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Lasbury Tracy Realty Inc

Rotonda West Oakland Hills homes for sale

25 homes for sale in Rotonda West Oakland Hills, Rotonda West. 24 lots for sale →

Living in Rotonda West Oakland Hills

Oakland Hills is one of the original sections of Rotonda West's famous wheel — the master-planned circle whose pie-slice neighborhoods are named after storied golf links. Homes here run from early-1970s originals to brand-new builds, with canal-front lots threading through, and the mandatory community association costs about as little as HOAs get. Golf at the Rotonda Golf & Country Club courses is pay-to-play or membership, never baked into your dues.

HOA / fees
$16/mo median on current listings (Rotonda West Association — roughly $190/yr, billed annually) — Community-wide upkeep and deed-restriction enforcement — golf is entirely separate.
Amenities
Rotonda Golf & Country Club courses nearby · Freshwater canals through the section · Community parks & trails · Short drive to Boca Grande and Englewood beaches
Know before you fall in love
Deed-restricted through the Rotonda West Association · RWA dues apply community-wide even when a listing shows $0 — treat that as an entry gap, not a no-fee home · The canals are scenic freshwater — this is not gulf-access boating water
Flood story
Canal-adjacent lots vary by zone; check each listing's reported zone.

Drafted from listing records and community sources; pending verification by Lasbury Tracy Realty. Spot an error? Tell us.

Rotonda West Oakland Hills by the numbers — current listings

$289,900

Median asking price

$205,000–$509,900

Current range

$16/mo

Median monthly fees

1971–2026

Built

36%

With private pool

28%

Waterfront

24

Buildable lots listed

29 Oakland Hills Pl
Active
$329,000
11 days on market
4 bd · 3 ba · 2,126 sqft
29 Oakland Hills Pl, Rotonda West, FL 33947
Pool
Flood AE · Fees $25/mo · Built 1971

Listing courtesy of CENTURY 21 SUNBELT REALTY · MLS# D6149434

60 Rotonda Cir
Active
$246,500
15 days on market
3 bd · 2 ba · 1,231 sqft
60 Rotonda Cir, Rotonda West, FL 33947
Flood AE · Fees $16/mo · Built 1980

Listing courtesy of RE/MAX ALLIANCE GROUP · MLS# D6149302

28 Golfview Rd
Active
$248,900
15 days on market
2 bd · 2 ba · 1,333 sqft
28 Golfview Rd, Rotonda West, FL 33947
Flood AE · Fees $16/mo · Built 1973

Listing courtesy of DALTON WADE INC · MLS# C7532523

90 Oakland Hills Ct
Active
$339,000
26 days on market
4 bd · 3 ba · 2,305 sqft
90 Oakland Hills Ct, Rotonda West, FL 33947
Flood AE · Fees $16/mo · Built 1974

Listing courtesy of PARADISE EXCLUSIVE REAL ESTATE · MLS# D6148919

158 Annapolis Ln
Active
$499,900
30 days on market
4 bd · 2 ba · 2,153 sqft
158 Annapolis Ln, Rotonda West, FL 33947
Waterfront · 73 ftPool
Flood AE · Fees $16/mo · Built 2017

Listing courtesy of REALTY ONE GROUP INNOVATION · MLS# A4709484

114 Caddy Rd
Active
$360,000
43 days on market
4 bd · 2 ba · 2,520 sqft
114 Caddy Rd, Rotonda West, FL 33947
Flood AE · Fees $32/mo · Built 1974

Listing courtesy of MICHAEL SAUNDERS & COMPANY · MLS# N6145994

162 Annapolis Ln
Active
$360,000
45 days on market
3 bd · 2 ba · 1,784 sqft
162 Annapolis Ln, Rotonda West, FL 33947
Waterfront · 80 ftPool
Flood 8AE · Fees $16/mo · Built 1981

Listing courtesy of BAYPORT PROPERTY GROUP · MLS# C7530996

130 Annapolis Ln
Active
↓ $10,000
$329,000
31 days on market
3 bd · 2 ba · 1,701 sqft
130 Annapolis Ln, Rotonda West, FL 33947
Waterfront · 80 ftPool
Flood AE · Fees $16/mo · Built 1973

Listing courtesy of PAPE PROPERTIES REALTY · MLS# C7530975

160 Annapolis Ln
Active
Open Sat, Nov 21 1–4 PM
$274,000
56 days on market
3 bd · 2 ba · 1,777 sqft
160 Annapolis Ln, Rotonda West, FL 33947
Waterfront · 73 ft
Flood AE · Fees $16/mo · Built 1974

Listing courtesy of CENTURY 21 ALLPOINTS REALTY · MLS# C7530949

199 Caddy Rd
Active
$314,900
80 days on market
3 bd · 2 ba · 2,018 sqft
199 Caddy Rd, Rotonda West, FL 33947
Waterfront · 80 ft
Flood 8AE · Fees $16/mo · Built 1984

