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Rotonda West Real Estate

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Rotonda West Oakland Hills Homes and Lots for Sale

Oakland Hills is one of the established sections of Rotonda West, featuring residential streets and homes near the area's golf courses, canals and neighborhood recreation. This neighborhood is part of Rotonda West in Charlotte County, Florida, near Englewood, Placida, Boca Grande and Gulf Coast beaches.

Living in Oakland Hills

Rotonda West is known for its distinctive circular layout, freshwater canals, golf courses and deed-restricted neighborhoods. Oakland Hills is one of seven principal Rotonda West sections, alongside Broadmoor, Long Meadow, Oakland Hills, Pebble Beach, Pine Valley, Pinehurst and White Marsh. Buyers should compare lot sizes, home ages, flood zones and property-specific features rather than assume every home has a canal or golf-course view.

Oakland Hills HOA Fees and CDD

CommunityAnnual HOACDD
Rotonda West - Oakland Hills$180-$190$0

HOA fees and included services may vary by property and are subject to change. Figures are based on available real estate listing data as of October 2026 and are believed reliable but not guaranteed. Buyers should verify fees, assessments, deed restrictions and included services directly with the association before purchasing.

Golf, Recreation and Nearby Attractions

Residents enjoy access to the greater Rotonda West area's parks and recreation, while golfers can explore nearby public and membership-based courses. Golf memberships and greens fees are separate from homeowners association dues. Englewood beaches, Boca Grande, boating, fishing, shopping and dining are accessible by car.

Explore More Rotonda Communities

Visit the Rotonda area guide for an overview and HOA comparison, or explore Rotonda Lakes, Rotonda Heights, Rotonda Meadows and Rotonda Sands.

Current Oakland Hills Real Estate Listings

Browse available Oakland Hills homes and lots below. Contact Jason Ester with RE/MAX to compare properties and arrange a showing.

Rotonda West Oakland Hills Homes for Sale

191 Rotonda Boulevard W, Placida image
191 Rotonda Boulevard W, Placida $870,000

Brand-New Construction Triplex located in the Oakland Hills section of Rotonda West, offering a versatile opportunity for a variety of living and investment goals. This n...

  • 9 Beds
  • 6 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
195 Rotonda Boulevard W Unit 1-3, Rotonda West image
195 Rotonda Boulevard W Unit 1-3, Rotonda West $720,000 ▲

Brand-New Construction Triplex located in the Oakland Hills section of Rotonda West, offering a versatile opportunity for a variety of living and investment goals. This n...

  • Rotonda West Oakland Hills SubDv.
  • 33947 Zip Code
55 Rotonda Circle, Rotonda West image
55 Rotonda Circle, Rotonda West $599,000 ▼

Discover modern Florida waterfront living at its finest in this stunning brand-new 2026-built 4-bedroom, 2-bathroom pool home with 2-car garage, perfectly situated on a f...

  • 4 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
130 Boundary Boulevard Unit A&B, Rotonda West image
130 Boundary Boulevard Unit A&B, Rotonda West $549,000

Exceptional and fully updated modern duplex property located on Boundary Boulevard in Rotonda West, offering a turn-key layout designed for maximum appeal and effortless ...

  • 6 Beds
  • 6 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
240 Caddy Road, Rotonda West image
240 Caddy Road, Rotonda West $509,900 ▼

Welcome To your Golf Course Facing Dream Home with an Oversized Pool. This 4 Bedroom 2 Bath Rotonda West Home is Perfect for any Golf enthusiast. The home is located on a...

  • 4 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
158 Annapolis Lane, Rotonda West image
158 Annapolis Lane, Rotonda West $499,900

This 2018 built 4 bed 2 bath home with a heated pool is amazing. on the water canal. It boasts over 2100 sq ft of living space under air. With easy access to golf course...

  • 4 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
49 Boundary Boulevard Unit B, Rotonda West image
49 Boundary Boulevard Unit B, Rotonda West $499,900

Fully leased and generating immediate income, this beautifully remodeled duplex is a turnkey investment in one of Southwest Florida's fastest-growing yet still quiet and ...

  • 6 Beds
  • 4 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
182 Boundary Boulevard Unit B, Rotonda West image
182 Boundary Boulevard Unit B, Rotonda West $459,000 ▼

WOW!!! What a great investment opportunity, weather you rent both sides or live in one and rent the other, can't go wrong with this kind of investment!! Fully furnished, ...

  • 4 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
18 Caddy Road, Rotonda West image
18 Caddy Road, Rotonda West $451,100 ▲

Under Construction. Step into luxury with this brand-new BEAUTIFUL GOLF COURSE 4-bedroom, 3-bath, 3-car garage home with the CR elevation, designed with an exceptional op...

