8560)

Remarks: Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural light throughout. The modern kitchen is equipped with top-of-the-line appliances and give plenty of storage space. Enjoy the serene outdoor area with a beautifully landscaped yard, appropriate for relaxation and entertainment. Situated in a desirable neighborhood, this property provides easy access to Pineview Gifted School. Don't miss this exceptional opportunity to own this beautiful marvelous 4 bedrooms with a dent and 3 and 1/2 baths opportunity. The circle pool is beautiful and you can see it in Dinnig Room. The master bedroom is spacious with the beautiful marble Venetian team. There are 2 medium room next door. The washer and dryer are new in the laundry room. All the bathrooms are newly installed marble and high luxury tiles. The floor is beautiful with fancy travertine tiles for the whole downstairs floor and the upstairs are high end luxury plank vinyl all new floors and bathrooms

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: PRICE TO SELL. One or more photo(s) has been virtually staged. Exceptional opportunity in highly sought-after Rivendell, one of Osprey’s most desirable communities known for its scenic lakes, preserves, walking trails, and beautiful natural surroundings. Ideally located just steps from top-rated Pine View School, offering the rare convenience to walk or bike to one of Florida’s most acclaimed schools. This beautifully maintained home features a durable tile roof, tranquil lake views, and a spacious lanai overlooking the water, perfect for relaxing or entertaining. Enjoy stunning lake views from the dining room, creating a bright and inviting everyday setting. HOA maintained lawn care adds convenience and low maintenance living. The backyard is a tropical retreat with fruit trees including sugar apple, guava, and plum. Prime location near Oscar Scherer State Park, Casey Key beaches, shopping, dining, and the Legacy Trail. Rare combination of location, lifestyle, views, and school district appeal.

Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)

Listing Agent: Linh Pham (941-900-6789)

Remarks: Under contract-accepting backup offers. **BEAUTIFULLY UPDATED AND MOVE-IN READY, THIS SPACIOUS 4-BEDROOM + OFFICE/DEN HOME OFFERS NEARLY 2,900 SQUARE FEET** of thoughtfully designed living space with potential for a private in-law or multi-generational suite. Featuring 3 full baths and a coveted 3-car garage, this reconfigured floor plan provides flexibility, privacy, and comfort for today’s lifestyle. Situated on an ideal corner lot, the home enjoys peaceful water views from the rear and a lovely park view from the front. Major updates include a brand-new kitchen with granite countertops and stainless-steel appliances, fresh interior and exterior paint, and new flooring throughout, including luxury vinyl plank, etc. Plantation shutters add timeless charm and style. Newer ROOF (2021). Located in the highly sought-after community of Rivendell, known for its tree-lined streets, serene lakes, and natural preserves spanning 380 acres adjacent to Oscar Scherer State Park. This home is just minutes from nationally ranked Pine View School, Sarasota’s nationally ranked gifted school, as well as The Legacy Trail for miles of biking, walking, and skating. Enjoy the best of Florida living just 6 miles from Nokomis Beach and approximately 20 minutes to Siesta Key Beach. Rivendell is a deed-restricted community offering residents a community pool, playground, park, and gazebo. This exceptional home combines location, lifestyle, and luxury—schedule your private showing today!

Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)

Listing Agent: Mark Lyda (941-586-2670)