Listing courtesy of KELLER WILLIAMS ISLAND LIFE REAL ESTATE · MLS# D6148550

113 Annapolis Ln
Active
Can tour today
$219,000
99 days on market
3 bd · 2 ba · 1,743 sqft
113 Annapolis Ln, Rotonda West, FL 33947
Flood AE · Fees $16/mo · Built 1973

Listing courtesy of KW COASTAL LIVING III · MLS# A4702348

144 Rotonda Cir
Active
$205,000
73 days on market
2 bd · 2 ba · 1,192 sqft
144 Rotonda Cir, Rotonda West, FL 33947
Flood AE · Fees $16/mo · Built 1985

Listing courtesy of EXIT KING REALTY · MLS# N6145251

27 Annapolis Ln
Active
$275,000
102 days on market
3 bd · 2 ba · 1,839 sqft
27 Annapolis Ln, Rotonda West, FL 33947
Flood AE · Fees $16/mo · Built 1973

Listing courtesy of BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY · MLS# D6148112

192 Annapolis Ln
Active
↓ $10,000
$225,000
113 days on market
2 bd · 2 ba · 1,270 sqft
192 Annapolis Ln, Rotonda West, FL 33947
Waterfront
Flood AE · Fees $16/mo · Built 1984

Listing courtesy of SAVVY AVENUE, LLC · MLS# A4700869

18 Caddy Rd
Active
Can tour today
$443,300
130 days on market
4 bd · 3 ba · 2,265 sqft
18 Caddy Rd, Rotonda West, FL 33947
Flood AE · Fees $17/mo · Built 2026
New construction · Under construction · Adams Homes of NW FL

Listing courtesy of ADAMS HOMES REALTY · MLS# C7528140

23 Annapolis Ln
Active
$209,000
127 days on market
2 bd · 1 ba · 1,330 sqft
23 Annapolis Ln, Rotonda West, FL 33947
Flood AE · Fees $16/mo · Built 1973

Listing courtesy of RE/MAX ALLIANCE GROUP · MLS# D6148013

82 Rotonda Cir
Active
$399,990
126 days on market
3 bd · 2 ba · 1,712 sqft
82 Rotonda Cir, Rotonda West, FL 33947
Pool
Flood AE · Fees $16/mo · Built 1972

Listing courtesy of KELLER WILLIAMS REALTY- PALM HARBOR · MLS# TB8521009

52 Annapolis Ln
Active
$244,500
174 days on market
2 bd · 2 ba · 1,055 sqft
52 Annapolis Ln, Rotonda West, FL 33947
Waterfront
Flood AE · Fees $190/mo · Built 1973

Listing courtesy of FIVE STAR REAL ESTATE OF FL · MLS# O6410119

240 Caddy Rd
Active
$509,900
184 days on market
4 bd · 2 ba · 2,145 sqft
240 Caddy Rd, Rotonda West, FL 33947
Pool
Flood AE · Fees $16/mo · Built 2021

Listing courtesy of REALTY ONE GROUP INNOVATION · MLS# A4693678

12 Golfview Ct
Active
$289,900
215 days on market
2 bd · 2 ba · 1,596 sqft
12 Golfview Ct, Rotonda West, FL 33947
Flood AE · Fees $16/mo · Built 1974

Listing courtesy of PARADISE EXCLUSIVE INC · MLS# D6147006

295 Annapolis Ln
Active
$270,000
201 days on market
3 bd · 2 ba · 1,200 sqft
295 Annapolis Ln, Rotonda West, FL 33947
Pool
Flood AE · Fees $18/mo · Built 1981

Listing courtesy of VIGOREON INVESTMENTS LLC · MLS# A4687428

4 Golfview Rd
Active
$305,000
296 days on market
3 bd · 2 ba · 1,675 sqft
4 Golfview Rd, Rotonda West, FL 33947
Pool
Flood AE · Fees $16/mo · Built 1973

Listing courtesy of BEYCOME OF FLORIDA LLC · MLS# O6375854

271 Annapolis Ln
Active
$379,900
362 days on market
3 bd · 2 ba · 1,599 sqft
271 Annapolis Ln, Rotonda West, FL 33947
Flood AE · Fees $32/mo · Built 2010

Listing courtesy of BRETT BARBER & COMPANY REAL ES · MLS# D6144771

124 Caddy Rd
Active
$285,000
373 days on market
4 bd · 2 ba · 1,839 sqft
124 Caddy Rd, Rotonda West, FL 33947
Flood AE · Fees $7/mo · Built 1973

Listing courtesy of LANDMARKS INTERNATIONAL REALTY, INC. · MLS# D6144573

Want a closer look at Rotonda West Oakland Hills?

Listing information is provided in part by Stellar MLS, as distributed by MLS GRID. Based on information submitted to the MLS as of Nov 14, 2026, 7:51 PM (ET). All data is obtained from various sources and may not have been verified by broker or MLS. All information provided is deemed reliable but is not guaranteed and should be independently verified. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some IDX listings have been excluded from this website.

Lasbury Tracy Realty Inc. · [email protected]