  • 4 Beds
  • 3 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
151 April Road, Rotonda West image
151 April Road, Rotonda West $439,900

Under Construction. New Construction Nearly Finished in Rotonda Heights! Welcome to your new dream home, spacious open layout with 4 bedrooms, 2.5 bathrooms, enjoy a 3 ca...

  • 4 Beds
  • 3 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
108 Boundary Boulevard Unit B, Rotonda West image
108 Boundary Boulevard Unit B, Rotonda West $425,000

FULLY RENTED WATERFRONT DUPLEX IN ROTONDA WEST! Add a turnkey income-producing property to your portfolio with this beautifully renovated duplex overlooking the water, pa...

  • 4 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
3 Golfview Road, Rotonda West image
3 Golfview Road, Rotonda West $425,000

Exceptional development opportunity in the Oakland Hills subdivision of Rotonda West. This approximately 3.43-acre parcel offers nearly 149,500 square feet of land, subst...

  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
82 Rotonda Circle, Rotonda West image
82 Rotonda Circle, Rotonda West $399,990 ▼

Move-In Ready GOLF COURSE POOL HOME with NO REAR NEIGHBORS! Welcome to this beautifully maintained 3-bedroom, 2-bath ranch home overlooking the golf course in the heart ...

  • 3 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
51 Boundary Boulevard Unit B, Rotonda West image
51 Boundary Boulevard Unit B, Rotonda West $399,900

Fully leased and generating immediate income! This well-maintained duplex features two 2-bedroom, 2-bath units, each with a 1-car garage, making it a turnkey addition to ...

  • 4 Beds
  • 4 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
114 Caddy Road, Rotonda West image
114 Caddy Road, Rotonda West $380,000

Welcome to this spacious 4-BEDROOM GOLF COURSE HOME situated on a RARE DOUBLE LOT in the desirable Oakland Hills section of Rotonda West. Offering 2,520 square feet of li...

  • 4 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
271 Annapolis Lane, Rotonda West image
271 Annapolis Lane, Rotonda West $379,900 ▼

Pride of Ownership is what you will see with this Peaceful Retreat! This 3 bedroom 2 bath home with a bright and cheerful open floorplan is in mint, move-in condition....

  • 3 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
241 Annapolis Lane, Rotonda West image
241 Annapolis Lane, Rotonda West $375,000 ▼

This 2020 NEW BUILT stylish and move-in ready three-bedroom, two-bath home with a heated saltwater pool is located in the sought-after community of Rotonda West. Offering...

  • 3 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
162 Annapolis Lane, Rotonda West image
162 Annapolis Lane, Rotonda West $360,000

Start your morning with coffee on the inviting front patio, then step through to a home built around Florida waterfront living. This move-in ready 3-bedroom, 2-bath home ...

  • 3 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
130 Annapolis Lane, Rotonda West image
130 Annapolis Lane, Rotonda West $349,000

Welcome to your dream Florida oasis in the highly sought-after community of Rotonda West. This turnkey furnished beautifully updated 3-bedroom, 2-bathroom pool home sits ...

  • 3 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
90 Oakland Hills Court, Rotonda West image
90 Oakland Hills Court, Rotonda West $339,000

Space to Live. Room to Relax. A Florida Lifestyle Ready to Enjoy. Welcome to 90 Oakland Hills Court, where the hard work is already done, and the laid-back Florida lifest...

  • 4 Beds
  • 3 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
199 Caddy Road, Rotonda West image
199 Caddy Road, Rotonda West $314,900

Welcome to your effortless Florida getaway or lucrative investment opportunity! This beautifully updated 3-bedroom, 2-bathroom, 2-car garage home in Rotonda West’s desire...

  • 3 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
231 Caddy Road, Rotonda West image
231 Caddy Road, Rotonda West $305,600 ▼

WATERFRONT • HEATED POOL • 4 BEDROOMS • TURNKEY OPTION Welcome to your Florida waterfront escape! This spacious 4-bedroom, 2-bath home combines relaxed indoor-outdoor ...

  • 4 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
4 Golfview Road, Rotonda West image
4 Golfview Road, Rotonda West $305,000 ▼

Nicely updated 3 Bedroom Home with pool, A. C. Kitchen with wood cabinets, Granite counters and Stainless Steel Appliances. Large Rooms with Living Room and Family Room. ...

  • 3 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
124 Caddy Road, Rotonda West image
124 Caddy Road, Rotonda West $296,000 ▲

Welcome to paradise located inside the circle of Rotonda West Community, wether you want to be a owner or a investor, this fully furnished, remodeled 4 bed, 2 bath home ...

  • 4 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
27 Annapolis Lane, Rotonda West image
27 Annapolis Lane, Rotonda West $285,000

If you're searching for a full-time residence, seasonal getaway, or investment opportunity, this move-in-ready home deserves a spot at the top of your list. Located in th...

  • 3 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
165 Rotonda Boulevard W, Rotonda West image
165 Rotonda Boulevard W, Rotonda West $280,000

165...167...169...171 Rotonda Blvd W are all included in listing price. 1.55 acre +/- parcel in highly desirable Rotonda West. Multi-Family zoning RMF 15 (up to 15 units ...

  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
160 Annapolis Lane, Rotonda West image
160 Annapolis Lane, Rotonda West $274,000

BRAND NEW 2026 ROOF!!! ** WATERFRONT HAVEN WITH CURB APPEAL IN ROTONDA WEST ** DO NOT MISS!!! From the moment you pull up the sweeping, expansive driveway, this property ...

  • 3 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
30 Oakland Hills Court, Rotonda West image
30 Oakland Hills Court, Rotonda West $260,000 ▼

Welcome to this beautifully reimagined 3-bedroom, 2-bath home, where nearly every detail has been thoughtfully updated to provide a fresh, modern living experience. From ...

  • 3 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
258 Annapolis Lane, Rotonda West image
258 Annapolis Lane, Rotonda West $254,900

Updated finishes, beautiful water views, and inviting outdoor space—258 Annapolis Lane is ready for your Florida lifestyle! Being sold furnished, this Rotonda West home m...

  • 2 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
9 Annapolis Lane, Rotonda West image
9 Annapolis Lane, Rotonda West $249,900 ▼

Peaceful pool home with preserve view! Nestled in a serene setting, this delightful 2-bedroom, 2-bathroom home offers the best of Florida living with lush preserve views ...

  • 2 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
52 Annapolis Lane, Rotonda West image
52 Annapolis Lane, Rotonda West $244,500 ▼

Live your best life at this WATERFRONT home in the highly sought after ROTONDA WEST community! This 2-BEDROOM, 2 BATH home is a true hidden gem, nestled along the tranqui...

  • 2 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
192 Annapolis Lane, Rotonda West image
192 Annapolis Lane, Rotonda West $235,000 ▼

Enjoy peaceful waterfront living at this beautifully updated canal-front home in Rotonda West. This move-in-ready 2-bedroom, 2-bath residence features tile flooring throu...

  • 2 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
113 Annapolis Lane, Rotonda West image
113 Annapolis Lane, Rotonda West $219,000 ▼

Welcome to Rotonda West Oakland Hills, where this turnkey furnished 3 bedroom, 2 bath home sits on a quiet street with a tranquil nature preserve just beyond the backyard...

  • 3 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
66 Oakland Hills Court, Rotonda West image
66 Oakland Hills Court, Rotonda West $215,000 ▼

Virtually Staged. BEAUTIFULLY RENOVATED and MOVE-IN READY! Enjoy a fantastic GOLF COURSE VIEW from this spacious 2-bedroom, 2-bath home in desirable Rotonda West. This ho...

  • 2 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
23 Annapolis Lane, Rotonda West image
23 Annapolis Lane, Rotonda West $209,000 ▼

Full of charm and character in the Oakland Hills section of Rotonda West, this 2 bedroom, 1 bathroom home combines colorful coastal style with valuable updates including ...

  • 2 Beds
  • 1 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
144 Rotonda Circle, Rotonda West image
144 Rotonda Circle, Rotonda West $205,000 ▲

Short Sale. SHORT SALE – ACTIVE BANK APPROVED PRICE! Fantastic Opportunity to Own a Golf Course Home in Rotonda West! If you've been dreaming of affordable Florida golf...

  • 2 Beds
  • 2 Baths
  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
142 & 144 Boundary Boulevard, Rotonda West image
142 & 144 Boundary Boulevard, Rotonda West $200,000

A beautiful multi-family lot. Central water, central sewer, electric, cable. These 3 waterfront lots were originally zoned for 2 condo buildings and a pool.

  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
241 Rotonda Boulevard W, Rotonda West image
241 Rotonda Boulevard W, Rotonda West $149,900

Rare opportunity to own an oversized 1.02-acre homesite in Rotonda West, offering a level of space and flexibility not often found within this highly desirable Gulf Coast...

  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
121 & 123 Boundary Boulevard, Rotonda West image
121 & 123 Boundary Boulevard, Rotonda West $130,000 ▼

TWO ADJOINED BUILDABLE VACANT LOTS in popular and growing Rotonda West. Each lot has a parcel ID, and RMF15 zoning allows you to use them for multifamily construction pro...

  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
137 Boundary Boulevard, Rotonda West image
137 Boundary Boulevard, Rotonda West $120,000

A beautiful multi-family lot. Central water, central sewer, electric, cable.

  • Rotonda West Oakland Hill SubDv.
  • 33947 Zip Code
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Jason Ester
RE/MAX Alliance Group

14850 Tamiami Trail
North Port, FL 34287

941-376-6626
Email Jason

© 2026 Jason Ester. RE/MAX Alliance Group.
Equal Housing Opportunity.
Information deemed reliable but not guaranteed.

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